The wave crashed down and took me with it, tumbling head over heels in what some would call, an oxygen-poor environment. The ocean didn’t seem particularly happy with me, deciding to punish my insolence by sending the surfboard into the back of my head... more than once. Thanks, Poseidon.

While not concussed, I did have salt water in every orifice of my head trying to clear me of any ideas of trying to stand up on the board again with the sinus cleanse no one asked for. And despite every sign telling me to pack it in for the morning, I took myself out into the ocean to try once more.

As a general rule, I hate not being good at things. Like really hate it. As a semi-competitive person (read: extremely competitive), I have often chosen not to play games I know I won’t win. Why play my brother in tennis when there’s not a snowball’s chance in hell I return a serve more than once? At that point, it’s like Nadal playing against a golden retriever who’s learned to hold a racket in its mouth. I’ve seen Air Bud (and he is a very good boy), but that would be a beat-down.

And yet, much of my experience over the past few years in jiu-jitsu, surfing, rock-climbing, and a few other areas tells me that deliberately choosing to expose ourselves to the things we are not good at is not only valuable but incredibly necessary. If we are to reach more of the best that we carry within us, we need the feedback from something that we still have more to learn.

For example, I’ve been doing jiu-jitsu for 1.5 years now. That belt is whiter than my pale skin, and that’s saying something. (Updated edit: I’m now a blue belt, and I’m still trash).

For the first 1.4 years of that, training consisted of me showing up to practice, getting the shit kicked out of me, going home sweaty and despondent asking myself “Why do I do this?”, and then coming back to do it over again. I rarely felt like I was making progress, and it was difficult sometimes to convince myself to even go to training. I skipped more than one session at the prospect of another beat-down.

And yet, eventually, I trudged back. And eventually, I started to get better. I started to put the pieces together. I even started to not be smothered by people in their weird pajamas for the entire time we were rolling. Have you ever just breathed normally during practice? I highly recommend it.

So there was physical improvement in this one specific domain in my life, but what carried over to other arenas was more calm and more confidence. It’s hard to be upset about an email when someone has tried to snap your arm in half that morning, and it’s easier to feel good about yourself when you’ve done a hard thing. Even if you haven’t always ended up on top, you chose the challenge. Not many people do that.

It is easy to choose comfort. Your brain does not like pain in any form, real or imagined. There’s good reason for that; historically, pain has meant something is trying to harm you. Stabbing your hand with a knife has rarely led to an improvement in overall well-being.

This human tendency to avoid pain is also a crucial aspect of almost every story we ever tell. Author Donald Miller points out that:

“A general rule in creating stories is that characters don’t want to change. They must be forced to change. Nobody wakes up and starts chasing a bad guy or dismantling a bomb unless something forces them to do so. The bad guys just robbed your house and are running off with your last roll of toilet paper, or the bomb is strapped to your favorite cat. It’s that sort of thing that gets a character moving.

The rule exists in story because it’s a true thing about people. Humans are designed to seek comfort and order, and so if they have comfort and order, they tend to plant themselves, even if their comfort isn’t all that comfortable. And even if they secretly want for something better.”

That’s why there is something particularly valuable about finishing a workout that you absolutely did not want to do. You dragged your feet. You moaned. You whined. You bitched. And you still dragged your ass to the gym, started, and finished. Sometimes you even showed up harder than you thought you could.

In today’s world, rarely is the pain we face of real, physical danger. Legitimate threats to your survival (big scary animals, bad weather, an angry God, an infestation of demons from hell) are harder to find in modern-day society. However, your brain is still looking for threats. And still finding them.

In most cases, the danger exists solely in our minds. Usually, the threat is something author Steven Pressfield would call “The Resistance’. It is fear that locks us in place, rather than a true need to survive. In contrast, when we choose to do the workout, or go to training, what feels good in that moment is a victory over your self, a win over the limiting stories in your brain that tried to tell you it is better to just stay here. When we choose to skip out on that pain, we miss a chance to put pain in perspective and to grow into something our brain never thought possible.

So if there is any message to receive here, it is to intentionally put yourself in challenging situations. Create deliberate opportunities for pain (or chaos, confusion, uncertainty) as that forges an opening for us to step outside our fragile conception of who we are and become something more. Enduring through a struggle we created helps us find better internal answers in the responses we choose and the meaning we assign to external hardship.

Short version: do hard shit.

Popular examples include (it doesn’t have to be physical):

• Run a marathon (or a half, or a 5k).

• Take a cold shower.

• Do a 500 calorie workout (burning 500 calories).

• Go to therapy.

• Have a tough conversation with someone.

• Publish something you wrote.

• Meditate for time period you find uncomfortable.

• Wake up early.

Whatever it looks like for you, find ways to throw yourself in the deep end*. When you’re there, look at what’s right in front of you (just one more step, just one more perfect stroke, just one more practice). You keep moving forward with a focus on the only thing you can do in that moment until you look up and don’t even recognize where you are or who you are anymore. All it took was pain, and it is always worth it.

(*I will take this time to say, please don’t hurt yourself. I’m not the kind of doctor that matters, so consider this a note to please do sensible things when it comes to your health).

I should be very clear about something: I am still not good at surfing. And I’m still not particularly good at jiu-jitsu either. Or rock-climbing. It will continue to take me a while before I approach anything resembling competence in those arenas. And yet, I will continue to go out into the waves, onto the mats, and up the walls, because who I am when I do those things is a better version of myself than the one who chooses to stay comfortable.

Where will you choose to suffer?

Leave a comment

And you’re still doing the thing you swore you’d stop doing.

Unfortunately, pure knowledge changes nothing on its own.

I learned this at 2 AM in a Sydney hotel hallway, hunched over my laptop doing environmental statistics homework that just so happened to be due in six hours.

Environmental. Statistics. At 2 in the morning.

For context, my family had also just flown halfway around the world to see me. They were inside the hotel room, sleeping off their jetlag. And I was in a hallway. Doing homework. About trees and numbers.

Even worse, this was the third time that semester I’d turned a manageable assignment into a crisis through procrastination. I’d had all week to knock this out and instead I stared out the window and told myself I’d do it later.

Potentially even more infuriating, I knew better! I spent a great portion of my outside reading time on behavior change, able to explain the neuroscience of habit formation, cite every strategy for getting yourself to do what you know you need to do.

None of it changed the fact that I kept ending up here. Stealing time from people I loved. Time I couldn’t get back.

Ten years later, the lesson still hasn’t fully sunk in. And it is my literal job to teach these strategies to C-Suite executives.

All of it to say… Knowing the right answer and choosing the right answer are completely different skills. One lives in your head. The other lives in your bones.

I didn’t need more information. I needed wisdom.

The ancient Chinese philosopher Confucius laid it out 2,500 years ago: “By three methods we may learn wisdom: First, by reflection, which is noblest; Second, by imitation, which is easiest; and third by experience, which is the bitterest.”

Bitter. That’s the right word for the taste of wasted time with people you love. Disappointing, shameful, bad bad not good would also be acceptable answers.

To prevent this, let me show you why understanding these three paths to wisdom might finally close the gap between what you know and what you actually do and save you a lot of pain in the process.

Part 1: Experience is the bitter teacher

Confucius called experience “the bitterest” path to wisdom. Experience is bitter because it demands payment upfront and it usually takes the longest to sink in.

Sometimes you touch the hot stove, feel the burn, then learn not to touch it again. Sometimes you need to run your head into the wall repeatedly before you work out a different route. In either case, the lesson comes after the damage.

And the painful experience does not guarantee you will learn the right lesson.

I didn’t learn anything useful in that Sydney hallway at 2 AM. The initial lesson was: “I can still pull it off under pressure.” Because it worked. I scored an HD (high distinction = A on the assignment for all you non-Aussies) which pretty much guaranteed I would do it again.

Most people don’t extract lessons from experience. They accumulate experiences, each one sitting isolated in memory, without spending the time to digest and understand the connection between them, the recurring pattern, the principle or insight that is worth extracting and acting on to make your life better.

Experience is raw data about reality. Data without interpretation is just noise. That’s not helpful.

What this pattern was actually protecting

Later on in the trip, I was walking to the grocery store with the family in Sydney. My dad was in an uproar over outrageous prices before I reminded him that the price for a kilo of turkey was twice that of the pound, and the currency conversion actually meant it was cheaper here to eat his daily lunch of a turkey and cheese sandwich. He calmed down. Sort of.

As we were walking back, and my siblings are giggling at the old man’s peculiarities, I felt something that did not match

Anger.

I was furious with myself. Not because I’d procrastinated, but because I’d stolen time from people who mattered the most to me.

And in that anger, a question emerged:

“What am I actually protecting by doing this?”

Not “Why did I procrastinate?” That’s too easy. The answer is always “I was tired” or “I didn’t feel like it.”

The real question: What does this pattern serve? Why would I be complicit in creating the conditions I say I don’t want?

The answer that came back surprised me: Control.

When I procrastinate until the last minute, I create artificial urgency. I manufacture a crisis where only execution matters. Where there’s no time to doubt. The deadline becomes my permission to ‘lock in’ and do the work without judging it.

I was using procrastination to protect myself from my own perfectionism.

Well, shit.

That realization, that single question that forced me to look deeper, that’s when experience started becoming wisdom.

But it took days of sitting with the discomfort before I could even ask the right question. And it would take years before I could consistently catch myself early enough to choose differently.

Why I kept learning the wrong lesson

Without reflection to guide it, experience teaches you whatever lesson is easiest to learn. And that lesson might be completely wrong.

You get rejected once and learn: “Never put yourself out there again.”
A better lesson: “That approach didn’t work. What might?”

You achieve something hollow and think: “I need to achieve more.”
The real insight: “I’m climbing the wrong mountain.”

After that Sydney night, I could have learned: “Don’t procrastinate when family is visiting.”
For the rest of the master’s degree, I learned: “Just be more strategic about when I procrastinate.”

The experience was trying to teach me something about values. The emotional ‘discord’ (for me it’s heightened emotions like anger and frustration) signalled a mismatch between what I was choosing and what I actually cared about.

Turning pain into wisdom

If you want experience to teach you something useful:

• Notice the emotional intensity. When you have a disproportionate reaction like extra anger or unexpected anxiety, your system is trying to tell you something matters. Pay attention to those signals.

• Ask what the experience revealed. Not “What happened?” but “What pattern became visible?” The hallway revealed that I choose ego protection over connection.

• Look for the deeper lesson. The obvious one is usually wrong. “I failed because I’m not good enough.” The root cause goes deeper. “I failed because I was solving the wrong problem.”

• Connect it to other experiences. I started noticing patterns: I procrastinated often to ‘guarantee’ my focus. It worked during my master’s. It couldn’t work during my PhD, which required me to completely rewire how I worked and what the work meant to me. It became much more about ‘committing to the process’ and showing up, not last minute rushes to the deadline.

Experience is the bitter teacher. The bitterness can be medicinal if you’re willing to taste it fully. But you don’t have to learn everything the hard way. Some insights can be borrowed from others.

Part 2: Imitation borrows wisdom from others who’ve already paid

You don’t have to learn everything through experience. We’d die first.

That’s where borrowed insight comes in. Confucius called imitation “the easiest” path because you can learn in hours what took someone else years to understand. You can avoid obvious pitfalls by studying those who’ve already fallen into them.

Unfortunately, most of us are doing it wrong.

Why I was just the “Well, actually...” guy at parties

For years, I accumulated insight like other people collect stamps.

I had notebooks full of ideas. I swear to you there’s still a Google Doc titled “Sharpen the Saw’ full of my notes from the books I was reading on habit formation, personal development, and self-help. I could quote Naval Ravikant on leverage, Ryan Holiday on Stoicism, James Clear on habits.

I was basically the “Well, actually...” guy at parties. Nobody wants to be that guy. (Please don’t be that guy).

The shift happened during my PhD funding crisis. I’d been reading Annie Duke’s work on decision-making and “outcoming” - the idea that you judge decisions by the quality of your process, not by the result you get.

When my funding got pulled, my first instinct was panic-driven: “Should I quit? Should I transfer? What if I’m wasting my time?”

But then I caught myself. Instead of deciding based on fear, I asked a question inspired by Duke: “What’s the best decision-making process I could commit to that I’d feel good about having done, regardless of what I ultimately choose?”

So I researched transfer options. Talked to people who’d finished PhDs in similar situations. Designed experiments to test whether I could actually fund it myself. Gathered real data instead of catastrophizing.

I made my decision based on the best process I could design, not on whether it would definitively work out.

That’s when I learned the difference between collecting wisdom and using it.

The books weren’t failing me. I was failing to actually learn from them because I wasn’t letting them change my behavior.

The teachers who actually changed my behavior

Find people who’ve handled problems like yours.
When I needed to understand procrastination, workshops at the university told me to just start earlier. Ah yes. Brilliant. Why didn’t I think of that? Go closer to the source of experiences like yours. If they don’t exist in reality next to you, go to the books. Use the internet. You have more access to people like you than at any point in human history. Find them.

Look for practitioners over theorists.
General Stan McChrystal writes about character after decades of leading people in impossible situations. He’s reporting from the field of living high-stakes. My friend Ted hasn’t missed a workout in years. My friend Seb is a role model of warmth for any room he enters is made brighter by his entrance. These people live qualities I admire, they don’t talk about it.

Find those who challenge rather than comfort.
My coach would say things that hurt to hear: “You’re using productivity as a way to avoid dealing with your fear of being ordinary.” I didn’t have to like it for it to be true, though. This can be in therapy, it can also be your closest friends getting real with you. Cultivate a circle of people willing to tell you the hard stuff.

What actually transferred to my life

• From the Stoics: Separating what you control from what you don’t.

  I don’t control what happens to me or what’s already in the past. When I showed up to Sydney with the assignment unfinished, I needed to get the work done so I put my head down and did it. And in the future, I control whether I do the work that lets me be present when they visit. This distinction eliminates 90% of my anxiety.

• From Annie Duke: Judging process over outcomes.

  When facing big decisions, I ask: “What process would I respect myself for using, regardless of the result?” This kept me from quitting my PhD in panic and helped me make dozens of career decisions since based on quality thinking, not fear or hope.

• From my PhD peers: Showing up beats surging.

  My PhD had no tests, no courses, no deadlines for years. Just the work. I had to learn how to work without urgency, which went against everything that had gotten me to that point. Every week, I’d go to “Shut Up and Write” sessions - two hours of work, four pomodoros, free coffee at different cafés around campus. I learned from watching the people who finished their dissertation: they just showed up. Day after day. Office. Head down. Consistent cadence.
  

  They became my role models for the long-haul. Steady people who treated it like a job. That model of consistency - borrowed from peers I never even talked to much - got me to the finish line.

When the advice finally clicked into action

Borrowed understanding isn’t yours until you’ve tested it against your own life.

• Choose 1-3 guides whose wisdom resonates deeply.

  • Ideally, these are actually people close to you. I’ve found books to be good insight for the qualities I might desire or the things I need to work on, but it’s much more powerful for me to look at my brother or my friend Ted as my examples for discipline, not James Stockdale. I can see my people in ‘color’, whereas historical figures feel more distant. They’re still better than nothing though. So I can be inspired by the Stoics and Ryan Holiday’s writing for the importance of accepting reality as it is, then I try and find somebody who role models that (it’s my dad for me).

Extract principles over prescriptions.

• “Wake up at 5 AM” is a prescription. “Do your most important work when your energy is highest” is a principle.

  • The principle is portable to the changing conditions of your life and to your unique wiring as a human. As someone who has consumed every bit of productivity advice that’s out there, there was no one book that perfectly worked for me. But the system I created from their knowledge and what I extracted from their principles to suit me is what got me to the finishline for my PhD.

• Test everything.

  • I tried the Pomodoro Technique because everyone swore by it. Turns out 25-minute intervals were good for a while, but started to be too short and broke my flow. I ended up working to 90-minute blocks. The principle (focused work in time-bounded sessions, do this work or do nothing) was sound. The specific implementation needed adjustment.

Borrowed insight from others is accessible. The raw material of what to do, how to do it, and life lessons worth replicating are everywhere in the role models, mentors, authors, and friends all around us.

But you can fill notebooks with ideas, highlight dozens of books, follow all the right teachers and still make the same mistakes.

You haven’t done the work of integration. That work is reflection.

Part 3: Reflection turns information into power

Two weeks before I submitted my PhD thesis, I was once again walking to the grocery store in Sydney, but this time, the question was different:

“What if nothing changes?”

I’d been working toward this degree for five years. The finish line was finally visible.

And I realized: when I hit submit, I’d still be the same person. Still procrastinate. Still struggle. Still have the same patterns, the same fears, the same problems. The degree wouldn’t fix me. It wouldn’t make me superhuman. It never could.

That realization could have been devastating. And for a few hours, it was.

Eventually it became liberating. Because suddenly I could ask a better question: “Am I a better version of myself for having gone through this experience?”

Yes. Completely yes.

The becoming mattered more than the degree.

That’s what Confucius meant when he called reflection “the noblest” path to wisdom.

Reflection makes experience and imitation actually yours because you give time and space to allow the lessons, insights, and principles to fully sink in.

Without reflection, experience is just things that happened. Without reflection, imitation is just ideas you borrowed and tried on, but never made them a permanent part of your wardrobe.

The split second that changes everything

Reflection is not meant to be silent contemplation far off on a distant mountain. Reflection is work. Reflection is active synthesis where you are working hard to test yourself, to push yourself, to reveal where you’ve done well and where you’re falling short. You know you’ve done well when you feel like you’ve punched yourself in the stomach with insight.

A few different methods to bring reflection into your life. I’ve done them all, you just have to find the right mix that works for you.

1. Meditation: Building the attention muscle.

   Every time you notice your mind has wandered and bring it back—that’s a rep. That’s the awareness muscle getting stronger. This muscle lets you catch yourself before you’re hiding in a hallway at 2 AM. It creates space between impulse and action, that allows you to ‘decide to decide’ in alignment with your vision, values, strengths, and best self. That space is where your best choices live.

2. Journaling: Making the invisible visible.

   Your thoughts are fog until you write them down. Morning pages capture the noise. Evening reflections ask: “What energized me? What drained me?” Weekly reviews spot patterns. I tend to journal in cycles. Three months of consistent practice with a particular prompt, then I tend to switch. Honestly, sometimes I fall off. That happens. And it’s important that for more than 10 years now, I always come back to writing stuff down.

3. The “How Would I Know?” Framework: Reflection as science.

   This is the most powerful tool I’ve built. When facing uncertainty, ask: How would I know if this is true? What would I need to see? What evidence would contradict my assumption? What small experiment could I design? This question saved my PhD. When funding got pulled and I thought I should quit, instead of deciding based on emotion, I asked: “How would I know what my actual options are?” Then I researched. Talked to people. Designed experiments. Made a decision based on reality instead of fear. This was when I became a real scientist, using questions to interrogate my understanding of reality before allowing my reactive emotions to make all my decisions for me.

4. Coaching/Therapy: External perspective.

   Sometimes you can’t see your blind spots alone. My coach catches me in rationalizations on a weekly basis: “You just spent ten minutes explaining why you’re too busy to work on your book. But last week you told me the book is your most important project. So which is true?” Other people can sometimes see our patterns more clearly than we can (it’s why we know Susan and John shouldn’t be together, but they insist on dragging us all into a doomed relationship). Having a professional whose job it is to create productive confrontation forces clarity we desperately need.

The spiral that never ends

These paths (experience, imitation, reflection) do not need to be sequential. They’re at their most powerful when they spiral together, like three separate threads weaving something stronger together.

Experience brings up signals that lead to you asking questions. Questions that drive you to seek answers from others. The insights of others (live or from reading) gives you frameworks. But the frameworks don’t become real until you reflect on them. Test them. Integrate them.

Which creates new understanding. Which leads to new actions. Which creates new experiences. Which generates new questions.

Experience → Imitation → Reflection → Wisdom → On Repeat, forever and ever.

Each revolution takes you deeper, closer, and higher. Deeper into knowing yourself, closer to the gap between what you say and what you do, higher to the best version of yourself that we all know you’re capable of.

The ancient traditions called wisdom “the principal thing.” Wisdom makes everything else meaningful.

Intelligence got you here. Discipline built your skills. Work ethic created your achievements. But your wisdom determines what you do with all of it and whether it means something to you or not.

Ten years after that Sydney hallway, I still procrastinate sometimes. The pattern hasn’t disappeared.

But now when I catch myself putting something off, I pause, and within a few breaths, I know where it’s coming from. Fear of it not being good enough. Anxiety about being judged. Discomfort with vulnerability. Usual suspects.

Naming it doesn’t always make it go away. But now I have three paths working together:

• Experience signals when something’s off - the anger, the anxiety, the disproportionate reaction that says “pay attention here.”

• Imitation gives me the frameworks to interpret what I’m feeling, borrowed wisdom from others, to see what answers, insights, and principles might already exist to adapt to my situation.

