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How Taylor Tomlinson Writes Jokes | How I Write with David Perell

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30,497 views vs a median of 167,559 across the channel's last 8 long-form uploads · as of Oct 29 · 2 days old, early

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Comedian and author Taylor Tomlinson joins David Perell on 'How I Write' to discuss the architecture of crafting stand-up comedy, the differences between stage specials and prose writing, and the discipline required to turn raw personal experience into universal humor. She details how immediate audience feedback hones comedic premises, how she uses crowd work constructively, and how embracing vulnerability and self-doubt drives long-term creative development.

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    The explainer

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    A 2-minute read. Each underlined phrase opens the video at that second.

    In this deep dive into the comedic craft, David Perell hosts stand-up comedian and author Taylor Tomlinson to dissect the disciplined mechanics of comedic writing. Tomlinson begins by detailing her joke writing process1:05, rejecting the notion of casually discovering jokes on stage and instead relying on extensive notebook brainstorming centered on subjects that spark strong emotional conflict, such as indecision around having children or everyday irritations. She explains that while comedic ideas must originate from deeply personal specifics, the artist's challenge is finding the universal overlap2:55 that allows audiences to recognize their own lives in the premise, as illustrated by her baby laughing on a plane joke4:41.

    Tomlinson emphasizes that comedic success heavily depends on understanding audience perception6:05 and managing stage likability. Rather than assuming an aggressive persona that does not match her natural Midwestern warmth, she shapes jokes to fit how she is perceived. She treats crowd work not as reckless improvisation, but as a structured live interaction9:45 integrated every fifteen to twenty minutes to anchor audiences in a unique shared room while maintaining clear transitions back to her written hour. This immediate onstage testing offers an instant feedback mechanism13:05 that drastically contrasts with the solitary, multi-year delay of writing her essay collection, Actually, Nevermind.

    Transitioning from stand-up to literature required Tomlinson to invert her instincts. In stand-up, the objective is ruthless sentence economy18:40 and a laugh every twenty seconds, whereas prose demanded expanding upon emotional subtleties and accepting slower, private reader engagement. Drawing inspiration from memoirs by Tina Fey, Mindy Kaling, and Amy Poehler15:40, she learned to treat writing as rigorous work. She credits Anne Lamott's Bird by Bird with dismantling her debilitating perfectionism20:55 by reminding her that striving for flawless output only robs life of joy.

    quote
    'A masterpiece incomedy writing...I was hooked fromthe first word'Sunday Telegraph
    ▶ 15:45
    On screen at 15:45

    Tomlinson also recounts pivotal career adjustments, notably discovering that unbalanced self-deprecation23:00 alienated audiences who identified with her, prompting her to counterbalance self-effacing remarks with playful arrogance. When addressing personal tragedies—such as losing her mother at a young age in her Netflix special Look at You—she found that jokes about grief27:20 only land once the comedian is genuinely healed and in control. Rather than indiscriminate oversharing40:30, she insists that true vulnerability allows artists to protect core personal boundaries while still delivering authentic art.

    Finally, Tomlinson discusses her practical workflow, which includes listening to audio voice memos of every set36:45 to distinguish genuine visceral laughs from mere polite "clapter" or partisan cheers. She highlights the necessity of road collaboration with trusted peers like Sophie Buddle and Dustin Nickerson46:30 to discover joke tags. Reflecting on Ann Patchett's essay The Getaway Car, she embraces the poignant metaphor of the pinned butterfly52:10—accepting that turning a vibrant mental idea into words will always feel somewhat diminished, yet continuing to write through persistent self-doubt remains the artist's only viable path forward.

    Highlights
    1. 0:45Crafting jokes from notebooks to stage
    2. 20:50Perfectionism and Anne Lamott's Bird by Bird
    3. 27:20Refining material about grief and personal loss
    4. 46:30Collaborating on the road and defining comedy tags
    5. 52:10Ann Patchett's pinned butterfly metaphor
    Chapters across the 54:01 runtime
    How it's told

    A studio conversation exploring comedy and writing craft

    Format: Interview. Host David Perell interviews comedian Taylor Tomlinson about how the iterative stagecraft of stand-up comedy informs drafting books and managing vulnerability. The discussion moves from notebook joke-building and audience feedback to prose discipline, collaboration, and overcoming artistic self-doubt.

