Raising Boys Who Can Feel Things with Ruth Whippman

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.ResourcesCaitlin's Rec: The Will to Change, bell hooksBen's Rec: Shuggie Bain, Douglas StewardRuth's book: BoyMom: Reimagining Boyhood in the Age of Impossible Masculinity---Let us know what you thought of this episode! Find us on Instagram at @simplifypod. Subscribe to our newsletter on beehiiv here. Also, you can email us at [email protected] 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.ResourcesJasmine Sun's articleBill Burnett - designing your lifeEmail us at [email protected] on YouTube Simplify on InstagramSubscribe 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.

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. ResourcesHeather'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 MeHeather's campaign: #EverydayLookism Heather's website: heatherwiddows.com Coming soon: Selfie Culture by Heather WiddowsAlso 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 TolentinoMore from Simplify on this topic: our episodes with Amy Key (Arrangements in Blue) and Elise Hu (Flawless)See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

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 [email protected] 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.ResourcesBabushka 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 [email protected] on InstagramSubscribe 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.

What did you make on the internet, back before anyone was paying you to?This time around, Ben takes the interview chair. He's talking with Joanna Walsh, writer, artist, arts activist, author of twelve books, several of them co-written with AIs she coded herself (badly and on purpose <3). Her new book Amateurs! is a philosophical history of the internet we all built for free: the Tumblrs, the blogs, the aesthetic wikis, the momentary flashes of hilarity. Her starting point is the French sense of the word—amateur, from amour. Not a beginner or someone who isn't any good, but someone who does the thing for love, without expecting to be paid.Joanna and Ben get into what happened to the braided conversation of early Twitter, the difference between paying attention online and performing it, and why Joanna's answer to "should we just log off?" is an immediate and emphatic no. There's a thread about vulgarity—she means it as a compliment—and what it revealed when people started mashing up Girl with a Pearl Earring.Then there's the dead internet: how we'd know we'd arrived, and whether we'd know at all. Joanna's image for it involves the sea, and it's the best thirty seconds in the episode.Her advice for anyone starting out right now isn't optimism. It's a union card.ResourcesGuest's book: Amateurs! How We Built Internet Culture and Why It Matters by Joanna Walsh (Verso, 2025)Ben's Rec: New Dark Age: Technology and the End of the Future by James Bridle. Also worth your time: Ways of Being.Caitlin's Rec: What to Save and Why: Identity, Authenticity, and the Ethics of Conservation by Erich Hatala Matthes (Oxford University Press, 2024)New: we're putting outros and bookends up on video. Find the Simplify page on YouTube and tell us what you think — we're experimenting with all of it.Let us know what you thought of this episode! Find us on Instagram at @simplifypod. Subscribe to our newsletter on beehiiv here. Also, you can email us at [email protected] episode of Simplify was produced by Caitlin Schiller, Ben Schuman-Stoler, and Molly Hart. 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.

What if almost everything you're doing to "optimize" your health is, at best, doing nothing at all?Caitlin sits down with Dr. Nicola Guess—dietitian, Oxford nutrition scientist, and quite possibly the best BS detector in the wellness space. She studies blood sugar and diabetes for a living and dismantles nutrition nonsense for fun. The twist that makes her worth listening to: she used to believe the hype herself, so she doesn't lecture—she just sets the record straight.Together they run the wellness interent's current greatest hits through her unsentimental filter—the cortisol cocktail, apple cider vinegar, the glucose goddess, creatine for your brain, the whole "maxxing" carnival. Some of it survives. Most of it doesn't. There's a thread about the one supplement Nicola actually keeps in her cupboard, and another about why the genuinely good advice is doomed to stay boring forever.The best part: Nicola shares a debunking framework that you can use on anything at all, from a nutrition reel to a headline to a guy trying to sell you on extra insurance.ResourcesGuest's Rec: work on nutrition misinformation by Alex Ruani, UCL researcher Ben's Rec: Salt, Fat, Acid, Heat by Samin Nosrat Caitlin's Rec: Calling Bullshit: The Art of Skepticism in a Data-Driven World by Carl T. Bergstrom and Jevin D. WestAlso mentioned: Dr. Guess's Substack, Dr Guess's Blog; Stuart Phillips (protein researcher); the Being Well podcast with Rick and Forrest HansonLet us know what you thought of this episode! Find us on Instagram at @simplifypod. Subscribe to our newsletter on beehiiv here. Also, you can email us at [email protected] episode of Simplify was produced by Caitlin Schiller, Ben Schuman-Stoler, 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.

AI replacing our colleagues, feeling lonelier than ever despite enforced physical presense at the office. What is going on with the workplace?Caitlin sits down with Christine Armstrong, researcher, author, and founder of Armstrong & Partners, who has spent years doing something refreshingly unfashionable: actually asking people what's happening at work, instead of just theorizing about it. Christine is one of the world's top voices on the future of work, and she goes well beyond boardrooms and TED stages. She visits call centers in the north of England and local authority offices drowning in AI-generated letters to study the quiet erosion of the relationships that used to make work feel like it mattered.The conversation moves through two tangled questions: what is AI actually doing to our working lives (as opposed to what we've been promised it will do) and why are we so lonely, even when we're technically surrounded by colleagues? There's a thread about the gap between what CEOs think their companies are doing with AI and what workers on the ground are experiencing. A thread about what happens when the "human" becomes the luxury tie, and a surprising riff on gossip.ResourcesBen's Rec: The Anxious Generation by Jonathan Haidt Caitlin's Rec: Better Offline podcast by Ed ZitronAlso mentioned:Armstrong & Partners — Christine's research and speaking consultancyThe Mother of All Jobs: How to Have Children and a Career and Stay Sane(ish) by Christine Armstrong (Bloomsbury, 2018)Let us know what you thought of this episode! Find us on Instagram at @simplifypod. Subscribe to our newsletter on beehiiv here. Also, you can email us at [email protected] episode of Simplify was produced by Caitlin Schiller, Ben Schuman-Stoler, 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.