• Reflection is where I create the space to sit with the questions, ex; “What am I protecting by doing this?” It takes time, but it’s worth it for what deeper patterns it reveals.

That’s the spiral. Experience creates the signal. Imitation provides the language. Reflection reveals the pattern. Then I get to choose differently.

Not perfectly. Not every time. But more often than I used to.

Ten years after that Sydney hallway, I still procrastinate sometimes. But I don’t steal time from people I love anymore. Because I’ve built a system for turning bitter experience into actual wisdom.

Ole wise boy Confucius was right about all three paths. And ultimately, wisdom isn’t about reaching perfection. It’s learning to choose better, more often, with less collateral damage.

The patterns don’t disappear. You just get better at catching them before they steal what matters most.

Your turn: One question to bring you closer to wisdom

Right now, think of one pattern that keeps repeating. One place where you know better but keep doing it anyway.

• Experience: When did you last feel that disproportionate emotional reaction? What was your system trying to tell you?

• Imitation: Who do you know who’s handled this better? What would they do?

• Reflection: Write this down and answer it honestly: “What am I protecting by keeping this pattern alive?”

Five minutes. No phone. Just you and those questions.

That’s how knowledge becomes wisdom. That’s how you close the gap.

More importantly, it was mine. And if I squint hard enough, I can see the throughline leading from that silly little story from a second grader who thought he was funny and trace it all the way to me sitting in this cafe in DC writing a newsletter for you all.

That throughline matters because most of us lose it somewhere along the way. We stop asking “What do I want to make?” and start asking “What am I supposed to do?

In some ways, we are fortunate. Because the world does hand you a recipe: Focus on the job, the salary, the promotion. The house, the marriage, the kids.

None of these things are bad. Many of them are good. But the list is incomplete. There's something missing from this formula, something essential that no career counselor and only a great executive coach will tell you about.

You must create.

I don't mean you need to become a professional artist or quit your day job to write the great American novel. I mean you need to make space in your life, starting today, for the act of bringing something into existence that wasn't there before.

Subscribe now

Why Creation Is Your Best Medicine

Right now, you’re trying to figure out how to matter. Every human being is. The difference is that most people accept someone else’s definition of mattering: external validation, recognition, the approval of strangers who will forget about you the moment you step down from whatever podium you’ve climbed.

I know I did.

Creation offers you something different. It is a rebellion against a transactional world that says your worth is measured by your output, your salary, your productivity metrics. When you create, whether through writing, painting, music, or whatever calls to you, you’re saying “this matters because I made it, not because someone else validates it.”

You went from ‘zero to one’, from nothing to something, from absence to existence. Just because. I want you to believe that matters.

This is medicine for a life that will otherwise be spent chasing achievements that never satisfy. The promotion that feels hollow within minutes of receiving it. The constant question of “what’s next?” that never gets answered. The Sunday night dread that settles in no matter how “successful” you become.

The act of creating, of reaching within and expressing something authentic, tunes you into your own voice. Not what you think people want to hear. Not what gets the most likes. What YOU have to say. That authentic voice becomes your compass for every other decision you make.

This is how you stop optimizing for someone else’s definition of success and start building toward your own.

How to Find What Wants to Emerge Through You

"But Danny," you might say, "I don't know what I have to create. I don't know what I have to say."

That's exactly why you have to start.

You don't discover what you have to say by thinking about it in your head. You discover what to create through the process of creating. The act of reaching within, of wrestling with your thoughts and ideas, of expressing something, anything, is how you tune into your authentic voice.

Look Backward: The clues from your past

There are clues everywhere about what you are called to create. You may not be cleaning out your parents house, but signals will call to you from your past if you pay attention.

• When did you lose track of time as a kid?

• What made you light up?

• What did you love doing before anyone told you whether you were "good" at it?

Look backward at those moments. Look forward to who you want to be on your deathbed. Meet in the middle from both directions to harness those signs about what wants to emerge through you right now.

Share

If all else fails, remember a young Mike Myers on SNL for a deep cut reference.

Look for Flow: When time disappears, pay attention

As you experiment, you’re looking for flow states, moments when time disappears, when you're so immersed in what you're doing that the rest of the world fades away. That's an important signal.

It might not be what you expect. My friend found it drawing Pokemon during our Artist's Way challenge. For me, it's writing in cafes on Saturday mornings, coffee in hand, trying to articulate an idea that feels important.

The key is imperfect play and experimentation. Try different things. Write morning pages. Take an art class. Learn an instrument. Go on "artist dates," an idea from author Julia Cameron, as dedicated time just for creative exploration, no outcome required.

When you find something that creates that sense of being "plugged into the source," pay attention. That's a unique frequency of ‘resonance’ about something you deeply care about, believe in, or identify and it’s worth noticing.

Permission to Create Badly (And Privately)

Let me give you permission for something…you can create and never show it to anybody.

You can write and never publish it.
You can paint and never hang it on a wall.
You can make music and never perform it.

This isn't about becoming Instagram-famous or building a personal brand (although it can be if that’s your bag, baby. +10 to me for a second Mike Myers reference).

What this is about, is the inherent value of the creative act itself. It's about having time in your day that isn't transactional, isn't measured, isn't optimized for productivity.

You need that in your life. We all do.

So much of our lives is about trading your time and energy for outcomes. That’s fine. It has it’s place and I have neither the time nor the inclination to engage you, dear reader, in anti-capitalist screed right now.

But there must be a space for creation. Because creation gets to be different. It gets to be the space where you rebel, in small or big ways, against machine minds, metal hearts, and a message that says only productive work makes you worthy.

You don't have to be "good enough." Who's holding you accountable for that anyway? And even if you never make money from it, even if you never become professional-level, isn't it enough, in this one precious life you have, to simply enjoy doing it?

The Social Media Trap (And How to Escape It)

Popularity is a survival signal. Wealth is a signal of prosperity. These aren't bad things, but they're incomplete. If you only listen to what gets rewarded online, you're optimizing for someone else's definition of success, not your own. Social media metrics appeal to our survival instincts, not our deepest selves.

Social media has actually democratized creation in amazing ways—you can find your people, no matter how niche your interests. Someone is writing about medieval women's literacy in a small part of France, and they've found their community. But you have to be intentional about not letting the metrics hijack your deeper motivations.

The practice is this: look up occasionally to check your direction to see ‘is this resonating with people? Is this helping?’ Then focus back on your feet. Back to the work. Back to what you have to say. Back to expressing it more beautifully, more truthfully, more authentically.

If Not Now, When? (Spoiler: Never)

"But I need to focus on practical things," you might say. "I need to get a job, pay rent, be responsible."

When will you have time for this if not now? When you have more bills? A family? Kids? When your job becomes more demanding?

If you don't create space for yourself (and this is an expression of caring and attention to yourself) the world will not create it for you. It will not be handed to you out of the blue.

This is how you get off somebody else's path and start walking your own. Everyone has time for some version of this. It doesn't have to be hours every day. It can be an hour on weekend mornings. It can be thirty minutes before work. It can be whatever you can carve out consistently.

But you have to carve it out. Because this is how you get closer to your own measure of what a successful life looks like that includes time for creation, for expression, for bringing forward what's uniquely yours.

Five Years From Now

Five years from now, wherever you are, I hope you'll have a practice of creativity that energizes rather than depletes you, that connects you to that well of authenticity more often.

I hope you'll know the feeling of being "plugged into the source," of creating something that expresses your unique way of seeing the world. Not because it will make you famous or wealthy or impressive to others, but because it will make you more fully yourself (bad teeth and all, good god he’s done it again).

This is rebellion against a culture that wants to reduce you to your resume. This is medicine for a world that will constantly try to tell you what success should look like. This is how you tune into what you actually care about, what you have to say, what you want to express and definitively not what you think others want to hear.

So start somewhere. Start today. Create the space, however small. Listen for what wants to emerge through you. Trust that you have something unique to offer, even if you don't know what it is yet.

You must create, not because the world demands it, but because something in you does.

Grr Baby,

Danny

P.S. Let me know what you’re committed to creating in the comments. No step is too small.

Leave a comment

Growing up, my dad would leave handwritten notes on the kitchen counter before he left for work, simple messages and quotes of encouragement for my brother and me to find at breakfast. One phrase appeared more than any other, written in his careful block letters:

"If it is to be, it is up to me."

This became my north star.

When I needed to improve my grades, it was up to me.
When I wanted to make the varsity team, it was up to me.
When I faced rejection, setbacks, or challenges, the answer was always the same: figure it out, work harder, rely on yourself.

This message was incredibly powerful for who I became as a growing young man. It built resilience, work ethic, and the confidence that I could handle whatever life threw at me. It helped me achieve things that seemed impossible at the time, playing college soccer, doing well at school, securing scholarships that eventually sent me to Australia for 7 years.

That quote and the advice contained within helped me achieve everything I thought I wanted. It also left me carrying weight that was never mine to bear.

I found myself automatically carrying every weight alone - not because I had to, but because I'd forgotten I had any other option. The promotion decision? Up to me. The family crisis? Up to me. The career transition? Up to me. The relationship challenge? Up to me.

I had become so good at self-reliance that I lost sight of something even more powerful:

You get to choose the people in your life who carry the weight with you. And that choice changes everything.

The Choice You Didn't Know You Had

Here's the brutal truth marketer and businessman Alex Hormozi identified about getting advice:

Your family loves you unconditionally but may not understand the complexities of your career decisions. Your college friends care deeply but might not grasp the challenges you're navigating now. Your colleagues can offer professional insight but may not know your deeper values or long-term vision.

Meanwhile, the people who have the wisdom and experience you need - the ones who've walked similar paths and could actually guide your next steps, well they don't know you personally. They can't tailor their insights to your specific situation, your unique strengths, or your authentic goals, knowing exactly what makes you tick or what pisses you off.

Most people accept this gap between who cares versus who can help as inevitable. They take well-meaning advice from people who love them but can't help them. Or they consume generic wisdom from people who could help but don't know them.

The transformation happens when you refuse to accept this gap as permanent.

Instead of settling for well-meaning but inadequate support, you can seek the rare overlap. Find people who both care about your success AND have the wisdom to help you achieve it.

Most of us inherit our support network by accident. We stay close to people from our hometown because they were there first. We lean on family members because they're family. We seek advice from colleagues because they're convenient. We maintain friendships from college because of shared history.

None of this is wrong. If your groups work for you, please keep them. What I hope to convey is that in that scenario, none of the groups and relationships we inherit are particularly intentional either. So I ask:

• What if you didn't have to settle for whoever was around when you were growing up?

• What if you could choose who influences your biggest decisions?

This is the choice most people never realize they have: the power to intentionally shape who influences your life.

Building your Personal Board of Directors is one of the most important investments you can make. If you're ready to systematically design the relationships that will shape your next chapter, I help high-performers do exactly this through 1:1 coaching. Message below to hear more about working together.

Let me show you what this looks like in practice through three different ways this has transformed my own experience.

The Wisdom Collective: When Growth Becomes Shared

Time with high-quality friends is invaluable. Our calendars never reflect that truth.

Two years ago, I decided to change that by creating intentional time with two of my dearest friends in what became version 1.0 of our mastermind. Last year, we expanded by adding two more excellent humans to our gathering, and we just completed the 2025 version in early August.

In those masterminds, we did yoga, we worked out, we shared meals, and at one point, even visited the Denver Broncos practice facility to have a chat with their President. But the heart of our long weekends has always been "Ask and Offer" - dedicated time where each person could share whatever challenge they were facing and receive input from the group. It is the perfect culmination of time spent with people who care and people who can help.

Everyone always shows up for these conversations with curiosity, vulnerability, generosity, and the occasional loving "get your shit together" when needed. Some of my past takeaways have been:

1. The world is not served by you playing small

2. Knowing your story is the start of owning your story

3. You build legacy with action

4. How we choose to spend our time is how we choose to create value in the world

These weekends, (available to all of us with a shared space and time on the calendar), were intentional development with people who both cared about my authentic success and had the wisdom to challenge my thinking in productive ways.

Another way we can leverage this care/counsel dyanmic is the power we can create by simply being present for people in our lives going through tough times.

I've experienced this through creating space for a friend to be witnessed during a difficult personal crisis. Crucially, it was never about trying to fix or solve the issue. The point was to simply hold space for him to be fully human in his struggle without having to perform strength or competence. The healing wasn't in getting answers; it was in not carrying the weight alone and it required no lengthy experience or specific expertise to care or to help in that moment.

We can all be doing this more for the people in our lives.

The final way I’ve seen this intentional network is through strategic relationships opening doors.

This one is a little bit more transactional but when I was looking for a new role, one conversation with someone who understood both what I was seeking and what organizations needed led to the position I ultimately accepted. My current role is a natural result of having cultivated relationships with people who could support my growth when opportunities aligned, a perfect product of somebody who could help with enough investment in me to take action on it.

Regardless of which path you might experiment with yourself, here's what I learned the hard way: for every relationship like this that serves your authentic path, you might have three that don't. And the biggest chokepoint might actually not be finding new people but instead focusing on getting incredibly honest about the relationships already influencing your decisions in the wrong directions.

The People Sabotaging Your Success (And They Love You)

The first step is getting honest about who's actually influencing your big decisions right now.

Take a moment and think about your last few major choices - career moves, relationship decisions, financial investments, life direction changes. Whose voices were in your head during those deliberations? Whose approval were you seeking? Whose disappointment were you trying to avoid?

Now ask yourself these questions about each of those influences:

1. Do they want what's authentically best for me, or what looks good to others?
   Some people in your life are more invested in your image than your actual fulfillment. They give advice based on what they think success should look like rather than what would serve your unique path.

2. Have they successfully handled problems like what I'm facing?
   Love and good intentions can't substitute for relevant experience. The person giving you career advice - have they built the kind of career you want? The relationship guidance - are they in connections you admire?

3. Do they understand my values and long-term vision?
   Even well-meaning advice can be misaligned if it doesn't account for what you actually care about. The best supporters help you make decisions consistent with your authentic self, not their version of who you should be.

4. Do they challenge my thinking or just validate my existing beliefs?
   Growth requires someone who challenges your thinking. The people who only tell you what you want to hear might feel supportive in the moment, but they're not serving your development over time.

This audit isn't about judging your existing relationships or cutting people out of your life. It's about getting clear on which relationships are actively serving your growth and which ones might need different boundaries or expectations.

How to Attract People Who Actually Help You Win

Once you understand the gap between your current support network and what you actually need, you can begin building more intentional relationships.

Start with Your Current Circle

Before seeking new relationships, see if you can deepen existing ones.

The most powerful tool I've discovered is introducing "Ask and Offer" into regular gatherings - dedicated time where each person shares a real challenge they're facing and receives input from the group. This isn't casual advice-giving but structured vulnerability: one person presents their situation (the Ask), everyone else contributes perspectives, resources, or connections (the Offer), and the presenter chooses what resonates.

What makes this work is the combination of genuine problems (not hypotheticals), diverse perspectives (everyone contributes), and no pressure to take the advice. You'll quickly discover which relationships have the depth and wisdom for meaningful mutual support, and which ones prefer to stay surface-level.

Identify Your Growth Edges

Where do you most need wisdom, challenge, or support right now? Career transitions? Creative pursuits? Relationship skills? Financial strategy? Parenting? Physical health?

Different areas of growth may require different kinds of support. Be specific about what you're looking for rather than hoping one person can meet all your needs.

Seek the Overlap

Look for people who occupy that rare intersection of caring about your success AND having relevant experience or capabilities. This might include:

• Mentors who've walked similar paths and can offer wisdom from experience

• Peers who are slightly ahead of you in areas you want to develop

• Friends who share your values but bring different perspectives and skills

• Professionals who understand your industry, challenges, or aspirations

Create Structures for Connection

You need more than accidental interaction with your most valuable connections. Consider:

• Regular one-on-one conversations with key mentors or advisors

• Annual retreats with 3-4 people committed to shared growth (This is my mastermind retreat with 5 of us traveling to a shared location for a long weekend once a year)

• Quarterly dinners with a 6-8 people focused on mutual development

• Monthly accountability partnerships around specific goals (I often use this to read books with a partner I’ve been putting off, having a call on the calendar to check in on what we’re learning/applying from it)

Where High-Value People Actually Hang Out

If you think your current relationships might already meet the bar:

Start with deeper conversations about real challenges. Share something you're genuinely struggling with and see how people respond. Do they listen with curiosity? Offer thoughtful perspectives? Challenge your assumptions in productive ways? These are signals of relationship potential and you can start to deliberately invest more time on the calendar towards these relationships. Even 60 minutes more on the calendar than currently exists = progress.

If you're in the "lonely chapter" and need new connections:

• Join communities aligned with your values and interests. Look for book clubs, hiking groups, professional organizations, volunteer opportunities, or hobby clubs where you'll meet people who care about similar things.

• Start your own gathering. Host dinners, create reading groups, organize outdoor activities, or launch discussion series around topics that matter to you. Being the convener allows you to attract the kind of people you want to know.

• Look for ways to serve others' growth. Mentoring, teaching, or supporting other people's development often leads to reciprocal relationships where they contribute to your growth as well.

The Permission You've Been Waiting For

Here's what I need you to understand: You don't have to carry the weight alone, and you were never supposed to.

The self-reliance that helped you achieve what you have achieved is a powerful tool. But like any tool, it has its appropriate applications. Some challenges are best handled independently. Others require collaboration, diverse perspectives, or capabilities beyond what any one person can provide.

The wisdom isn't choosing self-reliance or community. It's choosing consciously based on what serves your growth.

You have permission to:

• Set boundaries with relationships that drain more energy than they provide

• Seek out people who've handled problems like yours

• Choose your companions for the journey rather than accepting whoever happens to be around

You don’t need to abandon the self-reliance that got you here. You do, however, need to evolving that self-reliance into something even more powerful: "If it is to be, it is up to we - and I get to choose who 'we' includes."

The Compound Effect of Choosing Your Circle

When you take responsibility for choosing the relationships that shape your life, something profound happens: you stop being a passive recipient of whatever support happens to be available and become an active architect of the community that serves your highest growth.

What's remarkable is that my mission has become so important—and so big—that there's no way I could achieve it alone. The people I get to go through life with now genuinely care about my success and offer counsel that actually matters. Every conversation becomes a gift, every minute I carve out for them on my calendar a source of both learning and joy. I can't imagine a better way to move through the world.

So who needs to be on your board? Who do you need more time with? And when are you going to carve out space on the calendar for the people who care and who can help?

Leave a comment below—I read every one and often respond.

Leave a comment

Your personal board of directors is waiting to be assembled. If you're ready to stop carrying the weight alone and start building intentional relationships that accelerate your growth, I'd love to help.

I work with accomplished professionals who've achieved external success but want relationships that serve their authentic path forward. Through our work together, you'll identify your current relationship gaps, design strategies to attract the right people, and create structures that turn surface-level connections into your most valuable assets.

Ready to build your board? Book a conversation to explore working together below.

The conversation happened on a Tuesday morning in Sydney, 9,000 miles from home. Short sentences that demolished two years of blood, sweat, and a single tear slowly tracing its way down my cheek: my PhD funding had been pulled. No explanation, no appeal process, no backup plan. Good luck.

My emotional brain had an immediate, crystal-clear response: Quit. Pack your bags. You've been screwed over and humiliated. Cut your losses and gtfo.

The intensity of my reaction surprised me. I felt peaks of frustration, anger, sadness, and bitterness that were higher than normal. All emotional overreactions that, thanks to years of meditation practice, I recognized as a signal that something was off.

What I came to realize was that these emotions were my ancient, primal wiring trying to grab the wheel, control the radio, and choose the final destination of my entire academic career.

That's too much power to give to the most animal-like parts of my brain.

Instead of letting my emotional brain make a decision that would reshape my entire life, I realized I needed a different approach. I needed to channel the newest part of my brain, (the prefrontal cortex if ya fancy), to think like a scientist.

In that moment of crisis, one question cut through all the emotional noise:

"How would I know what the right decision actually is?"

That question became the foundation for everything that followed.

Three years later, I finished that PhD (finally), launched a consulting career, and now help executives navigate their own complex decisions for the organizations and people they lead. The systematic thinking framework that saved my academic career has since transformed how I approach every major choice from career transitions to where to live to how I evaluate information in our increasingly noisy world.

It is one of the gifts of my PhD, a way of thinking more valuable to me than the letters behind my name.

Which brings me to you.

What if I told you that most of the decisions shaping your life right now are being made by the wrong part of your brain?

Think about your last major decision.

Did you agonize over it for weeks, flip-flop between options, or rush toward what "looked right" because sitting with uncertainty felt unbearable?

You're not alone. The very traits that made you successful in one domain often sabotage you when facing genuinely uncertain choices.

Subscribe now

Why Smart People Make Terrible Decisions

Here's the uncomfortable truth about people who've tasted excellence in at least one domain: We're exceptional at execution but surprisingly terrible at decision-making under uncertainty.