    Story arc

    1. 0:00IntroductionDavid introduces Taylor Tomlinson and explains what writers across genres can learn from the rapid feedback cycles of stand-up comedians.
    2. 0:48The Joke Writing EngineTaylor details her notebook habits, finding charged premises that trigger anger or absurdity, and navigating specific versus universal topics.
    3. 5:48Persona, Likability, and StagingTaylor examines audience perceptions, keeping crowds comfortable, and structuring the crucial first minute of a special.
    4. 9:22Structured Crowd WorkTaylor explains integrating planned crowd interactions into live sets without derailing narrative structure.
    5. 14:12Sponsor InterludeDavid presents a mid-roll spotlight on Alpha School.
    6. 15:32Comedy Memoirs and Craft BooksThe conversation shifts to lessons from memoirs by Tina Fey, Amy Poehler, and Mindy Kaling, alongside Anne Lamott's Bird by Bird on beating perfectionism.
    7. 22:49Vulnerability vs. TherapyTaylor describes framing heavy personal experiences like grief into punchlines without oversharing or alienating listeners.
    8. 29:25Routines and Writing EnvironmentsTaylor and David compare working in public coffee shops to Hasan Minhaj's monastic, distraction-free writing office.
    9. 33:25The Modern Comedy LandscapeTaylor discusses listening to set audio, discerning real laughs from 'clapter', and adapting to social media clip promotion.
    10. 45:47Drafting, Collaborating, and Pushing Through Self-DoubtTaylor explores trading comedy tags with touring partners, the necessity of living life to generate material, and Ann Patchett's pinned butterfly metaphor.

    Setups and payoffs

    1. 0:42Setup David establishes the maxim that 'quantity leads to quality' in stand-up comedy.
      ↳
      45:37Payoff David highlights Taylor's quote emphasizing that overcoming writer's block requires simply writing volume and living life.
    2. 6:08Setup Taylor notes that her stage persona cannot successfully sustain being unlikable.
      ↳
      23:01Payoff Taylor explains learning that excessive self-deprecation repels audiences, forcing her to adjust her delivery.
    3. 17:34Setup Taylor remarks on the grueling, slow nature of drafting long-form prose books.
      ↳
      30:40Payoff Taylor details the rigid daytime drafting schedule she had to invent specifically to finish her book.
    4. 20:41Setup David and Taylor point to a visual stack of writing manuals.
      ↳
      51:40Payoff The interview concludes with a deep dive into Ann Patchett's essay book The Getaway Car.

    Devices

    • Kinetic Quote GraphicsVerbatim excerpts from Taylor's essays displayed full-screen with stylized text framing.21:1844:0645:37
    • Stand-up Performance B-rollClips from live comedy performances and specials illustrating comedic timing and delivery discussed in the conversation.0:080:2746:50
    • Book Cover InsertsVisual book cover graphics appearing on screen when specific writing craft guides and memoirs are mentioned.2:0315:4520:4451:41
    • Direct MetaphorComparing early creative drafting to turning on an old tap until brown muck clears out.33:40

    From the video's own structure, matched to the transcript and on-screen text.

    Teardown

    A long studio interview that earns clicks from Taylor Tomlinson's celebrity, but holds viewers with specific, unglamorous mechanics of drafting, editing, and protecting boundaries.

    Below the channel's typical: 0.2× its typical views (30,497 vs a median of 167,559 across the channel's last 8 long-form uploads, as of Oct 29) · Long-form interview · 2 days old, early

    The promise

    Viewers expect to learn practical comedy and writing lessons from comedian Taylor Tomlinson to make their own writing funnier.

    Packaging

    How it looks in the feed

    Show the feed as
    54:01

    How to Make Your Writing More Funny (Taylor Tomlinson Interview)

    David Perell30K views · 2d agoLearn more about Alpha School at ⁠https://go.alpha.school/howiwrite Taylor Tomlinson is on the show today, and she is one of the world's top comedians with…

    Views and age as of the teardown, Oct 29, 2026. Other videos are blanked out.

