Why You Never Feel Like Enough of a Man

I chased a definition of manhood I wrote at 13, and the finish line moved every time I got close.

One Saturday morning a while back, I was drinking coffee with Spotify on shuffle when “What Was I Made For?” came on. The Billie Eilish song from the Barbie movie.

I started crying. Out of nowhere. A former Marine in his 50s, crying into his coffee over a song from Barbie.

What spilled out of that morning was a long look back at my own life. I want to hand it to you with one request: read it about you.

Somewhere in here is a thread of your story too. So as you go, ask yourself a few things. What did you decide about success before you were old enough to question it? How has your definition changed since you were 15? Since 25? What are you still chasing that some kid version of you signed you up for? And what are you settling for, quietly, in place of what you actually want?

Okay. Here’s mine.

Somewhere in my first 13 years, without ever saying it out loud, I wrote a definition of what a real man is. Strong. Competent. Tough. Doesn’t cry. Achieves. Perseveres. Wins. Leads. Serious, smart, quick, fit, good with his hands. Handles everything himself and would rather die than take a handout. Preferably with a beard.

I got it from my grandfather, from books, from movies. My family had zero part in it (they were my biggest cheerleaders, actually, which somehow made no dent). The judge lived in my head, and he’d written the rulebook himself.

One problem. By my own scorecard, I had almost none of it.

Here’s who I actually was. A joyful, curious, creative kid who felt everything and cried easily, which I learned to stop doing. And a musician, in a way that felt like the reason I existed. By 10 I played violin, piano, drums, baritone, french horn, and trumpet. By the end of high school I’d added trombone, cello, string bass, and electric bass.

Freshman year of college, ear training class, 8am Tuesdays and Thursdays. The professor would play an interval on the piano and call on someone to name it. For most of the room it was work. For me it was like being asked the name of the street I grew up on. I’d be half asleep (my classmate Lynn used to nudge me when I got called on) and I never missed one. It drove everybody a little crazy.

Music was that natural to me. It vibrated through me. And everything that came with it, beauty, sensitivity, emotion, softness, joy, sorrow: none of it fit the rulebook. It never once occurred to me that those things could live inside a real man.

So I hid it. Literally, once.

At 13 I went to Boys State, a 5-day leadership camp for boys. I brought my trumpet, then buried it at the bottom of my foot locker under everything I owned, because I figured if the other guys found it, everything would change. They found it. And everything changed, exactly the way I was afraid it would.

A few years later I was at the Eastman School of Music, a trumpet major, 6 hours from home and out from under my family’s musical world for the first time. And I did the thing that should have been impossible and turned out to be weirdly easy. I walked away from music completely.

Then I went chasing the rulebook. The Marine Corps, where I led a platoon in Desert Storm. Skiing, snowboarding, mountain biking, whitewater kayaking, mountaineering, rock climbing, outrigger paddling. Adventure racing with a Red Bull sponsorship. I founded CrossFit LA, one of the first 10 CrossFit gyms in the world, and grew it from 8 members to more than 350. We fielded a team at the CrossFit Games. Later I co-created the Whole Life Challenge, an online health program built from scratch that reached more than 250,000 people.

People saw a guy who loved the mountains, the ocean, and pushing his body. I did love those things. And running underneath, the whole time, was a quieter engine: prove it. Prove you’re a real man. If I saw another guy doing something hard and sufficiently manly that I hadn’t done yet, the pull to go do it was almost physical.

Here’s the part that took me 40 years to see.

I never felt like I got there. Ever. I’d win the race or the award, and the feeling lasted somewhere between an hour and a month. Then it reset. I’d reach real mastery in one sport and cheerfully start over as a complete beginner in another, and I could never explain why.

Now I can. When your identity is built on lacking something, you’ll manufacture lack wherever you go. Even while you’re winning. There’s always a domain where you don’t measure up, and you get very good at finding it. I’d check the boxes in one arena and immediately pick a new arena full of unchecked boxes. The system I’d built had two jobs: remind me I still wasn’t a real man, and keep me grinding to become one.

And the destination doesn’t exist. That’s the punchline. Every step toward it feels like progress, and the horizon keeps perfect pace with you, so you never actually arrive.

A few years back, the Universe gave me a swift kick in the ass. The Whole Life Challenge, the business that was supposed to be my proof and my exit, fell apart underneath me. It took me about a year just to get reoriented.

The work since then has been simpler and harder. Trusting my own intelligence, my intuition, my heart. Listening, to myself and to other people, like it matters. Treating myself as whole and complete, including every part I’d labeled a defect. Dropping the need to prove anything to anyone. Giving myself the kind of compassion I had no trouble giving my son when he was 6 months old. Swimming with the current for once.

Dorothy had it right. There’s no place like home. Home was in my heart the entire time, and the pursuit was the very thing keeping me from seeing it.

So here I am, on the record.

I’m a big softie. I run on love, joy, fun, and curiosity. Given a free evening, I’ll take the couch, a movie, and a good book over just about any adventure. I cry, happily and often. I love music that makes me feel something: melodic, melancholy, soft, soaring, even in the middle of a workout. My favorite color is purple. I love early mornings. I love doing hard things nobody else wants to do, even when part of me doesn’t want to either. I love the inward trip, meditation, spiritual practice (yes, sometimes including psychedelics), the big questions about consciousness and purpose and why any of us are here.

I’m still pretty good at all the adventure stuff. 40 years of it will do that. And I’d trade any of it for a deep conversation over coffee. A slow walk in the woods. A night of music with people I love. A long, real hug.

And all of that, and all of me, is enough.

If something in this landed, go back to those questions at the top and give yourself a quiet hour with them. Somewhere in your first 13 years, you wrote a rulebook too. It might be time to read what’s in it.

With love, Andy

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