166. Questlove: The Art of Self-Sabotage

Ira Glass has appeared on the Working It Out podcast three times before, and usually it’s Mike asking Ira for advice, whether it’s about podcasting or storytelling. But now the tables have turned: Ira recently listened to a stand-up set he performed years ago, he has the itch to try it again, so he’s come to Mike for comedy advice. On this episode, Mike and Ira listen to Ira’s old stand-up set in real time, break down what worked and what didn’t, and brainstorm ideas for Ira’s next set.Please consider donating to your local public radio or television station.

Zarna Garg first appeared on the Working It Out podcast in 2022 and since then her popularity has continued to rise. Zarna explains to Mike how she has built her comedy career like a business, and why performing for an audience of one or two is no different for her than performing for an audience of thousands. Mike and Zarna discuss free speech in Zarna’s native India, and what it’s like for her to raise her kids in America. Plus: why no one in Zarna’s family has been allowed to read her memoir This American Woman.Please consider donating to Unicorn Island

After decades of being a beloved comedian’s comedian Jessica Kirson has broken out in the last few years with viral crowd work videos and a brilliant new special on Hulu called “I’m The Man.” Mike and Jessica dig deep into the nuts and bolts and emotional work of being a stand-up comic, including overcoming stage fright and dealing with hecklers. Jessica breaks down the difference between her on stage and off stage personas, and recalls her childhood which was spent listening in, with her stepbrother Zach Braff, on her therapist mother’s sessions. Plus, Mike has an awkward experience in a steam room and Jessica tells the story of when she put a heckler up against a wall.Please consider donating to The Children's Heart Foundation

This week the legendary Ahmir Thompson (aka Questlove) sits down for his first appearance on Working It Out. Mike and Questlove discuss touring with his father’s band as a kid, every DJ’s worst nightmare, and how jealousy and self-sabotage can affect even a member of a band as iconic as The Roots. Plus, what it was like accepting an Oscar after The Slap and the behind-the-scenes process of Quest’s new documentaries Sly Lives! and Ladies & Gentlemen... 50 Years of SNL Music.Please consider donating to: The Food and Finance High School

Rachel Feinstein recently appeared as a surprise guest on one of Mike’s shows at the Beacon Theatre, where Mike observed after the show that everything Rachel said in the green room could be a bit. Now, on the heels of her Netflix special Big Guy, and in her third appearance on Working It Out, Rachel spills all the details about living with other comedians, the time she moved in with a Bengali family she met on a bus, and all the red flags she ignored in her previous relationships. Plus, Mike shares an unflattering movie offer he received and Rachel defends her pre-schooler’s permanent record.Please consider donating to Friends of Firefighters

This week Andrew Schulz comes on the podcast and Mike and Andrew break apart why the two of them are unlikely work friends. They discuss Andrew having Donald Trump on his podcast, Andrew’s new deeply personal Netflix special, “Life,” and the politics of free speech in comedy. Plus, Andrew reveals the guest he regrets having on his podcast, “Flagrant.”Please consider donating to The Carlos Rodon Foundation

Comedian Josh Johnson is a writer and correspondent for The Daily Show and his stand-up sets have millions of views on YouTube. Josh talks with Mike about cultivating a fan base via the YouTube videos, why he thinks chasing success in the comedy industry is sometimes antithetical to the art form, and shares the advice he got from Trevor Noah. Plus, Josh helps Mike work out a new story about animals living in Mike's walls.Please consider donating to Feeding America

At the top of this Best of WIO episode featuring Elizabeth Gilbert, Mike reads a new piece that he wrote for Elizabeth's Letters From Love Substack.(Recorded November 2024) Author Elizabeth Gilbert wrote one of Mike’s favorite books about creativity, Big Magic. She also wrote a book that, to her surprise, become a cultural phenomenon: Eat, Pray, Love. Mike and Liz discuss the unexpected impact of Eat, Pray, Love, and what it was like for Liz to watch Julia Roberts portray her on the big screen. Liz gets candid about the ups and downs of a creative life, including the reasoning behind the cancellation of a novel she wrote that took place in Russia. Plus, some bawdy jokes and stories care of Liz’s uncles and grandfather, and the surprising reason why Liz was stopped at airport security. Please consider donating to The Loveland Foundation

For this all-new Working It Out Q&A, Mike fields listener questions about people fainting at his shows, how to write comedy about topics that are painful to you, and balancing a day job and creative life when starting out. If your question didn’t get answered on this week’s Q&A, stay tuned for another one soon where Mike answers the rest! Got a new question? Email [email protected] with a VoiceMemo asking your question.

Pete Holmes returns to help Mike punch up some last minute jokes before the premiere of Mike’s show The Good Life at the Beacon Theatre in New York. What follows is a heated debate about puns, an attempt to define and dissect the nature of “clean” comedy, and, yes, a nuts and bolts joke writing session. Plus, Pete psychoanalyzes the state of Massachusetts, and Mike recalls the time he opened for Tracy Morgan.Please consider donating to Homeboy Industries