Timeless Conversations: The Best Books I Read in 2023
M. Andrew McConnell • December 26, 2023
“The reading of all good books is like conversation with the finest men [people!] of past centuries,” wrote René Descartes, he of “I think therefore I am” fame, 400 years ago. If this was true in his own day, how much more so is it in our own when we can tap into that accumulated wisdom and add to it the millions of books now published each year?
Having “consumed” (read or listened to) more than 150 books over the past 12-months, as we close the year, I wanted to share some of my favorites in case you are building your own reading list for 2024. I also ask that you share any particularly great reads you came across as I am currently in the process of building out my own!
So, without further ado:
Bold Beginnings
Two books published by friends of mine are a great way to start the list, and to start your year. Begin Boldly: How Women Can Reimagine Risk, Embrace Uncertainty & Launch a Brilliant Career by Christie Hunter Arscott and The Bold Ones: Innovate and Disrupt to Become Truly Indispensable by Shawn Kanungo are the perfect pairing. Whether you are just starting your career or are looking to kick it up a notch in your already established career, both are filled with insightful and practical advice as well as inspirational stories of the recommended practices being used IRL.
Making a House(l) a Home
I was no doubt late to Morgan Housel’s The Psychology of Money: Timeless Lessons on Wealth, Greed, and Happiness having only recently read it, but it was so good I had to immediately pick up his new book, Same as Ever: Timeless Lessons on Risk, Opportunity and Living a Good Life, as well. The first does a great job in helping distinguish “rational” versus “reasonable,” making the case for not setting your bar too high, and demonstrating that wealth is not what you spend, but rather what you save. The second is perhaps even more relevant today as questions (and fears) regarding the rise of AI and more come to the fore. Rather than focusing on what will be different, the book makes the case that the more important, and helpful question is instead what will stay the same.
Better Breathing
Another natural pairing, Breath: The New Science of a Lost Art by James Nestor and Jaws: The Story of a Hidden Epidemic by Sandra Kahn and Paul R. Erhlich had immediate and measurable positive impacts on my life. For something we do more than 20,000 times a day, we give surprisingly little thought to breathing, until, e.g., with COVID, we find it more difficult than usual. The books make a compelling case for how and why we are getting so much of this wrong and are filled with many free ways we can address this immediately. I have implemented several of the practices recommended in my own life, and my calendar now includes 2 separate daily reminders to stop and do 4-7-8 breathing.
TED Talks
Preparing for my own TEDx talk in May, I of course had to revisit the phenomenal TED Talks: The official TED guide to public speaking: Tips and tricks for giving unforgettable speeches and presentations by the Head of TED, Chris Anderson (for the third time!). As is evidenced by the fact I read this book twice before this year, it is relevant for anyone, not just a TED speaker. The lessons in storytelling, presenting, and communicating more broadly will make you better and more effective regardless of your role or objective.
It's Sophie’s World, We Just Live in It
I am not sure what it says about me that a children’s introduction to philosophy book is one of my favorites of the year, but there you have it. Philosophy literally means “the love of wisdom,” but when written by philosophers, for me at least it can be intimidating, confusing, and oftentimes inaccessible. Sophie's World by Jostein Gaarder is the exact opposite. It makes philosophy and the history of philosophy accessible, entertaining, and thought provoking, and teaches you quite a bit in the process.
A Man for All Times
My fascination with Paul Newman stemmed not from his acting, but rather from reading In Pursuit of the Common Good: Twenty-Five Years of Improving the World, One Bottle of Salad Dressing at a Time by Neman and his friend and business partner, A.E. Hotchner, a few years ago on the recommendation of Tim Ferriss. Thus, when his memoir came out (The Extraordinary Life of an Ordinary Man: A Memoir), I had to pick it up immediately, and boy am I glad I did. If you only know of Paul Newman through his acting, or through his salad dressings, or through his philanthropy, or through his car racing, or through his…you get the picture, then you are missing out. What a man. What a life.
Getting Back to Our Roots
How is it that it took me until my forties to read Roots by Alex Haley?! I read his The Autobiography of Malcolm X: As Told to Alex Haley in college, so clearly knew he could write. I also knew the PBS show Roots was a cultural phenomenon, though I still have never watched it. And yet, it took me until this year to pick up Roots the book. My conclusion? The best time for any of us to read it was we were in school learning history. The second-best time? Right now! Why is this not part of the standard school curriculum?
Shine a Little Light on Me
I have said it before and will continue to say that one of the most under-appreciated gifts of the Obama Presidency was that it brought Michelle Obama into our lives. The former First Lady’s The Light We Carry: Overcoming in Uncertain Times is a beautifully written book that will leave you with all the feels.
Look at Me
Jennifer Egan is probably best known for her novel, A Visit from the Goon Squad. As good as that book and its sequel are, reading her even earlier written work, Look at Me, this year I was left wondering: “Is THIS the great American Novel of the 21st century thus far?” Written in 2001, Egan’s prescience on what our future holds is astonishing when read in hindsight. Any of her books are worth picking up, but this is my favorite.
Musings
Are you looking to read a great book? The Tenth Muse by Catherine Chung is just that. Need I say more?
The Navalmanack
Anyone who can get Tim Ferriss to write an introduction is onto something. The Alamanack of Naval Ravikant by Eric Jorgenson is the closest thing I have found to a modern Tao Te Ching. This book is available for free but I bought a hard copy immediately after finishing and plan to revisit it frequently, like I do the Tao Te Ching and Marcus Aurelius’s Mediations.
Keeping the Covenant
Abraham Verghese’s writing is simply beautiful. The way he crafts and tells a story leaves me in awe. I also have a fascination with India going back decades. It is truly a world within a single country, and a lifetime of reading about it, learning about it, and traveling and living around and within it would not be enough to fully understand it. Bringing Verghese’s writing virtuosity together with an epic multi-generational novel set in India is basically the Venn diagram of all of my favorite things. The Covenant of Water was always going to be on this list.
Healthspan > Lifespan
We often get two major things wrong when it comes to health. The first is that we equate health with an absence of disease. That is missing the point. The second is that much of health is focused on longevity/lifespan, i.e., extending the number of years we live, rather than the far more applicable and inspiring Healthspan, i.e., extending the number of HEALTHY years we experience. As perhaps the most well-known proponent of a Healthspan-focused approach, Dr. Peter Attia’s Outlive: The Science and Art of Longevity could not come at a better time, even if it could have done with a better subtitle :). Attia’s final chapter on mental health brings much needed breadth to the subject of what health is and requires, and poses a question too rarely asked: why do want to live longer if you are not living a life you love?
