the curse of knowing how to win

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May 20 • 1 min read

Hot dog #2131


Back in my college days, I hated the cafeteria food.

So, I lived off of ramen and hot dogs.

I’m not breathing like a French bulldog yet, but I suspect the two thousand hot dogs I’ve had will pay a toll later in life.

When it came time to leave college and get my first job, I became a teacher in Brooklyn at 23.

Our fourth-floor walk-up, 325-square-foot apartment in the Lower East Side, was empty on day one.

As a farm kid who visited New York two years earlier, I’d stopped in the middle of a busy crosswalk and said to myself, “I have to live here.”

Now, I was using my clothes as blankets, lying on the wood floor, waiting for the furniture to be delivered, and too nervous to eat.

When the next day arrived, and it came time to grab a bite, I thought…comfort.

Back then, that was meat in tube form.

Pop into the bodega, grab some hot dogs, buns, ketchup, and mustard. Walk back up the four floors and microwave the dog.

Then take a bite…

What the hell?

I was so out of my element that the thing I’d bought my whole adult life was the wrong product.

I was eating a veggie dog.

Standing in the new place. Alone. I start laughing.

Years later, I still love New York.

It’s one of the only places I’ve lived that I’d go back to.

But in the beginning, I was just a dude holding a veggie dog, feeling incompetent as hell.

That’s the annoying thing about getting what you asked for.

You don’t just become new at the big stuff.

You become weirdly bad at things you thought you knew.

Like buying a hot dog.

So we stay where we feel competent.

The same room with the same players.

The same business with the same rules.

The hot dog in the familiar dorm room, not the veggie dog in the big city.

I see this in 1:1s constantly.

Someone tells me they want the next level.

Then, eventually, it becomes obvious: they’re afraid to look stupid.

So I encourage them to go look stupid.

Being new sucks because it makes you look worse than you are.

That’s the tax.

And once you’ve gotten used to being impressive, you’ll do all sorts of weird shit to avoid paying it.

But every hugely profound experience in my life started with me looking like an idiot in the beginning.

So maybe the question isn’t:

“How do I make this feel good faster?”

Maybe it’s:

“Am I willing to be new here long enough for this to become mine?”

I miss New York now.

Kinda funny, because the beginning was an empty apartment, no furniture, and a microwaved veggie dog I bought by accident.

Terrible start.

The right move.

-C


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