Diets fail us all the time, and yet we usually blame ourselves. This physician says that neither the blame nor the failure are necessary.In the episode, Caitlin sits down with Dr. Yoni Freedhoff—Canadian physician, obesity expert, and one of the first doctors in his country board-certified in obesity medicine—for a conversation about his book, The Diet Fix. Dr. Freedhoff's book really isn't a diet book at all. Its premise is simple: any diet can work, and the trick is understanding the handful of reasons they usually don't.They get into why a diet built on hunger is doomed before it starts, why food is so much more than fuel, and why exercise—for all its gifts—is a surprisingly lousy engine for weight loss. There's a thread about the marshmallow test, a reframe of willpower as biological rather than a measure of your moral fiber, and a 10-day reset built on one radical instruction: notice your own patterns before you try to change them.The part that lingers is the gentlest: Yoni's phrase, "your best weight" that isn't a number at all, but the healthiest life you can honestly enjoy. Not "can I eat less," but "can I happily eat less?"ResourcesFeatured Book: The Diet Fix: Why Diets Fail and How to Make Yours Work by Dr. Yoni FreedhoffBen's Recs: A small stack of willpower-and-habits books: The Power of Habit by Charles Duhigg, The Willpower Instinct by Kelly McGonigal, Atomic Habits by James Clear, and Tiny Habits by BJ Fogg. Plus his Guardian piece on refusing to be a salad purist: "French beans good, cucumber bad. Please, no."Caitlin's Rec: Eat to Live by Dr. Joel Fuhrman, which is a callback to an early Simplify episode and the origin of the immortal "G-BOMBS" (greens, beans, onions, mushrooms, berries, seeds)Also mentioned: Dr. Yoni Freedhoff's blog Weighty Matters.Let us know what you thought of this episode! Find us on Instagram at @simplifypod. Subscribe to our newsletter on beehiiv here. Also, you can email us at [email protected] episode of Simplify was produced by Caitlin Schiller, Ben Schuman-Stoler, 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.

10,000 downloads a month. 11 episodes. 6 months of independence. Caitlin and Ben sit down for a bonus episode to talk about where Simplify has been and where it's going. They bought the show back from Blinkist at the end of last year, set some ambitious goals, and hit all of them. This episode is a chance to catch up, say thank you, and let you in on what's coming next.They get into the ins and outs of funding Simplify and why neither of them is interested in a race to the bottom. There's also a thread about what Simplify has always been—a lens, not a quick fix—and how that's becoming more true, not less, as the show evolves.And they have a couple of things to ask of you.Those Two things:1) Please fill out the Simplify listener survey—it takes just a few minutes and genuinely shapes the show.2) If Simplify brings something to your life and you'd like to help keep it going, you can donate at buy us a coffee. It means more than you know.You can find us on Instagram at @simplifypod. Subscribe to our newsletter on beehiiv here. Also, you can email us at [email protected] episode of Simplify was produced by Caitlin Schiller, Ben Schuman-Stoler, 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.

What if the thing standing between you and a better day at work isn't a new habit—but just knowing which play to run?Amy Morin is the psychotherapist behind the 13 Things Mentally Strong People Don't Do series, which has sold over a million copies and sparked one of the most-watched TEDx talks of all time. Her new book, The Mental Strength Playbook, takes a different tack. Where her earlier work was preventative, this one is urgent care. Fifty plays you can run in the moment you need them: before the presentation, during the spiral, in the middle of a task that feels completely pointless.Caitlin and Amy get into why positive thinking can actually leave you less prepared, what happens in your brain when you step away from a problem and the answer shows up in the shower, and a surprisingly simple vagus nerve trick that can drop your anxiety in thirty seconds. You'll also hear how Amy arrived at this work through personal loss that reshaped everything she thought she knew about helping people.Mental strength isn't about pushing through pain at all costs. It's about having enough clarity on your own values to know which battles are yours—and enough flexibility to let the rest go.ResourcesAmy's new book: The Mental Strength Playbook by Amy MorinAmy's rec: How to Not Know—launching May 2025 Caitlin's rec: Wanting: The Power of Mimetic Desire in Everyday Life by Luke Burgis Ben's rec: Indistractable: How to Control Your Attention and Choose Your Life by Nir EyalAlso mentioned: Amy's podcast Mentally Stronger, the 13 Things Mentally Strong People Don't Do series (6 books), Man's Search for Meaning by Viktor Frankl, Four Thousand Weeks by Oliver BurkemanLet us know what you thought of this episode! Find us on Instagram at @simplifypod. Subscribe to our newsletter on beehiiv here. Also, you can email us at [email protected] episode of Simplify was produced by Caitlin Schiller, Ben Schuman-Stoler, Molly Rose Hart, and mixed & mastered 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.