I Quit My Job at 29. Was I Brave or Foolish?
A guest who left a safe, respectable career with no plan B. We spend an hour deciding whether they are a cautionary tale or the only person in the room making sense.
Published 9 July 2026
About this conversation
Quitting looks heroic from a distance. Up close, it looks like spreadsheets, panic, and explaining yourself to relatives. This conversation is about the decision before the LinkedIn announcement, the invisible costs of staying, and why the bravest part of a career change is rarely the day you leave.
“Everybody claps for the leap. Nobody sees the months of walking toward the edge.”
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Ambition, ladders, money, and the uncomfortable possibility that professional progress can move you further away from the life you actually wanted.
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One of us thought product management was just being bossy with slides. Then we invited someone who actually does it, and none of us were sure what we do all day anymore.
Why Did Nobody Tell Us About These Careers?
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