The World in a Book
Simon Sebag Montefiore’s rollicking The World: A Family History strikes me as obvious required reading for life at any age, and wherever in the world you find yourself. Spanning the globe, and human existence, Montefiore makes our common story one well worth reading. It is an amazing story, so well told, so thorough, so expansive, and is an astonishing accomplishment.
Sovereignty
Am I allowed to put The Sovereign Individual: Mastering the Transition to the Information Age by James Dale Davidson and Lord William Rees-Mogg on my list? Perhaps Lord Rees-Mogg’s son’s politics will turn off some, while Peter Thiel’s new preface will prove anathema to others. And yet, like Ray Dalio’s Principles for Dealing with the Changing World Order: Why Nations Succeed or Fail last year, this book made me see the world in an entirely new light, question many things I took for granted as true, and months later I am still not sure what to think (or do!). Anyone who reads this and wants to talk about it with someone, please give me a call!
Dinner Reading
Mother for Dinner by Shalom Auslander is by far the most bizarre, hilarious, and original book I read this year. I have never come across anything quite like it, and I mean that in a good way.
Anne with an “E”
I originally came across Anne of Green Gables by Lucy Maud Montgomery when I was in Mrs. Rainy’s third grade class at Shades Cahaba Elementary School in Homewood, AL. After lunch, she would read the book to our entire class. When Talulla received this book as a birthday present, it took the place of our Wizard of Oz series (since we have now read all of the 14 books in the series written by L. Frank Baum), and it is even better than I remembered. Talulla laughed out loud several times, loves Anne (with an E!), and as soon as we finished the first, we headed to the bookstore to pick of Anne of Avonlea. Whether we will also make it to the end of this series is still to be seen, but we are enjoying it thus far.
Not so Hidden Potential
It is hard to think that "the man who does everything," as Tim Ferriss described him, could have had a time when his potential was hidden, but in what is perhaps his best book yet, in Hidden Potential Adam Grant shares incredibly personal stories of overcoming his own doubts and circumstances throughout his life to get to where he is. Like with his other books, he also includes lots of evidence to back up his assertions, compelling and original stories from all over the world, and actionable insights on how we can all be better at unlocking that potential hidden within each of us.
Christmas Bonus
While in London over the summer I ducked into a bookstore across from the British Museum and picked up a replica first edition of Charles Dickens' A Christmas Carol. I would have forgotten about it, but fortunately as we got close to the big day, Talulla reminded me. As many times as I have seen A Christmas Carol performed live or on television, I think this was my first time reading it myself, though with this classic, I doubt it will be my last.
As you can tell, the reading was as varied this year as in prior years. Hopefully there is something you find interesting or useful here.
Books are truly remarkable - they allow us to commune with some of history's greatest minds. The living and the deceased sit equally on our shelves, ready to impart hard-won wisdom. I very much look forward to continuing the centuries-long conversation in 2024 by learning from both contemporary thought leaders as well as enduring voices from the past.
In an age obsessed with novelty, repetition can feel… boring. We crave the new workout plan, the new diet hack, the new productivity method that promises overnight transformation. But here’s the quiet truth: real change rarely arrives in a flash. More often, it’s built in silence—through small actions repeated with intention, day after day, year after year. Discipline and ritual get a bad rap. Some see them as shackles—restrictions that box in our freedom. But the irony is, the right routines don’t limit you. They free you. And the science backs it up. The Science of Small, Consistent Steps Big, dramatic moves—like crash diets or jumping from zero exercise to two-hour workouts every day—make great headlines. But research shows they rarely stick. In his book Atomic Habits , James Clear distills decades of behavioral research into one simple idea: small habits, repeated consistently, compound into remarkable results. He writes, “Every action you take is a vote for the person you wish to become.” The votes don’t have to be huge—just steady. B.J. Fogg, a behavior scientist at Stanford, teaches the same through his Tiny Habits Method: lasting change starts with actions so small you can’t fail. When they’re easy, you repeat them. When you repeat them, they become identity. And in 2009, a study by Phillippa Lally published in the European Journal of Social Psychology found that, on average, it takes 66 days to make a behavior automatic. Not one heroic effort—66 days of small repetitions. So while bold transformations are tempting, they rarely last. It’s the quiet consistency that changes who you are. Rituals Shape Identity When you commit to small, repeated actions, you’re not just changing what you do—you’re changing how you see yourself. Think about your own rituals: your morning walk, your daily journaling, your regular workouts, your mindful bedtime wind-down. These aren’t random tasks. They’re anchors. Each repetition is a tiny reminder: I’m someone who cares for my body. I’m someone who makes time for stillness. I’m someone who keeps promises to myself. This is how repetition becomes transformation. Not by forcing you into a box—but by giving you an identity you trust. Discipline Is Freedom, Not a Cage Here’s the paradox: the more discipline you have, the more freedom you gain. Jocko Willink, a Navy SEAL turned author, says it best: “Discipline equals freedom.” It sounds harsh until you realize what he means—discipline frees you from chaos, distraction, and decision fatigue. A 2011 study in the Journal of Personality and Social Psychology found that people with strong self-control don’t constantly resist temptation—they avoid it by automating their choices. They build routines that run on autopilot. They spend less energy deciding, because the decision has already been made. When you repeat good actions by default, you free your mind to focus on what truly matters: your work, your relationships, your purpose. The 80/20 Principle of Rituals: Be Consistent, Not Perfect But here’s where people get stuck: they think discipline means perfection. It doesn’t. True discipline lives in the 80/20 rule: if you follow your rituals 80% to 90% of the time, you get nearly all the benefit and the freedom to loosen the reins for the other 10%–20%. Look at Tim Ferriss’s Slow Carb Diet: he famously built “cheat days” into the plan. Not as failures, but as part of the system. Or consider athletes: they schedule rest days because recovery is part of growth. If you train hard every single day, you break down. If you rest with intention, you build back stronger. Life will test your routines. You’ll travel. You’ll have family emergencies. You’ll celebrate holidays. You’ll hit seasons of burnout or unexpected surgeries (like I did recently). Not long ago, I had an operation that took me completely out of my normal groove—no swimming, no lifting, not even my daily stretching and mobility practice. It rattled me. Was I worried about losing momentum? Of course. But it also reminded me that discipline isn’t a prison. In that season, letting go of my routine was the discipline. Pushing would have set me back. Pausing was how I kept faith with the bigger goal: long-term health. So here’s the truth: your rituals are powerful, but they’re not stone tablets. They’re tools. The goal isn’t perfect streaks forever—it’s meaningful consistency over time. Seasonality: Know When to Hold On, Know When to Let Go A wise routine respects the seasons of your life. Sometimes you tighten your grip. Sometimes you loosen it. Maybe work or family needs more from you for a while. Maybe you’re traveling, grieving, healing, or simply living. Rituals should adapt to serve your life, not the other way around. Discipline, at its best, isn’t rigidity—it’s discernment. The skill isn’t just in doing your rituals, but in knowing when to break them, when to return, and when to evolve. Repetition Is How We Become When you strip it all down, repetition is not redundant. It’s how we become. There is quiet power in doing the same meaningful things, well and often. In showing up for yourself not just once in a burst of motivation, but over and over again, when nobody’s watching. That’s where depth lives. That’s where the big changes hide. So embrace your routines. Love your discipline. Use them to shape your days—and, piece by piece, your identity. But remember: do it for the life you want. And never let your rituals become the walls that keep you from living it.
