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Behind Every Win Is a Stack of Losses

As you know by now, I love to gamble. I don't have to go into it. I'm a fan of gambling. I love slot machines, and I love placing sports bets. It might not be for you, I'm ok with that, but I love the rush, the thrill, the entertainment, and the experience that comes with all aspects of gambling.

What's funny about a gambler, though, is that they don't tell you the losses. The old adage is that a gambler only tells you when they win.

The story always goes like this. A gambler wins a few thousand dollars, and they share the story with their friends.

"I won $5,000 in Las Vegas!" said the gambler.

"Oh wow, how much did you lose?" asked a dickhead friend.

"Oh, way more than $5,000...." said the gambler.

But the gambler didn't lead with the losses; they led with the win. Why? Who wants to announce they lost $20K when they can announce they won $5K?

The exact same thing happens in our careers, and it's a problem. Everyone wants to announce the big win. "My business is a success!" Great, how many businesses did you fail at before this one? "I got promoted!" Outstanding, didn't you grind in your previous role for seven years? "I'm working my dream job!" Cool, how many applications did you get rejected from before you finally found this one?

These are all hypothetical questions and scenarios because no one would actually ask these in return, but the reality is, maybe sometimes we should.

Maybe we need to normalize the conversation around success and failure.

When we read the headline, our minds usually go to a place of positivity first, and we forget all of the struggles that may have gone into that situation previously. We then start to compare ourselves to the individual, and we second-guess our own journey.

Instead, we don't celebrate all of the losses along the way that these people had. We don't talk about the struggles as if they mattered; we only talk about the win as if it's the only outcome that took place.

The losses, the challenges, the struggles, the problems, the stress, the anxiety, the failures are all where the real magic happens. It allows us the space to learn, to tinker, to figure shit out, and without these moments, we are never able to actually learn the path to success.

The part we forget is that the win is usually the smallest part of the story. It's the headline, sure, but it's never the whole article. The win is the screenshot on Instagram, the LinkedIn announcement, the humble-brag text your buddy sends from the airport lounge.

The losses sit underneath it like the foundation of a house, completely invisible unless someone decides to pull up the floorboards. Most people never do. Most people never will.

And because no one talks about the floorboards, we walk around thinking our own mess is some kind of personal failure instead of the tuition everyone pays. We pretend the journey should be linear, polished, simple, and clean. We forget that every meaningful success was built on a pile of mistakes no one advertised. We forget that confidence is usually just the byproduct of surviving the stuff that almost broke us, not the thing we naturally started with.

If we were more honest about that, we'd probably give ourselves a lot more credit. We'd stop comparing our behind-the-scenes to someone else's highlight reel. We'd recognize that losing isn't proof you're off track; it's proof you're actually in the game. And maybe, just maybe, we'd start celebrating the losses the same way a gambler celebrates that lucky five-grand win, because without the losses, the win doesn't feel like anything at all.

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