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The Delivery Man. Authentic Random Life/Work Musing. · Jun 16, 2026

Between Reinvention and Retirement

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Sebastien Taveau · The Delivery Man. Authentic Random Life/Work Musing.

There is an old joke that worrying is like paying interest on a loan you may never take out.

The uncomfortable answer is that most people never completely stop worrying.

At 20, you worry about finding your place.

At 30, you worry about building a career and a family.

At 40, you worry about keeping what you built.

At 50, you worry about whether what you built will last.

At 70, you worry about time itself.

The target was never a life without worry. The target was learning which worries deserve rent-free space in your head and which ones should be politely shown the door.

What tends to change with age is not the amount of worry but the relationship with it.

You eventually realize:

  • Most disasters never happen.

  • Most failures are survivable.

  • Most people are too busy worrying about themselves to spend much time judging you.

  • The perfect moment to start something rarely arrives.

  • Time is the only asset you cannot earn back.

For many people, the shift happens after a health scare, a layoff, a loss, children leaving home, or simply noticing that there are fewer years ahead than behind. The math becomes impossible to ignore. You start asking a different question.

Not “What if this goes wrong?”

But “What if I spend the next ten years waiting for certainty?”

That question changes people.

I suspect this is particularly relevant to many people in tech right now. There is a generation that feels caught between reinvention and retirement. Too young to stop. Old enough to know the market can be brutal. Smart enough to see the risks. Experienced enough to know that worrying doesn’t actually reduce them.

The irony is that living was never waiting on the other side of certainty.

Living was always the thing happening while you were trying to become certain.

A Scottish proverb says, “Be happy while you’re living, for you’re a long time dead.”

Not bad advice from a people who invented both whisky and existential weather.

So perhaps the moment you start living is not when the worry disappears.

It’s when you decide that the worry no longer gets to make the decisions.

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Read the original on thedeliveryman.substack.com

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