There’s a certain beauty in the quiet things we do each day. The 6 a.m. walk before emails begin. The decision to skip the drive-thru and make something fresh. A moment of stillness before bed. They don’t feel groundbreaking. But they echo—sometimes for decades. We often think of longevity as a gift granted to a lucky few—people with “good genes.” But what if living longer—and better—wasn’t about chance, but about the ripple effect of today’s smallest choices? Superagers: Proof That It’s Not Just in Your DNA In the book Superagers, the research is clear: it’s not just genetics that determine who thrives in their 80s and 90s. In fact, only about 20–30% of our lifespan is determined by genes. The rest? It’s lifestyle, mindset, and the way we show up each day. These “superagers” aren’t elite athletes or lottery winners of the genome. They’re people who make movement a daily habit. Who engage socially and stay mentally curious. Who work their bodies and brains consistently—not perfectly, but persistently. What these studies revealed is powerful: the way we live shapes the way we age. And the best part? It’s never too late to start. The Healthcare Echo: What Our Choices Cost Let’s talk numbers. In the U.S., nearly 1 in every 5 dollars in our economy is spent on healthcare. That’s about $4.5 trillion annually. Of that staggering total, 90% goes to chronic and mental health conditions —many of which are preventable and often reversible through lifestyle changes. Yes, reversible. Conditions like type 2 diabetes, hypertension, heart disease, and certain autoimmune disorders have all shown dramatic improvement—or even full remission—through sustained changes in nutrition, movement, sleep, and stress management. That means the ripple of our collective habits isn’t just biological—it’s financial. Our daily choices, multiplied across millions, shape not just our bodies but our budgets and society at large. This is not about blame. It’s about opportunity. Today’s Choices Echo Forward I like to think of every habit as a pebble tossed into a still lake. The effect might seem small now. But over time, those ripples stretch out wider than we ever imagined. A 20-minute walk each day might not feel heroic. But stack that over 30 years? You’re looking at thousands of hours of cardiovascular health, better mood, stronger joints, and more resilient longevity. Cooking a simple, whole-food dinner might not feel Instagram-worthy. But do it consistently and you’re changing your gut health, metabolism, energy, even your cognitive function. Sleep, stress management, strength training, hydration, laughter, friendships—these aren’t just “nice to haves.” They’re foundational. They are the long-game investments that compound over time in the most valuable asset we’ll ever own: ourselves. The Superager Blueprint So what do the superagers actually do differently? Here’s what the research—and real life—shows: They move daily. It’s not about marathons. It’s about movement: walking, dancing, lifting, stretching. They stay mentally engaged. They learn languages, play music, read, challenge their thinking. They connect. Loneliness is as dangerous as smoking. Superagers cultivate deep relationships. They have purpose. They wake up with a “why,” whether it’s family, service, or curiosity. They don’t retire from life. Many keep working or volunteering well into their 80s and 90s. These habits don’t just keep people alive. They keep them vibrant. Capable. Present. A Mindset Shift: From Fixing to Building Too often we treat health reactively—waiting until something breaks before we fix it. But longevity requires a builder’s mindset. The superagers didn’t stumble into strength. They laid the bricks one habit at a time. And that’s the invitation. To stop seeing habits as chores, and start seeing them as blueprints. As personal architecture. As investments in the person we’re becoming. Your habits today are the foundation your future self will stand on. What Will Your Echo Sound Like? Pause and reflect: What’s one habit I’m practicing today that my 80-year-old self will thank me for? What belief am I holding that says “it’s too late” or “too hard” to change? How can I make my long-term well-being part of my daily rhythm, not just a New Year’s resolution? This isn’t about perfection. It’s about consistency. It’s about choosing, again and again, to honor the future you. Because the echo is already forming. Your Future Self Is Listening In 10, 20, or 40 years, you will become the result of what you practiced—not occasionally, but regularly. You’ll carry the benefits of sleep routines, strength training, a joyful plate, and purpose-filled days. Or you’ll feel the burden of their absence. The good news? That future is not fixed. You shape it today—with every step, every bite, every breath. So take the walk. Choose the greens. Call the friend. Learn the thing. Small ripples. Big echoes.
