Do You Have to Grind to Be Great?

The Truth About Sacrifice and Success

"Do you think it's possible to achieve greatness and be happy?"

Jason Jacobs asked me this on The Next Next podcast a few weeks ago. We were talking about what it takes to build something great later in life—when ambition collides with new realities. Kids, aging parents, and deepening responsibilities at home shift our attention and capacity, making the all-in, obsessive approach of our twenties less feasible.

Jason pressed further. "To perform at that level, it requires immense sacrifice. Do you think any of those people are actually happy? Do you need to be tortured, at some level, to make the level of sacrifice that cuts so much into the bone of daily joy?"

I sat with it for a moment, letting the weight of the question sink in.

"I don’t know if the highest performers in the world are tortured," I said. "But I do know that achieving greatness requires sacrifice—constraints, commitment, and focus."

At the time, I framed greatness as a question of tradeoffs—that some things require going all in, and suffering is just part of the deal. But sitting with it now, I wonder: Are we even asking the right question?

Because the more I think about it, the more it seems like we’ve been handed a narrow, incomplete version of greatness—one that worships effort, struggle, and sacrifice, while ignoring other ways people create extraordinary lives and impact.

What if greatness isn’t about how much we sacrifice, but about how fully we live?

Why Do We Believe We Have to Be the Best

We're not born believing we have to be the greatest. There's no biological blueprint encoded within us that says we're destined to become hyper-achievers, strivers, or winners. Instead, we inherit success scripts—stories handed to us by our family, peers, and culture that tell us what it means to be worthy, what it takes to be "enough." Over time, these scripts become our operating system, silently shaping our choices and determining what we chase.

The most haunting of these scripts whispers: "Success is proof of your value. Without it, who are you?"

Other versions quietly vibrate in our unconscious:

• Work harder than everyone else, or you'll fall behind.

• You have to be the best to be taken seriously.

• Your worth is measured by your achievements.

• If you slow down, you'll become irrelevant.

We don’t wake up one day and decide to adopt these beliefs. They take root long before we even recognize them.

Maybe in our families, love felt tied to performance—affection flowing more freely when we excelled, running dry when we fell short. Maybe praise only came with straight A’s, championships, moments of standing out. Or maybe we watched a parent struggle, trapped in patterns of stagnation or self-destruction, and we silently vowed to carve out a different path, to escape from their shadow.

Over time, we internalize a quiet but powerful message: To be worthy—to be loved and accepted—you have to be exceptional. Being good isn't good enough. Only by achieving more, proving more, being more, do we earn our place.

Then we step into the world, and that message is no longer quiet—it’s everywhere.

American culture glorifies winners. Workplaces reward endless hours and constant achievement. Social media transforms every aspect of life into metrics to be optimized—followers, likes, and views. Those who rise to the top become case studies, while those in the middle fade into the background. Over time, the work itself stops mattering—it becomes merely a way to prove our worth, to be seen, to matter.

And when we look for role models, we see the same story repeated: the sacrificial greats. We glorify the ones who push through pain, who outwork everyone, who sacrifice their bodies, relationships, and well-being in the name of excellence. These stories become blueprints for how we believe we need to operate. Over time, they don’t just shape how we measure success; they shape how we measure ourselves.

Without realizing it, we absorb our culture’s success scripts as our own. We chase the accomplishments, follow the rules, and accept the tradeoffs offered to us—rarely questioning whether they align with what we actually want. The more we internalize them, the harder it becomes to imagine another way. And so we keep running, measuring ourselves against standards we never chose, sacrificing without stopping to ask: Is this even mine?

And that’s how it shows up—not as a conscious choice, but as a feeling you can’t shake. A quiet, gnawing pressure that follows you everywhere. In moments that should feel restful—on the couch, in the car, at the dinner table, with your family—it never fully lets you exhale. When your sense of worth is tied to achievement, anything other than work feels like falling behind.

And so we keep climbing, pushing, proving—never pausing long enough to ask where this path actually leads. We don’t question the game. We just keep playing harder, believing that if we suffer enough, we’ll finally arrive.

The Games We Play

In 1986, James Carse introduced a simple but profound idea: There are two kinds of games in life. “A finite game is played for the purpose of winning, an infinite game for the purpose of continuing the play.” Decades later, Simon Sinek popularized this concept, but its essence has been around for generations—some pursuits are about winning, while others are about staying in the game as long as possible.

As a venture capitalist, I was playing a finite game. There were clear winners and losers, and I wanted to win. There was only so much room on a cap table in the hottest deals, only so many phenomenal opportunities each year. Success wasn’t just about making smart investments—it was about securing my place in my firm and industry, because there was always someone else ready to take it.

That meant constantly scanning, competing, and proving myself. Every pitch email, every meeting, every investment decision felt like a test—one more chance to prove I belonged. The stakes felt high because, in a finite game, they are. There wasn’t enough to go around. If I wasn't moving up, someone else was taking my place. And when I was in it, I didn’t question the rules—I just played harder.

