170: Billy Lahr | Grit, Quit, or Pivot?

Billy Lahr returns to The Prestigious Initiative for a deeply honest conversation about living in the in-between. After 21 years as a teacher and dean, Billy stepped away from education—and four years later, he’s still experimenting, freelancing, promoting others, and wrestling with a question many high performers quietly carry: What if I don’t have a niche?In this episode, Billy and Chris explore what it means to be a generalist in a specialist-driven world, the tension between quitting and gritting, and the emotional toll of constant experimentation and rejection. They talk about identity, generosity, self-promotion discomfort, and why wanting to see others win can be both a gift and a challenge. This is a real conversation about purpose, resilience, and staying in the arena when the path forward isn’t clear yet.https://mindfulmidlifecrisis.systeme.io/jumpstartconvo This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit theprestigiouspod.substack.com