We've been trained to have the right answer, to be the person others turn to for solutions, to figure it out quickly and move forward with confidence. This serves us well when we're operating in familiar territory: the sport we've mastered, the academic subject we've studied, the professional domain where we've built expertise.

But when facing genuinely uncertain decisions (career pivots, relationship choices, life direction changes), this same performance, success, and achievement oriented mindset becomes a liability.

Instead of asking "How would I know if this is right for me?" we rush toward what looks impressive based on external markers of success rather than what actually serves our authentic path.

We make decisions to maintain our image as someone who "has it figured out" rather than admitting we're navigating uncharted territory.

We let inherited stories and unconscious biases drive our choices because slowing down to examine them feels like weakness.

The identity component here is crucial. For someone whose self-worth has been built on competence and having answers, saying "I don't know" feels like admitting failure. The terror of appearing incompetent often drives us to make quick decisions based on incomplete information rather than designing systematic ways to gather better data.

This is how smart, capable people end up in careers that look impressive but feel hollow, relationships that check the right boxes but lack genuine connection, or life paths that satisfy everyone else's definition of success while leaving us feeling empty.

The Scientific Method for Life Decisions: Mini-Experiments and "How Would I Know?"

There's a better way to navigate uncertainty, one that starts with a simple but powerful question: How would I know?

This matters more than you might think.

We live in a world where everyone has infinite options and nothing feels permanent. Most people respond to this by either getting stuck in endless research mode or making quick decisions they later regret. Meanwhile, you'll be the person who actually knows what they're talking about because you've tested your assumptions. You'll be making moves that serve your authentic path instead of just looking good on paper.

This approach is grounded in what philosophers call critical realism: the understanding that while reality exists independently of our perceptions, we can only know it imperfectly through systematic inquiry.

There's an old parable from India about blind people trying to understand an elephant. One person touches the trunk and says "An elephant is like a snake." Another feels the leg and says "No, it's like a tree trunk." A third touches the ear and insists "You're both wrong. It is like a fan."

Who's right?

Everyone is.

And no one is completely right.

Here's what this teaches us about life decisions: When you're trying to decide something important like what career to pursue, there ARE real answers about what would contribute to your happiness and fulfillment. There's likely a whole category of jobs that would fit you well, and many more that won't. But you can't see the complete picture from where you're standing right now. You only have partial information. The elephant exists, it's real, but your current experience isn't the whole truth.

So instead of pretending you know the complete truth ("I KNOW this specific job will make me happy") or throwing your hands up to the gods of nihilism because perfect certainty is impossible ("I can't know anything for sure so fck it"), you ask: How would I know?

You try different experiments.
You look from different angles.
You test small pieces of your assumptions.

Each experiment gets you a little closer to understanding what actually works for you. You'll never have perfect information, but you can have much better information.

In practical terms, this means approaching major life decisions the same way a scientist approaches research questions: with curiosity rather than certainty, experiments rather than assumptions, and evidence alongside emotion as the primary guides.

The scientific method, one of the greatest inventions of humanity, is a framework for cutting through our own biases and stories to make decisions aligned with reality rather than wishful thinking. And you don't need an advanced degree, a laboratory, or 7 years of a doctorate overseas to use it in your own life.

Here's how it works in practice:

• Observation: Notice what's actually happening, not what you think should be happening or what others expect to be happening.

• Question: Formulate specific, testable questions rather than vague anxieties or assumptions.

• Hypothesis: Make educated predictions based on available evidence, not just gut instinct or social pressure.

• Mini-Experiments: Design small, low-risk tests to gather data rather than betting everything on one big decision.

• Analysis: Examine results objectively, including data that contradicts your preferences.

• Iteration: Use what you learn to refine your understanding and design a better life.

Share

The key insight is in the "mini-experiments": small, designed tests that help you gather real-world data about your assumptions.

Instead of agonizing over whether a career change is right for you, you design ways to test it through informational interviews, volunteer projects, part-time work, or shadowing someone in the field, all to give you insight and better answers to the question “How would I know?”

Worried about whether you'd enjoy living in a different city? How would you know? Maybe you spend a month there, talk to locals, explore different neighborhoods, experience the daily rhythms rather than just visiting as a tourist.

Uncertain whether a relationship has long-term potential? Well, how would you know? Perhaps you travel together, see how you handle conflict, spend time with each other's families, observe how they treat service workers when they're stressed.

The beauty of this approach is that you can learn something valuable regardless of the outcome. Even "failed" experiments provide crucial data about what doesn't work for you.

Real-World Tests: When Experiments Surprise You

Let me share how this plays out in practice, showing how this approach transforms messy uncertainty into manageable experiments.

The LinkedIn Experiment

After six months of writing once weekly on LinkedIn (which I loved), I decided to scale up to five times a week for six months. My question became: How would I know if more frequent posting would actually serve my goals? My hypothesis was that more frequent posting would accelerate audience growth and business opportunities. Part of the pressure came from ideas about branding and reach that I'd absorbed from the platform.

I upheld the commitment for the full six months, but the analysis revealed something unexpected: the increased frequency was pushing me to write too superficially, crafting posts for "the market" rather than expressing authentic insights. I was optimizing for engagement rather than truth. And it burned me out.

The experiment taught me that more isn't always better. It led me to Substack (we’re here right now!) where I could write longer, more thoughtful pieces less frequently, which felt far more aligned with my authentic voice.

The Jiu Jitsu Investigation

After a back injury ended my soccer playing days, I needed a new physical practice. Ironically, despite being a martial art where people actively try to choke you and break your limbs, jiu jitsu seemed like a potentially safer pursuit than the sport that had led to my injury. My hypothesis was that Brazilian Jiu Jitsu would provide the competitive outlet and community I was missing. I joined the first gym I found and struggled for months, feeling lost, overwhelmed, and convinced I was terrible at it.

The question became: How would I know if jiu jitsu wasn't for me, or if this particular environment wasn't serving my learning style?

I tried a different gym with smaller classes, more personal attention, and instructors who learned my name. Same sport, completely different experience. The mini-experiment of switching gyms revealed that my initial struggle was about environment and instruction quality, not my aptitude for the sport.

The PhD Strategy

Back to that funding crisis. Once I recognized my emotional overreaction as a signal rather than a directive, I approached the decision systematically. My question was: How would I know what my actual options were for completing this degree or transitioning to something else?

I researched other universities I could transfer to, investigated alternative funding sources, and had conversations with people who had completed their PhD programs to understand their career trajectories. My hypothesis was that with strategic planning, I could find a way to complete the degree that aligned with my financial and personal constraints.

The experiments included applying to transfer programs, taking on multiple part-time jobs to fund my studies, and networking with professionals in fields I might want to enter.

The analysis revealed that while finishing the PhD would require significant sacrifice, it was achievable and provided both valuable skills and kept more doors open for my next career phase.

None of these experiments went exactly as planned, but each provided crucial data that informed better decisions and ultimately improved my life.

From "Having Answers" to "Finding Answers"

Making this transition from emotional to systematic decision-making requires a fundamental identity shift, especially for those accustomed to having the right answer.

You have to move from "I should know the answer" to "I can design a way to find out."

This isn't just a cognitive change but an emotional one that challenges core beliefs about competence and worth.

Here are four mindset shifts to be aware of:

1. Permission to Not Know: Excellence in systematic thinking means embracing uncertainty as the starting point, not something to be quickly eliminated.

   
   The phrase "I don't know, but here's how I could find out" becomes a statement of competence, not inadequacy.
   

2. Comfort with "Failed" Experiments: When a test doesn't deliver the results you hoped for, that's not failure but successful data collection.

   
   The goal isn't to be right about your initial hypothesis; it's to learn something useful regardless of the outcome.
   

3. Patience Over Action Bias: High-achievers are wired to solve problems by working harder and moving faster. Systematic thinking sometimes requires slowing down, gathering more data, and testing smaller hypotheses first.

   
   This can feel like procrastination but it's actually a more sophisticated form of problem-solving.
   

4. Good Evidence Over Perfect Information: The goal isn't to eliminate all uncertainty before acting but to gather enough good evidence to make reasonably informed decisions.

   
   Critical realism reminds us that we'll never have perfect information about complex life choices.

   
   And that's okay.

   
   The question "How would I know?" isn't meant to paralyze you with endless research but to give you confidence that you've done your due diligence. Sometimes a bad outcome reflects circumstances beyond your control, not a flawed decision-making process.

   
   The standard is "good enough evidence to act wisely," not "perfect prediction of outcomes."

The identity shift is from seeing yourself as someone who should have it all figured out to someone who excels at figuring things out. That's a crucial distinction that transforms how you approach uncertainty from a source of anxiety into an opportunity for discovery.

Your Decision-Making Toolkit

The most powerful question in this entire framework remains: "How would I know?" Here's how to apply it systematically to your own decisions, whether you're navigating career transitions, relationship choices, or life direction changes.

Observation Stage Questions

• What's actually happening in my situation right now (versus what I think should be happening)?

• Where am I feeling emotional intensity that might signal important data?

• What patterns do I notice in my reactions or behaviors?

Question Formulation

• What specifically am I trying to decide or understand?

• What's the real question beneath my surface concern?

• How can I make this question specific and testable?

Hypothesis Development

• Based on available evidence, what do I predict will happen?

• What assumptions am I making that I could test?

• What would I expect to see if this assumption is correct?

Mini-Experiment Design

• What's the smallest, lowest-risk test I could design?

• How would I know if my hypothesis is accurate?

• What could I learn even if the experiment doesn't go as planned?

Analysis and Iteration

• What did the results actually show (versus what I hoped they'd show)?

• How does this change my understanding of the situation?

• What's my next action based on what I learned?

These questions work as coaching prompts for yourself or others. The goal isn't to eliminate intuition or emotion from decision-making but to ensure they're informed by evidence rather than driven by unconscious biases or inherited stories.

Making It Stick: Rationality as Your Superpower

Here's what's at stake: every major decision in your life will be made either by your highest self or your most primitive wiring.

When you don't consciously choose a decision-making framework, your choices default to whatever emotional pattern or inherited story happens to be loudest in the moment. It's the past, or the noise of the crowd, or limiting beliefs screaming over what you, real you, actually wants.

Again, this is how intelligent, capable people end up living lives that serve someone else's definition of success while leaving them feeling empty and unfulfilled. WE DON’T WANT THAT!

The alternative is rationality. Not rationality as cold, emotionless calculation, but as systematic thinking that integrates both logic and intuition in service of decisions aligned with who you actually are and what you genuinely value. It’s how you get to know which part of the elephant you’re actually dealing with.

Rationality is the human superpower. It's what allows you to step outside your immediate emotional reactions, examine the stories you've inherited about what's possible, and design experiments to test whether those stories serve your authentic path forward.

When you master this approach:

• Your decisions become expressions of your values rather than reactions to circumstances.

• You spend less time second-guessing yourself because you've systematically gathered relevant data.

• You recover faster from setbacks because you've approached choices as experiments rather than permanent commitments.

• You build genuine confidence rooted in your ability to navigate uncertainty rather than the illusion of having everything figured out.

Most importantly, you stop being at the mercy of whatever emotional pattern or social pressure happens to be strongest in the moment.

You become the author of your own life rather than a character in someone else's story.

The path forward requires courage. This requires the courage to admit you don't know, to question inherited assumptions, and to design experiments that might not deliver the results you're hoping for.

But it's also the path to a life that's genuinely yours rather than a performance for an audience you may not even respect.

Most people will keep making decisions with their emotional brain because it feels easier in the moment. But you're not most people. You're someone who chooses the harder path because it leads somewhere worth going.

The framework is simple:

Notice what's actually happening.
Ask "How would I know?"
Design a small test.
Act on the data.
Rinse and repeat.

Your next major decision is coming whether you're ready or not. The question is: who's going to make it? Your emotional brain operating on outdated programming, or your highest self armed with systematic thinking and evidence-based choice-making?

I'm Danny Kenny, and I've spent over a decade exploring the intersection of behavioral science, decision-making, and authentic achievement. If this framework resonates with you, subscribe below to receive new articles on living deliberately in a world designed to keep you reactive.

Subscribe now

Growing up in the Midwest, there were unspoken rules woven into the fabric of daily life. Don't knock on the neighbor's door before 9am on weekends. Don't invite yourself over to someone else's house. Don't be a bother. Don't impose.

These weren't harsh restrictions. They were presented as common courtesy: basic decency, the way good people behave in the world.

And I absorbed these lessons completely.

Fast-forward decades later to a sales conversation I’m having in downtown DC. I'm wrapping up what's been a great conversation with a potential client. They love the work we do, they're impressed with our approach, and they're ready to move forward.

This is the moment where any competent salesperson asks: "Who else do you know who might benefit from this kind of work?"

The words are right there. I know them. I’ve practiced them.

But I can't say them.

Instead, I thank them for their time, shake hands, and walk away, leaving money on the table and opportunities unexplored.

Why?

Because asking for a referral feels like imposing. It feels like being a bother. It feels like violating some deep code of conduct that was programmed into me decades ago in the suburbs of St. Louis.

This happened call after call, meeting after meeting. I'd built my entire career around helping others, but I couldn't bring myself to ask them to help me in return. Not because they wouldn't want to (most people love making valuable connections) but because a belief buried deep in my psyche whispered: Good people don't ask for things. Good people don't impose.

What I didn't realize was that this whisper wasn't truth. It was a limiting belief, and it had been quietly running my life for years.

Subscribe now

The Invisible Operating System

We all carry beliefs like this: stories we tell ourselves about who we are, how the world works, and what's possible for us. Most of them operate completely below conscious awareness, like an invisible operating system running in the background of our minds.

• "I'm not creative."

• "I'm bad with money."

• "I don't deserve success unless I work myself to exhaustion."

• "People will judge me if I fail."

• "I have to have it all figured out before I can start."

These beliefs feel like facts. They feel like reality.

But they're not.

These beliefs are constructions, carefully built by our brains over years of experience, reinforcement, and repetition. And for many of us, they've become the primary limitation, a chokepoint, on what we think we can achieve.

The challenge is that these beliefs are nearly impossible to see on our own. They're what psychologist Michael Shermer calls our "belief engine," the brain's evolved pattern-recognition system that connects dots and creates meaning from experience, often without our conscious involvement.

Here's the kicker: neuroscience research shows it's actually easier for our brains to believe something than to disbelieve it.

In a fascinating study, researchers put people in fMRI scanners and showed them various statements while monitoring their brain activity. What they found was remarkable: belief activated the brain's reward centers and happened faster than disbelief or uncertainty.

In short, believing is fast and feels good. Doubting takes work. And we almost always take the easy path.

This means our brains are naturally inclined to accept the patterns they detect as true, even when those patterns are incomplete or misleading. It’s easier for our minds to just accept a pattern, regardless of its accuracy or truth. And once a belief forms, we unconsciously seek out evidence that confirms it while ignoring evidence that contradicts it.

It's a perfect system for reinforcing whatever story we've already accepted about ourselves and the world.

But how do these invisible stories actually get written? Understanding the process reveals why they're so persistent and why they're so hard to change.

The Dopamine Loop of Self-Limitation

Here's how limiting beliefs actually form in your brain:

Early in life, you have an experience. Maybe you ask your dad for help with homework and he says "Figure it out. That's how you learn." Maybe you ask to join a group of kids playing and they tell you to go away. Maybe you never ask anyone for assistance, and you learn that self-reliance is a virtue.

Your brain, designed to keep you safe and help you navigate social situations, takes note: Asking for help leads to rejection/disappointment/judgment. Not asking for help leads to safety/approval/belonging.

Each time you encounter a similar situation and choose self-reliance over asking for help, your brain releases a small hit of dopamine (the "do that again" chemical). You've successfully avoided potential rejection. You've maintained your image as competent and independent. The neural pathway gets stronger.

Over time, this pattern becomes so automatic you're not even aware it's happening. The belief shifts from "asking for help didn't work that one time" to "I don't ask for help" to eventually "I can't ask for help. It's not who I am."

What started as a protective strategy becomes a core part of your identity.

That’s not all bad! Self-reliance is a good thing. People in the world could use more of it and good things can happen from a willingness to do good work and raise oneself up by the bootstraps.

However… the problem becomes when self reliance moves from ‘a truth’ to ‘the truth’. The very belief that once kept us safe often become the barrier that limits our growth. For me, the "I must do everything myself" belief that helped me avoid childhood disappointment was now preventing me from building meaningful business relationships and scaling my impact.

Subscribe now

Mental Archaeology: Digging Up Your Hidden Beliefs

So how do you find beliefs you can't see? How do you excavate stories that have been running in the background for decades?

The process starts with becoming a detective in your own mind, looking for the patterns that reveal your hidden assumptions about reality.

Four Patterns That Reveal Your Hidden Beliefs

Pattern #1: The Emotional Red Flags

Your emotions are often the first clue that a limiting belief is operating. Strong emotional reactions (especially the disproportionate ones: extra anger, frustration or sadness) usually signal your psyche bumping against a threatened belief.

For me, the red flag was anxiety every time I considered asking for referrals. Not just nervousness, but deep visceral discomfort, like I was about to violate something sacred.

When you notice these reactions, get curious: What story am I telling myself? What am I afraid will happen if I do the thing I'm avoiding?

Pattern #2: The "I Always/Never" Statements

Listen to your internal dialogue and the stories you tell others about yourself. Limiting beliefs often show up as absolute statements:

• "I'm just not a people person."

• "I never finish what I start."

• "I'm terrible at asking for what I need."

• "I always put everyone else first."

These totalizing statements are rarely accurate. They're usually beliefs masquerading as facts.

When you catch yourself using this language, pause and ask: Is this actually always true? Can you think of any exceptions?

Pattern #3: The Areas Where You're Stuck

Look at the places in your life where you consistently struggle or avoid taking action despite having the knowledge and skills to succeed. These stuck points often reveal limiting beliefs.

Can't seem to raise your prices? There might be a belief about your worth.

Avoid networking events? Could be a belief about bothering people or not being interesting enough.

Struggle to delegate? Might be a belief that you have to do everything yourself to ensure it's done right.

The pattern is usually: I know what I should do, I know how to do it, but I consistently don't do it. That gap between knowledge and action is where beliefs live.

Pattern #4: The Family Echoes

Many of our deepest beliefs were inherited from our families and cultures. The stories our parents told about money, success, relationships, and what's possible in life often become our stories… until we consciously examine them.

My "don't be a bother" belief was pure Midwest culture, filtered through values about self-reliance and not imposing on others. It served family members well in their context, but it eventually came to limit me in mine.

Ask yourself: What did my family believe about success, money, relationships, asking for help? Which of these beliefs did I adopt without question?

If this pattern resonates, try this exercise:

Write down five things your family believed about money, success, or relationships.

For each one, ask: "Is this serving me now, or is it limiting me?" Often, beliefs that made perfect sense in your parents' context become obstacles in yours.

Next, for any belief that's limiting you, trace it back: When did you first learn this? What was the original context? What was your family trying to protect you from or help you achieve?

Finally, write a new belief that would serve you better. Don't just flip the old one to its opposite. Create something nuanced and true. For example, my old belief "Good people don't ask for things" became "Asking for help creates opportunities for others to contribute and connect."

The goal isn't to judge old beliefs as wrong. It's to consciously choose which stories you want to carry forward and which ones you're ready to update.

Share

Once you start this excavation work, you'll likely experience what I call the awareness trap: the frustrating gap between knowing and changing.

Why Knowing Isn't Enough (The Awareness Trap)

Here's where it gets tricky: simply identifying a limiting belief isn't enough to change it.

I could clearly see that my reluctance to ask for referrals was holding me back. I understood intellectually that most people would be happy to make introductions. I even had evidence from the few times I did ask: it went fine, people were helpful, the world didn't end.

But the belief persisted.

This is because limiting beliefs aren't just thoughts. They're neural patterns reinforced thousands of times, connected to our identity, our sense of safety, and our understanding of how to belong.

Changing them requires more than insight. It requires rewiring.

The good news? Your brain is more malleable than you think. The same neuroplasticity that allowed these beliefs to form in the first place can be harnessed to transform them. But it takes the right approach. You need an approach that works with your brain's natural learning systems rather than against them.

The Science of Why Beliefs Resist Change

The research on changing limiting beliefs draws from several therapeutic approaches, but they all share common elements:

First, they create psychological safety. You can't rewire beliefs while your nervous system is in fight-or-flight mode. This means approaching the work with curiosity rather than judgment, and often working with a therapist, coach, or trusted friend who can provide external support.

Second, they challenge the evidence. Cognitive Behavioral Therapy has shown that beliefs often persist because we're selective about what evidence we pay attention to. Learning to question flimsy evidence and focus on concrete data can begin to loosen a belief's grip.

Third, they create new experiences. Narrative therapy recognizes that we can't just think our way out of limiting beliefs. We need to ‘live’ our way out of them. This means taking small, safe actions that contradict the old story and provide evidence for a new one.

Think of it like updating your brain's software. You can't just delete the old program. You have to install and run a new one until it becomes the default.

