The Most Radical Thing I’ve Done? Choosing Enough

Three books can change your Thursday. One book can change your world.

Hello,

This week marks the 100th anniversary of The Great Gatsby—a novel about ambition, reinvention, and the cost of chasing too much. It got me thinking about the idea of enough. Especially when it comes to money.

When I sold my business in 2021, the questions came quickly:

What’s next?

What’s the next company you’re building?

What are you going to do now?

Some of the offers were hard to ignore—lucrative, high-profile, full of possibility. But the truth is, I didn’t want to jump back in. Not because I was tired, but because—for once—I didn’t feel the need to keep climbing. I felt grounded. I was content. I had enough.

And that feeling? It came from a story I’d read years earlier. A conversation between Kurt Vonnegut and Joseph Heller that’s stayed with me ever since.

At a party hosted by a billionaire hedge fund manager, Vonnegut turns to Heller and says, “Our host made more money yesterday than you’ve made from Catch-22 over your whole life.”

Heller responds, “Yes, but I have something he’ll never have—enough.”

That one hit me. And when I sold my business, it became a compass.

Because I’ve seen what happens when people don’t have that compass. I’ve spoken to other entrepreneurs who were financially set—but within months of exiting, they were back in the grind. Not because they needed more—but because they couldn’t sit still. They didn’t know how to be content. They were still chasing, still measuring their worth by what came next.

Last week, I overheard my wife on a Zoom call with her inner circle—a group led by Dan John (whose work I can’t recommend enough). The topic of the day was enough. What is enough?

After her call, we talked.

And I shared something I’ve been sitting with for a long time—that when most people talk about enough, they talk in numbers. A target. A “freedom number.” A finish line that keeps moving. But one thing I’ve learned is this:

Enough isn’t a number. It’s a mindset.

Sure, we all need to meet our basic needs—safety, security, comfort, choice. But once those are covered (and perhaps a little more), enough stops being external. It becomes internal. It’s knowing what matters and tuning out the noise. It’s the discipline to stop sprinting toward “more” just because everyone else is. It’s the awareness to pause and say:

I’m already living a life that brings me joy.

I don’t need to chase what I already have.

This moment is enough.

It reminds me of the parable about the financier and the Mexican fisherman.

A Harvard MBA, who is on vacation, meets a local fisherman who catches just enough fish each day to support his family. The rest of his time? He spends napping, playing with his kids, taking siestas with his wife, and drinking wine with friends while strumming his guitar.

The MBA says, “You could scale this. Build a fleet. Sell to distributors. Launch an IPO.”

The fisherman asks, “And then what?”

“Well,” the MBA says, “then you’d retire. Move to a quiet village. Sleep late. Fish a little. Take siestas. Sip wine. Play guitar.”

We laugh at the absurdity. But how many of us are living that exact loop—trading away the life we already want in pursuit of the same life, just repackaged?

That story changed how I see everything.

Because enough isn’t small. It’s sacred.

It’s not about settling. It’s about choosing.

It’s about aligning your life with your values.

And enough doesn’t mean you stop growing, or learning, or creating. It just means you’re not trapped on the hedonic treadmill—the one that constantly moves the goalposts, dulls your joy, and whispers that the next milestone will finally make you whole.

Enough means you get to choose your pace.

You get to decide what matters.

You get to stop chasing what’s next—and start cherishing what’s now.

Welcome to this week’s Three Book Thursday.

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1. Fiction
The Great Gatsby

Buy this book

Summary
There’s a reason The Great Gatsby keeps showing up—on syllabi, in bookstores, in conversation—even a hundred years after it was written. It’s not just a book about wealth and parties and the jazz-soaked glamour of the 1920s. It’s a book about longing. About the distance between the life you dream of and the one you’re actually living. About the relentless, heartbreaking pursuit of something just out of reach.

Jay Gatsby is a man who builds an empire chasing the shimmer of a green light across the bay—the house, the clothes, the parties, all carefully constructed to win back a woman he once loved. But beneath that glittering surface is something far more universal: the aching desire to rewrite the past, to will a version of life into existence through effort, belief, and sheer force of hope.

And we’ve all been there, in some form.

Whether you’re a chasing your next idea, navigating the weight of expectation, or simply trying to find meaning in the middle of your success—it’s easy to mistake motion for purpose. Gatsby reminds us that not all hustle leads to fulfillment. That ambition without alignment can leave you hollow, no matter how good it looks from the outside.

What makes this book powerful isn’t just its critique of the American Dream—it’s the tenderness with which it handles that dream’s unraveling. It’s the quiet reflection from Nick Carraway, the narrator, watching the cost of obsession and illusion unfold. It’s the haunting realization that we often pursue what we’ve idealized, not what’s real.

The Great Gatsby is a cautionary tale—but not a cynical one. It challenges us to examine our own green lights. To ask what we’re chasing, why we’re chasing it, and whether the life we’re building reflects who we truly are.

Because in the end, the goal isn’t just to dream.

It’s to wake up and live.

Favorite Quote, Insight, & Principle

• Quote: “There are only the pursued, the pursuing, the busy, and the tired.”

• Insight: Whenever you feel like criticizing anyone, remember that all the people in the world haven't had the advantages that you've had.

• Principle: Let us learn to show our friendship for a man when he is alive and not after he is dead.

• All of my notes

Author: F. Scott Fitzgerald
Themes: Fiction

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2. Personal development
The 5 Types of Wealth: A Transformative Guide to Design Your Dream Life

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Summary
I’ve read dozens of books on self-reflection and personal development—but this one stands out.

