At the height of his success—8 Grand Slam titles, global fame, a marriage to Brooke Shields—tennis legend Andre Agassi was miserable.
In his autobiography, Open, he explained that despite being one of the greatest tennis players alive, he dreaded his craft. He felt trapped by a life that revolved around the relentless pursuit of achievement and external validation.
Matthew Perry was one of four actors to ever have a #1 movie and TV series at the same time. He dated Julia Roberts, bought the oceanfront house of his dreams, and made $1 million per episode of Friends. But as he repeatedly wrote in his memoir, Friends, Lovers and the Big Terrible Thing: none of it was enough.
Agassi and Perry are extreme cases in just about every way, but their stories illustrate a truth that affects everyone: you can have it all—but there is no greater trap than thinking external achievement will fulfill you.
The Success Trap
The human brain is wired to want more.
The neurochemical associated with wanting (dopamine) is much stronger than the one associated with liking (serotonin). It’s how we evolved. Back on the Savannah, our ancient ancestors that became content after a big hunt eventually died off during the next famine. It was only those who stayed hungry—literally and metaphorically—who survived to pass on their DNA, and it’s the DNA that all of us have inherited. We are a striving species. It explains our greatest innovations and contributions. It also explains our ceaseless longing for more.
We all have holes we are trying to fill. Every last one of us. Maybe it has to do with our parents. Or being bullied in elementary school. Or an older sibling. Or a specific coach or teacher. Or just being a person who exists in a media ecosystem with an overwhelming message that you always need more. But no achievement, income, fancy watch, or substance will fill the holes in any meaningful way.
Recognizing the arrival fallacy is liberating. You stop expecting the next accomplishment to finally make you feel like a finished product. It gives you permission to turn your attention to the process—finding joy, energy, and fulfillment in the work, not in the illusion of what might happen if (or when) you finally arrive.
Perry wrote: “I’m certain that I got famous so I would not waste my entire life trying to get famous. You have to get famous to know that it’s not the answer. And nobody who is not famous will ever truly believe that.”
The trap of fame, status, and success doesn’t just affect actors and athletes, but artists, musicians, entrepreneurs, writers, bakers, executives, doctors, nurses, educators, and coaches—which is to say it affects all of us.
If you can’t find joy and fulfillment in traveling, then the arrival won’t matter. As Agassi wrote at the height of his career, which coincided with the height of his emptiness and dread, “I feel like I’m standing on top of a mountain I never wanted to climb.”
Now there are tons of influencers, self-help authors, and TEDx gurus who extol the virtues of being content and having enough. The only problem is that these very same people seem far from content themselves—they are hustling harder than anyone to make bestseller lists, go viral on Instagram, or top the TED Talk charts.
In 2019, Arthur Brooks wrote a powerful piece for The Atlantic about how no amount of professional success will ever fulfill you, and how you have to find contentment outside of striving, especially in the second half of life. Since then, the 61-year-old has written three best-selling books, partnered with Oprah, appeared on hundreds of podcasts, and started a new company offering online courses for “high achievers who crave more than just success,” and who realize “the more we chase success, the more unhappy we become.”
Arthur Brooks is very smart, and his work is good. But he’s also a profound example that, for many people, one of the main ideas he’s selling—releasing from striving for success or achievement—seems to be a fiction.
This doesn’t mean we should all become soulless workaholics. But it does mean we’ve got to learn how to find happiness, fulfillment, and contentment in the striving itself.
Contentment In The Striving
After winning a gold medal in the 2021 Olympics, the runner Jakob Ingebrigtsen was asked if the emotional payoff was worth it. “It’s really strange because I trained for that specific race for basically my whole life,” he replied. “The peak is really high, but also right after the peak, there’s a big low. Because I’ve done it.”
Not even minutes later, in the same interview, Ingebrigtsen was thinking about what’s next: “I want to win the World Championship as well. And when I’m this fast, it would have been stupid not to go after some records.”
Psychology researchers differentiate between obsessive passion and harmonious passion, and knowing the difference is key:
Obsessive passion is when you are compelled to do something whether you want to or not. It’s when you get addicted to the external validation. Harmonious passion is when you choose to keep pushing. It’s when your motivation is predominantly intrinsic: it comes more from doing the work than the recognition you gain from it.

Success that’s driven by fear, expectation, and a need to feel validated will almost always fall flat. No trophy, record, or podium can compensate for an identity wrapped in the adoration of strangers. But success that is primarily driven by a love for the game, by joy and growth and self-discovery and challenge and community, is far more satisfying. After all, it was only when Agassi reconnected his craft to meaning—using tennis to mentor kids, to serve a cause beyond himself—did he find the sport fun again.
No one’s passion is completely harmonious. It’s human nature to want to achieve, succeed, and be praised by others. It’s totally normal to want to win. Results do matter. But it’s also important to realize the success trap, which is that you can get addicted to success—and just like any other addiction, it narrows your life, consumes you, and ultimately leads to emptiness and dread.
The way to give something your all without burning out, losing your mind, or becoming miserable is to savor the wins; grieve the defeats; and always come back to the work itself (and whenever possible, to do the work with good people).
In other words, the best shield against the trappings of success is building, maintaining, and protecting a process that you genuinely enjoy. It’s working toward goals that align with your values and the person you want to become. It’s rarely worth sacrificing a process that leaves you feeling satisfied at the end of the day for a high-status role, better title, bigger income, or some other bright and shiny object.
The only zen on the mountaintop is the zen you bring with you.
The only place you are going to find the love or wholeness you are looking for is by losing yourself in meaningful pursuits, expressing your innate gifts and creativity, and walking the path with good people.
— Brad and Steve