The Rewiring Process

For my "don't ask for help" belief, this meant starting with tiny requests in low-stakes situations. Asking a colleague for a book recommendation. Requesting an introduction to someone I was curious to meet. Each positive experience provided new data for my brain to process, slowly building evidence for a different story about what happens when I ask for things.

The process isn't always linear, and it requires patience with yourself as your brain learns new patterns. But it works, as long as you're willing to do the excavation work first.

Your Hidden Stories Are Waiting

The beliefs running your life right now aren't accidents. They were formed for good reasons, often by a younger version of yourself who was trying to navigate a complex world with limited information and resources.

That younger you did the best they could with what they had. But you're not that person anymore, and the strategies that once kept you safe might now be keeping you small.

The most liberating realization I've had in this work is that the story I was telling myself about not being able to ask for help wasn't protecting anyone. That story was actually limiting my ability to create value for others and build meaningful relationships.

When I finally started asking clients for referrals, something beautiful happened. Not only did my business grow, but my relationships deepened. People lit up when they could make valuable connections. They felt useful, appreciated, part of something bigger than themselves.

I had been so focused on not being a burden that I'd forgotten a fundamental truth: letting people help you is often a gift to them, not an imposition.

Your limiting beliefs are holding similar gifts hostage. What beliefs have been running your life from the shadows? Which stories that once kept you safe are now keeping you small? The most liberating realization isn't that you have limiting beliefs… everyone does. Freedom comes from realizing that you have the power to rewrite them.

The excavation starts now.

Share

The discovery process is just the beginning. Once you've identified your limiting beliefs, the real work of changing them begins… but that's a story for another article. For now, start with awareness. Notice your emotional red flags, listen for your "always/never" statements, and get curious about the inherited echoes in your own story.

Leave a comment

Nothing would change.

Two weeks before submitting my PhD, this truth hit me like a physical blow. After five years of work, 250 pages written, countless sacrifices made—when I finally hit send, I would still have the same problems. Still struggle to get up early. Still be the same person.

Years of sacrifice had led me here: working five part-time jobs while studying full-time, enduring depression and a back injury that left me unable to stand, missing weddings and births while living an ocean away from everyone I loved.

All for a moment that would change... nothing.

When I submitted this thing working on for 5 years, when I finally hit send on this 200,000 words and over 400 references, when I finally brought an end to years of existential dread and struggle… nothing would be different.

Absolutely nothing. Zero. Zilch. Nada.

In that moment, on my walk to the grocery store as the sun set on a Sydney sky, I almost stumbled to the pavement as I asked myself, "Has this whole this been fucking pointless? Has this all been for nothing?"

Fortunately, the feeling didn’t last.

Within about 20 minutes, something shifted. The fog of despair lifted enough for a different perspective to emerge…

The degree, the piece of paper, the moment of PhD submission... that was never the point.

The Shift That Changed Everything

The real question was: Am I a better version of myself for having gone through this hard, at times horrific, challenging experience?

One hundred percent yes.

I was a better Danny Kenny for having gone through that experience. For the struggle. For the realization, appreciation, and gratitude for the people who came out of the woodwork to help me. For realizing how lucky I am.

None of that happens if I don't go through the PhD.

It was always about the process. It was always about the journey.

This moment taught me something profound about this idea of ‘arrival’. I had been chasing a destination that didn't exist. The transformation I was seeking had been happening all along.

But I couldn't see this truth until someone asked me a question that changed everything.

Why the Oak Tree is Already Perfect

I first heard this question from coach Joe Hudson on Modern Wisdom. Hudson works with leaders in Silicon Valley, helping them navigate the same achievement traps that had ensnared me. His question is essentially a Zen koan designed to break your brain in the most useful way:

"Think of an acorn. Think of an oak tree. The acorn becomes an oak tree at some point.

Now ask yourself this: At what point is the acorn or the oak tree perfect?"

…

It's never perfect. It's always perfect.

There is no arrival point where perfection is achieved, and yet at every moment, it's exactly what it should be.

You are, in many ways, perfect for what you are right now. Not in some woo-woo, superficial mantras in a mirror type of way. In the way that you get to keep changing and growing because that is what it is to be human, but not because there's some fatal flaw that needs fixing. You were shaped by experiences you didn't choose. The only control you have is in this moment.

And you still get to choose what to do next.

This is the fundamental shift: from "I need to achieve to be worthy" to "I am worthy and I choose what to create from that place."

You don't have to earn your worthiness. Instead, you can create from it. That is moving in the world from a place of 'big magic'.

Understanding this intellectually is one thing. Actually living it requires confronting everything you've been taught about success.

So what does it actually look like to live from this place of inherent worthiness? For me, it meant completely reimagining my relationship with achievement.

Subscribe now

Achievement as Waypoint, Not Destination

For as long as I can remember, there's been a relentless internal voice: 'Better. Faster. More.' This was the soundtrack to my entire existence, playing on every radio station, 24/7, 365. Every achievement felt hollow within minutes of receiving them, immediately triggering the questions of “What's next? What's the higher level?”

I had confused being successful with being seen as successful. My entire identity was reputation management—crafting a story others would tell about my excellence. But when that reputation was recognized, I felt invisible. What was on the podium wasn't me; it was a projection, a ghost. The insanity? I took this emptiness as a sign to achieve more, AS IF THAT WOULD FIX THE PROBLEM. Lunacy.

Making Your Own Meaning

Like the oak tree that's perfect at every stage of growth, you don't need to reach some final destination to be worthy. The acorn pursuing its path to becoming an oak isn't 'incomplete.’ That acorn is exactly what it should be in that moment, growing toward its next stage of becoming exactly what it should be for the next moment.

Here's what I've learned: if there is no inherent meaning to existence, we get to make our meaning. The game we can instead choose to play is: what are the achievements we can focus on that ask us to become something more? That ask us to become a more purified, distilled, brighter, shinier, warmer, more powerful version of that essence we're bringing forward?

These become waypoints along the path, not destinations. As the Haitian proverb says: "Behind mountains there are more mountains."

The path becomes evolving into the most crystallized version of ourselves. That's what's worthy.

We don't have to stop pursuing achievements. We just have to change what they mean to us, how we go about getting them, and where we go about getting them from.

Understanding this intellectually is one thing. Actually living it requires practical frameworks to catch yourself in old patterns.

Here are three frameworks of questions that helped me make this shift and that I use with executives seeking to redefine their relationship with achievement.

Three Questions to Change Everything

The "What Does This Give Me?" Reality Check

Think about the next achievement on your list. Maybe it's the promotion you've been working toward, the fitness goal that's been nagging at you, or the recognition you think will finally validate your efforts. Write down:

• What does this give me?

• What changes from the moment before you get this thing to the moment after?

• What will be different about my life?

Then ask again: What does that give me?

Keep asking this question, following the logic train like a five-whys exercise. Some of it might still be true and worth it, but you need to see this story in black and white.

Then ask the crucial question: What am I willing to give up for this?

This question separates what we actually care about from what we don't. It reveals the hollowness of pursuing things for external validation versus internal alignment.

The From/To Practice

Before pursuing any achievement, check your fuel source by asking:

Am I pursuing this FROM worthiness or FOR worthiness?

FROM worthiness sounds like:

• "This challenge will help me grow"

• "This aligns with what I care about"

• "This will let me express more of who I am"

FOR worthiness sounds like:

• "This will prove I'm successful"

• "People will respect me if I achieve this"

• "I'll finally feel good about myself"

The goal isn't to eliminate all external motivations, but to ensure the primary fuel source is internal alignment rather than external validation.

The Waypoint Selection Framework

When choosing your next challenge or goal, ask:

1. Does this ask me to become more? Will pursuing this require me to develop new capabilities, deepen existing strengths, or express more of my authentic self?

2. Does this align with my values? Will the process of achieving this honor what I truly care about, or require me to compromise my integrity?

3. Will I be proud of who I become through this journey? Regardless of whether I achieve the specific outcome, will the person I become through this pursuit be someone I respect?

If the answer to all three is yes, you've found a worthy waypoint. If not, you might be chasing someone else's definition of success.

Subscribe now

These frameworks will help you see through the lies spun by the achievement trap. They're logical, practical, straightforward.

And yet, when most people try to implement them, they hit a wall. Because our relationship with achievement isn't just intellectual. This is deeply wired into our nervous system. Making this change requires confronting something most people spend their whole lives avoiding.

The Courage to Question Everything

Making this shift requires immense courage. And to be clear, it’s one I’m still working through.

From our earliest days as humans, belonging to the tribe was literally life or death. To be cast out of the tribe was to perish.

If we fast forward tens of thousands of years, so many of the signals of conventional success in our society now are signals of one’s ability to belong to a larger tribe: wealth, power, status, sex appeal - all signs of your ability to ‘survive’ in a group setting. It’s become so hardwired that to question those things can feel like questioning the tribe (do I really need to be that famous?) which, unfortunately for us, sits ever so close to questioning = a good way to get kicked out the tribe and die. probably super painfully.

This is why your nervous system screams that achieving, driving, striving is your path to success, to love, to respect. This is evolutionary programming designed to keep you alive and accepted. All at the cost of your happiness and flourishing. Your brain cares about you surviving, it does not care about your ‘thriving’.

You can see this in the very metrics that our culture uses to signal belonging (the promotion, the title, the perfect Instagram life) also being the things that leave us feeling most disconnected and listless. It’s a nice little one-two punch for experiencing existential feelings of not good.

The Warning Signal

This is the courage of the acorn that chooses to crack open and grow, even though it means leaving behind the safety of what it's always known.

For those wondering “how do I know if I’m in this?”, the question "Is this it?" is often the first warning sign. When you reach something, when you achieve, and you can feel this lack of satisfaction, this emptiness or unease that something's not quite right… that's usually your soul's first quiet signal that this current trajectory is not your ultimate path to fulfillment.

What all of this then requires is the willingness to listen to that signal.

To be willing to be curious, to ask questions, to be willing to be punched in the stomach by some of the answers you get back.

The stories you've told yourself about what life is and what success is mean that if you take this path fully, you're stepping onto the much harder route of determining what you actually care about. What does your definition of success look like: for you and you only?

That's terrifying. Because it takes really hard work to find that.

And there is nothing more worthy you could be doing.

But sometimes, before you can move forward, you need to have the conversation with the part of yourself that started this whole chase long ago. The scared achiever who believed his worth depended on the next award, the next recognition, the next proof that he mattered.

If I could sit down with that version of myself, (there might be a version of you that's been running this same race) here's what I'd want him to know:

What I’d Tell The Insecure Overachiever

Young Lad,

My heart breaks for you. You're trying so hard, and it's because you're so scared. Scared of being rejected, of failing in front of the people who love you most, of disappointing them in ways that feel unforgivable.

The story you're telling yourself (anything less than perfect will let everyone down and make you worthy of rejection) well it’s just not true. But I know you can't see that right now. The fear is too loud, too overwhelming.

You're throwing yourself at this project of achievement, but it's really just a project of futility. It never ends. It won't make you happy. You're working so hard to be loved by something that will never love you back. It couldn’t.

But here's what I need you to know: those people who love you? They already love you. They loved you before the first trophy, before the perfect grades, before any of it. And they'll love you after every failure too.

You are enough. You were always enough.

I'm grateful for the journey you're about to take, even the painful parts, because it will teach you what I know now. That your worth isn't earned. Your worth is inherent. Your essence, your curiosity, your humor, your heart, has nothing to do with what you achieve.

Keep that drive, that work ethic. But let it come from a different place. From worthiness instead of fear. From purpose instead of validation.

You're going to change the world, just probably not in the way you think.

Love,
Danny

Writing that letter was a key part of transforming my relationship to success and achievement. Reading it again now always reminds me of how far I've come, and how much further there is to go. Because part of me still wants the achievements. It’s just a quieter voice now.

If you see yourself in that scared striver, never satisfied, the good news is this: there are answers.

They're not easy to find, but the journey to discover them is the most worthy work you'll ever do. And that hard work and striving you've developed? That doesn't have to be wasted. You just need to burn cleaner fuel.

Burning Clear Fuel

What does "burning cleaner fuel" look like in practice?

• You can sit with success without immediately asking "what's next?"

• You take time to celebrate and mark your achievements with gratitude.

• You make decisions based on what lights you up rather than what looks impressive to others.

• You find flow states more easily because you're not constantly judging your performance.

• You celebrate the process, not just the outcome.

The people who make this shift become magnetic in a way that has nothing to do with their credentials.

The fundamental shift is this: from "I need to achieve to be worthy" to "I am worthy and I choose what to create from that place."

That is moving in the world from a place of ‘big magic’.

Two weeks before my PhD submission, I thought nothing would change when I hit send.

I was right.
And I was completely wrong.

Nothing changed about my external circumstances. But everything changed about how I saw them and the meaning I place upon them. The person who had been transformed through years of struggle, who had been supported by people who came out of the woodwork to help, who had learned gratitude in the face of despair… well he was already here. He always was.

Like the oak tree, you don't become perfect when you're fully grown. You're perfect as the acorn, perfect as the sapling, perfect in every stage of becoming.

You have already arrived. The question is: what will you create from that place?

Leave a comment

That scared achiever I wrote to? He's still part of me, just burning that sweet, sweet cleaner fuel now (most of the time…). The drive remains, but the source has shifted from fear to purpose. If you're ready to make that same shift, from achieving to prove your worth to creating from your inherent value, I offer coaching to support this transformation. If you're ready to stop chasing worthiness and start creating from it, let's explore what becomes possible when you finally understand you've already arrived.

The plane lurched violently upward.

"Ladies and gentlemen, we're making an emergency climb due to traffic in our flight path."

In other words, “there’s a plane where it’s not supposed to be and we’re gtfo here.”

The captain's voice was steady, but the g-forces pressing me into my seat and the fast climb told a diferent story. It was the kind of airplane experience where your mind races to conclusions you'd rather not reach.

As turbulence shook the cabin, I noticed something strange happening in my body. While others gripped armrests and exchanged terrified glances, I found myself focusing on my breath, to see how low I could bring my heartrate. Like a psychopath.

In for four. Hold for four. Out for four. Hold for four.

In that moment of potential ending, I needed to know: Am I ready?

My grandfather used to say, "Make sure to have your bags packed." Not to literally have your luggage by the door. He meant spiritually, emotionally, relationally. Be ready to leave this earth without regrets, without unfinished business, without words left unsaid.

So as Flight 447 to Orlando climbed through that storm, I did my check:

Am I good with all my people?

The answer surprised me.

Despite all my achievement-chasing and productivity-hacking, despite the endless striving I've documented in these pages... I was good. I'd added warmth, humor, and joy to the lives I'd touched. My relationships were in a good spot. The world was, perhaps, a slightly brighter place for my existence.

It honestly wasn’t the answer I was expecting. But it was a grounding one.

A few minutes later, the plane leveled off. Thirty minutes later, we were safely on the ground in Orlando.

But something had shifted.

The rest of that trip felt clearer, less anxious, more grounded. The obnoxious emails waiting in my inbox had lost their sting. The "urgent" meeting that wasn't really urgent revealed itself as something not to spend any additional energy on.

Death, it turns out, is an excellent bullshit detector. And we could be thinking about it way more often in our daily lives.

The Ancient Practice Modern High-Achievers Need Most

Memento Mori, literally means "remember you will die," sounds like the kind of thing that would send modern optimizers running for longevity protocols (ex; infrared light, collagen, and definitely some kind of algae) and the promise of immortality. But as Tim Ferriss observed:

"I think about death all the time and it's not a morbid, sullen exercise for me... I find it to be, and this might sound strange, but greatly encouraging because it drives a sense of urgency, or at least time sensitivity, to a lot of my decisions."

He goes on to describe looking at stars and contemplating that the light hitting your eye might be from a star that no longer exists. That realization isn’t an excuse for nihilism, it’s providing perspective, it’s clarifying, and it’s empowering. Suddenly, that workplace drama or Twitter beef reveals itself as the cosmic irrelevance it always was. "It's all dust," he Ferriss says. "Nobody gives a fuck."

Ryan Holiday puts it even more directly in his exploration of Stoic practices:

The ancients knew this. Emperor Marcus Aurelius reminded himself, "You could leave life right now. Let that determine what you do and say and think."

But here's what Ferriss, Holiday, and the Stoics are really pointing to, and what that moment on Flight 447 made visceral for me:

Death isn't the enemy. It's the life coach you desperately need but never ever ever wanted to hire.

From Denial to Dance: Befriending Your Mortality

Ernst Becker won a Pulitzer for "The Denial of Death" by arguing that human civilization is essentially an elaborate defense mechanism against our awareness of our own mortality. We build monuments, chase achievements, create legacies to somehow convince ourselves we'll find a way to overcome the one thing guaranteed by our biology.

This denial drives what Becker calls our "immortality projects", the ways we try to ensure we'll be remembered, that we'll matter, that our existence will echo beyond our inevitable end.

For me, it was the 4.0 GPA, the PhD, the six-figure consulting gig. For you, it might be the IPO, the bestseller, the perfect family photo that gets 500 likes. We're all running towards some imagined future, some imagined achievement, some imagined trophy that grants us immunity from dying. We’re scrambling to find the thing, and we’re scrambling to get the thing, and we’re scrambling to hold onto it forever.

We don’t have to do that.

This shift from seeing death as the enemy to recognizing it as a clarifying force has been gradual for me. Years of stoic practice, meditation, and honestly just watching life happen around me. People in my life passing on, some way too soon. People diagnosed with long-term illnesses. Consistent, regular reminders life is a finite, non-renewable resource.

The irony is that befriending death doesn't make life feel shorter or scarier. It makes it feel more vivid, more precious, more worth living authentically rather than performatively.

When you truly internalize that you could leave life right now—not as some abstract philosophy but as lived reality—several things happen:

1. Your real values emerge from the noise. Suddenly, being seen as successful matters less than actually connecting with people you love.

2. Fake urgency reveals itself. That "ASAP" email? Unless someone's actually dying, it can wait.

3. Your tolerance for bullshit approaches zero. Life's too short for meetings that should have been emails or relationships that drain more than they give.

4. What actually matters becomes blindingly clear. Hint: It's usually much simpler than your brain wants to believe.

The 90-Year-Old Test (Your Future Self Knows What's Up)

Here's an exercise I give to every coaching client as we start our work together. It never fails to cut through the complexity we create around our lives:

Close your eyes. Fast-forward to age 90. It’s a Tuessday and you're sitting on a porch (because apparently all 90-year-olds have moved south and have porches in our imagination). What's true about the best version of this moment?

When I do this exercise, the picture that emerges is remarkably simple:

• I'm healthy enough to move around and be active

• I'm surrounded by people and family I love

• I'm still sharp enough to write, teach, and serve others

That's it. That's the whole list.

Notice what's not there? The size of my bank account. The prestige of my job title. The number of LinkedIn followers. Whether I ever gave a TED talk.

None of it makes the cut when you're staring down the barrel of your own mortality.

This isn't about having low ambitions. It's about having accurate ambitions. When you know how your story ends, you can work backward to figure out what actually matters now.

The 90-year-old test is where I start my values work because it's the only perspective that can't be fooled by short-term thinking or social pressure. Your 90-year-old self doesn't give a single, solitary shit about inbox zero or Q3 targets.

They care about whether you were present for the people who mattered.
They care about doing about doing work you found meaning in.
They care about not dying with a live unlived.

Subscribe now

Practical Memento Mori: Tools for the Living

Here are a few more concrete practices that bring death's clarity into daily life:

• Write Your Own Eulogy Many people have heard of this but I recommend writing two versions: Write the eulogy for if you died today, then write the one you'd want read if you lived aligned with what truly matters. The gap between them is the work for you to do and the places for you to focus.

• The Deathbed Story Filter Before any major decision, ask: "On my deathbed, will I regret not doing this, or will I regret the things I sacrificed to do it? What’s the story I wish to be able to tell about this when I’m dying?" This question has helped me see through superfacial achievement traps and, on the other side, has helped me choose the short-term painful thing that benefits me in the long-term.

• Study the Stars and Get Outside Adapting Ferriss's advice, go outside at night and look up. Find a star. Consider that its light traveled years to reach you, that the star itself might already be gone. Find ways to be in grand scenes in nature. Find places that bring you ‘awe’. Let that cosmic perspective shrink your problems to their actual size.

When Death Becomes Your Productivity Hack

Here's what nobody tells you about memento mori: It's the ultimate productivity system.

Not productivity in the mercenary sense of cramming more into less time. But productivity in the truest sense: producing what matters, eliminating what doesn't.

When you truly grasp your mortality:

• You stop procrastinating on important conversations

• You quit optimizing systems that optimize nothing meaningful

• You delegate or delete the trivial many to focus on the vital few

• You stop trading time for money once you have "enough"

• You start creating things that might outlive you in useful ways

After that flight to Orlando, I noticed immediate changes. Emails that would have sent me into an hour-long response spiral got two sentences or silence. Arguments that would have escalated got met with "You might be right" or "This isn't worth our energy."