If you ever want to see how quickly a good thing can become a distraction, look at health in 2025. We have trackers on our wrists, apps on our phones, micro-optimized meal plans, sleep scores, HRV dashboards, supplements for every hour of the day — and more podcasts than we can listen to about “what to try next.” On two recent episodes of the Home of Healthspan podcast, I sat down with Michael Chernow of Kreatures of Habit and Ben Azadi. Both of these guys live and breathe health — the fasting windows, the cold plunges, the stacks of supplements. It was inspiring, but what struck me most was a simple, deeper question we circled back to every time: WHY? Why are we doing all of this? Because at some point, you have to ask: is all this optimization helping us live better — or is it just another thing to track, measure, and stress over? When “Better” Becomes Another Box to Check It’s an easy trap to fall into. I’m guilty of it too. A new supplement promising better sleep? Add it to the stack. A new protocol for muscle recovery? Let’s go. A new tracker? Strap it on. But somewhere along the line, “health” can start to feel like work — another project to manage. Another layer of “productivity.” The irony? All this busyness might just be pulling us away from the point of it all: actually feeling good and living our lives. A recent Vox article called out a perfect example: sleep trackers and “sleep anxiety.” More people are waking up groggy, not because they slept poorly, but because their wearable said they did. They check their score first thing in the morning — and if it’s bad, they spend the day feeling worse. The data becomes the experience. That’s not rest. That’s a report card. Tools Are Not Good or Bad — They’re Tools I’m not anti-tech. Wearables are neutral. So are supplements, apps, fancy beds, or ice baths. They’re not “good” or “bad” — they just are. They’re like smartphones or AI: in the right hands, they’re powerful. Used mindlessly, they can drain us. The same goes for anything in life. Even water — our most basic need — can be deadly in excess. These tools only work if we remember they’re just that: tools. They’re meant to serve us, not the other way around. The Productivity Trap — Health Edition Greg McKeown’s Essentialism changed how I think about this. In work, there’s always more you could do — more meetings, more emails, more Slack messages. But just because you’re busy doesn’t mean you’re moving the needle. The same is true in wellness. There’s always another thing you could add: ✔️ Another supplement ✔️ Another cold plunge ✔️ Another new training protocol ✔️ Another fasting tweak But does it serve you? Does it get you closer to what you really want? Sometimes, the time you’d spend on another biohack would be better spent on the basics: getting to bed earlier. Taking a nap instead of forcing a workout. Or — and here’s the radical part — skipping the gym for an unhurried dinner with the people you love. What Actually Matters Health metrics are not health itself. They’re proxies — signposts. They can help us see if we’re moving in the right direction, but they’re not the destination. No one lies on their deathbed wishing their sleep score had been a little higher, or their macros a little tighter. They remember moments. Laughter. A sunrise walk. Sharing a meal they didn’t obsessively log. It’s easy to forget: the reason we chase health is so we can live. Not just longer, but better. Essentialism for Your Wellbeing So what if we applied McKeown’s Essentialism to our health? ✅ Sleep well — consistently — instead of chasing hacks on no sleep. ✅ Train hard — but know when to rest. ✅ Eat nourishing food — but share meals without guilt when you want to. ✅ Track your data — but don’t let it dictate your day. More is not always better. Sometimes, more is just… more. My Own Reminder This lesson hit me recently. After a minor surgery, my routines went out the window: no swimming, no lifting, not even my daily stretches. For two weeks, my health “routine” was just resting — and yes, I hated it. I worried I’d lose momentum. But I realized: pushing would’ve made it worse. Sometimes the healthiest thing you can do is nothing at all. My wearables didn’t matter. My metrics didn’t matter. What mattered was letting my body heal so I could get back to living the life I want — not just checking boxes for the sake of checking them. Use the Tools — But Live the Life Health tracking, new gadgets, wearables — they’re amazing when they remind us to take care of ourselves. They’re dangerous when they convince us to live for the numbers. So here’s my gentle nudge — and the reminder I’m giving myself too: The data is helpful. The hacks can be powerful. But they’re never the point. The point is energy. Capability. Freedom. Presence. Joy. Connection. The point is living. A Simple Question If you ever feel caught in the swirl of health optimization, pause and ask: Is this serving me, or am I serving it? Don’t trade real life for perfect metrics. Use the tools to build the life you want — then go live it, fully.
There’s something fascinating about watching my parents interact with their grandkids. At 70+, they’re on the floor playing, running after them in the yard, or lacing up for a 10K like it’s just another Saturday. They golf almost daily, do the Peachtree Road Race every 4th of July, and still somehow seem more agile than folks 20 years younger. This isn’t the picture many of us were taught aging should look like—but maybe that’s the point. For so long, we’ve accepted a particular script about what it means to grow older. One where energy wanes, strength diminishes, and our best days are behind us. But what if aging isn't just a biological timeline, but also a psychological story—a narrative we’ve been taught to believe? Ellen Langer’s “Reverse Aging” Experiment Psychologist Ellen Langer once ran an experiment that feels almost like a scene from science fiction. In 1979, she invited a group of elderly men to live in a retreat designed to replicate life in 1959. Everything—from the music and newspapers to the television shows and decor—was a time capsule from two decades earlier. The twist? The men were told to act as if it actually was 1959. And something remarkable happened. After just one week, the participants showed measurable improvements in strength, posture, flexibility, even hearing and vision. They walked with greater confidence. One group photo taken at the end of the study was so compelling, a new observer guessed the men were younger after the retreat than they appeared in photos before it. Langer’s conclusion? Our minds deeply influence our physical state. When we stop acting old, we stop feeling old—and our bodies often follow. A Tale of Two Generations I’ve seen this truth play out in my own family. My grandparents and great-grandparents lived into their 90s and even to 100, which is incredible longevity. But their final decades were marked by fragility and immobility. They mostly stayed seated. Lifting grandkids was out of the question. The mindset was: “This is just what happens when you get old.” My parents, on the other hand, never subscribed to that story. They’ve rewritten the narrative for what 70 looks like—and what it can feel like. They never question whether they should run, golf, or play tag. They just do. The difference? Yes, some of it is due to physical habits—but much of it is belief. They never bought into the cultural story that says aging = decline. Instead, they wrote their own. The Myth of the Slowing Metabolism Here’s another story we’ve all heard: metabolism slows as you age. It’s framed as inevitable—as if, somewhere around 40, your body decides to run a little slower just because. But here’s the thing: science says otherwise. A groundbreaking international study that tracked over 6,500 people across a wide age range found that our metabolism remains remarkably steady from our 20s all the way into our 60s. The culprit for that creeping sluggishness? Not age—but muscle loss. As we get older, if we become less active, we lose lean mass—and it’s that lean mass that keeps our metabolism humming. In other words, your metabolism doesn’t slow down because the calendar says so. It slows down because you stop moving, stop lifting, stop challenging your muscles. And here’s the kicker: if you don’t stop—if you do the work to maintain muscle—you can preserve your metabolic engine well into later life. So next time someone chalks up weight gain or fatigue to “just getting older,” know that it’s not destiny. It’s a choice, rooted in a story that no longer holds up to scrutiny. Changing the Script The stories we inherit—from doctors, media, even our own families—shape how we live. And when those stories are built around limitation and inevitability, they can quietly become self-fulfilling. If we expect to slow down, we will. If we assume we’re too old to try something new, we won’t. But the opposite is also true. When you believe you can thrive at any age—when you treat your 60s, 70s, and 80s as full of potential rather than decline—you start to act in ways that reinforce that belief. You say yes to movement. You stay curious. You reach for weights instead of excuses. The Five Pillars—and One More Yes, we need to invest in the fundamentals of health: Fitness —move your body, build strength Nutrition —fuel wisely, eat for longevity Sleep & Recovery —honor rest Stress Management —stay grounded Social Connection —stay engaged with others But there’s a sixth, often overlooked pillar: the story you tell yourself about your age. Because even with perfect habits, if you believe you’re “too old” to matter, too old to grow, or too old to feel good—you’re putting a ceiling on your own potential. Final Thoughts: The Power to Choose Your Narrative We don’t control everything about aging. But we do control the mindset we bring to it. And mindset, as research and real-life have shown, is not a passive lens—it’s an active force. You get to choose the story. You get to decide whether “70” means winding down or gearing up for new adventures. You get to believe, as Langer’s work suggests, that we are far more capable than the age on our driver’s license would have us think. So if you care about your health, absolutely commit to the five pillars. But don’t forget the most powerful tool you have: your story. Because how we age starts, quite simply, with how we think we can.
