Podcast · ~90 min listen

How have I been complicit in creating the conditions I say I don't want?

Jerry Colonna (interviewed by Lenny Rachitsky) · Lenny's Newsletter Freemium Intermediate

Colonna, the coach founders go to when they are cracking, gives the question that actually moves boundaries: how am I complicit in creating the conditions I say I don't want? A founder who claims the startup demands 12-hour days often needs to notice how much of the always-on is self-imposed, attachment to outcome and identity fused to the company, not the business genuinely requiring it. That is the honest layer under a stop-time rule: the off-switch fails when your sense of worth is wired to the inbox. This is the self-inquiry that makes a boundary stick instead of collapsing the first stressful week.

• Much of a founder's overwork is self-manufactured, so the first move is asking how you built the conditions you resent
• Tying self-worth to the company's outcome is what makes an off-switch impossible to hold
• Boundaries hold when they come from identity work, not just a calendar rule you white-knuckle