Mike Birbiglia's Working It Out
Episode: Questlove – The Art of Self-Sabotage
Original Air Date: October 6, 2025
Guest: Questlove (Amir Thompson)
Host: Mike Birbiglia
Episode Overview
This episode of "Working It Out" features an inspiring, candid conversation between Mike Birbiglia and Questlove, spanning creativity, self-sabotage, music, documentary filmmaking, and personal journeys through fame and self-acceptance. The discussion revolves around how creatives grapple with vulnerability, rejection, and the fear of success, using Questlove’s own life and projects—especially his acclaimed documentaries and musical career—as the lens.
Key Discussion Points & Insights
1. Mistakes and the Creative Process
- Music vs. Comedy & Mistakes:
- Questlove distinguishes the musician’s relationship to mistakes from that of comedians. For musicians, performing every note perfectly signals something is wrong—unlike in comedy, where the "mistake" can become part of the act.
“People say something's wrong when I play it right. Like the Roots guys know I'm mad when I play everything correct.” — Questlove [02:14]
- Questlove distinguishes the musician’s relationship to mistakes from that of comedians. For musicians, performing every note perfectly signals something is wrong—unlike in comedy, where the "mistake" can become part of the act.
- The conversation ties into Questlove’s SNL documentary, emphasizing how rhythm and timing unite music and comedy [02:33].
2. Self-Sabotage and Fear of Success
- Relating to ‘Don’t Think Twice’ and Questlove’s Docs:
- Questlove shares that Mike’s film made him rethink how artists self-sabotage, sometimes unconsciously, out of a desire for control and fear of the unknown.
“I believe that most people self sabotage, you know, because we want to control. We want to know what's next.” — Questlove [05:46]
- Questlove shares that Mike’s film made him rethink how artists self-sabotage, sometimes unconsciously, out of a desire for control and fear of the unknown.
- Success as a Source of Anxiety:
- Both host and guest discuss how success can feel as frightening as failure—Questlove admits to times he’s rooted against his own success.
"Declines are familiar. Letdowns are familiar, disappointments are familiar...even success is scary." — Questlove [06:28]
- Both host and guest discuss how success can feel as frightening as failure—Questlove admits to times he’s rooted against his own success.
3. Making 'Sly Lives' and Dealing with Artists
- Getting Honest Contributions from Artists:
- Questlove describes the challenge of getting high-profile musicians (like D’Angelo and André 3000) to open up about vulnerability and self-defeating behaviors [08:01].
“There was 19 other artists that flat out said no or said yes. And seven hours later you’re on set like, are you coming or not?” — Questlove [08:35]
- Questlove describes the challenge of getting high-profile musicians (like D’Angelo and André 3000) to open up about vulnerability and self-defeating behaviors [08:01].
- Sly Stone’s Influence and DJ Culture:
- The episode dives into how Sly Stone shaped Bay Area youth culture and counter-culture as a DJ, paralleling Questlove’s eclectic, boundary-crossing style [13:12].
"Sly is an open format DJ...that was sort of unheard of, mixing rock and soul on the same radio station." — Questlove [14:40]
- The episode dives into how Sly Stone shaped Bay Area youth culture and counter-culture as a DJ, paralleling Questlove’s eclectic, boundary-crossing style [13:12].
4. Quests for Authenticity and Record-Collecting
- Roots of Questlove’s Musical Exploration:
- Growing up in a musical family, digging through both hit songs and “flops” shaped Questlove’s comprehensive, unpredictable sets.
“So I'm probably the first music expert that gravitated towards the flop song.” — Questlove [21:10]
- Growing up in a musical family, digging through both hit songs and “flops” shaped Questlove’s comprehensive, unpredictable sets.
- He describes being thrust into professional music as a child, learning from his father’s nightclub band [18:51].
5. Crafting Iconic Documentary Moments
- Editing and Curating for SNL Doc:
- Questlove recounts spending 11 months to assemble a seamless musical montage for his SNL doc, using deep musical theory and serendipitous lyrical links for transitions [23:40].
“Whenever I hear a song, the first thing I say to myself is, what key is this in? How many BPMs?” — Questlove [23:53]
- Questlove recounts spending 11 months to assemble a seamless musical montage for his SNL doc, using deep musical theory and serendipitous lyrical links for transitions [23:40].
6. The 2022 Oscars 'Slap' and Processing Fame
- Oscars Night and the Slap:
- Questlove reflects on the surreal experience of winning an Oscar right after the infamous "slap," including his own nervousness about winning and dread of being in the spotlight [29:10–34:16].
