September 1, 2025

If You’re Trying to Win, You’ve Already Lost

by | Business, Truths

Trophy broken on the ground

(Inspired by Simon Sinek’s The Infinite Game)

Most people run their life and their business like it’s a game they can win. That’s why they flame out, sell out, or disappear.

Sinek calls it the difference between finite and infinite games. Finite games have winners and losers. Infinite games don’t end, they evolve. The problem is, most of us treat life like a scoreboard, chasing quarterly wins, viral moments, or follower counts. We mistake cheap dopamine for meaning, and then wonder why it feels hollow.

Winning is a trap. The second you think you’ve “won,” the game shifts. The algorithm changes. The culture moves on. The title you worked for doesn’t matter anymore. Everything you thought was permanent evaporates.

Infinite players don’t care about that scoreboard. They care about building something that outlives them. They measure differently: Did this make someone better? Did it make someone feel? Did it add something to the world that wasn’t there before?

That’s why Relentless Creativity exists. Not to chase quick wins or viral moments, but to leave scars that last. I don’t care if a post sells today. I care if it changes how you see yourself tomorrow. I care if you remember it when the noise fades. That’s the infinite game.

So go ahead and keep chasing wins if you want. Stack up your trophies and metrics and follower counts. Just don’t confuse them for meaning.

If you’re trying to win, you’ve already lost.

My Relentless Creativity takeaway:
The short game dies with you. The infinite game outlives you. Stop chasing wins and start creating what matters.

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Jason Dauphinee

Jason Dauphinee

Jason Dauphinee is the creative force behind Relentless Creativity™—a designer, writer, and existential shit-disturber crafting brutally honest art and emotionally intelligent commentary. He builds brands, breaks rules, and occasionally makes people cry (in a good way).

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Jason Dauphinee

Jason Dauphinee

Empathetic inquisitor. Creative lifer. Bold feeler.

Underneath it all, I’m chasing something more human. I want the work to feel. I don’t care about clever unless it’s got heart.

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