I started to understand what Becker was really saying: We're all going to die, and no amount of achievement changes that. But instead of this being depressing, it's liberating.

But the biggest shift? I started prioritizing shared meals with loved ones like they were board meetings with God himself/herself. Because from the perspective of mortality, they basically are.

When you stop trying to outrun death through achievement, you can start using your limited time to contribute something meaningful. The question shifts from "How can I matter forever?" (an absurd exercise likely to lead to shallow, inauthentic answers) to "How can I matter right now?" (a powerful question for finding compassionate action to make the world a little bit better around you, in this moment).

Your Mortality, Your Mentor

As I write this, I'm thinking of my Uncle Ward. A kind, loveable, and humble man, he was an example to all who met him. And he passed, far too soon, in August 2023 after a horrific battle mixing throat cancer and Crohn’s disease that meant for months, he could not eat and barely speak. He was far too gentle, too kind, too good to have deserved a fight I wouldn’t wish on my worst enemy.

And yet, even as he lost weight and even when words became too painful to form, Uncle Ward still showed up for his family. Still managed to communicate love through presence alone. Still found ways to express care even as his body betrayed him.

I remember how he'd text me about the lastest Blackhawks or Cubs game, or to share the latest news on my one friend who made it to the MLB. For anyone he knew driving to or from Chicago, he would be checking the weather for them, letting them know the forecast and the ideal driving windows to avoid the worst of it. And there was nothing any of his many nieces or nephews could accomplish without Uncle Ward being one of the first to congratulate them for it.

By remembering my Uncle Ward, who is no longer with us, I remember to live. I remember how he loved his family and his friends. I remember the joy (and agony) of his Chicago Cubs fandom (as a Cardinals fan, I am contractually bound to submit an obligatory boooo here. Uncle Ward would understand). I remember the generosity of his spirit, the first to serve charity, to leave behind a bigger tip, to check in on his many nieces and nephews to congratulate them on their latest accomplishment.

And the reality is: My Uncle doesn’t get to do those things anymore on this earthly plane…

But I do.

While my Uncle is busy fishing with my grandpa in the afterlife, I, along with everyone who attended Uncle Ward’s funeral and everyone who has ever lost someone they’ve loved… we get to honor their passing for them and for ourselves with every action we choose in the time we have remaining.

This is the paradox of memento mori: The more we remember death, the more I remember and miss my Uncle, my Grandpas, or anyone else that’s gone before us… the more fully we live. The more we befriend mortality (our own or the people in our lives), the less it controls us.

Yes, this feels morbid. Admittedly, it feels weird. It feels like we need to be wearing way more black, dark eyeliner, and spikes on our clothing to fully embrace this.

But death is the feature of our existence that makes life meaningful.

Without scarcity, there's no value.
Without endings, there's no urgency to begin.
Without mortality, there's no reason to choose what matters over what's merely urgent.

So I'll ask you what I asked myself on that turbulent flight:

Are you ready? Are you good with your people? Have you said what needs saying, done what needs doing, loved who needs loving?

If not, what are you waiting for?

Death is waiting to help you figure out what actually matters.

All you have to do is listen.

"Better. Faster. More."

This was the refrain that lived in a constant loop in my head throughout high school and college (and beyond if I'm being honest).

Get a 5 on the AP test? Why weren't you taking more of those classes? What else can you be taking for college credit next year?

Be named captain? How is that going to help you get into college? Or when it happened in college, how will that help you go pro?

How can you be doing more extracurriculars? Why aren’t you doing more public service? Shouldn’t you be working and earning more? Why aren’t you getting stronger?

Nothing was good enough. For me, and in my head, for everyone else around me. No achievement lasted. No award endured.

I was in a state of perpetual dissatisfaction, and I felt that if I did not keep pushing my mind and my body to the breaking point, I would drown.

Story time.

The last B I received was in 4th grade. I maintained a perfect 4.0 until my senior year of college where all of this striving, all of this achieving finally came to a head. I finally broke.

At the start of my senior year of college, soccer season was going well. We were good — very good. A number of us had been starting every game since freshman year, and we ripped off a 6-0 start to the season for the first time in the program's history. My teammates, Franklin, Kyill, and I were two-year captains, committed to getting ourselves and the team to the conference tournament for the first time since we started playing together.

Meanwhile, I had both of my senior seminars for Environmental Studies and Hispanic Studies. At my university, senior seminars were essentially mini-master's theses. As a first introduction to formal research, they were not easy. Not even close.

I was also the Awareness Events Commissioner for Student Senate, President of the Student Athlete Advisory Committee, co-President for the GreeNetwork, and working on the side as a Spanish tutor, an assistant for the Environmental Studies department, and as an aide for the athletic department.

I barely slept.

The only nights I got more than 4-5 hours in were the nights before soccer games. I thought I’d be fine, because I thought out I was Superman.

Turns out, I’m not. Not even close. And for the first in-progress grade on my Senior Seminar, I see a letter I haven't seen since 4th grade:

B. For bitch-ass.

I freaked out.

I immediately (and I mean within 3 minutes) scheduled a meeting with the professor. Got my full Karen haircut ready to go and everything. What’s important to know is that this professor had been both my mentor, my advisor, and my boss for going on 4 years now. If anyone is going to have my back, it’s her.

When I walked into her office, I flopped down into the chair across from her, feeling something that might have been exhaustion deep in my bones. When she asked how I was doing, I gave some non-answer because it didn't matter how I felt. I had work to get back to the second after we sort this out.

"Professor," I said, "what can I do to bring my grade up?"

"Danny, before we get there, are you ok?"

“I’m fine. What can I do to bring my grade up?” I repeat.

Silence.

"I have to ask this... are you on drugs?"

Fkn wot?

My mentor, teacher, borderline friend, just asked me… what??? I almost couldn't answer. But the inside of my head went a little like this:

“YOU KNOW ME BETTER THAN THAT! I, Daniel C Kenny, who care so much about school, who is literally killing himself to do well in your classes, who has always given you 110% in every single one of your classes and every single little task you’ve given me for work, you think I could be doing drugs at the busiest, most vital time of my college career? Are you fucking serious?!?!?”

I didn't say all of that.

But the indignation came through as I explained, with some vehemence, that no, I'm not on drugs, thank you. I'm just not sleeping a lot with all that's on my plate. Can we, please, return to the matter at hand of how I can work to restore my grade and the universe to order?

In further proof of how little she understood me, she offered that maybe I should step back from soccer.

Death first.

Soccer was the only outlet keeping me sane at this point. Only on the field could I disconnect and not think, not hear the refrain of how much more I needed to be doing to survive and thrive, not just in this semester, but for every semester and year going forward.

I flatly rejected her proposal. "That's not on the table. I'll find a way to make it work. Now what can I do to bring my grade up?"

"Danny, there's nothing you can do. I don't know what to tell you, but I'm worried about your performance in this class and I'm worried about you."

"Great, well that doesn't help me, so I'll see you in class, I guess."

And I left.

I took my things, and I turned my back on her. She couldn’t, she wouldn’t help me, and so I would do it myself. I would save my grade, I would save my 4.0, and all would be right in the world again. I left convinced that all I needed to do was work harder to save myself, to prove myself worthy, because clearly, no one else was going to be helping me.

Fast forward: I lost my 4.0 that semester. I lost the perfection that had defined me at school for over 10 years at that point.

You know what happened?

Nothing.

The world kept right on spinning.
No one cut me out of their life.
I didn’t die.

Maybe achievement isn’t all that it’s cracked out to be…

This realization was just the beginning of questioning the achievement-driven mindset that had defined my entire life.

The Achievement Trap: Exposing the Lies That Keep You Running

The promise of achievement is this: give me your time, your energy, your focus, your heart, your mind, your sweat, your blood, and your tears, and I will give you the validation you seek. I will give you the love, the respect, the safety you crave. I will make you everything you ever wanted to be, give you everything you ever desired, secure the love and affection of the people around you. Forever.

Achievement is a liar.

It offers you a contract that says "If I achieve enough, I will finally be worthy." Achievement never had that power. Its pockets are stuffed with monopoly money that, when you finally reach the summit, finally win the award, finally get that trophy you've longed for, burns to ash in your wallet and in your mouth.

"Achievement makes you a mercenary, trading it all for the pursuit of a lie."

Achievement, left unchecked, will have you sell your soul to appease total strangers who will forget about you the second you step down from the podium. While the people who know and love you right now never cared about where you finished the race, they only cared that you did something that mattered to you.

Achievement is a charlatan, selling you quick fix cure-alls that do nothing more than provide 30 seconds of relief, so that when the feel-good feeling disappears, you turn like an addict to the next pursuit, thinking deep down that it didn't work because somehow it was your fault. You didn't deserve the lasting happiness.

I hate to break this to you, but there is no forever happiness. That was never an option.

Research on what psychologists call the "hedonic treadmill" confirms what philosophers have known for centuries—we quickly adapt to both positive and negative changes, returning to our baseline level of happiness regardless of what we achieve. The promotion, the award, the championship—they deliver a brief high, then fade, leaving us starving once more for the next fix.

Why are we so vulnerable to this lie?

Because it's not just in our heads—it's in the water we swim in. From gold stars in kindergarten to standardized tests to college admissions to performance reviews at work, we're indoctrinated and trained to be mercenaries from our earliest days.

This system isn't all bad—I wouldn't be where I am today without it—but it's incomplete. And it leaves many of us hollowed out, wondering why success feels so empty.

To be clear, this isn't about abandoning achievement.

It's about transforming your relationship with it—what I call the "Mercenary to Emissary Shift." This fundamental transformation changes not just what you achieve, but why and how you achieve it.

Think of it this way: a mercenary is a soldier who fights for whoever pays them, while an emissary is an ambassador representing something they believe in. The mercenary achieves to get validation; the emissary achieves representing something bigger than themselves, the belief in something more, something lasting.

I've lived both sides.

My most recent foray into writing publicly again began as a commitment with two friends to publish weekly on LinkedIn. Initially, I wrote pieces I truly believed in, saying things that felt meaningful and authentic. Those pieces were good. I stand by them.

But over time, LinkedIn's professional environment started warping my approach. My writing became extractive, performative—carefully crafted to appear valuable to ‘the market’ rather than true to my voice.

The shift was subtle but profound.

I boxed myself into what I thought people wanted to hear rather than what I needed to say. A little of this adaptation is natural, even necessary. But it's a dirty fuel.

You can burn it. It does work, at least for a little bit.

Eventually it runs out.

So after ramping up to posting five times weekly for six months, I simply... stopped.

In contrast, my work on Substack now comes from a different place. It's about writing what my younger self desperately needed to hear, with no achievement attached beyond the hope it might serve at least one other person. The work itself is the reward, not what it might bring me someday.

That's the game we have to play more often.
Not achieving.
But becoming.
Unveiling.
Revealing.

Your Invisible Armor: How You're Sabotaging Your Own Happiness

When we're caught in the pursuit of validation through achievement, we develop sophisticated patterns of resistance. These patterns keep us busy with the illusion of success but they also protect us from deeper vulnerability and deeper meaning. These same patterns are intelligent strategies that serve a purpose in your life.

In simple terms, resistance is how we protect ourselves from feeling vulnerable. It's the behaviors we develop to avoid facing our deepest fears about our worth and belonging.

Let's look at the common forms this resistance takes:

Perfectionism

Perfectionism isn't about excellence—it's about creating an impenetrable fortress against criticism. It says "If it's perfect, no one can question my worth." You recognize this pattern when you spend hours refining already-good work or feel devastated rather than constructive when receiving feedback. The result? You produce less, risk less, and grow less—all while exhausting yourself.

Productive Procrastination

This is the art of staying monumentally busy with tasks that look important but avoid the truly meaningful work that scares you. You might be using productive procrastination when you organize your desk instead of starting that challenging project or respond to easy emails while postponing difficult conversations. Your calendar is packed, your to-do list checked off, yet somehow the needle never moves on what matters most.

Overcommitment

Taking on too much trades depth for breadth—you're involved in so many responsibilities that you have a built-in excuse for never going deep anywhere. Look for these signs: you say yes to everything then resent the commitments, or your identity becomes tied to "being busy." The sad irony? The volume of work never fills the void of purpose, leaving you even emptier despite your heroic efforts.

Why Your Resistance is Actually Intelligent

Here's the thing about resistance: it's not your enemy. These patterns weren't designed to sabotage you—they were crafted to protect you.

Maybe perfectionism shielded you from criticism in a household where mistakes weren't tolerated. Perhaps overcommitment was your strategy for securing love from parents who only noticed achievement.

These patterns served you once. They helped you survive. They got you this far.

But protection always comes at a cost.

The very strategies that once kept you safe now prevent you from living authentically.

The Achievement Reflection: Seeing Your Patterns

Choose one significant achievement from your life (the degree, the promotion, the major raise) - something you worked hard for and finally attained. With this specific achievement in mind:

1. What happened next? After reaching this goal, how quickly did you move on to pursuing the next one? Did you truly celebrate, or did the satisfaction evaporate almost immediately?

2. What were you really seeking? Beyond the achievement itself, what were you hoping to feel or prove? Recognition? Security? Worthiness? Did the achievement deliver what you were truly seeking?

3. What did it cost? What parts of yourself or your life did you sacrifice to reach this achievement? Consider relationships, health, interests, or aspects of your identity that were set aside.

Take your time with these questions. The insights often emerge not in the first answer, but in the quiet space after you think you've answered.

For me, completing my PhD revealed that I wasn't celebrating achievements because I didn't believe I deserved them - each accomplishment was simply meeting the minimum standard I'd set. The cost was years of relentless self-criticism and isolation. What I was really seeking was indisputable proof of my worth, which no degree could ever provide. And this pattern protected me from the terrifying possibility that I might be ordinary, that I might not be exceptional.

Recognizing this pattern was uncomfortable but liberating. It allowed me to see that my relationship with achievement had become toxic - not because achievement itself is bad, but because of what I was asking it to do for me.

Once you recognize these resistance patterns, a choice emerges: continue as a mercenary burning dirty fuel, or transform into an emissary aligned with deeper purpose.

Choose Your Path: Mercenary Exhaustion or Emissary Fulfillment

The difference between these two paths isn't just philosophical—it's visceral. It shows up in how you feel when you wake up, how you approach challenges, and ultimately, what your life adds up to.

The Mercenary Path: Burning Dirty Fuel

The mercenary serves whoever pays the highest price. External validation, recognition, status, security—these are the currencies they accept. There's nothing inherently wrong with wanting these things. But when they become your primary motivation, you're burning dirty fuel.

A mercenary's life looks like:

• Working tirelessly for goals that feel hollow once achieved

• Constantly scanning for how others perceive you

• Feeling drained even by work you're "good at"

• Measuring success primarily through external metrics

• Asking "what should I want?" rather than "what do I want?"

"The mercenary path demands constant effort for diminishing returns. The emissary path creates fusion—a little input generates massive output."

This path demands constant effort for diminishing returns. Like a car burning contaminated fuel, you find yourself working harder and harder just to maintain the same speed. You might achieve impressive things, but at what cost? The fuel you're burning slowly pollutes your system, leaving residue of resentment, fatigue, and emptiness.

The Emissary Path: Finding Fusion

An emissary represents something they deeply believe in. They carry a message, embody a value, or serve a purpose that resonates at their core. This connection creates something akin to fusion—a little input generates massive output.

An emissary's life looks like:

• Working hard but feeling energized rather than depleted

• Finding flow states more frequently and easily

• Making decisions from an internal compass rather than external pressure

• Creating impact aligned with what matters most to you

• Experiencing satisfaction independent of recognition

"When you're aligned with your authentic purpose, work becomes less about effort and more about expression."

When you're aligned with your authentic purpose, work becomes less about effort and more about expression. The challenges don't disappear—they often intensify—but they feel worthwhile rather than burdensome.

One of the clearest signs you've found your emissary path is that energy balance. Work that aligns with your core values, strengths, and unique contribution creates energy rather than consuming it. You still get tired, but it's the good tired of meaningful exertion rather than the soul-sucking exhaustion of misalignment.

Can You Be an Emissary in a Mercenary World?

There's no denying we live in a world that rewards mercenary behavior. The system is designed to measure, quantify, and reward external achievement over internal alignment. Being an emissary carries risks and consequences.

Choosing and representing your mission makes you an outlier. In ancient times, emissaries could be killed for delivering unwanted messages. While you're unlikely to face a Spartan kick into an endless pit, there is still a price to pay—potential rejection, financial uncertainty, or the discomfort of forging your own path.

But consider the alternative—a life spent chasing validation that never arrives, achieving goals that never satisfy, accumulating credentials that never fill the void.

What makes the emissary path worth it is a life of meaning and purpose. It's about being able to die at peace with the mark you left on the world because you made your own meaning rather than accepting someone else's definition of success.

The irony? Many who choose the emissary path end up achieving remarkable things—not because they're chasing achievement, but because authentic purpose unleashes potential that mercenary motivation never could.

The world needs both paths. We need doctors who study medicine because it pays well, and we need doctors who practice because they can't imagine doing anything else. But only one of these paths leads to a life you won't regret.

So ask yourself: Are you a mercenary fighting for someone else's cause, or an emissary representing what truly matters to you?

"But Isn't This Just Privilege?"

Some might argue that focusing on meaning and fulfillment is a luxury for those who've already achieved financial security. There's truth here—it's easier to pursue purpose when basic needs are met.

But this isn't an either/or proposition.

The emissary mindset doesn't require abandoning practical concerns. Rather, it changes your relationship to them. You can pursue financial stability while being conscious of why you're doing it and how it connects to your deeper values. Many people find that authentic alignment actually enhances their material success rather than diminishing it.

The real privilege is awareness—understanding the water you're swimming in. This awareness is available regardless of your circumstances, though how you express it will naturally vary based on your situation.

Liberation: Turning Resistance into Fuel for Change

Death as the Ultimate Clarifier

Nothing cuts through noise quite like contemplating your impending doom as a mortal being. When I find myself caught in achievement loops, I turn to three powerful perspective-shifting practices on my own mortality:

• The Eulogy Exercise: Write your own eulogy as if you died today. Then write the one you hope people would read if you lived aligned with what truly matters to you. The gap between these two reveals where mercenary thinking has led you astray from what you genuinely value.

• Futurecasting: This is usually one of the first things I do with my coaching clients. Fast-forward to age 80. What are you doing on a Tuesday? A Saturday? Who’s around? Who’s missing? What matters to 80 year old you?
  
  From that vantage point, what would you tell your current self about how you're spending your limited time? Which achievements would still matter? Which relationships would you wish you'd prioritized?

• Memento Mori: The ancient practice of remembering we'll die isn't morbid—it's clarifying. Keep a physical reminder of mortality (a quote, an object) where you'll see it daily. This continuous reminder strips away the promise of success games that don’t matter and reveals what actually deserves your energy. (Hint: It’s never an email).

These practices aren't just philosophical—they're practical resets. They reveal the truth: the mercenary path pursues validation that ultimately means nothing in the face of our finite existence.

The Emotional Battlefield

The most challenging part of this transformation isn't intellectual understanding—it's navigating the emotions that arise when you try to change.

When you first step off the mercenary path, expect to feel:

• Fear: What if I'm not enough without my achievements?

• Grief: Mourning the identity you're letting go of

• Confusion: Without external metrics, how do I know I'm "doing well"?

• Unworthiness: The voice that says you don't deserve joy unless you earn it

These emotions aren't weakness—they're evidence you're dismantling the very structure that's been organizing your life. This is where working with a therapist or coach can accelerate your journey. Someone who can ask the questions you can't yet ask yourself:

• "What would happen if you were enough exactly as you are?"

• "What would you do if you weren't afraid?"

• "What would your inner child want for you right now?"

I needed someone (like my amazing leadership coach, Lauren Borden) to help me see how often I set impossible standards for myself, then brutally self-criticized when I inevitably fell short. Through the questions she asked, I realized I was stacking the deck against myself, then berating myself for losing a rigged game—like setting a goal to become a NYT bestseller by 35, and then treating myself like I'd failed at life when it didn't happen. Not all of us can be my former boss, Mark Manson. And that's fucking fine!

Practical Tools for Transformation

This shift isn't about abandoning achievement—it's about changing your relationship with it. Here are tools to begin that process:

• From Extrinsic to Intrinsic Motivation: As Naval Ravikant suggests, "The reason to win the game is to be free of it." The ultimate transformation isn't abandoning achievement altogether, but shifting why you achieve. When you operate as an emissary, your accomplishments become expressions of your authentic self rather than attempts to prove your worth. Success becomes a milestone along a path of self-realization, rather than the sole, ultimately unfulfilling, goal. This shift transforms achievement from something you chase for validation to something that naturally flows from who you are.

• The Childhood Reconnection: As Robert Greene suggests in Mastery, recall what absorbed you as a child before external expectations clouded your natural inclinations. What activities made you lose track of time? What were you doing when you felt most alive?