    • 3/5Thumbnail imageThe lighting and subject focus are crisp, but it looks like a standard interview frame without built-in drama or visual storytelling.Taylor Tomlinson framed on the left looking slightly off-camera mid-speech against a blurred indoor background.
    • 3/5Thumbnail text““Not Everything Is Writing Material””It pushes back against the common creative trope that everything is material, though it reads more like a quiet realization than an urgent hook.Five words in white serif font inside quotation marks on the right half of the frame.
    • 3/5TitleIt makes a clear skill promise and uses a recognizable name, but the phrasing feels plain and the parenthetical tag reduces momentum.Title structured as a direct how-to followed by '(Taylor Tomlinson Interview)'.
    • 3/5Title + thumbnailThey divide the work adequately with the title promising technique and the thumbnail giving a boundary, but neither generates strong urgency.Title focuses on making writing funny while thumbnail text warns against turning every experience into material.

    Curiosity gap: What experiences does a top comedian choose not to write about, and how does that filter make her writing funnier?

    The three hooks

    The title, the thumbnail text and the first words spoken each make a promise, and each does a different job.

    • Title“How to Make Your Writing More Funny (Taylor Tomlinson Interview)”How-toOutcomeCuriosityIt makes the viewer want actionable comedic techniques from a working professional to improve their writing.
    • Thumbnail text““Not Everything Is Writing Material””Contrarian takeCuriosityLoss aversionIt makes the writer want to know which topics or experiences they should avoid turning into material.
    • First words spoken“Taylor Tomlinson is on the show, who's one of the world's top comedians, with multiple Netflix specials and also a book...”AuthorityProofIt leverages Taylor Tomlinson's credentials as a top Netflix headliner and author to convince writers that her system holds elite creative value.
    • PairingDifferent jobsThe title promises a broad instructional craft lesson while the thumbnail quote presents a contrarian rule on what to leave out.
    • StakesFitsThe conversation accurately delivers practical, hard-won insights on translating stage discipline to written prose without over-dramatizing the stakes.
    • UrgencyNoneThe video presents an evergreen craft discussion without any manufactured time pressure or artificial countdowns.

    The first 20 seconds

    TimeWhat you seeWhat you hearWhat it does
    0:00Guest Taylor Tomlinson gesturing, graphic title card reading 'Taylor'.Host voiceover: 'Taylor...'Immediately introduces the featured guest visually and verbally.
    0:01Title card expands to 'Taylor Tomlinson' over guest smiling.'...Tomlinson is on the show, who's one of the world's...'Frames guest as a major figure in the industry.
    0:02Cut to host sitting in an armchair speaking to the camera.'...top comedians...'Establishes the host and the interview setup.
    0:03Host gestures with both hands explaining her accomplishments.'...with multiple Netflix specials...'Builds guest authority and credibility.
    0:04Poster graphic appears for Netflix special 'Look At You'.'...and also...'Provides visual proof of her comedy specials.
    0:05Poster graphic switches to Netflix special 'Have It All'.'...a book called...'Shows breadth of her produced work.
    0:06Graphic switches to book cover 'Actually, Nevermind'.'...'Actually, Nevermind.''Connects her comedy directly to written book publishing.
    0:07Book cover graphic remains on screen with subtle motion.Brief pause in narration.Lets the viewer register the writing credential.
    0:08Flash transition to b-roll of Taylor Tomlinson performing stand-up on stage.Host: 'Now, I love having...'Shows the guest in action in her primary craft.
    0:09Wide shot of comedy stage with spotlight on Taylor.'...stand-up comedians on the show...'Explains why comedians specifically are featured.
    0:10Wide performance shot continues.'...because there's such a purity...'Sets up the premise about comedic writing discipline.
    0:11Stand-up stage shot continues.'...to their creative process.'Anchors the core topic to the creative process.
    0:12Cut to medium shot of Taylor on stage holding the mic.Music and room tone under narration.Maintains visual interest with closer performance footage.
    0:13Medium shot continues as Taylor delivers a joke.Host takes a breath between thoughts.Showcases guest charisma and delivery.
    0:14Cut back to host in armchair speaking directly to viewer.'No matter what kind of writing you do...'Broadens the value proposition to all writers.
    0:15Host gestures outward with hand.'...you can learn from stand-up comedians...'Delivers the clear takeaway promise of the video.
    0:16Host points upward.'...because what are they doing?...'Plants an open question about comedy craft.
    0:17Host leans forward, gesturing with hands.'...Like any kind of...'Begins unpacking the universal writing mechanics.
    0:18Host continues speaking in armchair.Voiceover continues setting up the comparison.Sustains the setup leading into the conversation.
    0:19Flash transition to wide shot of host and Taylor Tomlinson sitting together on set.Host continues dialogue smoothly across the cut.Reveals the actual interview environment.
    0:20Wide studio shot with both speakers facing each other.Host finishes the transition thought.Enters directly into the core discussion.
    Click confirmation
    Yes, instantly. The opening frame shows Taylor Tomlinson and displays her name, fulfilling the title's guest promise at 00:00.
    Time to the point
    0:14
    Hook
    bold claim
    Reason to stay
    The promise that any writer, regardless of medium, can improve their craft by adopting the creative process of top stand-up comedians.
    Missing on purpose
    No channel bumper, no generic welcome greeting, and no plea to like or subscribe before delivering context.
    Pace and texture
    Fast and energetic. Cuts every 2 to 3 seconds between studio address, credential graphics, and stage performance b-roll over upbeat voiceover.