“I was just sitting there, like, frozen, totally channeling out what was happening...I just went back to, oh, God, it's all gonna be different.” — Questlove [32:18]
- He humorously notes his ex saying he got his “manifuckwish”—the "quietest" Oscar win ever due to the chaos overshadowing it [35:16].
- Questlove reflects on the surreal experience of winning an Oscar right after the infamous "slap," including his own nervousness about winning and dread of being in the spotlight [29:10–34:16].
7. Navigating Jealousy and the Tortoise-and-Hare Journey
- On Jealousy and Career Comparison:
- Both discuss envy experienced towards peer artists’ sudden success, the pain of being only “prestige” instead of “hitmakers.”
“Inside my voice I'm like, I do care about that shit.” — Questlove on being seen as not caring about hit status [42:59]
- Questlove recalls feeling Fugees- and Outkast-envy in the Roots' early days, only to realize, years later, the slow, steady journey is more rewarding [44:05–45:35].
“This was absolutely, positively the best storybook ending ever.” — Questlove [44:20]
- Both discuss envy experienced towards peer artists’ sudden success, the pain of being only “prestige” instead of “hitmakers.”
8. Turning Points: Embracing Leadership and Vulnerability
- From Second Banana to Center Stage:
- Questlove unpacks his longstanding pattern of hiding behind collaborators or instruments and how teaching at NYU forced him out of his comfort zone [53:15].
“I realized there's a level of leadership vulnerability that I've been avoiding by hiding in plain sight.” — Questlove [54:16]
- Questlove unpacks his longstanding pattern of hiding behind collaborators or instruments and how teaching at NYU forced him out of his comfort zone [53:15].
- Accepting and Challenging Himself:
- He describes his everyday battle to show up fully, engage directly, and not shrink from leadership or self-promotion [54:52–55:34].
9. Simple, Lasting Advice
- The Power of Showing Up:
- Questlove attributes much of his success to simply continuing to show up, even when he isn’t the first choice or doesn’t have the most accolades.
“A lot of things I just show up for is because someone else didn't show up for it... you just have to show up.” — Questlove [56:18]
- Questlove attributes much of his success to simply continuing to show up, even when he isn’t the first choice or doesn’t have the most accolades.
Notable Quotes & Memorable Moments
-
On Self-Sabotage:
“I’m probably the first person that would actually actively root against something good happening to him.” — Questlove [06:35] -
On DJing and Connecting Eras/Genres:
“In my mind, my thing is, how am I gonna connect Benny Goodman and Kendrick Lamar.” — Questlove [13:25] -
On the Roots’ status:
“We were critically acclaimed. But critically acclaimed doesn't necessarily mean that we're hit makers...” — Questlove [42:20] -
On Career Longevity:
“Would you rather your second album sell 12 million units and... crash and burn... Or would you rather tortoise and hare your way... and not realize that you’ve made it?” — Questlove [44:20] -
On Self-Acceptance and Showing Up:
“I know I’m the fifth person or the sixth person, but you just have to show up.” — Questlove [56:18]
Key Timestamps
- 02:14: The difference between mistakes in comedy vs. music
- 05:46: Self-sabotage as an artist's coping mechanism
- 08:01: Challenges of eliciting real vulnerability from documentary subjects
- 14:40: Sly Stone’s boundary-breaking DJ approach
- 18:51: Questlove’s childhood in professional music environments
- 23:40: Editing the SNL opening musical montage
- 32:18–35:16: Questlove describes his Oscars experience post-"slap"
- 42:59: Admitting desire for mainstream success (not just critical acclaim)
- 44:05–45:35: Reflection on the value of a slow-burning, enduring career
- 53:15–54:52: The shift to embracing personal vulnerability and leadership
- 56:18: Sage advice: the importance of consistently showing up
- 57:56: Spotlight on Food and Finance High School, Questlove’s nonprofit of choice
Resource Links
- Questlove’s SNL and Sly documentaries: Peacock & Hulu/Disney+
- Food and Finance High School: (link to be included in show notes)
Final Thoughts
This episode stands out as a deep-dive into the emotional and psychological lives of high-achieving creatives. Questlove’s candidness about insecurity, standing in one’s own way, and eventually learning to embrace vulnerability offers lessons not just for artists but for anyone striving for authentic success. The laughter and rapport with Mike Birbiglia, combined with honest stories of anxiety, competition, and fulfillment, make this conversation both grounding and inspirational.