“I had HIGH expectations of my first surf lesson; verdict: Expectations exceeded!” Those were the words I penned tweeted after my first surf lesson just a couple weeks ago in Santa Cruz, California. Of course, being the philosopher I am, I just had to be so verbose in my 140-character summary of my first surf experience, which was fulfilling a childhood dream. I couldn’t just say something like “I caught my first wave today learning to surf.” No, really, I couldn’t, because I didn’t actually catch a wave. Believe me, everyone asked! I feel like that’s what you’re really supposed to say after your first surf lesson, and while some that day in Santa Cruz no doubt did, I wasn’t one of them. I did in fact stand up, but only long enough to face plant into the water. But does that mean it wasn’t a successful day?

What is the standard by which we judge success in our lives? “Whoa now Traveling Philosopher; you just went from talking about surfing to dropping some knowledge about success.” I know, but stick with me here, it’ll circle back to surfing. So what defines success across our interests, careers, relationships, and personal lives. It’s likely a tangible measurement, something like wins or losses. If you’re a writer, it’s where you’ve been published. If you’re a publicist, it’s who your clients are. If an athlete, it’s the numbers that are in the win/loss column. And so it is, this is how success is often measured and the outcome is often the line between promotion/termination, gaining/losing clients, and happiness/sadness. Is it not?

I sometimes wonder if I and we as a society here in America have more to learn from those sports that aren’t exactly “our” sports. Take football soccer for example. The final result is often a tie. You kind of feel robbed. There should at least be sudden death, if not a penalty shootout, but anything but a tie. Yet as the players are walking off the field, it’s often as if they’ve won. They’ve got their heads up, high-fiving each other, and trotting into the locker room so gingerly. Yet while it’s not a win for either team, they both get a point for it, and that one point can be the difference at the end of the year between league champion and second place.

I was recently talking with a friend and they were asking me about some of my travels, both past and present. They had traveled abroad when younger, and had a desire to travel as much as I did, yet dismissed it now because as they put it, a stint of long-term travel like that would sidetrack their career. Is that the place we’ve come to, where the things that we want to do, those things that make us happy, hold a lesser position in our lives because it doesn’t result in the tangible outcomes such as a job affords?

Midway through my surf lesson in Santa Cruz, there came a moment; the moment. I sat up on my board for the first time in the middle of the water as the wind had died down, the clouds had parted, the sun was beaming down directly on the ocean, and there was a lull in the waves. I gently placed my hands on top of the calm ocean waters, closed my eyes, and took a deep sigh. This was it. This was my moment. There may have been a hundred people out there on the water, cars honking behind me on the main drag, and hustle and bustle one hundred yards to the left on the Santa Cruz Wharf, but as far as I was concerned, it was just me and my surfboard on the expanse of the ocean in a moment of bliss I won’t soon forget.

Some of you may know about the major risks I’ve taken, such as becoming a freelance writer, traveling for nearly a year, and moving across America to San Francisco. These were risks I went all-in on and won. But there have been other risks I’ve gone all-in on and lost. Some have been career risks, one of which was an assignment I was chasing last year in New Orleans and ended up eating hundreds of dollars on because nobody was interested in the story I was selling. Another was around the time of my birthday a couple months ago, in which I wanted one last hoorah for what had been my best year to date. I went all-in and lost. I texted my friend V: “I should’ve just taken a knee and gone into the locker room with the ‘W’.”

I had high expectations of my first surf trip, one of which was riding a wave, which didn’t happen. Instead something better happened. I confronted my fears of going deep into the ocean, and not just confronted, but conquered them and found myself in a moment of uninhibited bliss. And then before I was even out of my wetsuit, my instructor was helping me plan a surf camp in Spain. Today I booked a 9-day surf camp this summer in the Canary Islands on the island of Fuerteventura, translated “strong adventure”. As it turns out, I didn’t have to catch a ride for it to be a successful day.

The challenge then, both for myself and others, is a call to stop measuring success by wins and losses. Success doesn’t always mean holding up the trophy, winning the girl, getting the promotion, or riding the wave. What and where is it? It’s different for everyone. It took me traversing North America and moving to San Francisco to find it, and even then, I’m not sure what it exactly is. Or at least I can’t quite put it into words. It reminds me of the Donald Miller quote: “It wasn’t necessary to win for the story to be great, it was only necessary to sacrifice everything.” Go all-in, because often, the greater risk is not risking at all.