Alexander Hamilton, Winnie the Pooh, and the Wisdom of the Hermit Crab
Three books can change your Thursday. One book can change your world.
Hello,
Thank you to everyone who completed last week’s survey—your insights were incredibly helpful. And I hope you enjoyed my recommendation for The One Book I’d Gift to Every Graduate. Now, let’s jump into this week’s Three Book Thursday.
Growing up in Twin Rivers, New Jersey, I had a childhood friend named Dan Epstein. Our families were close, and our parents often helped each other out with childcare. I spent a lot of afternoons at Dan’s house, and there was something about being there that always felt exciting. His house was full of life. And by that, I mean animals. Not dogs or cats—those would’ve been too ordinary. Dan had tropical fish. A bird. A chameleon. And at one point, he had something I’d never seen before: a hermit crab.
I remember staring at that crab, completely mesmerized. There was something strange and captivating about it. A small, awkward creature living inside a borrowed shell. Always carrying its home on its back. I didn’t know much about them then, but something about that little crab stuck with me.
Years later—decades, actually—I found myself thinking about it again.
I was preparing to give a Grand Rounds talk at the University of Wisconsin–Madison, my alma mater and one of my favorite places on earth. The topic was learning and growth—how we learn best, how we evolve. And in the process of preparing, I fell down a research rabbit hole. I came across an article about hermit crabs, and it pulled me right back to that childhood memory. Except now, the metaphor hit me differently. This wasn’t just about biology. This was about life.
Hermit crabs are fascinating creatures. They’re not technically true crabs—they’re more closely related to lobsters. And unlike other crustaceans, their abdomens are soft and vulnerable. Exposed. Which means they need to live inside a shell. Not one they create—but one they find.
That’s already a metaphor in itself. But here’s where it gets better.
As hermit crabs grow, they must abandon their current shell and search for a new, larger one.
And here’s the part I can’t stop thinking about: Their protection becomes their prison if they don’t move on.
To grow, a hermit crab has to leave what once kept it safe. It has to step out—naked, unprotected, exposed to the elements and predators—while it searches for something new. Something that might not even be there yet. It risks everything for the chance to keep growing.
And if that’s not life, I don’t know what is.
There’s a moment in every meaningful transition where you have to step out of what’s comfortable. Where what once fit you perfectly—your job, your home, your routines, your identity—starts to feel tight. Starts to restrict instead of protect. Starts to hold you back instead of hold you up.
And so, if you want to grow, you have to risk exposure.
You have to let go of the shell that no longer fits.
Even if the next one hasn’t appeared yet.
That’s the part I keep returning to.
Sometimes we mistake that feeling—the discomfort, the tension, the questioning—as a step backward. Like we’re giving something up, leaving something good behind. But what if we’re not stepping back at all? What if we’re simply shedding a shell that no longer fits?
What if this is how growth feels in real time?
That’s what I love most about the hermit crab.
It doesn’t resist change—it moves with it. It knows that the risk of exposure is the price of growth. It doesn’t cling to the old shell out of fear. It listens. It feels the tightness. And when the time comes—it moves.
And maybe that’s the question we all need to ask from time to time: Is the shell I’m living in still protecting me—or is it starting to hold me back?
It’s not about chasing constant reinvention. It’s about being honest. About recognizing that safety and growth don’t always coexist.
About stepping out—even when it’s uncomfortable—because the cost of staying might be greater than the risk of going.
But here’s something I learned that made the metaphor even more powerful:
Hermit crabs never really stop growing.
Even decades into their lives, they keep searching for new shells. The process slows, sure—but it doesn’t end. There’s no final shell. No perfect fit that lasts forever. Just the next best one—for now.
Which means the moment of risk, the vulnerable in-between, isn’t a one-time thing.
It’s a lifelong rhythm.
So if you’re feeling like something doesn’t quite fit anymore—pay attention.
It might be time for a new shell.
Even if it hasn’t shown up yet.
Even if stepping out means being seen.
