So for a number of years here in Austin, I had the pleasure of training my friend Rio’s dad, Jack. Jack was in his 80s, had pretty advanced COPD, so our sessions involved lots of rest. And lots of talking. Jack had been around- in the NYC art scene in the 60s, abroad, but a story he always told me (and he tended to repeat some of the greatest hits) was how he shucked the corporate world to follow his own path. He’d gotten his start as a Wall Street trader, and one day—this is how he told it—he was sitting on the toilet, doing what one does, and he suddenly realized:
“This is all bullshit.”
And then he stood up, walked out the door, and never went back.
No dramatic resignation letter. No midlife-crisis convertible. Just a man in a bathroom stall having a moment of perfect clarity.
After he quit, he reinvented himself as a master carpenter and cabinet maker. He found a decrepit old industrial building in SoHo, fixed it up with his own hands, turned it into a proper workshop… and because it was SoHo, eventually sold it for—let’s just say—generational money.
But that’s not what stuck with me.
Because of his background and my slightly amateurish interest in building and fixing things, we’d often talk shop. We often talked about deeply philosophical things too- one of his first questions to me ever was “we do we self sabotage?” Whoa.
Anyway, we’d be sitting there, and he’d have some crazy idea about replacing a wall of the gym with foam or something and I’d be skeptical, and Jack would shake his head at me—good-naturedly—and say:
“You kids are terrified to be bad at things. You look at a challenge and ask, ‘What if I mess up?’
And then nothing you stall. We used to ask, ‘What’s the worst that could happen?’”
And… yeah. Guilty. I’d stare at some project—starting a gym, writing something new, learning a new skill—and feel that little internal clench. That fear of being less-than-perfect.
And I’d look at Jack, who had reinvented his life on a random weekday morning, and think: man… where do you get that kind of courage?
Turns out, there’s a place you can train it.
We were already at that place… is the gym.
Hear me out, because this is going to sound backward at first.
Gyms are places designed for you to fail. Over and over. Repeatedly. In public.
And somehow, you keep coming back.
Most places in life punish failure. The gym expects it. Encourages it. If you’re doing it right, it practically demands it.
Think about your first pull-up attempt. Or day one with a barbell. Or that moment the coach says, “Hey, today we’re learning the snatch,” and you silently look for the nearest exit.
And that’s the point.
The gym becomes this weird little laboratory for trying, failing, laughing at yourself, refining, and eventually succeeding.
It’s not punishment. It’s practice.
So today we’re gonna talk about why getting into a gym and doing something hard and failing is actually great- maybe not in the moment, but overall, for your lift.
Reason #1. Lots of “little” hard things
Real life can sometimes have two settings. We have the sort of boring normal and predictable day to day and then the OH SHIT EPIC challenges. Unless you’re in school or something you probably don’t have a lot of small to medium hard things to practice on, so you get lulled to sleep by your day to day and then overwhelmed when a big challenging thing pops up.
The gym is great because it’s full of hard stuff to do, but most of it is kind of “little”- a movement, a workout, even just showing up day after day. That gives us lots of practice points, opportunities to summon the mindset and resilience we need to overcome the hard things in life. So when that next OH SHIT EPIC thing comes along, you’ll feel a little more prepared for it.
2. There’s an expectation that you won’t be good at it.
Maybe your mileage varies, but I feel like I grew up with a pressure that I was immediately good at most of the things I tried- even if I had never done them before. Maybe it was school or peer pressure or whatever, but there was a subtle social pressure that probably kept me from trying some things I might have really liked or even excelled at. I didn’t want to look stupid.
Because there are so many different things to do in a gym, its inevitable that most days youll be doing something you aren’t great at. Most of us don’t walk into the gym thinking, “Today I will casually achieve athletic greatness.”
You walk in thinking, “Please don’t let me fall off this box.”
From day one, the social contract is:
You’re not good at this yet.
And that word—yet—is the magic spell.
Few places in modern life give you the space to start at zero, or to even lag behind on something even when it comes easily to others.
Gyms do.
3. Gyms reward effort AND output.
Most of the world is output focused. For so much of what we do as humans its almost impossible to accurately measure effort, so we default to looking at the finished product, and our little ape brains need to sort things, “more-good” “less-bad.” Whether someone got lucky or had weirdo savant natural talent or whether they worked themselves to the bone, we tend to see and value the finished product, and not much else.
