Comedian Caleb Hearon just turned 30 and he’s already got an hour-long HBO special, hosts a hit podcast (So True with Caleb Hearon), and was named one of the top social media influencers of 2025 by Rolling Stone. But it hasn’t been an easy road. Caleb talks with Mike about his battles with suicidal ideation, how improv comedy saved his life, and how he drew on the passing of his estranged father for his comedy special. Plus, Caleb and Mike discuss the value seeing stand-up live vs. on TV, and come up with a plan to go off the grid and live in a cabin in the mountains together.

Please consider donating to: https://kctenants.org/

Listen and subscribe to the Working It Out here:
https://podcasts.apple.com/us/podcast/mike-birbiglias-working-it-out/id1515419751

Find Mike:
Website: https://birbigs.com/
Instagram: https://instagram.com/birbigs/
Facebook: https://facebook.com/birbigfans
TikTok: https://tiktok.com/@mikebirbiglia

Find Caleb:
Website: https://calebhearon.komi.io/
Instagram: https://www.instagram.com/calebsaysthings/
Tiktok: https://www.tiktok.com/@calebsaysthings

Hosted and Produced by Mike Birbiglia
Producers: Peter Salomone, Joseph Birbiglia, Mabel Lewis, Gary Simons
Video Consultant: Graham Willoughby
Special Thanks: Marissa Hurwitz, Josh Upfal, David Raphael, Nina Cwik, J. Hope Stein, Oona
Music: Jack Antonoff and Bleachers