Because just like the hermit crab, the only way forward is through the vulnerability of change. And just like the hermit crab, there’s no final version of you.
Welcome to this week’s Three Book Thursday.
1. Biography
Alexander Hamilton
Summary
Hamilton has always been one of my favorite historical figures.
I still remember first learning about him in Russ Beaulieu’s high school history class. Even back then, something about him stood out. Not just the facts of his life, but the force of his presence. He was sharp. Restless. Relentlessly driven. He made things happen—often at great cost.
Years later, I picked up Ron Chernow’s Alexander Hamilton—a true tome, no doubt about it—when my kids were younger. Every night before they went to bed, we’d crawl into bed, books in hand. They’d read theirs. I’d read mine. One or two pages at a time. Given the length, I figured it would take me a year to finish. And it did. But I stuck with it. And I loved it.
This is a book that rewards patience. A portrait of what it looks like to live with velocity, purpose, contradiction, and fire.
Chernow captures Hamilton in full: orphaned, impoverished, self-made. He arrived in New York with no wealth, no family, no name—and within years was shaping the financial system, writing the Federalist Papers, serving as Washington’s right hand, and laying the foundations of modern America. His mind was as brilliant as it was combustible. He outwrote, outworked, and often outran those around him.
But the part of this book that stuck with me most wasn’t just his intellect. It was his urgency.
Hamilton lived like he knew he wouldn’t live long. He fought to shape policy, history, institutions—not just because he believed in them, but because he believed in doing. Even when it was messy. Even when it made enemies. Even when it burned him.
He was flawed. He was brilliant. He was human.
And finishing this book made seeing the Broadway show Hamilton that much richer. (I’ve now seen it three times—and a fourth is already on the calendar.) Because this isn’t just the story of a founding father. It’s the story of someone who refused to let his circumstances define him.
And if you’re someone trying to build something—your career, your business, your voice, your legacy—there’s so much here that will resonate.
Hamilton reminds us that you don’t need perfect conditions to make your mark. You need vision. You need urgency. You need to be willing to fight for ideas bigger than yourself.
And maybe most importantly: you need to write your story before someone else writes it for you.
Favorite Quote, Insight, & Principle
Quote: “A man stands tallest when he kneels before a vision larger than himself.”
Insight: He failed. He fell. He rose again with more fire, more urgency, more clarity.
Principle: The greatest ambition is not to gain power but to build something that lasts beyond you.
Author: Ron Chernow
Themes: Biography, History, Politics
2. Personal development
The Tao of Pooh
Summary
I first read The Tao of Pooh during my super senior year at the University of Wisconsin–Madison—a time when I was still trying to figure out who I was, what I believed, and how I wanted to show up in the world. I didn’t know it then, but this small, seemingly simple book would leave a lasting imprint.
It’s a quiet book. A gentle one. But don’t let that fool you.
Benjamin Hoff takes the beloved characters of A. A. Milne’s Winnie-the-Pooh and uses them to explain the fundamentals of Taoism—an ancient Chinese philosophy centered on simplicity, flow, humility, and balance. And the real magic is that he doesn’t just use them to explain it—he embodies it. Through the stories, conversations, and subtle wisdom of Pooh and his friends, Hoff delivers profound life lessons without ever preaching or overcomplicating.
In a world that often pushes us to go faster, work harder, chase more, and optimize everything, The Tao of Pooh offers something far more radical:
Stillness.
Presence.
Enoughness.
What struck me then—and stays with me now—is how much we overlook the value of doing less. Of trusting the process. Of not needing all the answers before we take the next step. Pooh doesn’t worry. He doesn’t chase. He simply is. He listens. He follows what feels right. He moves through the world with curiosity and quiet confidence—not because he has it all figured out, but because he’s not trying to force things that aren’t meant to be.
That’s what makes this book timeless. It’s not about giving up ambition. It’s about aligning it. About trading the constant striving for something steadier—clarity, peace, purpose.