I didn’t go to law school to become an entrepreneur. In fact, for most of my time there, I was laser-focused on the next obvious step: clerkships, law firms, maybe eventually a path into public service. But life has a funny way of unfolding—not by sticking to a carefully laid plan, but by veering into the unexpected. For me, it was a negotiation workshop during my second year that planted the seed. One of my professors shared an offhand anecdote that struck a chord, though I couldn’t have told you why at the time. Several years later, I found myself at lunch with some of my parents’ friends while on vacation, and that anecdote bubbled back up. That conversation, entirely unplanned, became the foundation of my first company, VacationFutures. From there, one thing led to the next—not through a tidy strategic plan, but through a series of meandering, curiosity-fueled steps. VacationFutures led to Rented Capital. Learnings from that led to Rented.com. None of it was straight. None of it was predicted. But each step, fueled by genuine interest, created the momentum for something new. That’s the thing about greatness: it doesn’t arrive by request. It emerges when you’re following what feels worth chasing—even if the destination isn’t clear. The Trap of the Plan This might sound counterintuitive. After all, we live in a world that worships plans. We set goals, chart paths, optimize for outcomes. But as Joel Lehman and Kenneth Stanley argue in Why Greatness Cannot Be Planned , that mindset can actually limit us. When we focus too much on achieving a specific objective, we often restrict ourselves to what feels like the next logical, incremental step. But true greatness? It’s rarely logical—and almost never incremental. Take computers, for example. They didn’t evolve from some straight line starting at Charles Babbage. The vacuum tube, an essential part of early computing, wasn’t invented to help build computers. It came from a completely different field. You could never have charted a course from Babbage to the laptop you’re reading this on, not without walking through dozens of other disciplines and accidental discoveries. It’s the same with flight. The Wright brothers relied on internal combustion engines—another unrelated invention—to bring their vision to life. Innovation is often less like climbing a ladder and more like crossing a river by jumping from stone to stone. The path isn’t visible until you look back. Even Evolution Isn’t Straightforward Stephen Jay Gould, one of my former professors, had a term for this in evolutionary biology: punctuated equilibrium . Rather than slow, continuous change, species often evolve in bursts—long periods of stasis followed by dramatic, sudden leaps. It’s messy. It’s unpredictable. And it’s how nature works. So why would we think that human creativity, innovation, or personal growth would be any different? When Metrics Mislead Sometimes, what we believe is progress actually moves us further from our goals. Ben Azadi, in his new book Metabolic Freedom , tells the story of a client who wanted to lose weight. Every morning, this person dragged themselves out of bed at 5am to hit the gym, determined to burn off the pounds. But they were also deeply sleep-deprived. The scale wouldn’t budge. The fix? Sleep more. Work out less. As counterintuitive as it sounds, shifting that focus led to real weight loss. The problem wasn’t discipline—it was direction. The client wasn’t lazy. They were just following the wrong metric. And this isn’t just a health issue. It’s a human issue. We chase what’s measurable—money, hours worked, followers, output—because it’s easier to track. But not everything that counts can be counted. A Holistic View of Health—and Greatness At Alively , we believe health isn’t a single number or habit. It’s built across five interconnected pillars. You can’t neglect sleep to chase fitness. You can’t grind through stress and expect resilience to magically hold. The system works best when you care for all of it. Greatness is the same way. You don’t achieve it by hammering one narrow objective. You achieve it by cultivating an ecosystem of ideas, experiences, and interests—and then following the paths that genuinely light you up. Follow the Interesting In Why Greatness Cannot Be Planned , the authors emphasize the importance of pursuing the interesting. Not the strategic. Not the efficient. The interesting. That’s how I built my companies—not through carefully calculated business school frameworks, but by paying attention to what sparked my curiosity. That unplanned class anecdote. That conversation over lunch. A pattern I noticed in an existing business that begged to be explored. I didn’t know what I was building until I built it. I just knew it was worth exploring. Curiosity isn’t frivolous. It’s foundational. The Risk of Easy Metrics The danger is when we let ourselves get hypnotized by easy metrics. Revenue. Growth charts. Round numbers. These are tempting because they’re tangible. But they can pull us off course. The truth is, not everything meaningful can be captured in a KPI. Sometimes progress looks like slowing down. Sometimes innovation looks like stepping sideways. And sometimes, the best decision you’ll make will seem, in the moment, completely irrational. That’s how greatness works. It doesn’t follow your plan—it rewards your attention. Leave Room for the Unexpected If there’s one takeaway I’ve learned, it’s this: make space for what you didn’t expect. Don’t let your calendar or your metrics crowd out your curiosity. If something feels interesting—even if it makes no sense right now—give it room. Because you never know. That conversation at dinner? That class you almost skipped? That itch you can’t quite name? It might just be the start of something great.