• The Worthwhile Trade-Off: Oliver Burkeman reminds us in Four Thousand Weeks that we have limited time. The question isn't "Can I fit this in?" but "Is this worth giving up something else?" This clarity around the trade offs we are willing to accept (or not) in our lives helps identify where our energy truly belongs.

• Experimental Living: Identify people whose lives contain elements that resonate with you. What specifically do they do that calls to you? Design small experiments to try these elements in your own life without full commitment. Ask yourself questions like, "How could I enjoy this moment 10% more?" Treat your life as a series of enlightening experiments rather than permanent decisions.

• Self-Understanding Over Self-Improvement: True transformation doesn't come from "fixing" yourself into someone worthy of love and respect. As Coach Joe Hudson emphasizes, it comes from understanding yourself deeply enough to recognize the worthiness that was always there. When you flip from self-improvement to self-understanding, you stop treating yourself as a problem to be solved and start approaching yourself with genuine curiosity. This shift alone often dissolves many of the resistance patterns that kept you trapped in mercenary mode.

The Practice of Noticing

Ultimately, this transformation is a practice of noticing—developing awareness of:

• Where you feel alive versus empty

• When you're acting from alignment versus seeking validation

• How your body feels when you're in mercenary versus emissary mode

• What stories you tell yourself about your worth and its connection to achievement

This noticing creates the gap between stimulus and response where your power to choose differently lives. It's not about perfection—it's about catching yourself earlier and earlier in the mercenary patterns, then making a different choice.

"The emissary path isn't about abandoning ambition—it's about ensuring your ambition serves something deeper than validation."

The emissary path isn't about abandoning ambition—it's about ensuring your ambition serves something deeper than validation. It's about creating from fullness rather than lack, about contribution rather than extraction.

Create Your World

Perhaps the most compelling reason to make this shift is captured in Joe Hudson's insight:

When you operate as a mercenary, constantly shaping yourself to meet external expectations, you build a life that fits someone you're pretending to be. No wonder it never feels right. The emissary path allows you to create a world aligned with who you truly are—not the person you think you should be.

This is how you build a life that actually feels like home.

Living as an Emissary: Real-World Examples of Transformation

This transformation from mercenary to emissary isn't just a philosophical shift—it's a practical one that shows up in how you spend your time, energy, and attention. The emissary path is marked by curiosity, meaning, and intentional challenge rather than the constant validation-seeking of the mercenary.

These tools for transformation aren't just theoretical—they manifest in practical, everyday choices. Here's what this looks like in real life:

The Creator Without a Deadline

For years, I pushed creative writing aside because it didn't immediately contribute to my "important work." It wasn't until I started waking up an hour earlier on weekends to write at a local café that I discovered what it felt like to create simply because something in me needed expression. No publisher waiting, no audience expecting delivery—just the quiet joy of putting words on a page that felt true.

What makes this emissary behavior? It's driven by internal alignment rather than external validation. The pleasure comes from the activity itself, not from what others might think of it.

The Curious Colleague

One of my coaching clients transformed her work experience by setting up weekly coffee meetings with people across her organization—not to network or advance her career, but simply to understand their perspectives on topics she found interesting.

"I used to avoid these conversations unless they directly benefited a project I was working on," she told me. "Now I realize how much richness I was missing by treating relationships as purely transactional."

What began as pure curiosity evolved into some of the most meaningful connections in her professional life—connections that eventually led to collaborative projects she never would have envisioned.

The Co-Learning Commitment

When I’m working on a course or reading a nonfiction book, I regularly set up a recurring Zoom call or weekly text message with a friend to work through and share the concepts that intrigued us—no achievement targets, just mutual accountability for showing up to explore ideas together. In different pairings, I’ve alternated choosing topics, from happiness to creativity, with no agenda beyond following my curiosity with a friend, and deepening our relationship as a result.

The DIY Retreat

Instead of waiting for the perfect workshop or retreat to attend, you can pull together a group of friends to create your own annual gathering. The easiest agenda to build is each person brings a challenge they're navigating for the group to help think through, along with something to teach everyone else—a skill, concept, or practice they find meaningful. Throw in some good meals, attending a show, probably a hard workout or two, and you will have one of the most powerful weekends of your year.

In our group, these retreats or ‘masterminds’ have evolved into spaces for authentic connection and growth, free from the achievement metrics that typically govern and infiltrate professional development events.

What all these examples share is agency expressed through curiosity, play, and meaningful engagement rather than achievement as the end all, be all. Whether carving out small pockets of time (a weekend morning, a lunch break) or creating larger commitments (weekly calls, annual retreats), the emissary finds ways to prioritize alignment over validation.

The key insight? When we engage in activities with no external reward—purely for the experience itself—we directly challenge the mercenary belief that our worth comes from our output.

Look at your calendar right now. Where could you create small openings for curiosity, play, or meaning without attachment to outcome?

You have agency here. Whether it's in the small spaces (the podcasts you choose to explore) or the larger commitments (hours blocked for creative practice), you get to decide what matters. And increasingly, as you practice the emissary path, what matters will be determined by your own internal alignment, the compass you create uniquely built for your life.

Recognizing these patterns and knowing what to change is just the beginning. The challenging part—and the most rewarding—is actually making this transformation stick.

The Journey Home: Your Invitation to Authentic Achievement

If parts of this article have felt like someone reached into your head and articulated thoughts you've had but couldn't quite name, you're not alone. The mercenary mindset is particularly common among high-performers, especially those who Brit turned modern philosopher Chris Williamson calls insecure overachievers.

But recognition is just the first step. The journey from mercenary to emissary isn't one you have to navigate alone.

The Blindspots We All Have

As I've walked this path myself, I've learned that our resistance patterns are often invisible to us. Like fish unaware of the water they swim in, we can't always see the ways we've been conditioned to equate achievement with worth.

This work often requires an outside perspective—someone who can shine a light on the patterns we can't see on our own and ask the questions we don't think to ask ourselves. This is where coaching becomes invaluable.

The Structured Path Forward

For those ready to make this transformation real, I offer two ways to work together:

Seeking Wisdom: You’re reading it right now. Every two weeks, receive practical insights and exercises to help make this shift from mercenary to emissary thinking. It's free, and you can subscribe below or share with someone who might find it useful.

Subscribe now

Share

1:1 Coaching: For those seeking comprehensive support, my 3-month coaching program provides personalized guidance through this transformation. We'll work together to dismantle your resistance patterns and design a life aligned with your authentic purpose. Read more below.

Whether or not we end up working together, remember this: You are already worthy, regardless of what you achieve. Your value isn't tied to your performance. And it is possible to create a life of meaningful contribution without sacrificing your entire wellbeing on the altar of achievement.

"Creating from fullness rather than lack, focusing on contribution rather than extraction."

The journey from mercenary to emissary isn't always easy, but it might be the most important work you ever do.

It's how you build a life that actually feels like home.

Introducing 1:1 Coaching for High-Performers

I work with a limited number of clients who are ready to transform their relationship with achievement—to shift from being mercenaries at war with themselves to emissaries aligned with their deeper purpose.

This coaching isn't about abandoning your ambition. It's about ensuring your ambition serves something deeper than validation.

Together, we'll:

• Identify your specific resistance patterns and how they've served you until now

• Develop awareness practices to catch yourself in mercenary thinking

• Create experiments to explore what truly brings you alive

• Design sustainable structures that support your emissary path

• Navigate the emotional terrain of this transformation with compassion

Who This Is For

This work is specifically designed for high-achievers who:

• Have a track record of external success but struggle with internal fulfillment

• Recognize the mercenary patterns in their approach to achievement

• Are ready to transform their relationship with productivity, worth, and success

• Want to maintain excellence without sacrificing wellbeing

• Are willing to experiment with new ways of showing up in their work and life

This isn't for everyone. If you're looking for quick productivity hacks or ways to squeeze more achievement into less time, there are plenty of other resources available. This work goes deeper—addressing the root patterns that keep you trapped in cycles of achievement without fulfillment.

The Next Step

If you're ready to explore whether coaching might be the right next step for you, I invite you to apply for a discovery call. During this conversation, we'll:

• Discuss your specific situation and goals

• Determine whether we're a good fit to work together

• Answer any questions you have about the coaching process

I'm selective about who I work with, not because I'm looking for perfect clients, but because I want to ensure I can genuinely help you transform your relationship with achievement.

Take the first step: Book a discovery call →

The day I accomplished more in 6 hours than I had in previous weeks of 40+ was the day I realized everything I knew about productivity was wrong.

During my PhD, I found myself working one full-time job plus five part-time gigs (bartending, TA for two classes, assistant for the HDR office, and, only in Australia, delivering the school’s tea service for longer classes) while studying full-time in order to raise $22,000 for one semester’s tuition. And I had two semesters left to go.

My schedule, unsurprisingly was compressed to breaking point. I would wake up early, work late after one or more of my jobs had finished, and weekend breaks were a myth.

The surprising part? In the mere 15-20 hours I had left for my PhD work each week, I was accomplishing twice as much as when I had 40+ hours available in the years prior.

Scarcity had created clarity.

With so little time available, I became ruthlessly focused on what would move the needle. Everything else was stripped away. There was no time for second-guessing or procrastination—only the essential remained.

Saturdays became my heavy work day. Wake up at 7am, meet my friend at the gym at 730, sit down for coffee, breakfast, and work at 9am and knock out 3-4 sessions of focused 120 minute working time, changing location (I am a notorious café hopper) to keep it fresh, and usually ending my day around 5pm with an insane amount of articles read, notes written, and next steps laid out.

In contrast, when I first started the PhD with all the time in the world to focus, I tracked my progress by counting deep work sessions—tallying each 25-minute focused block. At first, this input-focused approach helped build the focus muscle, slowly building to 90 minutes of pure, focused flow time.

But eventually, I had to ask: What was all this productivity actually producing? Sure I was putting time on the calendar, but was I moving the needle? Was I actually getting closer to producing a written thesis?

The answers were all a resounding no. And it took adding 60 hours of real job(s) to my calendar to finally do something about it.

This is the hollow chase that traps so many of us: we optimize our systems, track our metrics, implement the latest productivity hack to pursue recognition—all while avoiding the harder question of whether we're moving efficiently in the entirely wrong direction.

Now that I work in consulting, I find this focus even harder to maintain. Work, social life, identity, building my own business, and sales all blur together. The clear boundaries have disappeared, and with them, the clarity of purpose that had made those limited PhD hours so productive.

And it’s not something that can just be fixed by “WORK HARDER!” As a former athlete, and since my earliest days of soccer, I knew how to push through pain and work. I knew how to grind. I can white knuckle and throw long hours at a problem.

But hours worked can’t solve everything. It’s a good starting point, but it’s probably not enough on it’s own to get you to the finish line you need.

This struggle illuminates something essential about real productivity: it's not about doing more. It's about doing what matters.

Real vs. Shallow Productivity

Busyness as a badge of honor is bullshit.

"Being busy is a form of laziness—lazy thinking and indiscriminate action." — Tim Ferriss

There's lots of work we can do simply to make people leave us alone. Work that looks impressive but doesn't move the needle. Work that creates the appearance of productivity without the substance.

This was me early on the PhD attending workshops that had very little direct value to writing my thesis. This is everytime you open your inbox pretending to check emails in order to make it look like you’re doing something while at the office. In fact, part of why virtual work is effective is because it removed the need for this fake productivity virtue-signalling.

That's not fulfilling. That's not energizing. That's shallow, unecessary shenanigans.

Real productivity, by contrast, tries to tick as many of these boxes as possible:

• It's aligned with our meaning and purpose

• It helps us grow and improve

• It allows us to reach deep levels of concentration (flow)

Sometimes you only get one. The holy trinity is when you can reach all three—what I call "Value-Aligned Productivity." These are the supercharged hours where you accomplish in 60 minutes what used to take four hours, working at the intersection of flow, purpose, and mastery.

Value-Aligned Productivity means aligning your work with your core values at a time when you do your best work, creating a virtuous cycle where your actions reinforce what matters most to you, rather than depleting your energy on tasks that feel meaningless. Having just two hours of this type of work in your week can transform your experience from good to great. Having one hour of this every day can absolutely change your life—creating momentum that carries into all aspects of your work and personal development.

This is where our values enter the equation. When I approach sitting down to write as something I have to do versus this is a practice of my value of growth, in getting better at writing and documenting my own journey in order to better serve others, my relationship with the work transforms entirely. It becomes something I look forward to as opposed to dread.

The approach, the energy, and ultimately the output are fundamentally different when the work connects to what we truly value.

Think about the last time you were so locked in on a task that time seemed to disappear. Maybe it was writing a report on a topic you found fascinating, perfecting a slide deck just so, or solving a complex problem about trying to sell to a specific client. That flow state wasn't just about pRoDuCtIvItY—it was about alignment.

Share

The Awareness Connection

Awareness—that muscle we build through meditation, journaling, and mindful practice—is crucial to distinguishing real from shallow productivity. It gives us the "catch" for interrupting patterns that don’t serve us. We either:

1. Notice and choose our intention before approaching a task ("Even though this is a chore I dislike, I'm going to make it as enjoyable as possible" or "I'll approach this meeting by dialing up my warmth and playfulness.")

2. Notice what we're bringing to the table during the task and choose a reframe ("I hate this, it's pointless" becomes "This is about integrity—I said I would do this, so I must.")

One of the simplest practices is setting an intention before beginning work. "I'm going to do this as fast as possible." "I'm going to approach this with humor." "I'm going to pretend this is fun." You find what you look for, so use intention to create a nudge back toward who you wish to be and how you wish to move through the world.

Without this awareness, you'll find yourself grinding through tasks that drain your energy while wondering why you're exhausted at the end of each day.

The Flow State Checklist

Flow states serve as powerful signposts that you're engaged in Value-Aligned Productivity. Research from psychologist Mihaly Csikszentmihalyi (I dare you to try and pronounce his name) shows that people in flow states are up to five times more productive than when working under normal conditions, with neuroimaging studies revealing distinctive brain activity patterns during these peak performance states.

Here's what to look out for:

Typical Work:

• You check the clock constantly

• Your phone becomes incredibly interesting

• You find excuses to take breaks

• Ideas come slowly if at all

• You feel drained afterward

• You dread returning to it

Flow State Work:

• Time seems to disappear

• You forget to check your phone

• You have to remind yourself to eat or take breaks

• Ideas come more easily than usual

• You feel energized after, even if physically tired

• You look forward to returning to it

The challenge in modern workplaces is that they're often designed to inhibit flow. Open offices, constant notifications via email, slack, teams and whatever other messaging platform is out there now, back-to-back-to-back meetings, and the expectation of immediate responses… all of this is in a deep, full-fledged conspiracy against deep work. The enemy is inside the gates. The call is coming from inside the house.

The countermeasure?

Boundaries.

The Liberation of Limits

The hardest thing about boundaries is keeping them.

It's easy to say, "I want more time for things I care about—the gym, writing, going for a walk." But that requires sacrifice. It requires trading and choosing your opportunity cost.

Because you can do and accomplish just about anything you want.

But you cannot do everything you want.

To choose to go for a walk without your phone is to choose not to respond to emails or plan your work week. And you have to be okay with paying that cost.

This is what Oliver Burkeman in his best-selling book Four Thousand Weeks: Time Management for Mortals reminds us. Because we have a limited time on this earth with an infinite list of things to do, it means we have to choose, and we have to be ok with the price of those choices. That it’s not about more work, it’s about choosing the right work more often.

For me, it was so easy, for so long, to choose my job. Long hours and a lot of mental energy were dedicated to showing up and performing well as an exceptional learning designer and strategic consultant. For me, being good at my job guaranteed respect and safety. But eventually, that ran out.

Consistently choosing more work over the right work, especially the work that involved taking care of myself, is not sustainable. And it's not actually my job's responsibility to prioritize for me.

That's my job.

If I can, with a straight face and a genuine heart, tell work that I'm doing good work and that shutting my phone off at 6pm is going to help me sustainably produce great outcomes for them, then I have an obligation to protect that time.

Work is often the first place I have clients start to set boundaries, which can sound scary. Work takes up (usually) 8 hours of your day, 5 days a week. Work adds up to a third of your life, a third of the 4000 weeks you have on this planet. But at work, unlike in personal relationships, you have a job description and a contract that makes some expectations explicit about what needs to happen for "good work."

Because if you don't protect yourself and what you need to do your best work, no one will.

As long as your requests and boundaries are couched in clarity—"Here's my role, here's what I need to do my best work, and here's what I'm doing about it"—the conversation becomes much more productive. At best, they never cared in the first place. At worst, they push back strongly, and then you have every signal you need to know you're in the wrong environment.

"Daring to set boundaries is about having the courage to love ourselves even when we risk disappointing others." — Brené Brown

Where I am still a work in progress is setting boundaries with myself to protect my important-but-not-urgent time. Writing my morning pages, time for workouts—I don't treat these as sacred as I should. I get caught in immediate feelings ("I'm tired," "I want to meet friends," "I just have 30 mins of work left"). These occasional slips might be okay sometimes, but for me, they happen far more often than they should.

There's also an anxiety cost—the price you pay for not having done them in your day yet, reaching 5pm knowing you still need to workout, write a new post, and meditate. When you knock these things out early, it gives you freedom later.

This is why ritual and consistency—doing specific activities at specific times that you don't miss—are so important. They create room that you and others can plan around.

As scary bald man Jocko Willink says, "Discipline equals freedom."

Common Objections and Realistic Solutions

When discussing these approaches to productivity, I frequently hear three main objections specific to work (but hint, hint, it applies to life in general):

• "My job doesn't allow for this kind of flexibility." Even in highly structured environments, you often have more agency than you realize. Start with small boundaries—like taking a proper lunch break or blocking 30 minutes for deep work—before attempting larger changes. Research shows that even micro-breaks of 5-10 minutes can improve focus and sustainability. The key is to begin with changes so small they don't require permission, then gradually expand your autonomy.

• "I can't afford to work less in my competitive industry." This approach isn't about working less—it's about working differently. You have to be doing the work that only you can be doing. Your work, your team, your organization does not benefit from the time you spend on low-level tasks. We may not be able to cut out admin tasks entirely, but what and how are you working on the things that directly benefit the business? Outside of work, the same question remains. If you think you don’t have enough time, check your screen time on your phone and then re-evaluate that answer. The question isn't whether you can afford to change your approach; it's whether you can afford not to.

• "What about urgent demands and unexpected crises?" Value-Aligned Productivity doesn't mean ignoring genuine urgencies. It means having the awareness to distinguish between true emergencies and manufactured ones. Build what author and researcher Cal Newport calls "slack" into your system—buffer time that absorbs the unexpected without derailing your most important work. When emergencies do arise, having clear values actually makes triage decisions easier because you know exactly what matters most.

The Productive Pendulum

While boundaries protect your time and energy, they're only part of the equation. The question remains: how intensely should you work within those boundaries?

This is where finding your rhythm becomes essential.

There's a tension between the David Goggins endorsed "grind" mentality and a more ‘let’s just wing it’ approach to productivity. I've found that neither extreme works perfectly.

Grind is good to have on call. You want that capacity in your engine for the days you really need it, so if this is missing, it is certifiably the place to start.

My problem, and the problem of so many high-performers I see, is learning how to shut the engine off.

Currently, I’m suffering from a little of both extremes. Between having started a new full-time job 5 months ago, just added a sales target to the role which is totally new, and launching the substack, there is a lot on my plate, and I feel like I’m doing ok on some of it, excelling at none of it.

To address this, my current approach looks like entering seasons of "push" to step up to my line of capacity, possibly a little bit over it. I’m trying to increase my capacity to work because I know I’m selling myself short in that domain. So this looks like adding an hour before work on the Substack, sometimes 2 hours after work, and usually 5-6 hours across the weekend. Between the job and this extra work, it can end up at a 60 hour work week. One week of 60 hours is doable, 6 months of that could be a superhighway to burnout.

So after these intentional push periods, I flip the focus: Where and how can I concentrate only on the highest leverage activities?

The goal becomes sustainable effort on move-the-needle tasks rather than sheer volume of hours.

It's similar to how I approach training Brazilian Jiu-Jitsu. If I am always rolling at max intensity with competition-level rolls five times weekly, injury becomes inevitable. I’m 100% going to hurt myself (or be hurt by all the scary people engaging in death cuddles). And those months I would have take off injured, could have still counted if I had just dialed it back. Strategic intensity is key.

There's a rhythm and a balance to this work. Some weeks you push to your edge. Other weeks you recover. The goal isn't constant intensity, but rather a sustainable pattern and tempo that builds your capacity over time.

This approach aligns with what sports scientists call 'strategic overreaching'—temporary, planned training intensification followed by adequate recovery. Like a muscle under progressive overload, you stress your capacity, allow time to recover, and go-again, maybe just a little bit longer or harder this time. The same principles apply to cognitive work.

What's crucial here is setting a time limit for these "push" experiments. We don't want to grind indefinitely. So I might say: three weeks of doing two hours of focused work after my regular workday.

