The Success Paradox: Why Winning The Game Means Being Free Of It

Last week, I had coffee with someone who'd just sold their company for eight figures.

You'd expect them to be euphoric, right? Instead, they looked... empty. "I thought this would change everything," they said. "But I feel exactly the same."

This conversation unlocked something I've been thinking about for months. Here's the counter-intuitive truth about success that most people never learn:

The Two Paths to Happiness

There's an ancient story that changed everything for me.

Socrates walks through a marketplace filled with luxury goods. His response? "How many things there are in this world that I do not want."

That's freedom—not wanting something can be as powerful as having it.

Path 1: Get what you want (conquest)
Path 2: Stop wanting what you don't have (contentment)

Both work. Most people only try one.

Your Move: Pick one thing you desperately want right now. Spend 5 minutes imagining you already don't want it. How does that change your energy around it?

Win The Game to Be Free Of It

Here's my philosophy: The reason to win the game is to be free of it.

You play. You win. Then you get bored and stop needing to win. You either move to a bigger game or play purely for joy.

I see this with every successful person I know—once they prove they can do something, the obsession fades. The peace that follows is where real life begins.

Your Move: Think of one "game" you're playing obsessively right now. Ask yourself: "What would I do differently if I already knew I could win this?"

Stop Being a Suffering Addict

Here's the trap most ambitious people fall into: confusing pain with progress.

Some people get addicted to suffering. They think: "If it doesn't hurt, it's not working." They attach their sense of achievement to the struggle, not the outcome.

That's backwards.

The insight: Successful people's biggest regret is usually not enjoying the journey more. The work wasn't the problem—their relationship with it was.

Your Move: Pick one task you're currently "grinding" through with drama. This week, approach it with the same effort but zero emotional resistance. Notice the difference.

The 5-Year Reality Check

Try this mental exercise tonight:

Transport yourself back exactly 5 years. Remember your biggest worries, your goals, who you were with. Now ask: "What advice would I give my past self about approaching challenges?"

When I did this, my answer was clear: Do everything the same, but with less anger, less emotion, less internal suffering.

That suffering was optional. It wasn't necessary for the results.

Your Move: Write down three pieces of advice you'd give your 5-years-ago self about handling stress. Apply one of them to your current situation tomorrow.

The Bottom Line

99% of your time is spent on the journey, not at the destination.

You can choose miserable success or peaceful success. The outcomes might be identical, but your daily experience will be completely different.

The journey isn't just the reward—the journey is the only thing there is.

This Week's Challenge:

Pick one goal you're currently stressing about. For 7 days, pursue it with the same intensity but less internal drama.

Notice how this changes not just your results, but how you feel every single day.

Your Better Self,

Richard
Founder, Elevenstoic

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