    Story map

    Explainer. A writer struggles to make their written material sharp and funny without alienating their audience or burning out. The payoff is discovering how stand-up comedy's rapid test-and-discard loop can fix prose writing.

    TimeSectionNew tensionStakesTurnLoops
    0:00 –0:48Hook & The Stand-Up PremiseWhy should general prose writers care how stand-up comedians work?RiseStand-up seems loose and natural, but it relies on an unforgiving, rapid testing loop.Opens: How does a comic's rapid feedback process translate to the page?
    0:48 –5:48Mining Topics & The Airplane Baby JokeHow do you turn a personal annoyance into a joke an entire crowd agrees with?RiseGoing specific works, but complaining about a laughing child risks making the comic look terrible on stage.Opens: How do you protect your likability when delivering harsh observations?Closes: How does an annoyance turn into a stage bit?
    5:48 –9:22Stage Perception & First MinutesWhat happens if the audience dislikes your persona within the first sixty seconds?HoldYou cannot pretend to be an edgy character if your natural visual presence reads like an earnest Midwestern daughter.Opens: How do you control an audience without letting live crowd interactions derail the script?Closes: How do you balance harsh material with stage likability?
    9:22 –14:12Disciplined Crowd Work & Fast FeedbackDoes unscripted audience banter destroy the structure of an hour-long set?HoldCrowd work is not random riffing; it is a rigid 15-minute interval tool anchored to written themes.Closes: How to include live audience interaction without losing control of the set.
    14:12 –15:32Mid-Roll Sponsor BreakDoes the viewer want to sit through an education product pitch?FallSag: no turn
    15:32 –22:49Book Drafting vs. Stand-Up EconomyCan a stand-up comic survive writing a book where nobody laughs out loud?RiseStand-up forces extreme compression, therefore writing prose requires retraining yourself to expand instead of constantly cutting.Opens: How do you share dark personal history without turning a show into an uncomfortable therapy session?Closes: How comedic timing changes from the stage to the page.
    22:49 –29:25Self-Deprecation & Staging TraumaWhere is the line between relatable vulnerability and pathetic oversharing?RiseAudiences hate relentless self-loathing, therefore you must balance vulnerability with unearned arrogance.Opens: What physical routine produces this output without falling into the tortured artist trap?Closes: How to joke about grief without turning the set into therapy.
    29:25 –35:17Writing Environments & Internet ClipsDo viral short-form social clips destroy the artistic integrity of an hour-long special?HoldClips sell tickets, but you cannot write for the clip; you have to write for the full hour.Opens: How do you verify if material actually works when you are off stage?Closes: How to manage social media clip pressure.
    35:17 –40:25Audio Memos & Dissecting LaughsHow do you tell real laughter apart from polite applause?HoldCheering and clapping mean the audience agrees with your point, but it does not mean the line is funny yet.Opens: How much of your real private life belongs to the audience?Closes: How to tell real humor apart from audience agreement.
    40:25 –45:47Privacy Boundaries & The Creative TapDoes being authentic require selling every private detail of your life for content?HoldYou do not need to monetize every painful or joyful memory; some experiences must stay private.Closes: What experiences should never become material.
    45:47 –54:00Collaboration, Tags & Ann Patchett's ButterflyWhy does every brilliant creative idea feel ruined once put on paper?FallEven master essayists feel like they kill their best ideas upon writing them down, therefore self-doubt is just part of the job.Closes: How to survive creative self-doubt.