It starts innocently enough. You’re scrolling. Maybe LinkedIn, maybe Instagram. You see someone you know—maybe even like—posting their latest win: a funding round, a feature in a magazine, a new job, a bestselling book. You’re happy for them. Kind of. But also, if you're honest, something shifts in you. A subtle tightening. A quick glance at your own progress. A question you didn’t mean to ask yourself: Am I doing enough? That’s the quiet tax of comparison. It doesn’t scream. It hums. And over time, if you’re not careful, it starts to drive the ship. The Comparison Economy We live in a world built to rank us—by followers, titles, income, likes, and status symbols. We’re praised for being seen. And even when we tell ourselves we’re not measuring, we often are. That external scoreboard? It rewards the visible. But rarely the meaningful. And if we let it, it quietly shifts our motivation from intrinsic to extrinsic—from being driven by what we love to being driven by how we’ll be perceived. Intrinsic vs. Extrinsic: The Science of Motivation Let’s get clear for a second. Extrinsic motivation is when you do something for a reward or recognition—money, status, a gold star. Intrinsic motivation is when you do it because it’s meaningful, enjoyable, or aligned with your values. Research consistently shows intrinsic motivation leads to greater creativity, learning, and resilience. According to Deci & Ryan’s Self-Determination Theory, people thrive when they’re driven by autonomy, mastery, and purpose—not pressure or performance reviews. Daniel Pink put it plainly in Drive: carrot-and-stick motivation might work for rote tasks, but when it comes to meaningful work, intrinsic wins—every time. When the List Doesn’t Change You I’ve experienced this truth firsthand. When Get Out of My Head hit #5 on the Wall Street Journal Best Seller list, it was surreal. A milestone, no doubt. The kind of thing you maybe dream about. The kind of thing you think might do something—for your life, your mood, your sense of self. And then the next day came. And you know what? I felt the same as the day before. My life didn’t change. The air didn’t smell different. My coffee didn’t taste better. What had changed me was the process. The conversations I had with the amazing people profiled in the book. The months of research and reflection that stretched my thinking. The discipline it took to sit down, day after day, and wrestle with the blank page. That was the gift. Not the list. Not the accolade. The work itself. The Real Cost of Comparison Comparison doesn’t just dull our joy—it clouds our decision-making. When we chase extrinsic rewards, we often: Make short-term moves that look good on paper but don’t align with our long-term values. Stifle creativity , because we’re scared of looking foolish. Stop listening , because our ego already has the answer. Lose our voice , trying to sound like someone who’s already “winning.” And here’s the punchline: chasing external validation often undermines the very performance and fulfillment we’re after. Returning to What’s Real The best moments in my work—whether as a writer, founder, or just a human being—have come when I forgot there was an audience. When I wrote because something inside me needed to be said. When I built something because it mattered, not because it impressed. When I had a conversation with no agenda, just curiosity. These moments don’t get shared on social media. They don’t show up on leaderboards. But they’re the ones I remember. They’re the ones that shape me. How to Reclaim Intrinsic Motivation (and Your Joy) Want to step off the comparison treadmill? Here are a few practices that help me stay rooted: Ask yourself often: “Why am I doing this?” Be ruthlessly honest. If the answer is applause, dig deeper. Set identity-based goals. Not “I want to be a bestselling author,” but “I want to write with consistency and clarity.” Curate your inputs. If certain platforms or people trigger comparison, limit your exposure. Your peace is more valuable than their updates. Celebrate effort, not outcome. Keep a journal of what you’re proud of—especially when no one else sees it. Mentally subtract. Imagine losing the external reward. Would you still want to do the thing? If yes, that’s your compass. Talk to yourself like someone you respect. Would you judge a friend for not hitting a vanity metric? Didn’t think so. Final Thought: Let the Work Be the Reward There’s nothing wrong with goals. There’s nothing wrong with ambition. But when we let comparison or external validation steer the ship, we lose the very thing that makes the work meaningful in the first place. Let the work be the reward. Let the process be your teacher. Let your motivation come from the inside out. Because no list—no matter how high you climb—will ever give you what you can already give yourself: the joy of being fully, unapologetically engaged in your path.
“You McConnells just think you should be happy.” An ex once said that to me, and she didn’t mean it as a compliment. She said it with a bit of an eye roll, like the notion itself was naive—maybe even arrogant. And yet, I remember hearing it and thinking: Exactly . Yes. We do. We should be happy. She meant it as a criticism. I took it as confirmation that I’d inherited something truly valuable. I think back to a Christmas vacation years ago, sitting with my dad. He was a physician—brilliant, compassionate, steady. That day, he told me something with his usual clarity: “I won’t have a business to pass down to you. You’ll have to make your own way.” There was no trust fund waiting. No ready-made company to take over. No inheritance in the traditional sense. But that conversation wasn’t about lack—it was about abundance of a different kind. Because while I may not have had a financial inheritance to rely on, I got something better: a framework for living. A mindset. A calling. My dad loved his work. As a pediatric cardiologist, he saved lives and brought calm to chaos. But more than that, he loved what he did. And he made sure I knew it. “If you love what you’re doing, you’ll never work a day in your life,” he told me—repeatedly. And he meant it. My mom offered a different but equally powerful refrain: “This is no dress rehearsal.” In other words, this life? It's the only one we get. There’s no dry run, no do-over. So live it. Fully. Deliberately. With joy. This was the inheritance I received. And it has shaped every major decision I’ve made. When I finished law school and felt the gravitational pull of a legal career I didn’t want, I remembered: This is no dress rehearsal. And I pivoted, choosing McKinsey instead. When I left the safety of a corporate job to start my first company, I was told I was taking a risk. But it didn’t feel risky—it felt aligned. It felt right. And when I carved out time, in the midst of building that company, to write a book that was waiting inside me, it was because I couldn’t not do it. That’s what happens when your inheritance is a belief that you should be doing work that fills you up, not grinds you down. People talk about “the grind” like it’s a badge of honor. I’ve never understood that. Life isn’t meant to be an endurance test. It’s meant to be experienced. Fully. Joyfully. Honestly. And this doesn’t just apply to work. People sometimes comment on my fitness routine as if it’s some kind of hardship. “You must be so disciplined,” they’ll say, as if what I’m doing is punishment. But the truth is, I love it. I love being in the gym. I love swimming. I love being in the ocean, feeling part of something vast and alive. Case in point: a recent trip to French Polynesia. If you looked at my WHOOP strain scores from that week, you’d think I was training for an Ironman. But I wasn’t. I was in heaven—swimming with sea turtles, gliding alongside manta rays and stingrays, watching an octopus change colors right before my eyes. It wasn’t “exercise.” It was joy. It was wonder. It was play. That’s the thing—when people say they hate exercise, I want to ask: What do you mean by that? Do you hate running? Weightlifting? Fine—don’t do those! But that doesn’t mean you hate movement. Maybe you’d love yoga, or paddle boarding, or dancing in your kitchen. Saying you don’t like fitness is like saying you don’t like food because you hate licorice. There are so many flavors. So many ways to move, to feel alive in your body. Why settle for drudgery? The same goes for how we spend our days. Whether it's work, relationships, hobbies, or how we show up for ourselves—what if we believed we should actually enjoy these things? What if we believed happiness wasn’t some frivolous byproduct, but an actual goal worth pursuing? That’s the inheritance I received. And my ex wasn’t wrong. I do believe I should be happy. I believe you should too. And maybe even more importantly, I believe we get to define what “success” and “legacy” mean for ourselves. My parents gave me no business to run, no stock portfolio to manage. But they gave me something far more enduring. They gave me permission to pursue what lights me up. They modeled how to be present in your life, how to take joy in your work, and how to treat each day as a precious, non-renewable resource. That’s the right kind of inheritance. And now, as I think about what I hope to leave behind—not just for my family, but for anyone I impact—it’s this: a belief that your life is yours to shape. That you don’t have to grind your way through. That joy is not optional. It’s essential. So maybe ask yourself: What did you inherit? What beliefs about work, life, worthiness, and happiness did you absorb? And more importantly: What do you want to pass on? Because the most powerful legacy you can offer isn’t found in a will or a bank account. It’s in how you live, and what you model every single day. Choose joy. Choose meaning. Choose presence. That’s the inheritance that lasts.
