I am one of the least fit people in my gym.
I am one of the least experienced entrepreneurs in my mastermind.
…and that is just fine.
You see, I go to one of the main gyms in my town. But my town is a beach town, where people are disproportionally very fit since half of them are seen shirtless or in bikinis multiple times a week. And even then, I am in a gym… where by definition people are on average much more fit than random people walking down the street.
This means my warm-up looks like the local fire department showing up for a rescue drill. I jog for four minutes, look like a dying walrus for six, and then sit on the mat pretending to “stretch” while actually considering whether faking a leg injury is a valid exit strategy. Meanwhile, the person next to me is doing upside-down handstand push-ups on a balance ball while drinking a protein shake through a straw they fashioned out of their own determination.
And still… I keep showing up.
In my masterminds I sit next to people whose companies are listed on the NASDAQ, some who run (or have run) 9-figure businesses, and others who have PhD’s in fields I didn’t even know existed.
Like, one guy casually mentioned his PhD was in “computational linguistics applied to cognitive neuroscience” which sounds like a fake major you’d invent if you were lying on your resume. My contribution to the conversation was, “I once figured out how to get Excel to stop yelling at me with that little triangle thing.” To my credit, nobody booed. Out loud.
Sometimes I nod like I understand what’s happening, but mostly I’m the human equivalent of that dog in the back of the truck who just looks happy to be included, even though it has no idea where the truck is going or why everyone’s talking about Series A funding rounds like they’re Pokémon evolutions.
It is uncomfortable. It is humbling. And it is also great.
Because here’s the secret: the discomfort means you’re in a place where you can grow. If you’re always the fittest person in the gym, that’s a red flag that maybe you’ve accidentally wandered into a daycare. If you’re always the smartest person in the room, congratulations, you’ve successfully cornered yourself into being the unpaid Google for everyone else. Neither of those things make you stronger. They just make you smug and boring, like a cat who brags about how many birds it has killed while you’re just trying to eat your cereal.
But when you’re the least of something, you’re surrounded by people who drag you upward just by existing. They remind you that you’re not done yet. That you’re still capable of becoming better, even if today you mostly just became sweatier.
So yes, I am the least fit person in my gym and the least experienced entrepreneur in my mastermind. And it is, in fact, fine. Because I’d rather be the scrappy underdog in a room full of champions than the reigning champion of the kiddie pool.

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