    Payoff: delivered in part at 18:42. Taylor breaks down the exact mechanical difference between verbal punchlines and page prose, though much of the video explores broader creative routines rather than a tactical step-by-step tutorial. Ending: Ends abruptly on Taylor reflecting on Ann Patchett's metaphor of creative grief, without a formal sign-off, summary, or teaser for future episodes.

    Leaks

    Where a viewer might leave. Guesses from watching, not retention data.

    • 7:27 David shifts from specific writing techniques to broad thoughts on movie three-act structure and show setup, slowing the momentum.
    • 14:12 A full 80-second hard commercial break for Alpha School with unrelated school footage halts the conversation flow.
    • 32:10 The discussion drifts into generic lifestyle chat about touring diets and eating chicken tenders, straying from writing craft.
    • 45:22 Host reads generic platitudes ('you just need to write') that sound like common writing clichés rather than fresh tactical advice.

    Steal this

    1. Bespoke-to-Universal Transition Explains how starting with a narrow, unflattering personal reaction (annoyance at a laughing baby) uncovers a shared unspoken thought. 4:38
    2. Mock-Arrogance Counterweight Prevents deep vulnerability from feeling pathetic by pairing heavy confessions with playful, unearned boasting. 24:36
    3. Laugh vs. Clapter Diagnostic Gives creators an objective filter: applause or cheers indicate agreement, whereas involuntary laughter proves comedic punch. 37:33
    4. Scaffold-and-Tag Expansion Shows how to lock down one proven central line first, then freely riff secondary punchlines off that anchor. 48:49

    Skip this

    • Relying on traveling writing partners to test lines daily Only works because Taylor tours constantly with paid opening acts who are professional comedy writers.
    • Dismissing social media clip creation as an afterthought Only feasible when you already possess multiple hour-long Netflix specials driving organic theater ticket sales.

    Open questions

    • What specific notebook organization system does Taylor use to catalog premises across multiple years?
    • How does the host's audience breakdown between prose essayists and comedy fans affect overall retention?

    Teardown by Avail.video from the thumbnail, the title, the first 20 seconds and the report's notes on the whole video.

    On screen

    Everything the video showed you

    Slides, frameworks, quotes and formulas, captured verbatim with the moment they appeared. Tap any card to jump there.

    Reference shelf

    People, ideas and things mentioned

    Said means mentioned aloud; Shown means it appeared on screen.