Working on your fitness comes with a bucketful of ways to measure effort, progress, and then output. You track the things that will lead to the big sexy outputs, the reps and sets along the way and you and everyone else can see them add up and the grind of putting in the work.
Also, gyms tend to celebrate little intermediary steps along the path to super-fitness. Trust me when I say that I’ve seen the gym go absolutely bonkers for someone getting their first pullup, while an “elite” athlete is across the room cranking out sets of 10 at a time.
It’s not that the super athlete’s work goes unnoticed- but the high level accomplishments tend to be understood in totality- you see someone who is super fit, or finished first in a workout, or wins a competition. The more granular and easily understood wins- things like a first pullup, tend to be frontloaded, early steps on the way to the bigger picture.
Unlike in “real” life, at the gym we get to put eyes on both the struggle and the success, and we respect both parts equally.
4. Gyms make failure safe and low-stakes.
So you failed a rep?
Cool. Shake it off. Try again.
You get stuck at the bottom of a squat?
Shrug the bar off your shoulders, and stand up without the weight.
You know what’s never at risk?
Your bank account.
Your career.
Your relationships.
Failure becomes… harmless.
Almost fun. Well, even if its not fun, even if its frustrating, its just a data point- it doesn’t have any real, lasting consequences.
And like I said before, since there are so many reps or “opportunities” at the gym, the relative importance of any single one of them is diminished. They get lost in the sauce, if you will.
When failure isn’t fatal, you’re free to explore who you could be on the other side of it.
#5: Gyms cultivate identity humility.
This is one of my favorite parts, and nobody talks about it.
When you fail regularly—in front of people—you start loosening your grip on your ego.
You stop clinging to the identity of “I’m good at everything I try” or “I must appear competent at all times.” All the stuff I said before- it might not happen overnight, but eventually you tend to loosen your grip on some of the weird social lessons the world has etched on your soul.
You become:
- More curious
- More coachable
- More open
- More able to say, “I don’t know—teach me”
- More comfortable laughing at yourself
- More resilient when you mess up
Identity humility isn’t weakness. It’s adaptability.
People who cling to a rigid sense of who they are can’t grow.
People who practice humility—even accidentally—become unstoppable.
The gym is basically exposure therapy for your ego.
Every failed rep is a reminder:
“Hey, you’re human. And that’s fine.”
Before I wrap up, I’d be remiss if I didn’t talk about the big force multiplier of gyms. Because failing alone in your garage is one thing. You’ll definitely learn something from it, and hopefully you won’t pin yourself under a barbell benching and have to wait a few hours for your significant other to come home and free you.
But failing surrounded by other people who are also failing? That’s community. It’s said that what bonds soldiers together so effectively is “shared suffering with a sense of humor.” Sound familiar?
Because gyms build environments where effort is visible and shared, suddenly failure isn’t isolating.
It’s bonding.
You look around and think, “Oh… it’s not just me. Everyone’s human here.”
Humans are social learners, that sense of belonging is hardwired into us, and we’re braver together than we are alone.
So how will this change your life?
Everyone joins the gym to improve their health and fitness. But sometimes the most valuable returns often show up everywhere else.
The person who was terrified of a barbell becomes the person who can have hard conversations at work.
The person who was afraid to look silly trying a new movement becomes the person who signs up for a pottery class or learns guitar or starts writing again.
The person who couldn’t do a pull-up starts backing themselves in moments that used to make them shrink.
Confidence doesn’t only come from having natural talent or being effortlessly good, it comes from trying, failing, and realizing you survived and that it wasn’t as bad as you thought it would be.
So When I think about my conversations with Jack I think about what he saw that I didn’t yet:
You don’t need perfection to change.
You need courage.
And courage is a skill.
One you can practice.
So if you’re watching this and something in your life feels stuck, maybe the place to start isn’t a five-year plan or a grand declaration.
Maybe it’s just… the gym.
Or a class.
Or a challenge you might fail.
Because if there’s anywhere designed for safe failure, humble effort, and brave beginners… it’s there.
And you never know—your whole life might change on an ordinary day, doing something you didn’t think you were ready for.
Just ask Jack.
