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Jay Shetty Podcast

Taylor Tomlinson ON: The Quarter-Life Crisis & How to Let Go of Toxic Relationships

Jay Shetty talks to Taylor Tomlinson about why sometimes it’s okay to shift your focus on something else. Dropping out of college doesn’t really mean you’re wasting your time away.

Taylor TomlinsonguestJay Shettyhost

May 23, 20221h 24mWatch on YouTube

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CHAPTERS

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Chapter summaries

Success, grief, and chasing a parent’s approval
Taylor reflects on the bittersweet feeling of succeeding without her mom there to witness it. She describes how grief can create drive—wanting to become someone a parent would be proud of—while also leaving a lasting sadness that achievement doesn’t fully resolve.
- •Taylor shares how family members imagine her mom being proud and present for major moments
- •She says she’s unsure she’d be doing comedy if her mom were still alive
- •Taylor describes the strange mix of motivation and sadness that comes with success after loss
- •She frames it as chasing the approval of someone who’s gone
Jay’s introduction: why he wanted Taylor on the podcast
Jay welcomes listeners and explains how he reached out to Taylor through a connection. He shares what he admires about her work and outlines her background and major career milestones as context for the conversation.
- •Jay says he’s a longtime fan and wanted an excuse to invite Taylor on
- •He lists key moments in Taylor’s career and public profile
- •Jay frames the conversation as getting to know her beyond the highlights
- •Taylor responds with humility and notes she usually expects to be the one learning
How a church conversation led to stand-up—and the many paths of comedy
Taylor explains that her dad signed her up for a stand-up class after hearing about it at church, initially thinking she could help write material. She emphasizes how small moments can shape a life and describes the wide range of comedy work she did beyond the typical ‘special’ path.
- •Taylor says a woman at church mentioned a class and her dad brought her along
- •She describes the origin as unplanned and surprisingly consequential
- •Taylor lists different comedy circuits she worked: cruise ships, corporates, colleges, clubs, churches
- •She notes creative careers rarely follow one standard route
Stage fear, social anxiety, and building confidence through repetition
Taylor and Jay connect over being shy and introverted, and Taylor describes how terrified she felt early on. She explains how she pushed through because she loved it, and how frequent stage time turned fear into a manageable “muscle.”
- •Taylor says she was physically sick with nerves before performing early on
- •She explains she kept going because she wanted it more than she feared it
- •Doing multiple sets regularly reduced pressure and limited time to spiral
- •She notes fear returns when there’s a long break from performing
Quarter-Life Crisis: making uncertainty the material
Taylor describes how being young and feeling inexperienced became the foundation of her comedy. She realized audiences deeply related to the confusion and insecurity of their 20s, even those who looked like they were doing well.
- •Taylor says she didn’t feel she had enough life experience to speak with authority
- •She turned that into a premise: joking about not knowing anything
- •Audience responses showed many people shared the same uncertainty
- •She describes writing now as focusing on what she wants to talk about and finding the people who relate
Dropping out of college—and the harder shift away from being a “clean” comic
Taylor explains she left college because she had enough booked work that she couldn’t attend, while still telling herself she could return. She says the more difficult transition was moving away from being perceived as a clean, church-friendly comedian and dealing with the shame and identity conflict that came with it.
- •Taylor says she only left college after booking extensive college gigs and lacking online options
- •She held onto the idea of returning to school for years
- •She describes internalized shame tied to leaving a “clean comedian” identity
- •Taylor felt caught between church expectations and the broader stand-up world’s culture
Leaving the church comedy market: rigid expectations, doubt, and feeling like she was “lying”
Taylor shares why she chose to stop doing church gigs: the environment demanded a constant role-model identity and strict behavior standards. She describes questioning certainty in religion after her mom’s death, being judged for minor things, and deciding she wasn’t the right fit for that space.
- •Taylor says church gigs weren’t just about being clean on stage—they wanted her to be a Christian role model always
- •She recounts being scrutinized for small things, like language and a tweet with innuendo
- •She describes realizing early that people acted certain about religious answers while she felt nobody really knows for sure
- •Taylor concludes it wasn’t sustainable and that it’s okay not to be right for every audience
Losing her mom at eight: anxiety, imagination, and empathy