At this point in my life, I thought I’d already heard it all. The frameworks. The lists. The promises of transformation if I just meditated more, journaled better, or woke up a little earlier. But The 5 Types of Wealth felt different. It was fresh. Practical. Grounded in real life. And more than that—it helped bring to the surface so many truths we tend to forget when we’re busy chasing, building, or simply getting through the week.

Sahil Bloom redefines what it means to be “wealthy.” Not in the financial sense—though that’s one part of it—but in a deeper, more holistic way. He breaks it down into five types: financial, time, physical, social, and spiritual. And from the first page, it’s clear this book isn’t about achievement for achievement’s sake. It’s about designing a life that actually feels good to live.

This isn’t a high-minded philosophy book. It’s a playbook. It makes you stop and ask the right questions. Where is my time actually going? Who am I investing my energy in? Am I building a life that looks impressive, or one that feels aligned?

Bloom doesn’t preach. He nudges. He invites you to audit your habits, clarify your values, and remember that success without fulfillment is just another trap. And while financial freedom is important, it’s only one piece of the equation. What good is money if you have no time? What’s the value of time if your health is failing? What’s the point of success if your relationships are shallow and your inner world is starving?

That’s what I appreciated most—this book reminds you that true wealth is multidimensional. That chasing just one type often leaves us bankrupt in the others. That the richest life isn’t always the loudest—it’s often the most intentional.

The 5 Types of Wealth isn’t just a book to read. It’s a book to pause with. To reflect with. To build from.

Because the goal isn’t just to win—it’s to win on your terms. And this book might just help you figure out what those terms really are.

Favorite Quote, Insight, & Principle

• Quote: “It ain't what you don't know that gets you into trouble, it's what you know for sure that just ain't so. -Mark Twain”

• Insight: I wasn't playing the wrong game. I was playing the game wrong.

• Principle: Arrival fallacy - the false assumption that reaching some achievement or goal will create durable feelings of satisfaction and contentment in our lives. We incorrectly assume that we will finally experience the sensation of having arrived when we reach whatever we have propped up as our destination.

• All of my notes

Author: Sahil Bloom
Themes: Personal development, Living a full life, Health and wellness

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3. Entrepreneurship
Beyond The Exit: What Successful Entrepreneurs Do With The Rest Of Their Lives

Buy this book

Summary
Before I sold my business I read everything about the topic that I could get my hands on. Articles. Memoirs. Podcasts. Any story that gave me a glimpse into what came next. Because while there are hundreds of books on how to build something from the ground up, there are far fewer that explain what happens after. After the thing you spent years building is no longer yours.

There was a real gap in resources about what life after an exit actually looks like.

Beyond The Exit filled that gap.

Written by my friend John Rood, this was his first book—and it’s something I wish had existed even earlier. It’s a thoughtful, honest, and deeply useful collection of insights drawn from interviews with successful entrepreneurs who sold their businesses and had to answer the same question so many of us face: What now?

Some walked away with satisfaction. Others wrestled with regret. Some leapt into new ventures. Others had to sit still and figure out who they were without the title. What makes this book so powerful isn’t just the stories—it’s the clarity they offer. It’s a mirror held up to your own future, asking: what will fulfillment look like for you once the mission is complete?

Though I read this book after my own exit, it still gave me language for what I was experiencing. And for anyone even thinking about selling a business someday, I can’t recommend it enough.

John captured something that was missing in the world of entrepreneurial storytelling. Not the rush of the chase. But the meaning that can come after. The peace. The challenge. The rediscovery of who you are when the game board gets cleared.

It’s not just about what you built.

It’s about what you build next—with your time, your energy, your purpose, and your life.

Favorite Quote, Insight, & Principle

• Quote: “The greatest entrepreneurs don't just build businesses; they eventually learn to apply their gifts to building lives of meaning.”

• Insight: Your identity was never your company—it was always the vision, resilience, and purpose you brought to it.

• Principle: Success isn't measured by the sale price, but by what you build with the proceeds—both in business and in life.

• All of my notes

Author: John Rood
Themes: Entrepreneurship, Selling your business

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We spend years building, chasing, striving. We hit milestones and move the goalposts. We convince ourselves that peace will arrive when we finally cross the next finish line—only to discover that it’s been replaced by another.

But at some point, we have to ask the harder question—not “What’s next?” but “What’s enough?”

This week’s books circle that question in three distinct but powerful ways. The Great Gatsby shows us what happens when ambition loses its anchor—when we build a life around longing and illusion. The 5 Types of Wealth reminds us that true fulfillment isn’t found in a single number, but in a life balanced across time, health, connection, and meaning. And Beyond the Exit brings us into the lives of people who “won the game”—and then had to figure out what to do with the rest of their story.

And that’s the thread.

Enough isn’t about giving up. It’s about growing with intention. It’s about replacing the urgency to climb with the wisdom to ask why you’re climbing. It’s about recognizing that what we’re really chasing—peace, joy, freedom, love—might already be here, if we’d only slow down long enough to see it.

This doesn’t mean we stop building. It means we build differently. From a place of wholeness, not lack. From purpose, not pressure. We stop measuring our worth by what we’re producing and start measuring it by how deeply we’re living.

Because the greatest freedom isn’t having it all—it’s knowing you don’t need to.

So take a breath. Look around. You may not be at the end of the road, but that doesn’t mean you haven’t already arrived.

Always ❤️📚💡

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