Simplify

What do you do when you're not feeling creative? What do people like Lin-Manuel Miranda, Jenny Slate, and James Acaster do?
In this third installment of our new a/v format - EXTRA - Caitlin drives. Sparked by a supercut episode of Mike Birbiglia’s Working It Out podcast, she asks Ben what he knows about creativity and how he approaches it.
Together, Ben and Caitlin discuss how to discover your own unique voice, how ritual and reps beat raw motivation, and why creativity requires enough psychological safety and rest to actually bloom.
This episode was produced by Caitlin Schiller, Molly Rose Hart, and Ben Schuman-Stoler.
See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

What does a five-year-old boy learn from the word "buddy"?
When Ruth Whippman started shopping around a book about boys in 2021, publishers mostly shrugged—boys, surely, have it great. Ruth, a British journalist, former BBC documentary-maker, and raising three boys, suspected masculinity was full of blind spots nobody was bothering to look at. By the time BoyMom: Reimagining Boyhood in the Age of Impossible Masculinity came out in 2024, masculinity had become one of the defining arguments of an election year, and her hunch looked a lot like foresight.
Caitlin and Ruth start with some science neither of them has stopped thinking about—what boys need from the very beginning, and what we tend to give them instead. From there, the conversation moves through a first day of kindergarten, an all-boys classroom that fell hard for Mr. Darcy, and the strange math of an identity defined mostly by what it isn't.
Then it goes somewhere harder. Ruth spent months building rapport with self-identified incels, and what she found in those forums surprised them both. It's a tender, unsettling stretch of conversation, and it lingers.
Afterward, Ben—father of two sons—joins Caitlin in the bookend to talk through what landed. Ruth's parting thought is one line from the book that quietly rearranges the whole ledger of who wins under patriarchy.

Resources
Caitlin's Rec: The Will to Change, bell hooks
Ben's Rec: Shuggie Bain, Douglas Steward
Ruth's book: BoyMom: Reimagining Boyhood in the Age of Impossible Masculinity
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This episode of Simplify was produced by Caitlin Schiller, Ben Schuman-Stoler, and Molly Rose Hart, and engineered by João Lucas in Berlin, Germany, for Kollo Media.
See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Why do commencement speeches suck so often? That's easy. They suck when the speaker is out of touch with their audience - new graduates. That's why legendary ones like from David Foster Wallace and George Saunders and Steve Jobs are so good, because they balance personal experience in a way that connects with a new generation.
This year, multiple tech CEO commencement speakers were booed across the US for being so out of touch with new grads' realities. When you’ve spent four years paying up for a degree, hearing an ultra-wealthy AI sponsor tell you to "get on the rocket ship" or whatever while the entry-level job market evaporates feels less like inspiration and more like an insult. Honestly, I'm proud of the grads for booing.
In this second edition of our new format - we're calling it Simplify EXTRA - we look at why traditional career advice is failing Gen Z, and what a genuinely useful path forward looks like. Ben drives this episode and brought Caitlin Jasmine Sun’s Substack article, 🌻 the old world is dying: opinionated advice for c/o 2026 graduates which offers some tips from one Gen Zer to other Gen Zers toward building a meaningful life when the old rules no longer apply.
Then Caitlin and Ben trade some life advice and share what they think future grads need to hear.
And yes, we’re still testing out our new video format! We’re tweaking the studio setup, playing with lighting, and dialing in the camera angles, so please send us your feedback - we’d love to know what you think.
Resources
Jasmine Sun's article
Bill Burnett - designing your life
Email us at info@kollomedia.com
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This episode was produced by Caitlin Schiller, Molly Rose Hart, and Ben Schuman-Stoler.
See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

When did "I resolve to be a better person" get replaced with "I resolve to tone my arms" in the register of resolutions?
For a long time, philosophy treated caring about how you look as proof you weren't serious. Heather Widdows, Professor of Philosophy at the University of Warwick, thinks philosophy was simply wrong. In Perfect Me: Beauty as an Ethical Ideal, she argues that beauty has stopped being a matter of taste and become a moral framework—a thing around which we build our days, measure our worth, and feel we've failed at, morally, when we fall short. The self became the body.
In this episode, Caitlin and Heather get into the four ingredients of the global beauty ideal, why so much talk about beauty "diversity" is fluff on top of a narrowing mean, and how a beautification practice goes from optional to invisible to required.
Caitlin also pushes back. Pretty privilege is real—and so is the sixteen-year-old who believes being perfect would fix everything actually wrong? Heather's answer is more honest than comforting, and it takes a detour through Emily Ratajkowski's memoir. They're refreshingly candid about why the way we look matters and what it means to not make the normie cut.

Resources
Heather's Book: Perfect Me: Beauty as an Ethical Ideal by Heather Widdows Ben's Rec: Aesthetica by Allie Rowbottom
Caitlin's Rec: "I Wish I Could Have a Body in Private" by Amy Key, from her Substack So Glad I'm Me
Heather's campaign: #EverydayLookism Heather's website: heatherwiddows.com Coming soon: Selfie Culture by Heather Widdows
Also mentioned: My Body by Emily Ratajkowski; What's Wrong with Lookism? by Andrew Mason; Jia Tolentino's New Yorker essay on "Instagram face,” Trick Mirror by Jia Tolentino
More from Simplify on this topic: our episodes with Amy Key (Arrangements in Blue) and Elise Hu (Flawless)
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What if the fastest way out of the beauty standard is deciding you're a horse?
This is the first of a new thing. On the weeks there's no interview, Caitlin and Ben take turns bringing each other one idea they found out in the world – a new term, a newsletter, a cultural weather system – and turn it over together.
Caitlin drives this one, and she brings bimbo stoicism: a philosophy invented on TikTok by a thirty-year-old Georgian creator called Babushka, who took the two halves of her own personality – a bimbo and a stoic – and made three tenets out of them. Ben had never heard of it. By the end he can recite them.
Then there's the homework, which is the fun part: find your twin animal. Not a spirit animal, not a personality quiz but an actual look at your own face that asks you to see something other than a list of things to fix.
The format still doesn't have a name. So email us at info@kollomedia.com if you have a good idea!
We're trying the video format out, playing with the studio cameras and the lighting so please do send us your feedback, we'd love to hear what you think.

Resources
Babushka on TikTok: @babushka.en.
"Wtf is Bimbo Stoicism? Unpacking the internet's wildest new beauty trend" by Laura Pitcher for Dazed
Kibbe body types
Email us at info@kollomedia.com
Simplify on Instagram
Subscribe to our newsletter here.

This episode was produced by Caitlin Schiller, Molly Rose Hart, and Ben Schuman-Stoler.
See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.