This is an experiment with a clear endpoint and evaluation: How's my energy at the end? When was I drained? What did I learn about my best times to work and how to do it sustainably?

Recognizing these patterns is half the battle. Correcting it is the other half.

Systems as Servants

After years of experimenting with productivity approaches from authors like Oliver Burkemann, Cal Newport, James Clear, Charles Duhigg, Ali Abdaal, David Allen, and others (you name it, I’ve probably read it), I've distilled a set of principles that actually serve meaning rather than just efficiency.

These are systems designed to be servants to your purpose, not masters of your time:

• Single-task. Multitasking is the enemy of depth. Choose one thing and give it your full attention. This isn't just intuitive advice—it's backed by science. Heavy multitaskers pay a ‘focus tax’ for constantly switching between tasks compared to those who focused on one thing at a time. Put simply, people who believe they are 'good multitaskers' are lying to you, to me, and to themselves.

• Aim for deep work and flow. Structure your environment and time to minimize distractions and maximize your chance of entering a flow state. Turn off notifications, look at a blank screen, lock the door to your office.

• Know your prime time. Figure out when you work best. We can't always perfectly control our schedules, but we often have more influence than we give ourselves credit for. I'm not doing creative work in the afternoons—it has to be mornings, so I block that time out. I can meet and chat with people all day in the afternoons. This is a negotiation, not a dictatorship, but start moving your schedule toward the times and types of work that suit you best.

• Have a place to track incoming tasks. Write it down. This gets things out of your head, and by seeing everything in one place, priorities often become clear.

• Use the Pomodoro Technique. Start with shorter focused sessions (the standard time is 25 minutes) and increase the length as you strengthen your focus muscle.

• Work around people. This isn't for everyone, but I thrive when working around others who are also working. Focusmate is a great online tool for this, where you jump on a virtual call and both work on your own thing. During my PhD, we did something called "shut up and write" that was incredibly effective. You can also ask a friend to jump on a Zoom call or meet at a café (my girlfriend and I call this "parallel play.")

• Balance inputs with outputs. At the start, it's about revs and reps—how many can you do in a day/week and how do you increase those over time? Eventually, you need to shift to "What are you producing that moves the needle?" For example in sales, this means asking, "How is your activity helping to generate revenue?" This is your ultimate check against useless spinning or productivity for its own sake.

• Small and consistent beats perfect and nonexistent. Some people can jump in and go all-out right away. That might work for you—I've had moments like that, usually with impending deadlines. But it's rarely sustainable. What works better is the ramp-up. With Pomodoros, my goal was always 4 hours (or 8 sessions of 25 minutes)—3 hours was not great, 5+ was exceptional. I increased session length by 5 minutes every week until eventually I was doing 90-minute blocks, consistently hitting 4-5 of those daily (6-7.5 hours of deep work). But that took about 4 months to build up to, and then I maintained that pattern for nearly 4 years.

Subscribe now

Homework: Start by identifying one activity in your current schedule that energizes rather than depletes you. Schedule an additional 30 minutes for this activity next week, protecting this time as if it were your most important meeting. Small shifts in how you allocate your attention often trigger the biggest transformations in productivity and fulfillment.

Reimagining Productivity: The Path Forward

I still think about that period during my PhD—when financial pressure forced me to compress 40 hours of work into 15, and somehow doubled my output in the process.

The scarcity that once forced clarity can be recreated by choice. The boundaries that once felt like limitations can become the very structure that liberates your best work. What initially felt like a crisis became my greatest teacher.

These systems aren't just productivity tricks—they're unique, personal expressions of a deeper philosophy that prioritizes your alignment over sheer volume. When we step back from both the hustle culture and the work-less movement, a more nuanced approach emerges.

In the productivity conversation, most voices fall into one of two camps: the hustle-harder crowd promising that sleeping four hours a night is the secret to success, or the work-life balance advocates suggesting that the key is doing less.

Value-Aligned Productivity offers a third path—one that focuses not on how much you do, but on the alignment between what you do and who you are, and holding you to account for doing work on what you decide matters.

When I was tracking 25-minute Pomodoro sessions at the start of the PhD, I thought productivity was about showing up and putting in time. When I was juggling six jobs, I learned it was about focus and elimination. Now I understand it's about something deeper—the intersection of values, flow, and impact.

Working on this Substack has been a great example so far. It is deeply tied to my vision, mission, and values of who I wish to become in the world. It allows me to work on and improve the craft of writing. And I am able to enter deep states of flow when I set aside concentrated blocks of time - the 90-120 minutes spent writing on a Saturday morning, coffee in hand, is consistently some of my favorite and most productive time of the weekend.

For those of us who've experienced excellence in other domains—whether on the field, in academics, or early career wins—this approach offers a way to recapture that sense of purpose and mastery without sacrificing sustainability. The game has changed, but the fundamentals of meaningful achievement remain.

The path starts with awareness—noticing when you're caught in the hollow chase and choosing a different way. It continues with the courage to set boundaries, even when that means disappointing others or going against cultural norms. And it's sustained through systems that work with your natural rhythms and strengths rather than against them.

The question isn't whether you can squeeze more into each day. It's whether what you're doing matters deeply enough to warrant your limited time and precious energy.

The most productive day of your life won't be measured by tasks completed or hours logged, but by how aligned your efforts were with what truly matters to you.

What would it look like if your productivity served your purpose rather than replaced it?

What's one boundary you could set tomorrow to create space for what truly matters?

Leave a comment

The living room. I sat down on the couch, hands waving as I explained my PhD funding dilemma to my parents.

"So that's where I'm at," I concluded, gesturing with my glass. "I'm trying to decide whether to transfer programs or walk away entirely."

My mother tilted her head slightly. My father cleared his throat.

"Remind me again," he said, his voice careful, measured. "What exactly is your PhD about?"

The glass stopped halfway to my lips. Time seemed to freeze as the question hung in the air between us.

What is your PhD about?

From anyone else, it would be a straightforward question.

But from my parents—the people who had raised me, who had been hearing about my doctoral studies for two and a half years, who knew I was working six different jobs while studying full-time after my promised funding disappeared—it felt like betrayal.

My chest tightened. I placed the glass down carefully, though my instinct was to slam it.

How could they not have been paying attention, especially this crucial moment when I needed their guidance most?

"Behavioral science," I said flatly. "Studying how people change their behavior, working with farmers on the decision to adopt sustainable agriculture and why they might resist."

But inside, a storm was brewing. My thoughts raced to all the terrible stories I’ve always told myself: They don't care. They haven't been listening. They've never really understood me. I'm completely alone in this.

My mother must have noticed something in my expression. She reached toward me, but I shifted away slightly, standing up to refill my water.

Twenty minutes later, as we moved to the living room, something unexpected happened. The tightness in my chest had dissolved. The anger had vanished.

Instead, I felt a sense of clarity washing over me—and with it, a surge of love and appreciation for my parents stronger than ever.

What happened in those twenty minutes?

I realized three essential truths that marked my transition into actual adulthood:

First, my parents didn't know the details of my PhD not because they didn't care about me, but because they only cared about me. They weren't interested in the academic particulars—they were interested in whether I was okay, whether I was growing, whether I was becoming who I wanted to be. If I was doing what I needed to do, that was enough for them.

Second, even if my parents somehow knew everything about behavioral science, the politics of academia, and had both secretly completed their PhDs when I wasn’t looking, it wouldn't have mattered. Because at 27 years old, I stood before a decision that would define my life's direction, and I alone had to own that choice.

And finally, the most liberating realization: I didn't want them to save me. I didn't need them to. I had everything I needed to make this call, and while that didn’t mean it was easy, I wanted the power to choose my path.

My compass was within me all along.

The fact that I could recognize this—that I was prepared to trust my own internal compass—was itself a testament to their parenting. At every turn, my parents have encouraged my siblings and me to make our decisions and own the consequences of it.

In that moment in the living room, when I decided that not only do “I choose,” but I actually have to choose forever going forward, I became an adult in the truest sense.

For some people, this moment of internal authority happens earlier.

For some, it never occurs at all.

Having now worked with hundreds of leaders at the world's most prestigious organizations, I can tell you that the number of adults in the room rarely equals the number in attendance.

Those who know who they are, what they truly value, refuse to compromise their authentic direction to placate others, and embody the “I choose” energy—these people are rare and immediately recognizable.

Their internal compass points to their true north, regardless of who's watching.

Subscribe now

Beyond the Map: Why We Get Lost

We live in a culture obsessed with success. From our earliest years, society hands us a map for success—prestigious schools, lucrative careers, impressive titles, material acquisitions—without being taught how to read our own internal compass.

High-school Danny believed success meant an Ivy League degree, a professional soccer career, financial security, and shelves lined with impressive books.

College Danny, though not at an Ivy, thought a PhD represented the pinnacle of achievement as my guaranteed path to respect, opportunity, and yes, even more books.

PhD Danny became desperate to escape academia, convinced that a six-figure consulting salary and teaching executives would finally bring fulfillment. And books.

You can probably see where this is going.

I secured the consulting job and the six-figure salary. And far too quickly, I found myself wondering why, yet again, I did not feel fulfilled.

This pattern—achieving external markers of success only to find emptiness—isn't unique to me.

All of us could name people in our lives that achieved everything society values—wealth, status, power—and yet remain deeply insecure, perpetually restless, and profoundly unhappy.

The reality is stark but liberating: resume achievements cannot equal lasting satisfaction. They were never designed to.

Our brains evolved with a negativity bias—a survival mechanism that keeps us perpetually dissatisfied and scanning for the next challenge or threat. Research in behavioral science shows this neurological treadmill consistently returns us to our baseline happiness regardless of external achievements.

Meanwhile, our culture has amplified this dissatisfaction by over-emphasizing measurable accomplishments, from IQ tests to college admissions, creating a pressure that now begins in kindergarten.

What does this mean for you?

It means it's harder than ever to determine what YOUR version of success actually looks like. The measures we've been told matter—explicitly or unconsciously—are largely misaligned with genuine fulfillment. There's too much noise drowning out your internal signals.

The True Cost of Misalignment

We often discuss the consequences of misalignment in dramatic terms—midlife crises, burnout, existential despair. But the daily cost of following someone else's map rather than your own compass is far more insidious.

• It's the Sunday night dread that settles in your stomach as you contemplate another week at a job that looks impressive but feels meaningless.

• It's the reflexive comparison when you hear about a friend's promotion, followed by the immediate question: "Do I want that too? Should I?"

• It's the curious way accomplishments evaporate from memory almost immediately—the promotion, award, or milestone that was supposed to feel significant somehow doesn't register emotionally.

• It's the constant internal dialogue filled with "I should" rather than "I want" or "I choose."

These are the subtle manifestations of compass interference—creating a constant low-grade anxiety that many high-performers have simply accepted as normal, like background noise they've stopped noticing.

When you allow external interference to redirect your compass, two losses occur:

• First, you shape-shift to fit into a box of someone else's design. You cram yourself into a shape because of what you imagine others want from you. I watched myself become increasingly concerned with fitting in rather than asking what do I actually want here?

• Second, you gradually lose the ability to hear your own internal signals. Like a muscle that atrophies from disuse, your capacity to discern what genuinely matters to you weakens over time. The noise drowns out the signal until you no longer remember what your own true north feels like.

The combined cost is a life lived inauthentically—a draining, inefficient, and ultimately unsatisfying way to move through the world. It's death by 1000 paper cuts, where each decision not aligned with your values takes another small slice of your vital energy.

Even worse, if you do not figure this out—if you do not discern what it means for you to live a life of meaning:

• You will reach the end of your life.

• You will face that moment alone with your thoughts.

• Only you will know if your life felt meaningful, if it was filled with love, if it made a difference.

This is why defining your personal scorecard isn't optional—it's the difference between a life of authentic fulfillment and dying hollow and full of regret.

Don’t do that.

Contrast this with compass-aligned living—the state where your actions and choices follow your internal direction rather than external maps. This creates a positive feedback loop, an eternal engine generating its own momentum. When you're aligned with your compass, energy expands rather than contracts. Obstacles become interesting challenges rather than draining barriers.

This can sound cliche. It can sound unrealistic. After all, we have bills to pay, responsibilities to manage, and sometimes we simply need to adapt to circumstances beyond our control.

And yes, there will be seasons when compromise is necessary—where your compass points one way while your current reality demands another path temporarily. But even in these periods of compromise, your internal compass remains intact.

You already know what you truly want and need. It's carried within you—in your unique disposition, your natural inclinations, the things that genuinely light you up when no one's watching or measuring, the presence you bring to every room you walk into.

You just need to listen closely enough to hear it. You need to quiet the external noise to discern it. You need to do the inner work of separating what's authentically yours from what you've been told to want.

It's never too late to begin this work.

It's never too early to start.

And it's always worthwhile to revisit and refine as you grow.

Calibrating Your Compass: Finding True North

So we've identified the interference and recognized its cost. Now comes the essential question: How do you work with your compass to find your true north?

In its simplest form, this means identifying what you truly value—not what you've been told to value, not what looks good to others, but what matters deeply and authentically to you.

It means taking the things you believe to be sacred and being willing to sacrifice for their pursuit, protection, and power.

In an interesting bit of trivia, "sacred" and "sacrifice" share the same Latin root, sacer, meaning "holy." Don’t worry, I’m not converting anybody here. This matters because you show what is sacred to you by what you're willing to sacrifice for it.

If I value growth, I show it by what I give up for it (moving halfway around the world away from friends and family for 7 years), not by what I say. If I value my family, I show it every time I fly to see them for the events I wouldn’t trade the world to miss. If I value integrity, it means there is no amount of money people could give me for an action that sits outside of who I am.

If you're not willing to give anything up for something, it isn't truly a value—it's a preference. And if you can’t explain why you value this thing, that value isn’t yours, it’s somebody else’s.

My own journey to calibrating my compass wasn't instantaneous. It unfolded through years of reflection, values exercises, coaching conversations, meditation, and honest self-assessment. What has emerged is the start of something uniquely mine—a Danny Kenny compass that no one else could have calibrated for me.

And there are actions you can take now to start living a life more aligned. Just you, me, and Jack Sparrow following our compass. Savvy?

Identifying Your Values

1. The process begins with identification. Looking at a comprehensive list of values, start by circling the 8-10 that resonate most strongly.

2. Then comes the challenging part: narrowing that list to 3-4 core values. This constraint forces clarity and prevents the "everything is important" trap. If you value 10 things, you actually value nothing.

3. Note: How you define these values can be unique to you. I value learning and curiosity, but in my compass, these fall under the broader direction of "growth." I value connection and service, but these align under my commitment to "leadership" as I define it. You can move things underneath a ‘master’ value.
   
   The key is identifying what you actually value, not what you think you're supposed to value. This requires ruthless honesty and careful examination. If you say you value "health" but your underlying motivation is appearance or social approval, then your true value might be "confidence," not health itself.

4. You know you've identified a true compass direction when no external reward could persuade you to abandon it, and no external pressure could force you to compromise it. Test your values with these questions:

   1. Would you maintain this value even if it cost you financially?

   2. Would you hold to it even if it made you socially unpopular?

   3. When was the last time you sacrificed something for this value?

   4. Can you identify specific decisions you made because of this value?

For me, this calibration process revealed that my compass consistently points toward growth and integrity.

• Growth means constant evolution, learning, and development—both for myself and others.

• Integrity means wholeness, alignment between inner and outer, and the courage to do what's right even when it's difficult.

Once identified, these compass directions simplified decision-making tremendously. When faced with choices, I ask whether an option will facilitate growth and whether it aligns with integrity. If both answers are yes, my path is clear. If either is no, I know I'm being pulled off course.

Subscribe now

This clarity doesn't mean the path is always easy. Following your own compass often means departing from well-worn trails and familiar landmarks. It means disappointing people who expected you to follow their maps, and being ok with their negative feelings about it. It means embracing uncertainty.

But the alternative—continuing to follow directions to someone else's destination—guarantees arrival at a place that wasn't meant for you.

Regular recalibration is essential. Notice where you've made choices based on external expectations rather than internal alignment. Be gentle with yourself when you discover you've gone off course—the goal isn't perfect navigation but gradual improvement in reading your own signals.

This process isn't about rejecting all external input. Other people's maps can provide useful information about terrain and potential paths. The key difference is that YOU decide which direction to take, based on your own internal compass rather than external pressure.

Finding Your Traveling Companions

Once you've begun following your internal compass, you'll notice something surprising: the journey becomes less solitary. Just as my parents supported my independent decision-making (even when they didn't understand the specific details), you'll need people who support your authentic direction.

One of the most powerful aspects of compass-aligned living is that it naturally attracts others on similar paths. When you begin navigating by your authentic values, you draw in people who resonate with that authenticity and repel those who are threatened by it.

In my own life, the relationships that have sustained me through this journey haven't been based on shared credentials or professional affiliations, but on shared commitment to living purposefully and authentically. These connections provide both support and challenge—they celebrate when my actions align with my compass and gently question when I veer off course.

These traveling companions aren't necessarily headed to the same destination as you. They might value completely different things. What connects you is not the direction of your compass but your mutual commitment to following your own true north rather than society's prescribed routes.

To find these companions, two things you can do:

1. Ask deeper questions in conversations, moving beyond resume exchanges to values exchanges: "What's been most meaningful in your work recently?" or “What do you love about what you do?” instead of "What do you do?"

2. Create spaces for authentic conversation—dinner gatherings where phones are put away, walking meetings where nature slows the pace, or regular check-ins with trusted friends where you can all speak truthfully.

The unexpected benefit of finding these connections is that they serve as mirrors, reflecting back both your alignment and your blind spots. They help you calibrate your compass more accurately through their observations and questions. These relationships provide companions who care more about you staying true than reaching any particular destination.

That is priceless.

From Calibration to Navigation: Your Next Steps

The journey from external validation to internal alignment isn't completed in a day, a week, or even a year. It's an ongoing practice of listening to your signals, making choices aligned, and adjusting when interference pulls you off course.

This foundation—understanding what truly matters to you—is essential for finding your purpose and living an examined life of wisdom.

For now, your next steps are simple:

• Set aside 30 minutes this week in a quiet space with no distractions.

• Identify three moments in your life when you felt most aligned—when your actions, your values, and your sense of purpose seemed perfectly in sync. These might be moments of achievement, but more likely they're moments of presence or connection that wouldn't necessarily appear on a resume.

• For each moment, ask yourself:

  • What values was I honoring?

  • What was I creating or contributing?

  • How did alignment feel in my body?

These moments contain the first clues for your personal navigation system.

Remember: As you begin this calibration work, be patient with yourself, celebrate small course corrections, and trust that your authentic path will reveal itself through consistent practice and attention.

Your compass has always been within you. Now it's time to learn to read it.

The poet Mary Oliver perhaps captured it best when she asked: "Tell me, what is it you plan to do with your one wild and precious life?"

In that moment with my parents in the living room, I wasn't just making a decision about my PhD—I was choosing my path based on what I care about rather than following someone else's map. Your moment of choosing may look different, but the freedom it brings will be just as profound.

The answer won't be found on anyone else's map.

It can only be discovered by following your own compass.

The meditation app was just meant to be another box to tick that day - 20 minutes of the usual mental ping-pong between breath and distraction.

But something different happened.

As I sat, watching the Australian countryside pass by, my awareness seemed to both expand and disappear entirely. The feeling of the leather seat disappeared, the rumble of the bus faded, and the chatter of other passengers melted away. I wasn't me anymore.

I just was.

It felt like that SNL sketch where people get abducted by aliens - the good experience, not Kate McKinnon's "knockers" situation. Pure golden light and cosmic belonging.

It might have been two minutes or twenty. Time doesn't exist when you're touching the divine, or whatever the hell that was. This was it - the mythical "awakening" that every meditation app and mindfulness guru promises.

And you know what?

It isn’t the point.

That rare moment of transcendence wasn't special because it happened—it was special because I noticed it happening.

And that noticing—that awareness—is available to all of us in every moment, not just in peak experiences.

The ability to witness our own experience is our most underutilized superpower.

Your Success Loop is Secretly Working Against You

Chasing enlightenment is just another version of the same achievement trap I've been falling into my whole life. Hell, I got a whole PhD trying to optimize my way to personal growth. It's the same mindset that had me calculating exactly what score I needed on every test to keep my A.

If you ever cared about school like I did (obsessive, borderline insane), then all you wanted was a syllabus. That beautiful document helped you calculate the perfect formula for achieving the almighty A. Through highschool and college, I could tell you what score I needed on every assessment, updating my calculations throughout the year like some obsessive mad scientist.

Achieving that A was my respect and my attention, and my whole life had taught me that everything could be bought with hard work, time, and a little strategy.

So when I discovered meditation, guess how I approached it? Like another performance-enhancing drug - free and legal! - that would help me survive the PhD, boost my productivity, and magically transform me into an entirely better person.

I thought it was simple math: show up, accumulate time on the cushion, hold up my end of the deal, and eventually be rewarded with enlightenment. Please and thank you, I'd like my transformation now.

