Good One: A Podcast About Jokes

Episode: Phoebe Robinson Is Done Being a Girl Boss

Host: Jesse David Fox
Guest: Phoebe Robinson
Date: October 16, 2025

Episode Overview

In this episode, Jesse David Fox sits down with comedian, writer, and producer Phoebe Robinson to delve into her new YouTube special, "I Don’t Wanna Work Anymore," and her journey from self-proclaimed "girl boss" to a more content, self-aware creative. The conversation is wide-ranging, covering Phoebe’s standup origins, reflections on hustle culture, lessons from her time as a boss, the impact of 2 Dope Queens, personal relationships, and the current state of comedy and podcasting.

Key Discussion Points & Insights

1. Standup, Validation, and Ambition

• Phoebe reflects on her changing relationship to standup:

  “I think I needed standup in a way that I don’t need it now. And I think a lot of it was the sort of, like, external validation...Now I’m in a much more peaceful place where it’s like, I know I’m funny.” (00:40)

• Standup as initial identity: Phoebe describes how, early on, the grind and hustle culture felt normal and was “just a part of the culture” growing up and starting out in New York. (07:06)

2. The "Girl Boss" Reckoning

• Departing from the ‘girl boss’ identity

  “I’m 39, and I don’t want to be a girl boss anymore.” (06:19)

  • Phoebe shares how the girl boss era rooted in the early aughts encouraged overwork, especially for women of color feeling pressure to be twice as good.
  • Tina Fey’s “Bossypants” is cited as a key text that made bosshood appealing and accessible for women in comedy. (08:35–09:38)

3. The Cost of Hustle and Work-Life Balance

• Personal impacts of workaholism:
  – Phoebe looks back at times when her sense of worth was deeply intertwined with professional results, especially during the COVID-19 pandemic.
  – Therapy and introspection have helped her focus on a fuller life:

  “During COVID...I was 100% a workaholic...Now I’m like, there should be layers to my life...I went into therapy and had to do the work on that.” (26:19–27:38)

• The myth of hustling for fulfillment:

  “We were sort of, like, sold a bill of goods that this was going to set us free...We’re just all tired.” (14:35)

4. On Being a Boss

• Positive lesson:

  “I learned about being a boss is it requires a lot of different parts of you...vulnerability, tenderness...those things are feminine qualities and not celebrated as boss attributes. And I think a lot of them actually are.” (23:59–24:58)

• Hardest part:

  “Learning how to fire people...As a Libra, Scorpio moon and Pisces rising, I never want to be the bearer of bad news.” (24:59–25:49)

5. The Burnout and Anti-"Content" Stance

• Treadmill of productivity:

  “It was like a treadmill that you could not get off…I can’t slow down...if I stop, what happens?” (30:49–32:13)

• Exhaustion and boundaries: Her experiences dovetailed with the decline of "girl boss" as an aspirational brand and the rise of creative burnout.

• Phoebe’s anti-content sentiment:

  “Which is why I’m just so anti-content these days. Because I just don’t think that that is how you make good things.” (31:47)

6. Blending Writing and Performing

• Writer first:

  “I think I’m a writer first...I just love language so much. Any comic does.” (18:22–19:58)

  • Phoebe’s distinctive voice carries from her books to her standup.

7. Relationships, Breakups, and Parasocial Dynamics

• Being publicly in a relationship:
  – On her breakup and how the public processed it:

  “Even when we broke up and people were like, ‘You guys broke up?’ I go, I don’t know you, why you thought…I was going to DM every person who follows me and say, ‘I broke up.’” (33:16)

• Standup preceding self-awareness:
  – Previous jokes about her ex contained truths she didn’t fully process until later.
  – “I did love this guy...But in this latest special, it is me taking stock of, like, this person was kind of a hot mess and I was carrying him for too long.” (35:28–38:05)

• Buying her ex teeth (‘reverse colonizing’) and comedic self-deprecation
  – Memorable joke and listener resonance:

  “I bought it. So listen, I wouldn’t do that again...it was a good lesson to learn.” (38:08)

8. On Michelle Obama, Being Starstruck, and the Arena Tour

• Hosting for Michelle Obama and the joke about not farting in front of her:

  “I just held it in till I got back to my hotel room...just the longest fart into my toilet bowl.” (39:41–40:34)

• Responding to Bill Burr’s comments on Michelle Obama’s book tour:

