Overthinking About Millennial Optimism

Millennials... are we feeling hopeful again? After a week that gave us a rare dose of political optimism, we’re revisiting an episode about the generation that came of age during a recession and then somehow became embarrassing simply for existing online. In this re-air of Overthinking Millennial Cringe, Amanda is joined by Kate Kennedy (@katekennedy), host of Be There in Five and author of One in a Millennial, to unpack the side parts, skinny jeans, earnest internet behavior, and the fear of being cringe. But this time around, we’re listening with a slightly different question in mind: what if some of that earnestness, idealism, and refusal to stop caring is actually worth holding onto Consider this a little millennial optimism for anyone who thought we were permanently doomed to be the generation of “adulting” jokes and The Office references.Further Reading: One in a Millennial by Kate Kennedy Join the "Magical Overthinkers Club" by following the pod on Instagram @magicaloverthinkers. To access early, ad-free episodes and more, subscribe to the Magical Overthinkers Substack. Pick up Amanda's book The Age of Magical Overthinking: Notes on Modern Irrationality, or listen to the audiobook. Get 40% off select Lola Blankets products at Lolablankets.com by using code [MAGICAL] at checkout. Experience the world’s #1 blanket with Lola Blankets.  Go to https://BUYRAYCON.com/MAGICALOPEN to get up to 50% off sitewide during Learn more about your ad choices. Visit podcastchoices.com/adchoices

This week, Amanda overthinks capitalism with scholar, activist, and author Ash Bohrer (@ajbohrer), whose new book Capitalism and Confinement looks at the systems shaping so much of our daily lives. They get into why trying to be the “perfect” ethical consumer can become its own thought spiral, whether regulation is enough to fix what feels broken, and the super annoying reality that you cannot personally shop, save, or optimize your way out of a structural problem. Ash also talks about why so much of our anxiety around capitalism gets turned inward, when the bigger question is what we can actually change together. A surprisingly hopeful spiral about money, power, community, and whether there really could be another way.Further Reading: Capitalism and Confinement by A.J. Bohrer Join the "Magical Overthinkers Club" by following the pod on Instagram @magicaloverthinkers. To access early, ad-free episodes and more, subscribe to the Magical Overthinkers Substack. Pick up Amanda's book The Age of Magical Overthinking: Notes on Modern Irrationality, or listen to the audiobook. Get 40% off select Lola Blankets products at Lolablankets.com by using code [MAGICAL] at checkout. Experience the world’s #1 blanket with Lola Blankets.  If you’re ready to launch your business before Black Friday, go to https://SHOPIFY.COM/magical to start your free trial. Listeners of our show get an additional 35% discount when they go to https://SMILESET.com/MAGICAL Learn more about your ad choices. Visit podcastchoices.com/adchoices

Why do we feel guilty when we haven’t actually done anything wrong? This week, Amanda overthinks guilt with psychiatrist Dr. Jennifer Reid (@jenreidmd) , author of Guilt-Free: Reclaiming Your Life From Unreasonable Expectations. They unpack the difference between guilt that helps us repair something and guilt that tells us we’re never doing enough, plus the sneaky way it can make us feel responsible for things we can’t actually control. Then, listener thought spirals, like: moving away from aging relatives, feeling guilty for being too tired to enjoy nature, and more. Maybe the goal isn’t to get rid of guilt entirely, but to figure out whose expectations you’re carrying. A spiral about guilt, control, impossible expectations, and letting your own needs count. Further Reading: Guilt-Free: Reclaiming Your Life From Unreasonable Expectations by Dr. Jennifer Reid Join the "Magical Overthinkers Club" by following the pod on Instagram @magicaloverthinkers. To access early, ad-free episodes and more, subscribe to the Magical Overthinkers Substack. Pick up Amanda's book The Age of Magical Overthinking: Notes on Modern Irrationality, or listen to the audiobook. See Amanda, in person! Sounds Like A Cult is coming to you LIVE from The Elysian in LA on October 15th! Get tickets at soundslikeacult.com! If your glasses are overdue for a refresh, now is the time. Use code PODCAST15 for 15% off your first order at ⁠⁠⁠bit.ly/3OdtU5X Learn more about your ad choices. Visit podcastchoices.com/adchoices