Let’s talk about a weird contradiction we live with every day—one we rarely notice, even though it shapes our lives and our health outcomes in quiet but powerful ways. In most Western countries, the people—you and me—are the ones who get the personal benefits of good health. More energy, longer life, better sleep, clearer focus, fewer pills, and more joyful moments. But the economic costs of poor health? They usually land somewhere else: on employers, insurance companies, and governments. That’s the paradox. We live the benefits, but they pay the price. This disconnect matters, because it shapes how our systems are designed—and how we, as individuals, are nudged, pushed, and sometimes dragged toward better health. The trouble is: motivation that starts outside of us rarely goes the distance. So how do we fix this? How do we bridge the gap between outside incentives and inside drive—and maybe even get the best of both worlds? Let’s unpack it. Who Actually Pays? Poor health isn’t just a personal inconvenience—it’s incredibly expensive. Employers shell out billions each year in lost productivity, absenteeism, and higher insurance premiums. Governments foot the bill for preventable chronic diseases through Medicaid, Medicare, and public health programs. Insurance companies carry the costs of claims that could often be avoided through lifestyle changes. Ironically, individuals don’t always feel the immediate hit in their wallets. We feel it in fatigue, or mood, or a prescription refill—but not always in dollars. That makes it easy to delay action. The cost is long-term. The comfort of the couch? Immediate. And so we get wellness incentives: gym reimbursements, step challenges, even lower premiums for certain health behaviors. These can help—but they often don’t stick. Why? Because they’re built around someone else’s bottom line. Motivation That Works (and What Doesn’t) Research makes it clear: intrinsic motivation is the game-changer. Studies like those based on Self-Determination Theory by psychologists Edward Deci and Richard Ryan show that sustainable behavior change comes from autonomy, personal relevance, and a sense of competence. Translation? We stick with what feels meaningful, self-directed, and achievable. So while financial perks or pressure might kickstart a new habit, it’s internal motivation—what we want for ourselves—that keeps it going. Health Investment That Makes "Dollars and Sense" Here’s where things get interesting. Even though the benefits of better health show up on our skin, our sleep, our steps, the economic incentive to invest in that health often lives somewhere else. Employers save money when workers are well. Governments ease budget strain with healthier populations. So yes—it makes dollars and sense for them to invest in programs that help people eat better, move more, and stress less. But the key? Don’t stop at the spreadsheet. Programs that work best meet individuals where they are—not as line items, but as humans. Make the Individual the Hero Let’s flip the script. If we want people to care—and truly choose better health—we can’t just say “do it for the company” or “to reduce national healthcare costs.” That’s not a story anyone wants to live out. What works is this story: What does a healthier version of your life look like? Maybe it’s being able to lift your grandkid without back pain. Maybe it’s running a 5K or sleeping through the night without melatonin. It might be finally feeling good in your own skin, not for anyone else—but for you. The story of a better life is far more compelling than any third-party incentive. And that story needs to feel accessible now—not 30 years from now. That’s where design matters. Make It Real. Make It Visible. Make It Possible. We live in the golden age of wearable tech and health tracking. You don’t need to guess if something’s working—you can see it, sometimes in real time. Steps taken, heart rate lowered, hours slept, stress reduced. These tiny wins add up, and seeing them makes a huge difference in motivation. You feel momentum. You see proof. You can adjust when something isn’t working. Wearables, apps, and data dashboards aren’t just gadgets—they’re modern tools for building intrinsic motivation. They turn vague goals into visible, trackable change. Next Steps: Collective Responsibility, Personal Empowerment So how do we move forward? For organizations and governments: Keep investing. But invest smarter. Choose strategies that empower autonomy, not just compliance. Prioritize accessibility—healthy food shouldn’t cost more than fast food. Mental health care shouldn’t require a scavenger hunt. For individuals: Stop waiting for the perfect system. Start where you are. Anchor your choices in what you want—joy, energy, strength, peace—not just what others tell you is “good for you.” Use tools. Track progress. Celebrate tiny wins. Conclusion: It’s Your Life—and That’s the Point Yes, employers, insurers, and governments have skin in the game. And yes, they should continue to invest in helping people get and stay healthy. But at the end of the day, you’re the one living in your body. You’re the one who gets to feel the difference. You’re the one who wakes up with more energy—or not. That’s the real reward. And that’s why, even if you’re not the one paying the bill—you’re still the one who gets to choose the benefit. Your health. Your story. Your move.