  “I just find it interesting how easily men dismiss the contributions of women if it’s not tied to money...that is work.” (41:44–42:48)

9. Podcasting and the Shift in the Comedy Landscape

• Phoebe and the podcasting boom:

  “Everyone has a microphone...Most of these opinions are ass...You need to take a test before you can have a podcast.” (43:05–45:05)

• Intentionality behind 2 Dope Queens:
  – Started as a live show in 2015 at UCB East, grew organically with intention to spotlight overlooked talent, especially women and comics of color. (46:21–49:13) – Phoebe takes pride in how 2 Dope Queens opened doors:

  “It should be a platform for people who I think are brilliant and don’t have as much attention as they should.” (50:25)

• Relationship with Jessica Williams now:

  “We’re both, like, on our grind...But I have nothing but positive feelings.” (51:30)

10. The Comedy Industry’s Current State

• Cultural change and industry fear:

  “People are scared...They don’t want to do creatively left-of-center things.” (52:02) – Phoebe bemoans streaming culture’s impact and the pressure for continual output.

11. Contentment Over Success

• Redefining ambition:

  “If I don’t want to be a girl boss, what do I want to be? I want to be content.” (58:49)

• Pride and reframing independence:
  – Phoebe is proud of her self-reliance (buying her own apartment) and the impact of her book imprint, Tiny Reparations. (55:31–57:57)

Notable Quotes & Memorable Moments

• “I matched with this guy Kristoff in Berlin...He pulls out his phone to check the rate of the Westin Grand Berlin...This was in the first seven minutes. I’m just like, even if you’re like, ‘Wow, she’s fancy’, keep it on the inside!” – Phoebe (01:38–04:11)
• “If Michelle [Obama] can respond within five minutes, these dudes taking hours? Absolutely not.” – Phoebe (40:49)
• “I’m so voice driven I wouldn’t want to steal anyone else’s joke. But I love watching comics who are totally different from me, like Tig Notaro.” – Phoebe (67:11)
• “Lazy crowd work...If you aren’t going to put the effort in to the time you’re spending at your job, you are essentially wasting your time.” – Phoebe (71:48)
• “What I love about standup is it’s so much like life...It’s not focusing on, I gotta kill, it’s the process of doing it and figuring out what you learn about yourself.” – Phoebe (77:40)
• “Enough of this content. Enough of every year I gotta have a new hour. No, you don’t. Let us miss you. Let us fucking not hear from you for nine months. It’s great.” – Phoebe (77:40–79:29)

Timestamps for Key Segments

• On validation and outgrowing hustle: 00:40–01:11
• Defining ‘girl boss’ and its history: 06:19–09:38
• Impact of COVID and work addiction: 26:19–27:38
• Advice for bosses: 23:49–24:58
• Content burnout—‘treadmill you can’t get off’: 30:49–32:13
• Public relationships and breakups in standup: 33:16–38:05
• Podcasting and 2 Dope Queens’ origins: 43:05–49:13
• Reflections on the industry now: 52:02–53:51
• Contentment over ambition: 58:49–60:26

The Laughing Round (Q&A Lightning Round Highlights)

• Comedic influences: Janine Garofalo, Patrice O’Neal, Chris Rock, Wanda Sykes, Bill Burr (64:47)
• Best time you bombed: “Did standup between stripper acts. The men did not want to hear a woman talk. But it’s worth doing those shows…Now, if I have a bad show, it doesn’t faze me.” (74:45–77:40)
• Favorite YouTube song (funniest): “Vertigo—because they just count Spanish incorrectly!” (70:49–71:19)
• Comedy pet peeves: Lazy crowd work, content for content’s sake, lack of intentionality. (71:48–73:55)
• On allowing yourself to fail: “You don’t get good by always being good. What is that? Doesn’t make any sense.” (79:29)

Episode Takeaways

Phoebe Robinson provides a candid, hilarious, and introspective look at shedding the “girl boss” identity, choosing fulfillment and intentionality over external validation and hustle culture. She reflects on her pioneering work with 2 Dope Queens, her evolution as a performer and boss, and her desire for the comedy industry to slow down and value quality over quantity. Throughout, her distinctive comedic voice and commitment to honesty, both with herself and her audience, stand out.

For listeners new and old, Phoebe’s episode is a rich exploration of ambition, authenticity, and the cost of keeping up with culture’s relentless pace. It’s both a love letter to standup and a rallying cry for contentment and intentional creation.