And if you’re in a high-stakes profession, if you lead a business, a classroom, a team, or a family—this message matters. Because the pressure to do more, be more, fix more, is everywhere. And sometimes the greatest wisdom is in knowing when to not push. When to step back. When to trust that ease isn’t laziness—it’s wisdom in disguise.
The Tao of Pooh is simple. But it’s not simplistic.
It’s a reminder that life doesn’t have to be so hard. That clarity often comes when we stop forcing it. That who we are—at our core—is often already enough.
And sometimes, it takes a bear with very little brain to help us remember that.
Favorite Quote, Insight, & Principle
Quote: “Enjoy the little things, for one day you may look back and realize they were the big things.”
Insight: You can’t save time. You can only spend it wisely or waste it.
Principle: When you discard arrogance, complexity, and a few other things that get in the way, sooner or later you will discover that simple, childlike and mysterious secret to those of the uncarved block: life is fun.
Author: Benjamin Hoff
Themes: Philosophy, Personal development
3. Entrepreneurship
Escape From Cubicle Nation: From Corporate Prisoner to Thriving Entrepreneur
Summary
There are books that give you tips. Then there are books that give you permission.
Escape from Cubicle Nation is the latter.
Pamela Slim doesn’t just hand you a step-by-step manual on how to start your own business—she asks you to consider a deeper question: What would your life look like if you stopped waiting for permission to live it on your own terms?
For anyone who’s ever felt stuck in a job that looks good on paper but feels hollow in practice, this book meets you where you are. It’s honest about fear, thoughtful about risk, and relentless in its encouragement. Slim doesn’t glorify entrepreneurship. She just tells the truth: that staying in a safe, unfulfilling job can be far more dangerous to your long-term well-being than striking out on your own.
Reading it reminded me of so many conversations I’ve had—with colleagues in medicine who are quietly burning out, with entrepreneurs sitting on great ideas but paralyzed by doubt, with people who’ve built outwardly successful lives that feel disconnected from who they really are.
Slim gets it. She’s been there. And she walks with you, not ahead of you. She explores the mental models that keep us stuck—fear of failure, the illusion of job security, the weight of others’ expectations—and offers clarity, not hype. Her writing is grounded, wise, and full of stories that make you feel less alone.
What stood out to me most is this: freedom doesn’t come from leaving something—it comes from choosing something. And that act of choosing, of stepping out of a structure that no longer fits and into the unknown, is where transformation lives.
This book isn’t just about career change—it’s about reclaiming agency.
It’s about taking ownership of your time, your energy, and your purpose. It’s about understanding that entrepreneurship isn’t for everyone—but intentionality is.
If you’re at a crossroads—if the shell you’re living in feels too tight—this book offers more than advice. It offers perspective.
Because escaping the cubicle is never really about the walls around you.
It’s about the boundaries you’re willing to challenge within yourself.
Favorite Quote, Insight, & Principle
Quote: “Don’t wait for permission to live the life you want.”
Insight: Entrepreneurship is not a job, it’s a way of being.
Principle: When you align your work with your values, everything changes.
Author: Pamela Slim
Themes: Entrepreneurship
There’s a moment between shells—a space of discomfort, vulnerability, and uncertainty—that every hermit crab must pass through to grow.
This week’s books remind us that real growth doesn’t happen when everything is secure and predictable. It happens when we’re brave enough to step out of the roles, routines, and identities that no longer fit—and reach for something larger, even if we can’t fully see it yet.
Hamilton teaches us to live with urgency, to create before the clock runs out. Pooh reminds us that clarity and peace often come from not forcing things. And Pamela Slim shows us that freedom begins the moment we stop waiting for permission.
We can’t grow if we cling to what once served us.
We have to leave the shell behind—even if the next one hasn’t appeared.
Because in that exposed space between where we’ve been and where we’re going…
That’s where transformation begins.
Always ❤️📚💡
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Yes, it's a fun read!
Thanks, I’ve never read “The Tao of Poo”🤦♀️Always knew about it, but you’ve recommended at exactly right time for me!