    People16

    • Taylor TomlinsonStand-up comedian, author of 'Actually, Nevermind', and host of 'After Midnight'.0:00Said + shown0:02Shown0:08Said + shown0:21Said + shown0:45Said + shown42:19Said + shown43:24Said + shown47:07Said + shown
    • David PerellHost of the 'How I Write' podcast, writer, and writing instructor.0:00Said + shown0:02Shown0:45Said14:18Said + shown42:12Said + shown
    • Judy CarterComedian and author of 'The Comedy Bible'.2:02Said + shown2:03Said + shown
    • Dustin NickersonStand-up comedian, friend, and touring partner of Taylor Tomlinson.4:42Said4:47Said46:45Said46:52Shown46:53Said47:08Said
    • Mitch HedbergStand-up comedian known for surreal humor and one-liners.11:44Said + shown
    • Tina FeyComedic writer, actress, and author of 'Bossypants'.15:36Said15:38Said15:44Shown15:45Said + shown
    • Mindy KalingActress, comedy writer, and memoirist.15:40Said15:46Shown15:47Said + shown
    • Amy PoehlerComedic actress, producer, and author of 'Yes Please'.15:48Said15:56Said + shown16:07Said
    • Anne LamottAmerican novelist and nonfiction author of 'Bird by Bird'.20:42Said20:43Shown20:44Said + shown20:45Said + shown20:46Said + shown
    • Neal AllenAuthor who co-wrote 'Good Writing' with Anne Lamott.20:45Shown20:46Shown
    • Hasan MinhajStand-up comedian and writer known for high-concept specials.29:33Said29:45Said
    • Ed SheeranEnglish singer-songwriter.33:40Said
    • Sophie BuddleStand-up comedian, touring partner, and monologue writer.46:42Said46:50Said + shown46:57Said
    • Brian ReganAmerican stand-up comedian known for theater touring.49:42Said + shown
    • Kathleen MadiganAmerican touring stand-up comedian.49:43Said + shown49:44Said
    • Ann PatchettAmerican author of 'The Getaway Car' and numerous novels.51:15Said51:40Shown51:41Said + shown53:02Said

    Ideas & frameworks7

    • Actually, NevermindBook of comedic essays authored by Taylor Tomlinson.0:05Said + shown0:06Shown15:35Said42:20Said + shown
    • The Comedy BibleComedy craft guide book written by Judy Carter.2:02Said + shown2:03Shown
    • BossypantsAutobiographical comedy book written by Tina Fey.15:44Shown15:45Shown
    • Is Everyone Hanging Out Without Me?Humorous memoir collection authored by Mindy Kaling.15:46Shown15:47Shown
    • Yes PleaseMemoir book by Amy Poehler.15:56Shown
    • Bird by BirdInfluential book on writing craft and life by Anne Lamott.20:41Said20:43Shown20:44Said + shown
    • The Getaway CarMemoir essay on writing and life by Ann Patchett.51:15Said51:40Shown51:41Shown

    Organizations1

    • Alpha SchoolK-12 educational institution featured as podcast sponsor.14:13Shown14:32Said + shown14:33Said + shown15:26Shown

    Things on screen4

    • Look at YouTaylor Tomlinson's 2022 Netflix stand-up comedy special.0:03Shown0:04Shown2:43Shown27:20Said
    • Have It AllNetflix comedy special by Taylor Tomlinson.0:05Shown2:44Shown
    • Quarter-Life CrisisComedy special by Taylor Tomlinson.2:42Shown
    • FleabagBritish comedy-drama television series created by Phoebe Waller-Bridge.50:05Said50:11Shown
    Video description

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    By the numbers

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    The video

    Views
    30.5K
    Likes
    484
    Comments
    40
    Published
    Oct 26, 2026
    Length
    54:01
    Category
    People & Blogs
    YouTube's topics
    Entertainment, Humour
    Captions
    No
    HD
    Yes
    Language
    English
    Paid promotion
    None declared
    Made for kids
    No
    License
    Standard YouTube

    Creator's tags

    • writing advice
    • how to write
    • writing guide
    • writing
    • advice
    • writing lessons
    • writing books
    • writing online
    • writing essays
    • writing articles
    • knowledge
    • productivity
    • david perell
    • how i write
    • podcast

    The channel

    Subscribers
    333K
    Videos
    771
    Total views
    26.3M
    Channel age
    9 years (since Jan 2017)
    Country
    United States
    Uploads
    about every 6 days
    Across the last 8 long-form uploads
    Before this video
    5 days after the previous long-form upload

    Calculated by Avail.video from YouTube's public numbers

    Outlier score
    0.2× · Too early to tell
    Views against the median of the channel's last 8 long-form uploads
    Views per subscriber
    0.09
    Likes vs the channel's usual
    1.1× the channel's usual
    1.6% of views vs a usual 1.5%
    Comments vs the channel's usual
    1.1× the channel's usual
    0.13% of views vs a usual 0.12%
    Rank among recent uploads
    #9 of 9
    By views: this video and the channel's last 8 long-form uploads
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    Watched by Avail.video · 2026-10-29