If your trauma helped shape who you are, what happens to you when you start healing it? This week, Amanda is joined by complex trauma expert, therapist, and NYU adjunct professor Dr. Gillian O’Shea Brown, LCSW (@dr.gillianosheabrown), author of Psyche’s Awakening, to untangle some of the questions that tend to get flattened into therapy-speak online. They overthink the difference between acute and complex trauma, why certain songs can send us straight back into an old emotional reality, whether being cheated on can be traumatic, and how to know if you’re actually processing your pain or just overwhelming yourself all over again. They also get into closure fantasies, talking to the parent who hurt you, the strange ways old wounds can become ambition or perfectionism, and the fear that healing might erase the person you fought so hard to become. An eye opening spiral about triggers, coping mechanisms, closure, and becoming more yourself instead of less. Further Reading: Psyche’s Awakening by Dr. Gillian O’Shea Brown, LCSW Join the "Magical Overthinkers Club" by following the pod on Instagram @magicaloverthinkers. To access early, ad-free episodes and more, subscribe to the Magical Overthinkers Substack. Pick up Amanda's book The Age of Magical Overthinking: Notes on Modern Irrationality, or listen to the audiobook.See Amanda, in person! Sounds Like A Cult is coming to you LIVE from The Elysian in LA on October 15th! Get tickets at soundslikeacult.com! Thanks to our Sponsors: Download Whatnot today and get $20 Off and free shipping on your first purchase.  If your glasses are overdue for a refresh, now is the time. Use code PODCAST15 for 15% off your first order at ⁠⁠⁠bit.ly/3OdtU5X Learn more about your ad choices. Visit podcastchoices.com/adchoices

Would you ever date an AI boyfriend? Before you say absolutely fucking not, consider this: plenty of people who swear they’d never have an “AI relationship” are already turning to chatbots for reassurance, emotional processing, difficult conversations, or the occasional late-night spiral. This week, Amanda is joined by Bridget Todd (@bridgetmarieindc), host of There Are No Girls on the Internet and author of Love at First Prompt: AI and the Future of Intimacy, to overthink what happens when technology starts creeping into our most private emotional spaces. They talk about women using AI for romance because dating men feels increasingly hostile, neurodivergent people using chatbots to rehearse human connection, the appeal of a boyfriend who literally never gets tired of talking about books, and the very real misogyny baked into “girlfriends who never say no.” But in the world of large language models, who gets to own, shape, and profit from the parts of us that feel most intimate. An inquisitive spiral about loneliness, desire, digital intimacy, and who gets access to our inner worlds.Further Listening: Love at First Prompt by Bridget Todd Join the "Magical Overthinkers Club" by following the pod on Instagram @magicaloverthinkers. To access early, ad-free episodes and more, subscribe to the Magical Overthinkers Substack. Pick up Amanda's book The Age of Magical Overthinking: Notes on Modern Irrationality, or listen to the audiobook. See Amanda, in person! Sounds Like A Cult is coming to you LIVE from The Elysian in LA on October 15th! Get tickets at soundslikeacult.com! Use code MAGICAL at jonesroadbeauty.com to get a Free Gift with your first purchase! #JonesRoadBeauty #ad If your glasses are overdue for a refresh, now is the time. Use code PODCAST15 for 15% off your first order at ⁠⁠⁠bit.ly/3OdtU5X Learn more about your ad choices. Visit podcastchoices.com/adchoices

What if you actually get your dream job... and then realize you're not living the dream you thought you would? This week, Amanda is joined by Cherie Brooke (@cherie.brooke) and Jean (@_jeanluo), hosts of the Tiger Sisters podcast (@tigersisterspodcast), who both left impressive corporate careers after discovering that the jobs their younger selves would have killed for no longer fit the lives they wanted. Together, they overthink golden handcuffs, the privilege built into pursuing passion, and why a job doesn’t have to provide purpose, identity, money, joy, and self-actualization all at once. They talk about taking sabbaticals, experimenting before making a giant career leap, letting yourself “fade in and out” of ambition, and why a perfectly good job that pays the bills might actually be part of your dream life.  A thoughtful spiral about ambition, career pivots, and building a dream life instead of obsessing over one perfect job.Further Listening: Tiger Sisters Podcast - Join the "Magical Overthinkers Club" by following the pod on Instagram @magicaloverthinkers. - To access early, ad-free episodes and more, subscribe to the Magical Overthinkers Substack. - Pick up Amanda's book The Age of Magical Overthinking: Notes on Modern Irrationality, or listen to the audiobook. Learn more about your ad choices. Visit podcastchoices.com/adchoices

