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May 19
What happens when your brain is loud, your schedule is chaotic, and your best coping skill is making people laugh?
Jessica Michelle Singleton is a no-filter comedian, podcast host, and the kind of ADHD woman who can command a stage, lose her keys, and write a killer joke—all before lunch. She’s dropped two #1 comedy albums, racked up millions of views with her stand-up, and performed alongside comedy heavyweights like Mark Normand and Melissa Villaseñor. But behind the laughs? A woman who always knew her brain worked differently, even if it took years to get a name for it.
Diagnosed in college after nearly losing her scholarship, Jessica shares how undiagnosed ADHD shaped her identity, her anxiety, and her early drive to do it all—four sports, a packed schedule, and straight As. She and Tracy talk about how ADHD shows up in her comedy, why perfectionism nearly sidelined her special, and how growing up in chaos made her both resilient and hilarious. They also unpack family dynamics, trauma, and the real reason so many comedians come from childhoods that were anything but funny.
If you’ve ever felt like a hot mess with a high-octane brain, Jessica’s story is a powerful reminder: sometimes the traits that made you feel “too much” are the exact ones that make you unforgettable.
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"I was doing everything right, and still felt like I was failing. That’s when I realized this wasn’t about effort. It was about understanding my brain."
- Jessica Michelle Singleton
"Stand-up [comedy] gave me back my voice. On stage, I can be messy, raw, brilliant, and unfiltered. I don’t have to hide anything there."
- Jessica Michelle Singleton
"I’m not lazy. I’m not broken. My brain just works differently and I’m allowed to work with it, not against it."
- Jessica Michelle Singleton
"The more real I am, the more the right people find me. That’s true in comedy, and it’s true in life."
- Jessica Michelle Singleton
"I used to think I had to make everyone like me. Now I just want to be fully myself and find the people who love that."
- Jessica Michelle Singleton
- Jessica Michelle Singleton, a successful comedian who has released two #1 comedy albums, shares how she was diagnosed with ADHD during college when her academic performance unexpectedly declined despite previously excelling in school.She explains that in high school, she managed her undiagnosed ADHD by staying extremely busy—playing four sports and joining numerous clubs, which naturally provided the structure and physical activity her brain needed, but in college, without those outlets, her symptoms became unmanageable.
- Jessica recalls early signs from childhood, including a third-grade teacher telling her mother "she's not like the other girls" and could "afford to be more organized," planting an early seed of feeling fundamentally different despite her academic success.
- Jessica Michelle Singleton describes growing up with a brother who was diagnosed with ADHD early, noting how his obvious symptoms overshadowed her quieter manifestation of ADHD, particularly since she was a "peacekeeper" in a chaotic household with a mother who had borderline personality disorder.
- She reflects on her relationship with her mother, who once proudly told a teacher criticizing Jessica's organization that "if she was more organized, she wouldn't be my daughter," showing both acceptance of Jessica's differences but also creating complex family dynamics.
- Jessica shares her medication journey, starting with Strattera which gave her stomach pain, then trying Adderall which helped tremendously with focus but made her irritable, leading to on-and-off medication use before eventually settling on Vyvanse until a heart condition forced her to stop stimulants entirely.
[27:00 - 1:28:15] Comedy Career and ADHD as a Creative Superpower
- Jessica Michelle Singleton discusses how her ADHD manifests in her comedy, explaining that many of her best jokes come from spontaneous thoughts during performances, and notes how the comedy industry is filled with neurodivergent people who've turned their differences into creative strengths.
- She describes the challenges of being a female comedian with ADHD, addressing how men with chaotic personalities are seen as "geniuses" while women face harsher judgment, and shares how maintaining authenticity has helped her find the right audience.
- Jessica talks about her upcoming hour-long comedy special filmed in New Orleans, her career aspirations to tour at theaters with dedicated fans, and her realization that she needs to delegate travel arrangements and business tasks to allow her ADHD brain to focus on what she does best—creating comedy that connects with audiences.
