Mike Birbiglia's Working It Out 188. Caleb Hearon: Improv Saved His Life
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Oct 20, 2025 Caleb Hearon, a stand-up comedian and podcaster known for his HBO special, delves into the transformative power of improv and how it saved his life during tough times. He candidly shares his struggles with suicidal thoughts and the impact of losing his estranged father on his comedy. The conversation also highlights his journey from SNL auditions to a successful career, the importance of live stand-up, and the balance between ambition and mental health. Plus, Caleb dreams of off-grid living with Mike amidst comedic insights.
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Don't Think Twice Shaped Improv Realities
- The film Don't Think Twice resonated with Caleb's improv group by confronting the possibility of 'making it' and its emotional impact.
- He and friends revisited scenes that mirrored their own experiences years later.
Quitting For Comedy During COVID
- Caleb quit his ad-agency job in January 2020 to pursue comedy, then drove for Uber Eats when COVID hit.
- He later moved to LA, landed remote writing work, and progressed into TV and specials.
Contradictory Feelings Can Coexist
- Caleb holds contradictory feelings: ambition and past suicidal ideation coexist rather than cancel out.
- He frames happiness and despair as simultaneous truths that one must manage, not mutually exclusive states.