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Cancelling 30 Under 30

The Tyranny of Thirty

6 min readMay 14, 2025

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→ Read the next essay: Your Thirties Aren’t What They Used to Be

The tyranny of thirty has become the most pernicious deadline of our culture — a guillotine over the necks of ambitious twenty-somethings at tech startups in Silicon Valley, artist studios in Bed-Stuy, and influencer houses in West Hollywood.

All of them chanting the same frantic mantra:

“I gotta make it by thirty.”

Thirty is the line in the sand — the point beyond which “high potential” resolves into undeniable achievement or probable irrelevance.

And there’s a hint of truth in their words. Early success enables you to compound your gains and many of our culture’s most iconic figures got their start at a young age:

  • Taylor Swift won her first Album of the Year Grammy at age 20.
  • Mr. Beast became the world’s most subscribed YouTuber at age 26.
  • John and Patrick Collison became the world’s youngest billionaires at ages 26 and 28.
  • Kehinde Wiley began his iconic Rumors of War series at age 29.

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Jason Shen
Jason Shen

Written by Jason Shen

Executive coach and author of The Path to Pivot & weirdly brilliant. 3x startup founder, NCAA gymnast, and Brooklyn resident.

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