Taylor explains how her mom’s death shaped her life, worldview, and creativity. She shares the ongoing complexity of grief—how it affected her anxiety and sense of safety, while also pushing her into imagination and making her more empathetic and driven.
- •Taylor calls it the most important event in her life and wonders who she’d be without it
- •She describes heightened anxiety and nightmares after realizing life can change suddenly
- •Taylor says retreating into imagination as a kid likely strengthened her creativity
- •She emphasizes holding both the difficult and the meaningful effects of loss at the same time
Misconceptions about relationships: dealbreakers vs. what you can work through
Jay shares a story about a vivid dream of betrayal, then asks about beliefs about love that change with age. Taylor talks about learning that even strong relationships face issues, and that it’s often hard—especially in your 20s—to know what’s a true dealbreaker versus something that can be repaired.
- •Jay tells a personal story about dreaming his wife was having someone else’s baby and waking up emotionally affected
- •Taylor shares how a friend in a long-term relationship would pursue therapy to understand cheating rather than immediately leave
- •She says many couples quietly work through problems others assume never happen
- •Taylor highlights how trust and shared history change how conflict and disappointment are handled
The ‘cheated on me in my head’ twist: late confession, gaslighting, and closure
Taylor reveals that the partner from her earlier joke eventually admitted to cheating and apologized, including acknowledging he gaslit her. She explains how the truth shifted her feelings—bringing clarity, compassion, and a sense of putting that chapter to rest, even while recognizing the harm.
- •Taylor says the person from her earlier bit did later admit he cheated
- •She describes receiving a detailed apology that explicitly named gaslighting
- •Taylor explains how the admission complicated her therapy narrative and validated her instincts
- •She reflects on how time and empathy changed her ability to process the relationship
Back-to-back relationships and learning to be alone
Taylor describes realizing she’s been in relationships almost continuously and wants to do the work of being alone. She talks about not being a casual dater, leaning on career focus to avoid personal work, and reframing success as separate from being “worth loving.”
- •Taylor says she’s had back-to-back relationships and suspects it hasn’t been healthy
- •She describes discomfort with casual dating and a pattern of year-to-two-year relationships
- •She says reaching major career goals has pushed her to develop hobbies and self-growth beyond achievement
- •Taylor reflects on believing she had limited time because her mom died young, which fueled rushing and pressure
Adult solitude, long-distance marriage, and the post-show comedown
Taylor and Jay discuss how little time many adults spend single or living alone, and how solitude can become peaceful rather than scary. They also explore the unique contrast between on-stage validation and returning to quiet, emphasizing the need for a steady relationship with oneself.
- •Jay describes asking people to calculate time spent single versus in relationships and what that reveals
- •Taylor shares noticing she’s appreciating living alone more than expected
- •Jay discusses long stretches apart from his wife and adjusting to sleeping alone as habit changes
- •They explore the emotional drop after performances and the importance of being okay with yourself afterward
Comedy, identity, and mental health: jokes aren’t the same as healing
Taylor explains how she once believed turning pain into jokes meant she’d dealt with it, but therapy taught her otherwise. She describes doing consistent private work with a therapist and psychiatrist, and how sharing mental health material brought messages from people who felt seen or encouraged to seek support.
- •Taylor says intellectual understanding doesn’t equal emotional resolution
- •She describes learning that trauma responses can persist physically and emotionally
- •Taylor explains she was nervous about sharing mental health experiences in her special but felt grounded because she was doing the work
- •She frames comedy as expression and skill—not a substitute for healing
Final Five: advice, values, friendships, and journaling as a daily habit
Jay closes with rapid-fire questions that prompt Taylor to share concise personal principles. She highlights flexibility in life decisions, rejects fear-based urgency, values deep trust in relationships, and names journaling as a habit she thinks everyone should do—especially noting how relationships can disrupt it.
- •Taylor’s best advice: you can always change your mind
- •Taylor’s worst advice: if you take time off, everyone might forget about you
- •She says she cares less about being seen as “cool” and more about being happy with her people
- •Taylor describes choosing friends who are hardworking, kind, trustworthy, and willing to talk through conflict
- •She recommends journaling daily and notes she stops journaling when in relationships

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