 We say we want more human connection, so why can texting “want to hang?” feel weirdly like begging? This week, Amanda is joined by ICU nurse, New York Times bestselling author, and Stories from a Stranger host Hunter Prosper (@hunter_prosper), whose work interviewing strangers has taught him that connection often starts with something deceptively simple: actually listening. Together, they overthink why we assume we’re burdening our friends, the case for the humble 20-minute “micro hang,” and how to be vulnerable without accidentally oversharing your way into an intimacy level you never signed up for. They also get into our increasingly unrealistic expectations around constant communication, why one awkward social moment probably isn’t being dissected in the group chat, and how many potential friendships die because everyone is waiting for someone else to make the first move.A thoughtful spiral about loneliness, vulnerability, and being brave enough to say hi first. Further Reading: Stories From A Stranger by Hunter Prosper - Join the "Magical Overthinkers Club" by following the pod on Instagram @magicaloverthinkers. - To access early, ad-free episodes and more, subscribe to the Magical Overthinkers Substack. - Pick up Amanda's book The Age of Magical Overthinking: Notes on Modern Irrationality, or listen to the audiobook. Thanks to our Sponsors: Download Whatnot today and get $20 Off and free shipping on your first purchase.  If your glasses are overdue for a refresh, now is the time. Use code PODCAST15 for 15% off your first order at ⁠⁠⁠bit.ly/3OdtU5X Sign up for your one-dollar-per-month trial today at ⁠⁠⁠https://SHOPIFY.COM/magical Save 20% Off Honeylove by going to https://honeylove.com/Overthink Learn more about your ad choices. Visit podcastchoices.com/adchoices

Are you ambitious... or just exhausted? This week, Amanda is joined by award winning journalist and author of The Ambition Penalty, Stefanie O'Connell (@stefanieoconnell), to unpack one of the most misunderstood words in our vocabulary, ambition. They explore why ambition isn't a fixed personality trait, how corporate culture rewards some people while penalizing others for the exact same behavior, and why women are so often expected to walk an impossible tightrope between being "too much" and "not enough." They answer listener thought spirals about external validation, comparison, girlboss burnout, trad wives, capitalism, and whether it's possible to want a big life without letting your achievements define your worth. A validating spiral about redefining success and realizing your ambition was never the problem.Further Reading: The Ambition Penalty by Stafanie O'Connell - Join the "Magical Overthinkers Club" by following the pod on Instagram @magicaloverthinkers. - To access early, ad-free episodes and more, subscribe to the Magical Overthinkers Substack. - Pick up Amanda's book The Age of Magical Overthinking: Notes on Modern Irrationality, or listen to the audiobook. Get 20% off at https://BUYRAYCON.com/MAGICALOPEN Sign up for your one-dollar-per-month trial period at https://SHOPIFY.COM/magical  Learn more about your ad choices. Visit podcastchoices.com/adchoices

This week, Amanda is joined by entrepreneur, former supreme court attorney and professional poker player, and author of You Can Just Do Things, Cate Hall, to unpack why starting over feels so terrifying and why it might be the very thing that leads us toward a more authentic life. Together, they chat about the fear of quitting, the sunk cost fallacy, why we crave a tidy life story, and how to tell the difference between running away from something and running toward yourself. They also answer listener thought spirals about toxic jobs, divorce, changing careers, moving across the world, getting "too old" to begin again, and whether it's ever really too late to start over.Further Reading: You Can Just Do Things by Cate Hall with Sasha Chapin - Join the "Magical Overthinkers Club" by following the pod on Instagram @magicaloverthinkers. - To access early, ad-free episodes and more, subscribe to the Magical Overthinkers Substack. - Pick up Amanda's book The Age of Magical Overthinking: Notes on Modern Irrationality, or listen to the audiobook. - If your glasses are overdue for a refresh, now is the time. Use code PODCAST15 for 15% off your first order at ⁠⁠⁠bit.ly/3OdtU5X ⁠- Download Whatnot today and get $20 Off and free shipping on your first purchase.  Learn more about your ad choices. Visit podcastchoices.com/adchoices

Why are we so afraid of getting older? Is it really about wrinkles... or are we actually afraid of losing our purpose, our identity, and the people we love? This week, Amanda is joined by oncologist, bioethicist, and Eat Your Ice Creamauthor Dr. Ezekiel "Zeke" Emanuel (@drezekielemanuel) to unpack our culture's obsession with staying young. Together, they explore why the wellness industry's promises of longevity miss the point, why curiosity matters more than looking 25 forever, and why some of the happiest, most meaningful years of life may still be ahead of us. They answer listener thought spirals about Botox, becoming "invisible," feeling behind in adulthood, retirement, and whether getting older has to mean becoming less yourself. A hopeful spiral about learning to fear aging a little less... and living a little more. Further Reading: Eat Your Ice Cream by Ezekiel J. Emanuel, MD - Join the "Magical Overthinkers Club" by following the pod on Instagram @magicaloverthinkers. - To access early, ad-free episodes and more, subscribe to the Magical Overthinkers Substack. - Pick up Amanda's book The Age of Magical Overthinking: Notes on Modern Irrationality, or listen to the audiobook. Thanks to our Sponsors: Sign up for your one-dollar-per-month trial today at ⁠⁠https://SHOPIFY.COM/magical Learn more about your ad choices. Visit podcastchoices.com/adchoices