I tend to think of my life in two distinct periods: the first, when I didn’t know anything. And the second, when I realized I didn’t know anything. That shift—from unknowing to knowing I didn’t know—changed everything for me. Not overnight, but over time. It transformed how I approach learning, how I run a business, how I have conversations, and how I show up in the world. In that first period, I was full of confidence in my beliefs. Whether it was politics, philosophy, spirituality, or whatever big idea was on the table—I had an opinion, and I held it tightly. If you disagreed, well, then it was time to debate. And I didn’t enter debates to exchange ideas. I entered them to win. That need to be right? It didn’t come from malice. It came from a place I thought was noble: conviction. Passion. Purpose. But the older I got, the more I started to realize that certainty, especially in excess, is a form of blindness. When the Cracks Started to Show Somewhere in my late twenties, things started to shift. I couldn’t help but notice how often I was wrong. How frequently new information came in that challenged the views I’d held tightly. I’d read something, hear a new perspective, or live through a situation that forced me to re-evaluate what I thought I knew. And each time I changed my mind, I didn’t shrink. I grew. The more I embraced that, the more liberating it became. I stopped needing to win arguments. I stopped needing to plant a flag on every topic. And I started getting curious. Not curious in a performative way, but deeply, sincerely curious about what I didn’t yet understand. That was the beginning of the second period of my life: the one where I realized just how much I don’t know—and how powerful that realization really is. A Lesson from the Startup Trenches That mindset got put to the test when I built my first company. If there’s ever a crash course in letting go of ego, it’s entrepreneurship. You go into a startup with ideas—strong ones. Beliefs about what customers want, how the product should look, what pricing should be, how to market. But the market doesn’t care how right you think you are. It only cares about what actually works. That’s when I discovered a powerful mental framework: strong convictions, loosely held . It means believing passionately, but not rigidly. Testing boldly, but adapting quickly. Holding your ideas like clay, not concrete. This mindset saved me—more than once. It helped me pivot when a product wasn’t working, listen more closely to customers, and evolve faster than I ever could have if I’d stayed locked into “being right.” The Joy of Not Knowing Something else happened, too. As I became more curious and less certain, I started having better conversations. Instead of listening just to find an opening for my rebuttal, I started listening to understand. Instead of needing to prove a point, I asked more questions. And guess what? I learned more. Not just facts, but about people. About where they come from. What they’ve lived through. Why they believe what they believe. And I think—I hope—I became more enjoyable to be around. Because let’s be honest: nobody likes talking to someone who always needs to be right. It’s exhausting. But talking to someone who’s open, who’s learning in real-time, who’s curious? That’s energizing. Curiosity makes you lighter. Certainty is heavy. Why This Mindset Matters (Now More Than Ever) We live in an age where certainty has become a kind of performance art. Social media rewards the boldest take, the strongest stance, the snappiest takedown. Nuance? Not so much. But here’s what I’ve found: choosing curiosity over certainty has made me not only happier, but more effective. In business. In relationships. In life. Here’s why: You learn faster. When you’re not defending old ideas, you’re open to better ones. You connect more deeply. People feel safe with someone who’s listening, not judging. You become more creative. Certainty narrows options. Curiosity expands them. You find more peace. There’s no internal tension when you don’t need to be right all the time. As the Stoics would say, we suffer more in imagination than in reality. And much of that suffering comes from our belief that we’re supposed to know everything. That’s a trap. And it's one you can step out of at any time. Practicing Curiosity Daily So how do you start? Here are a few things that help me: Adopt the mantra: “I could be wrong.” Say it often. It softens your grip on certainty. Ask more questions than you make statements. Especially when someone disagrees with you. Listen to understand, not to reply. Don’t tie your identity to your ideas. You’re allowed to evolve. Consume content that challenges you. Not to argue with it, but to learn from it. Celebrate mind-changing moments. They’re signs of growth, not weakness. The Freedom in Uncertainty At this point in my life, I don’t want to be the guy with all the answers. I want to be the guy who asks good questions. Who learns out loud. Who changes his mind in public and is better for it. Because the truth is: I don’t know. And neither do you. Not fully. Not forever. That’s what makes life interesting. So if you’re stuck in a mindset of always needing to be right, try loosening your grip. You might just find, like I did, that there’s a whole world waiting on the other side of certainty—full of wonder, wisdom, and the quiet joy of not knowing.
When I started my first company, I thought freedom would follow. No boss, no office hours, no one telling me what to do. Just me, my laptop, and the wide-open promise of autonomy. Instead, I found myself working more than ever. The irony of our age is that we’ve made breathtaking progress—technological, medical, and otherwise—under the banner of freedom and ease. Yet many of us feel more trapped, more anxious, and more overwhelmed than ever before. The things designed to liberate us—the smartphone, the cloud, the work-from-anywhere ethos—have also shackled us to a perpetual mental treadmill. We can work from anywhere, which now means… we work everywhere. The Great Prediction That Got It Wrong Nearly a century ago, John Maynard Keynes predicted we’d all be working 15 hours a week by now. Automation, he said, would eliminate the need for toil. Machines would handle the dirty work, leaving us to explore leisure, art, and family. What happened? Well, we did make the machines. But instead of slowing down, we sped up. We started multitasking and “optimizing.” And instead of choosing peace, we chose productivity—over and over again. Because beneath the convenience and speed of modern progress lies something far older and deeper: craving. The Craving That Never Quits Buddhism and Taoism understood something that our data-driven culture still hasn’t fully grasped: craving is insatiable. The moment we hit one milestone—title, income, square footage—we see another gleaming just out of reach. So we push forward. And the more we achieve, the more convinced we become that just one more thing will bring peace. Spoiler alert: it won’t. This is the hedonic treadmill. You climb one peak of accomplishment only to see a higher one waiting. So you climb again. And again. Until you realize you’re not chasing success—you’re being chased by it. As the Tao Te Ching reminds us: “He who knows he has enough is rich.” And yet, how few of us ever pause to truly ask, “Do I already have enough?” Imagining Loss to Remember What We Have There’s a Stoic practice called premeditatio malorum —imagining the loss of the things you hold dear. It sounds morbid at first, I know. But bear with me. Imagine losing your eyesight. Or your partner. Or your health. Not as an exercise in anxiety, but in appreciation. When you truly see how fragile everything is, you also begin to see how precious it is. How enough it already is. We rarely do this in our progress-obsessed culture. We focus on what's next. But peace doesn’t live in what’s next. It lives in the gratitude for what is. Yes, Progress Is Amazing—But It’s Not the Point Don’t get me wrong. I love progress. I’m fascinated by what AI can do, by what science is curing, by what we’re building together as a species. Progress is a gift. But it’s a terrible master. If you tie your happiness to outcomes, you’ll always be at their mercy. Win the deal? Joy. Lose it? Misery. Get the promotion? Elation. Miss it? Defeat. This rollercoaster is exhausting. It’s also unnecessary. In Get Out of My Head , I talk about this exact trap. We give away our peace—not to bad things, but to good things. Success, ambition, growth. These aren’t enemies. They just make lousy landlords when we let them rent out our minds. Work for the Process, Not the Prize The ancient Stoics, Buddhists, and Taoists weren’t against progress. They were just clear-eyed about where happiness comes from. Not in the external world, but in how we relate to it. As I learned firsthand building my company, the moment I stopped obsessing over the outcome—and focused on how I was showing up each day—everything shifted. I found more clarity. More presence. Ironically, more success too. The key wasn’t more hustle. It was more equanimity. Progress should be pursued for the love of the process, not the thrill of the prize. And when the prize does come? Great. Celebrate it. Then let it go. Don’t let it define you. Because nothing outside of you can. What to Do With This So how do we escape the trap? Here are a few things that help me: Set boundaries. Just because you can work from bed doesn’t mean you should. Your mind needs places and times to rest. Practice negative visualization. Picture losing what you have—not to scare yourself, but to spark gratitude. Check your craving. Ask: “Am I chasing this because it brings me joy, or because I think it will finally make me enough?” Return to now. The only place you ever really own is this moment. The future is a dream. The past, a ghost. Owning Your Journey Progress will continue. It should. But let’s not confuse having more with being more. Let’s not mistake motion for meaning. You are not your job title. You are not your calendar. You are not your inbox. You are the thinker behind the thoughts. The being behind the doing. And when you can root yourself in that identity—not in your outcomes—you become unshakeable. So climb that next mountain. Build that next company. Write that next chapter. But do it because it brings you alive—not because you think it will finally make you whole. You already are.