And sure, it helped with all those things. Just not the way I expected.

Because awareness doesn't work like that.

Awareness is defined as “the capacity to observe your thoughts, emotions, and behaviors objectively—without immediate judgment or reaction”.

It's the space between what happens and how you choose to respond.

If it helps, you can think of awareness as the muscle that lets you notice your thoughts, emotions, and reactions without being controlled by them. And like any muscle, it grows stronger with consistent training.

In meditation, the real work happens when you catch yourself thinking about the grocery list, that project at work, or that mean thing Tina said last week (fkn Tina).

You notice.
You bring it back to the breath.
You get distracted again.
You notice.
You bring it back to the breath.

Those are the reps. That's the muscle you're building.

And it is the same underlying muscle with with journaling - catching the patterns in your morning pages or your weekly reviews. Similar with therapy or coaching - noticing what makes you react, what lights you up, what stories you keep telling yourself.

The 'catch' is awareness. And it's not just another skill to optimize - it's the foundation that makes every other change possible.

Research from neuroscientists like Richard Davidson at the University of Wisconsin-Madison shows that regular meditation practice actually changes brain structure, particularly in areas associated with attention, emotional regulation, and self-awareness. These aren't just subjective benefits—they're measurable changes in how your brain functions.

You are building your ability to notice. When you notice something, like “I’m pretty pissed off right now” or “that really upset me” or “I feel incredible,” you get to ask questions about where that comes from. You get to engage in what poet and philosopher David Whyte calls 'the courageous conversation' - the real work of asking what you actually want when no one else is looking.

The work of 'breaking free from domestication' begins precisely here - in these small moments of noticing when we're following our programmed agreements to meet someone else’s expectations rather than choosing consciously. Each time we catch ourselves, we're questioning what author Don Miguel Ruiz calls the 'fog' - the chaos of competing voices we've internalized.

Instead of just following those invisible scripts from our past, you get to act, like author and poet yung pueblo says, “like a detective in your mind.” You get to ask questions to deeply investigate the source of your problems, joys, and tensions.

And then you get to choose what happens next.

Subscribe now

From Reactive Patterns to Strategic Choices

Sitting at the bar, I could feel the steam pouring out of my ears. This mother french-fry stood me up again. Calls himself my best friend, and yet, last minute, chose to not show up to the group sesh that he arranged to hang out with a girl.

I will kill him for this.

Before I can stop myself , I shoot off a text in the group chat to let him know what’s up. “Mate, get absolutely fucked. If you keep abandoning your friends for a girl, you’re going to stop having friends. Get your shit together.”

His response, surprisingly, is less than cordial. “Don’t be upset that I can have a relationship and you can’t.”

In the group chat.

Fast-forward and it’s been a week since we’ve last talked. It’s the longest period of silence we’ve ever had in our friendship.

As I’m walking that day, I make the mistake of looking up the last text exchanges we’ve had, and I can sense my blood boiling at the memory. Heart rate rising, breath getting shorter, you’d think I’d have just finished a sprint workout.

And then I notice what’s happening.

“What the fuck is going on right now? I never get this angry.”

I’ll skip the self-inquiry to the answer, where my friend had touched my deeply ingrained hot-button of ‘respect’. By both not showing up, (wasting my time), failing to acknowledge or apologize, and then double down with an insult, my best mate sent a message that he didn’t respect me, and I allowed myself to internalize that as maybe I wasn’t worthy of respect, ultimately leading to capital-R Rage.

Note: For those of you keeping score at home, I am 3-0 on the gif game right now.

Now that I had it in hand though, visible in front of me as to what was going on, I now had choice.

I could choose to stay mad.
I could choose to let it go.

What serves me best?

Ultimately, we had a chat, we both apologized and we moved on, actually stronger for having brought out the worst in each other and then gone through the process of repair. Some of that is a credit to my friend and how willing he was to own his piece.

Some of that was the choice afforded to me by the awareness muscle I’d been building in the background for years.

In a more positive light, this same principle applied when I found myself in the middle of burnout and disengagement at work. I’d been traveling to Decatur, Alabama every two weeks for 6 months, managing multiple roles on multiple projects, not getting the support I’d asked for, generally in a miserable mood for days on end.

It was a bad time.

Again, the work was I caught myself feeling bad. And not just bad but angry.

At myself. At work. At just about anyone who got too close to me, a snarling animal with his foot trapped.

I was working long hours, couldn't workout, and definitely wasn't eating the way I wanted to. I was trapped in a glass case of emotion.

And then a question arose in my mind, "Who's fault is this? And what should you do about it?"

The answer was clear but difficult to accept: My fault.

I may not have created the conditions, but I alone owned my response.

My emotions, particularly my anger, warned that something was out of balance between the way the world was and the way I wanted it to be. But I was also choosing to stay in the lane of not accepting the responsibility to change anything.

The frustration and the bitterness underneath my anger revealed a deep-seated belief that I thought I was 'too good' to be doing this, putting my expectations ahead of reality.

My anger was not useful because I was using it to complain, not to fuel doing something about it. If I was being honest with myself, I had way more options at my disposal than I was giving myself credit for, more options than "endure and whine" vs "quit".

I needed to ask "What would need to change for me to be in a better place and more empowering headspace?" The answers led to doing that work to either create more space for the things I enjoyed or to be creative in extracting more out of the situation I found myself in.

None of this means that I liked what I found in reality. Or enjoyed pointing the finger straight back at my own face.

But I needed a perspective that was useful, and one where I have the power to make things different is surely more empowering in the short and long-term.

Anger is a signal, alerting us to discrepancies between our expectations and reality, and highlighting areas in our lives that need attention or change.

By acknowledging my role in my anger, I could find (at least more) peace in the acceptance of things I could not change, while working diligently to change what I could.

And it made all the difference.

Practice to Break Mental Autopilot

So what the hell do we actually DO with all this?

Good news and bad news there.

• Bad news: it takes time to build this muscle.

• Good news: you can start right now, and you'll see results faster than you think.

If you're thinking 'I don't have time for this' or 'My mind is too busy to meditate,' you're in good company. Everyone feels this way at first.

That's why starting with just 10 minutes matters—it's accessible to anyone, even the busiest or most skeptical among us. And ironically, the people who feel they have the least time for these practices are often the ones who need them most.

Each of the below practices serves a single purpose: to cut through the fog of competing voices, expectations, and conditioning that clouds your judgment about what it is that you want. This noise isn't just external; it's internalized to the point where you can't distinguish between your authentic desires and the echoes of your past.

The key is not treating this as another productivity 'hack,' but as a committed practice to clear away this fog. As Don Miguel Ruiz puts it in The Four Agreements, personal freedom requires quieting this noise to hear your own voice beneath the programming.

This is not about perfection or achievement—it's about discovery and reclaiming your ability to choose consciously.

A note of caution: Awareness isn't always comfortable. Sometimes you'll notice patterns you've been avoiding for years. You might discover that your anger has deep roots in childhood experiences, or that your procrastination is actually fear in disguise. Be gentle with yourself in these moments.

If painful insights arise, consider having professional support through therapy. The goal isn't to judge yourself for these discoveries, but to meet them with compassion while creating space for new choices.

I've tested these paths extensively, and each offers a different entry point to the same destination: greater awareness and choice.

Pick ONE practice. Block 10 minutes on your calendar for the next 7 days. Set a reminder on your phone. After a week, reflect on what you noticed.

That's it. Don't overcomplicate it.

Meditation: The Attention Gym

This is where we practice the fundamental "rep" of catching our wandering mind.

• Why it works: Neuroscience shows that meditation strengthens the prefrontal cortex while reducing activity in the amygdala—essentially building up the brain's 'pause button.' Each time you notice your attention has drifted and bring it back to your breath, you're physically rewiring neural pathways that enable self-awareness. It's not about "clearing your mind"—it's about noticing when your mind wanders, without judgment.

• How to start: 10 minutes daily. That's it.
  Use an app like Waking Up, Headspace, or Ten Percent Happier if you want guidance. Or just set a timer and focus on your breath.

• The challenge: You will get bored. You will get frustrated. You will think "am I doing this right?" at least 47 times. This is all normal and part of the process.

Journaling: The Mirror

This practice creates space to see your own patterns on paper.

• Why it works: Externalizing your thoughts forces you to articulate what's actually happening beneath the surface. The page becomes a mirror reflecting back patterns you couldn't see before. Studies show that expressive writing reduces intrusive thoughts and helps process emotions, creating cognitive space for new insights.

• How to start: Morning pages (3 pages of stream-of-consciousness writing first thing), or a simple evening reflection answering: "What energized me today? What drained me? What surprised me?"

• The challenge: Consistency. Most people journal intensely for a week then abandon it. Commit to 30 days minimum before deciding if it works for you.

Coaching/Therapy: The Skilled Observer

Sometimes we need an external perspective to see our blind spots.

• Why it works: A skilled therapist or coach brings both professional training and emotional distance from your situation. They can identify patterns you're too close to see and provide a safe space to explore them. The relationship itself becomes a laboratory for practicing awareness in real-time conversation, with immediate feedback.

• How to start: For therapy, check if your insurance covers mental health services. For coaching, look for someone with credentials and experience working with people like you.

• The challenge: Finding the right fit. You might need to try a few different people before finding someone who gets you and challenges you in the right ways.

The path you choose matters less than your commitment to it. Start small, but start somewhere. Your awareness muscle grows with consistent practice, not intensity.

Share

The Pause That Changes Everything

Whichever path you choose, you'll begin to notice subtle but powerful shifts in how you respond to life's challenges.

Spoiler alert: success doesn't look like permanent enlightenment or never getting triggered again.

You'll recognize real success when:

• Your catch time decreases. You used to stew in anger for three days before realizing you were upset about something entirely different than what you thought. Now you catch it in three hours. Eventually, you might catch it in three minutes.

• You notice patterns in real-time. "Oh, I'm doing that thing again where I take on too much work because I'm afraid of disappointing people."

• You gain space between stimulus and response. That breath between feeling triggered and acting on it grows wider. It might only be seconds at first, but those seconds make all the difference.

• Your recovery accelerates. You still get knocked down, but you get back up faster. The time spent in unproductive emotional states shortens.

• You make different choices. Not always, not perfectly, but increasingly often. You catch yourself before sending that angry text. You pause before agreeing to another commitment. You notice when you're avoiding important work. You notice yourself reaching for your phone out of boredom rather than necessity, and consciously choose to stay present instead. You recognize when you're making decisions from fear rather than values. You catch yourself about to stress-eat and pause to identify what you're actually feeling.

These micro-moments of awareness might seem small, but they compound over time into dramatic shifts in how you experience your life.

What won't happen: You won't become a permanently zen buddha-like figure floating above human emotions. You'll still get triggered. You'll still have bad days.

You just won't stay stuck there as long.

Remember: awareness isn't about eliminating feelings or never feeling angry or afraid or hurt again—it's about not being controlled by them, to recognize those feelings as information rather than instructions.

Choose Who You Become, Not Just What You Do

So why does all this matter?

Why spend years building this awareness muscle, catching your thoughts on the bus, or noticing when you're about to send that angry text to your friend?

Because that moment of noticing—that tiny pause between stimulus and response—is where your freedom lives.

We spend our lives being shaped by forces we rarely notice—culture, family patterns, media, social expectations. Most of us live on autopilot, responding to life with the same unconscious patterns we've always used. Remember that anger on the bar stool? That wasn't a random reaction—it was a pattern built over decades, waiting for the right trigger.

As Pressfield observes, 'The amateur believes he must first overcome his fear; then he can do his work. The professional knows that fear can never be overcome.' Similarly, the goal isn't to eliminate our patterns and reactions, but to recognize them as we work, creating space for different choices despite them.

Awareness is the first step toward authorship. Toward writing your own story instead of living one handed to you.

Whyte suggests that finding your path isn't about making the right choice but about listening to what's already calling you: 'What you can plan is too small for you to live.' The awareness practices we've discussed aren't about manufacturing meaning, but about clearing away the noise to hear what's been calling you all along.

This isn't just personal development fluff. The gap between what we say matters to us and what we actually do—that say-do gap—is the source of much of our dissatisfaction. When we value connection but spend our days doom-scrolling, when we claim health is important but work ourselves to exhaustion, when we value honesty but avoid difficult conversations—we create internal friction that erodes our wellbeing.

Psychological research backs this up. Dr. Sonja Lyubomirsky's work on happiness shows that this internal friction—what psychologists call 'cognitive dissonance'—is a significant source of psychological distress. Her studies demonstrate that people who align their actions with their stated values report significantly higher levels of life satisfaction and lower levels of depression and anxiety.

Awareness doesn't just feel good philosophically—it creates measurable improvements in mental health outcomes.

Yung pueblo writes, "Your past becomes your trauma; your trauma becomes your autopilot."

Awareness creates the space to step off autopilot.

Is it work? Absolutely.

But it's the most important work you'll ever do.

Because ultimately, each moment of awareness is a moment of freedom. A chance to choose who you're becoming instead of simply repeating who you've been.

And that's the whole game.

Now it’s your move.

What will you notice today?

“Is this it?”

The accolades grow, the responsibilities expand, the profile rises - you’re builidng your legacy, making progress, kicking ass and taking names. The metrics all point up and to the right. By all accounts, you’re “killing it."

And it sure as shit doesn't feel like it.

Something nags at you.
Something is off.

When you gain the recognition at work, it feels great for about 5 minutes before it wears off. The promotion might even feel good for a week, before you go right back to asking "What else? What's next?"

You might grow irritable, feel exhausted, and you certainly don't feel fulfilled.

At the core of all of this, you ask…

"Is this it?"

The Call to Do Something

The whisper in the back of your mind grows louder until you can't ignore it anymore. Alarms sound as you start to realize that maybe, just maybe, more 'success', more 'achievement' might not be the thing to pursue.

To correct this, you listen to Modern Wisdom and Tim Ferriss. You read about stoicism and habit formation. You watch all of the Youtube videos (all of them) on finding your life's purpose.

And what all of those things have to teach you, (aside from Meditations being the most important book in Western canon), is that something has to change.

There's a gap between what you say you value and what you do everyday.
This misalignment cannot continue.

Now the question is... where to start?

Resistance is Inevitable

Here's the thing: What you're fighting against is the habit of being who you were yesterday. And unfortunately for you, and for me, we all happen to be world-class champions in that particular pursuit.

The things keeping you in this place of existential dissatisfaction are the deeply ingrained voices of your past telling you what life is 'supposed to look like':

• Stability

• Financial security

• The right profession

• The ideal partner

• The appropriate after work activities

Over decades, you've taken opinions in on all of these, and not by choice. Inputs from your parents, teachers, coaches, friends, and definitely the video games you used to play that told you violence was cool.

Those inputs led you to land on this spot in the map incredibly far from where you, real you, wants to be.

It's not their fault.
They were all trying to help.

It's not your fault.
You didn't know any better.

It is, however, your responsibility to do something about it. And that's Scary Terry because what it will ask from you is the sacrifice of what you claim to know, what you believe, and what you hold dear in the blind faith that what lies beyond is worth the terrifying leap.

Even worse, the fear will fight back.
It will be clever.
It will be devious.

This capital R Resistance will shape-shift to sing you its sweet siren song of "can't you just be satisfied with what you have right now?", to drag you into the depths of complacency and mediocrity.

Fuck that.

There is Hope

Now here's the good news.

• Number 1: To go through this, to endure this trial, to survive in the hopes of one day truly thriving... this is what it is to be human. This pursuit of living a fully realized life is a beautiful good that the world so desperately needs more of.

• Number 2: You are not alone. You are not the first person to go through this. For thousands of years, this has been the central question of philosophy, of mankind's search for wisdom, of prayer, of the written word, of meditation, and it continues this day with the addition of science as our friend and ally, of social media to help us normalize this struggle, of therapy and coaching to partner.

What real insight in this space feels like is the passage you read that feels like you've been punched in the stomach.

For me it was "What is your condition to be loved?" and the instinctive, split second response inside me said "to be seen as successful."

I almost threw up hearing myself say it it.

Not even to be successful. To be seen that way.

Because wrapped up in that seemingly innocuous statement was a little boy's desire to protect himself from the pain of the world and incredible, unending achievement was the only way he knew how to do it.

In that moment, sitting at the end of the bar I worked at before my shift started, my heart broke into a thousand tiny pieces for that child who learned to believe that story, as if he wasn't enough already.

So while they are enormous resources, the self-help and personal development genres, with all their books, their podcasts, and their endless videos on their latest experiments, also balance on a knife's edge.

On one hand, much of what they have to say is a reminder of how far you are from perfect, a constant reminder of the gap that exists between where you are and where you wish to be in living authentically.

On the other hand, they are a gift, from somebody who knows intimately the struggle and who learned something along the way that can help. It could be a quote. It could be a practice. It could be a question that flips your entire world upside down.

And it helps.

These aren't the only places this insight and support can come from. I've had countless people in my life who believed in me, who saw more, who gave a hand to pull me on my feet, and a nudge forward to keep moving towards the mountain that matters.

Some came from sheer dumb luck that is the lottery of life (my parents, my coaches, my teachers), some came from people I sought out (and sometimes paid), academics, my therapists, my executive coach, meditation teachers, online courses.

So if life didn't give you a great hand, you can find it anyways.

Because of how 'human' this struggle is, there is actually an overwhelming amount of resources and insights available to help us find our way. Now you just need to choose.

Moving to Action

The game we wish to play is to live a life closely aligned to what it is we truly, deeply value so much so that as much of the 24 hours we have each day directly contributes to our growth and practice to that personal scorecard of what success means for us.

Do we know what those values are? Probably not.

Even if we did, would we know how to practice them? Gah!

Is there a bunch of external shit that's going to get in the way of that, like making money, putting food on the table and savings in our Roth IRA? Fuck!

Is there a bunch of internal shit that's going to be really scary and pernicious to uncover about our patterns and we might totally have a public breakdown at an inconvenient time? Almost certainly.

And...we still have to do something.

Because the alternative is living for decades with "just fine".
The status quo leads to a deathbed full of regret.
The path of least resistance leads straight to a life half-lived.

That is hell on earth.
And you, and I, will not live that way.

So we're going to act.

Imperfectly.
Often cluelessly.
Even though we're scared.

What's important here is that any action we take will teach us.

Any action we take will move us closer to the mountain that matters, to bring the picture of our realized self a little more into color, to step a little more fully into being who we always were.

This transformation, this unveiling starts with the realization that you have the power to do something about this, to write your own story, and the commitment to act on it.

Imperfect Progress is the Goal

This has been my obsession of the last 15 years.

It started with the 5-1 shellacking Wheaton gave us in the CCIW tournament to end my senior season and my lifetime as a student-athlete, ripping out soccer as the defining feature, purpose, and practice of my calendar.

It led to a relentless pursuit of productivity, countless journal pages filled with scribbles, hundreds if not thousands of books read and podcasts listened to, minutes meditated, courses purchased for the small total price of funding another liberal arts degree, and 6 years of a PhD where I did nothing but read, learn, and think about changing human behavior for the better.

This obsession now fuels my work in leadership development facilitation for businesses and executives, and coaching high-performance individuals - helping others navigate their own journey of alignment and growth.

Over time, I’ve discovered tools to practice:

To practice this looks like weekly reviews to find out your wins, challenges, and lessons learned were for the week and to plan out your next one.

To practice this looks like an early morning wake up to go for a walk or a late night to write that blog post you've been thinking about.

To practice this is to be overwhelmed by all there is to read, listen to, and watch and not know where to go to next.

To practice this looks like spending time building your personal knowledge management system on Roam, or Notion, or Obsidian or whatever software is hip these days.

To practice this looks like forgiving yourself for all the terrible things you've said inside for years, and to love yourself as you are because you are enough.

To practice this is to wake up one day realizing that you of 5 years ago could never have handled a difficult situation the way you just did.

Here to Help

What's crucial to remember in all of this is that you already have everything you need.

Yes, we're going to make changes, yes, we're going to do some things different, and this is absolutely not about reaching for something that's not you while beating yourself up for not having it already.

I'm going to save you 10+ years of banging your head against that particular wall now.

This is about becoming more you. Peeling back the layers and blasting away the darkness that's been hiding the light you uniquely bring to the world.

It will be hard.
Like really fkn hard.

And it is so worthwhile because even though I am nowhere close to being fully realized, I am significantly closer than I once was and my life is exponentially more mine as a result. And the world I hope for is one where everyone lived this way a little bit more every day, embracing their own unique light to illuminate a better path forward for all of us.

If any of this sounds like you, I'm here to help.

I'll be writing here about what helped me on my journey, what's currently helping me on the path, and all of the mistakes, mis-steps, and failures I've had along the way so you can bypass them.

Follow me for this call to adventure where we'll be bringing philosophy, wisdom, science and every other tool at our disposal to living a fully realized life, for ourselves, and for everyone around us.

Subscribe now

Subscribe now