I lived in a world where success was measured in markups, returns, exits, and rankings. But doing a good job wasn’t enough—I had to stay constantly plugged in, track the latest trends and companies, build a following, and earn the respect of entrepreneurs and co-investors. Because in a world where scarcity ruled, if I wasn’t winning, I was falling behind.

I told myself I was playing for the founders I backed, for the rush of making big bets, for financial security, for the intellectual challenge of the game itself. And maybe I was. But beneath that, there was something else—a quiet exhaustion, a creeping sense that no matter how much I strived or how many times I won, the game would never really end. There would always be the next deal, the next fund, the next wave to chase.

And that was the part that drained me the most—not just the effort itself, but the knowing that it would never stop.

I didn’t fully understand the difference between a finite and infinite game—until I started coaching. There's no “winning” in coaching. No ranking system, no scoreboard, no IPO moment that signals arrival. The only real measure of success is depth—depth of craft, depth of connection, depth of self-mastery.

In infinite games, there is no finish line. No point where you can declare victory and be done. The meaning isn’t in the outcome—at least for me, it’s in the continuous unfolding, the endless discovery of what’s possible, the deepening of one’s capacity to learn and serve.

To Win or to Live? The Tradeoffs We Ignore

There’s no final scorecard for who lived most meaningfully, no ultimate ranking of who made the biggest difference, no gold medal for who mastered life itself. And yet, we often approach our work and lives as if there were—as if every day is a competition, every achievement a test of our worth rather than a step in an ongoing journey.

We try to "win" at things that were never meant to be won. We chase the title of "best creator" when no such title exists. We compete to be the “top coach” in a field where excellence isn’t a zero-sum game. We strive to be the “most successful entrepreneur” as if some definitive ranking determines our success and worth.

It’s like trying to "win" at watching your child grow up. The very framing misses the point entirely. And yet, that's exactly what we're doing in so many areas of our lives. We exhaust ourselves chasing success, believing that if we just push hard enough, sacrifice enough, achieve enough, we’ll finally earn the love, security, or fulfillment we crave. But in the process, we sacrifice the very things we’re running toward.

We grind harder, work longer, push faster—believing it’s the only way forward. We mistake motion for progress, busyness for purpose. We keep climbing mountains that don't exist, never stopping to ask: What if the thing I’m chasing is already here? Am I sacrificing what I truly want in pursuit of something I think I need?

If you feel the pressure to be "the best," take a step back. Ask yourself:

• Is this truly a finite game, or am I applying the wrong rules?

• Am I running old success scripts that no longer serve me?

• What would success on my own terms actually look like?

• Am I still chasing external validation, or am I playing for the love of the craft?

• If there were no rankings, no scoreboards, no trophies—would I still be doing this?

You don't need anyone's approval to stop playing games that drain you and start playing ones that energize you. You can step off the treadmill of endless competition and into the infinite game of continuous unfolding. You can shift from asking "How do I win?" to wondering "How do I keep this journey interesting?" From "How do I beat everyone else?" to "How do I make this sustainable for a lifetime?"

You can simply choose—right now—to play a different game.

What Happens When You Stop Playing the Wrong Game?

Shifting from a finite to an infinite game reshaped how I approach my work—and my life.

I have zero interest in being the best coach in the world—because that title doesn't exist. There’s no singular definition of success. What I care about is connection, impact, and longevity. I care about sharpening my skills, being of service, continuing to learn, and staying engaged in the work for decades to come.

This shift isn’t about lowering ambition—it’s about redirecting it. Playing an infinite game doesn’t mean you stop striving, it means you strive differently:

• Instead of beating the competition, you focus on your own growth—because the competition doesn’t define your success.

• Instead of proving yourself, you deepen your craft.

• Instead of racing toward an endpoint, you embrace the process—because there is no endpoint, only evolution.

• Instead of chasing short-term wins, every action becomes a long-term investment.

We’re told that greatness requires sacrifice. That to reach the top, we have to give up something—our time, our energy, our health, our relationships. And yes, meaningful work requires commitment. But if the game you’re playing forces you to sacrifice the very things that make life worth living—what exactly are you winning?

And that’s what I started to see in others who had built careers with longevity—not just in coaching and writing, but across pursuits. Watching my coaching clients shift from finite to infinite games, and rewrite the rules altogether, I’ve learned time and again how many options we truly have for how to live and how to define greatness and a great life. We’ve been taught to believe that greatness has to be grueling. That impact has to come at the expense of ease. That to achieve anything meaningful, we have to push ourselves to the brink. But there are other ways to play, and games you have never even heard of.

Jason asked if greatness and happiness could coexist. But maybe that’s not the real question. Maybe the real challenge is redefining greatness itself—so that it’s not about sacrifice for its own sake, but about the pursuit of what truly matters. That way, you get to decide what the rules and opportunities are for your own life.

The goal shouldn’t be to win a game that costs you everything. Instead, you could build a game you really want to play.