Michelle Weise: Be a Skills Translator, AI-proof Your Future

Do you want to live forever? Bryan Johnson - the gazillionaire tech entrepreneur who started the "don't die" movement - created headlines (and some schadenfreude giggles) when he announced he was diagnosed with autoimmune gastritis, which is incurable. The don't die website says: "We are at war with death and its causes. We are building towards an infinite horizon. We are fighting for the freedom to exist as long as one chooses. Why? Because we have things to do tomorrow. And tomorrow’s tomorrow. Until we no longer want tomorrow." But Ben brought this topic to Caitlin because it's kicked off a discussion about the risks of longevity and the legitimacy of longevity in general. Caitlin shares what she thinks of longevity *routines* and what's legit vs. what's baloney. There's one thing everyone can agree on though: we love our black plastic spatulas, even if the microplastics are killing all of us slowly. Dr. Ingrid Yang's article for Outside is here. This episode was edited by Molly Rose Hart.

If you’ve ever listened to NPR’s Planet Money, you know the vibe: They take dense, eye-glazing economic theories and turn them into cinematic, human-driven stories. Whether following a t-shirt across the global supply chain, buying a barrel of crude oil, or creating a shell company, Planet Money has spent over 15 years proving that economics isn’t just for academics - it impacts our lives every single day. In this episode, Ben talks to Planet Money reporter and host Alex Mayyasi, author of the New York Times bestselling Planet Money: A Guide to the Economic Forces That Shape Your Life. They talk about the counterintuitive lessons from classic Planet Money cases, like why ATMs actually increased bank teller jobs and what that teaches us about automation. Plus they talk about some of the structural issues with the economy today, how markets are underrated, and why restaurants are so important. Check out Alex's Substack and new show, Gastronomics. See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

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.

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 [email protected] Simplify on YouTube Simplify on Instagram Subscribe to our newsletter here.