The Relentless Pursuit of Enjoyment

The Relentless Pursuit of Enjoyment

A catchphrase that became a philosophy, and then a purpose.

I started realizing that travel and adventure didn't have to be the reward for real life. They could be part of real life

I have been using that phrase for almost a decade. The relentless pursuit of enjoyment. Anyone who knows me would say it fits. But what it actually means has changed more than I expected over the years, and I think the evolution is worth talking about.

In the beginning, it was a reaction. At the height of my career in television and entertainment, life was intense. Long hours, constant pressure, and if you live in Los Angeles, even getting across town feels like work. When I first started Reject Average, it was a small executive group, just a handful of people trying to break that pattern by doing more interesting things outside. Getting into the mountains. Getting on the water. Getting out of the city and into something that actually felt alive.

Back then the relentless pursuit of enjoyment was a target. Something I was reaching toward. And the thing I was reaching toward looked a lot like what most people imagine retirement to be, a life where you wake up and do the things you actually want to do. That idea is deeply ingrained in how people think. Work for decades, build security, and then one day you get to enjoy it. The problem is that version of life rarely plays out the way people expect. For some, by the time they get there, the body and mind have moved on and the things they dreamed of doing are no longer things they can actually do. A week in the Dolomites, a sailing trip through Croatia, riding horses in Iceland, those things require a version of you that doesn't wait fifty years. For others, they have spent so long building a life around work that when it's gone, they lose their sense of purpose entirely. I knew early on I didn't want either outcome. So the goal became simple. Move that version of life forward. Don't wait for some distant point in the future. Build it into the present.

Those early years were some of the most rewarding of my life. It felt like discovering a dimension that had always been there but that I had never looked directly at. I started realizing that travel and adventure didn't have to be the reward for real life. They could be part of real life. By 2019 I had taken people on nearly forty different adventures in a single year, from snowbiking in Whistler to shark diving in Fiji to ripping through the sand dunes of Qatar. At that point it had stopped being something I did occasionally. It was what I did.

Then something unexpected happened. My original goal had been to take the intensity and focus I brought to my professional life and apply it to my personal life. To show up for adventure the way I showed up for work. What I didn't expect was that it would run in both directions. The joy I was finding out in the world started flowing back into my work. The curiosity, the enthusiasm, the sense of possibility. It came with me everywhere. And that is when I realized that work life balance is one of the great myths. It's a phrase designed to make you more productive, not happier. What actually works is harmony. Not in some abstract sense, but practically. You find a way to live with a certain energy and you bring it to everything. The same presence you bring to a boardroom, you bring to a trail in Patagonia or a boat in the Adriatic. The same intentionality you bring to an adventure, you bring back to your desk on Monday.

I saw this clearly when I worked with a professional sports organization on high performance. The athletes who were truly elite brought the same intensity to practice that they brought to games, because the brain gets comfortable with what you repeat. The goal was helping them understand that same drive belonged in every part of their life, as husbands, as fathers, as friends, not just on the court. Now the relentless pursuit of enjoyment has taken another turn entirely. It has become about sharing it.

Every article, every trip, every invitation I put out into the world is driven by the same thing. If I can point someone toward more joy, show them what is possible, drag them a little closer to the version of life they actually want, that is what gets me up in the morning.

Someone told me recently that the phrase seemed a little superficial. That relentless didn't quite fit. So I explained my definition of happiness, which I genuinely believe is one of the most useful things I have ever worked out.

Happiness is an equation.

Happiness equals joy applied over time.

That is why people feel so intensely alive when they travel, because you are compressing enormous amounts of joy into a short window. That week in Japan, that road trip down the Amalfi Coast, that morning you watched the sun come up over Wadi Rum from the back of a camel... you look back and think, I was so happy. Of course you were. You were experiencing more joy per hour than most people get in a month. The mistake is thinking that only counts on vacation. It doesn't have to be. If you increase the joy you experience day to day, you increase your overall happiness. It becomes your baseline, not something you visit occasionally.