Matthew Perry and the Holes We Try to Fill

Why having it all never feels like enough—and how to find meaning in the climb instead.

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: none of it was enough.

You can have it all—but there is no greater trap than thinking external achievement will fulfill you.

The neurochemical associated with wanting (dopamine) is much stronger than the one associated with liking (serotonin). The human brain is wired to want more. It’s how we evolved.

Back on the Savannah, our ancient ancestors who became complacent got selected out whenever there was a famine. Those who were constantly on the lookout for more and better opportunities, who were never satisfied for too long, they were the ones who survived and passed on their DNA—and that chain runs all the way down to us, today.

We are suckers for the chase. We struggle to be content.

We all have holes we are trying to fill, but no achievement, income, fancy watch, or substance will fill those holes in any meaningful way.

The Arrival Fallacy

Recognizing the arrival fallacy is liberating.

It helps you to stop expecting the next accomplishment to finally make you feel like a finished product. You 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 “arrive.”

Perry wrote in his 2022 memoir:

“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 and status doesn’t just affect actors, but artists, musicians, entrepreneurs, writers, chefs, and athletes—many of whom have made it to the proverbial mountaintop.

It affects all of us.

Win gold: you are on the medal stand for 3 minutes, and celebrate for a few weeks. Get a big promotion: you feel good about it for a day or two before it’s time to work again. Hit the New York Times bestseller list: you toast to your success, maybe even frame it and put it on the wall, but then it’s back to facing the blank page.

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.”

This nature is a gift and a curse: it's the source of innovation, progress and growth, and it's also the source of longing and emptiness.

One of the most important mindset shifts there is: stop expecting something magical to happen at the peak and instead focus on making the climb as satisfying as possible, otherwise none of it is going to matter. Be where your feet are. Celebrate success and grieve defeat, but then get back to doing the work itself.

In the words of the great Robert Pirsig: "There is no zen on the tops of mountains. The only zen you find on the tops of mountains is the zen you bring up there."

So yes, set goals and try to achieve them. But don’t fall for the trap of thinking they will somehow fulfill you.

The only place you are going to find the love you are looking for is losing yourself in meaningful pursuits, expressing your innate gifts and creativity, and walking the path with good people.