Podcast · ~2 hr listen

Jerry Colonna, How to Reboot Yourself and Feel Unrushed in the New Year (#554)

Tim Ferriss and Jerry Colonna · The Tim Ferriss Show Free Intermediate

Colonna is the founder coach (Reboot, ex-Flatiron VC) who works with the exact person this question describes, and he closes the loop the peer conversations cannot. His central challenge is why the answer says talk to a coach, not just other founders: how have I been complicit in creating the conditions I say I do not want. He normalizes rest as the whole point (the number one rule of a sabbatical is Sabbath, rest), models it with a two-month annual break, and names the startup-land reflex where taking even a weekend off feels terrifying, the exact reflex that has to change for recovery to hold.

• A coach asks the question peers will not: how am I complicit in creating the conditions I say I do not want, which turns recovery from waiting-it-out into a redesign
• Rest is the deliverable of a break, not the warm-up to more work; if a weekend off feels terrifying, that fear is the problem to fix
• Burnout ties your identity to the company's results; separating the two is what lets you rebuild without quitting