Why Trying Harder Never Gets You There

What you practice, you perfect. So it’s worth asking what you’ve been practicing.

There’s a saying every coach knows: what you practice, you perfect.

I’ve been practicing something since I was 7 years old. 50 years of daily reps. And for most of those years, I had no idea I was doing it.

I’ve been practicing trying.

They say mastery takes 10,000 hours. I blew past that a long time ago. If trying were an Olympic event, I’d have medaled in the 90s.

And to be fair, the trying produced things. I led a Marine platoon in Desert Storm. I built CrossFit LA, one of the first 10 CrossFit gyms in the world, from 8 members into a community of more than 350. I co-created the Whole Life Challenge, an online health program that reached over 250,000 people. Trying has a resume.

Here’s how trying operates, as best I can tell.

First it convinces you something’s missing in you. Then it hands you a plan: do this, win that, and you’ll finally have proof you’re okay. So you do it. You get the thing. And before the ink dries, trying has already located the next hole to fill.

That’s the whole machine. It can never sign off on you, because signing off would put it out of a job. A treadmill with a finish-line banner painted on the wall.

So here’s a partial inventory of my 50 years on it.

Trying to get it right. Trying to get noticed. Trying to fit in. Trying to prove I was smart. Trying to be liked. Trying to be worthy of love.

Trying to find a partner who’d impress everyone, including me. Trying to be perfect enough to deserve one. Trying to make up for whatever I’d decided was wrong with me.

Trying to get into the cool group. Trying to be extraordinary. Trying to disappear into ordinary. Trying to be envied, trying to avoid being envied, and trying to stop envying everyone else. (That trio alone is a full-time job.)

Trying to make enough money to keep up. Trying to feel morally superior for caring less about money. Trying to win. Trying to avoid losing. Trying to know more than the guy across the table. Trying to outdo everyone, and trying to keep up with everyone, sometimes in the same afternoon.

Trying to conquer the next physical challenge. Trying to stand out. Trying to stay invisible. Trying to be good at everything. Trying to look interested when I was bored. Trying to stay productive. Always productive.

If you’ve built a company or run one, I’d bet your list overlaps mine by about 80 percent.

And the sneakiest version of all: trying to improve myself out of the trying. I’ve done 30 years of inner work. A spiritual teacher for 15 of them. Nearly 7 years at the Santa Monica Zen Center. A Master’s degree in Spiritual Psychology. All of it genuinely changed me, and for long stretches, trying ran that show too. Meditate better. Awaken faster. Become the guy who’s beyond all this.

The self-improvement treadmill is still a treadmill. It just has nicer scenery.

And somewhere in my late 50s, I finally said the quiet thing out loud: I’m tired. Tired of trying. Tired of the treadmill. Tired of a thirst that can’t be quenched because unworthiness is the well it drinks from. Tired of chasing self-acceptance with a method that starts by assuming there’s something to fix.

Which brings me back to the coaching saying, because it has teeth.

Every one of those reps was also rehearsing something underneath the goal. Practicing hurry. Practicing bracing. Practicing the low hum of not-enough. Run those reps for 50 years and you get world-class at them. That hum you feel at 6am before your feet hit the floor? That’s skill. You earned it, one rep at a time.

Which raises the questions that stopped me cold.

Who am I if I’m not trying?

Who am I if there was never anything to make up for?

My reflex, of course, was to build a plan to fix the trying. Which is more trying. The ego loves that move; it gets to keep its job and look enlightened doing it.

So I’m running a different practice these days. Being with it. Sitting with the restlessness without turning it into a project. Letting the discomfort be there, just as it is, for as long as it wants to stay.

And reminding myself, gently, that the path unfolded exactly the way it needed to. Every year of it, including the wasted-looking ones, taught me something I couldn’t have learned cheaper. From here, I’d change none of it.

Some days I can even celebrate the whole mess. The ache, the striving, the ridiculous 50-year audition for a part I already had. There’s something almost exquisite in seeing it clearly. (I know how that sounds. Stay with me anyway.)

A to-do list would defeat the purpose here, and you’d just add it to the pile anyway.

So I’ll leave you with one question. What have you been practicing?

Watch a single ordinary day for the answer. The hurry into the car. The inbox refresh. The jaw you notice clenching at dinner. Whatever you find, you’ve probably gotten very good at it.

And the practice you choose next is the one you’ll perfect.

With love, Andy

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