Should I move or stay where I am? Take the job or turn it down? Text back or disappear into the ocean? This week, host Amanda Montell (@amanda_montell) is joined by Vicki Tan (@vickiheart), a digital product designer and author, to gently spiral about indecision: why it’s so hard to choose, what’s actually hiding underneath all that back-and-forth, and how much of it is really fear dressed up as logic.
Together, they unpack the mental clutter, perfectionism, and quiet grief that decision making so often stirs up, and ask what it would feel like to choose without trying to be perfect. A spiral into possibility, analysis paralysis, and the sacred mess of not knowing what comes next.
Further Reading: Ask This Book A Question by Vicki Tan

- 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 a hard copy of Amanda's book The Age of Magical Overthinking: Notes on Modern Irrationality, or listen to the audiobook.

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In the digital age, the people we feel closest to sometimes don’t even know we exist. This week, host Amanda Montell (@amanda_montell) is joined by Jessica Zier and Lizzie Li, PhD students at Northwestern University who study parasocial relationships, to spiral about the emotional life of one-sided intimacy. Together, they explore how digital closeness blurs the line between connection and projection, and why it makes perfect sense that we feel so seen by people who’ve never met us. A soft spiral into loneliness, identity, and the very human instinct to reach for connection, even through a screen.

- 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 a hard copy of Amanda's book The Age of Magical Overthinking: Notes on Modern Irrationality, or listen to the audiobook.

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The case of Amanda, a writer whose internal monologue won't stop narrating her life, instead of just letting her live it.

Listen to Proxy with Yowei Shaw

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What happens when the future is something you have to build, but others get to inherit? This week, host Amanda Montell (@amanda_montell) is joined by journalists Wailin Wong and Stacey Vanek Smith (@svaneksmith) to overthink the emotional, historical, and spiritual weight of generational wealth: what it gives, what it withholds, and who it was never designed for. Listen as they explore the systems that have kept generational wealth out of reach for so many marginalized communities, the guilt of those who inherit it and do care, and the quiet alienation of watching others take it for granted.
A layered spiral into privilege, precarity, and what it means to want stability in a world that’s never been fair.
Further Listening: The Indicator from Planet Money
Further Reading: Machiavelli For Women by Stacey Vanek Smith 

- 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 a hard copy of Amanda's book The Age of Magical Overthinking: Notes on Modern Irrationality, or listen to the audiobook.

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In an age where everyone has to have a hot take, how does this shape our inner voice? This week, host Amanda Montell (@amanda_montell) is joined by journalist Fortesa Latifi (@hifortesa) to unpack the emotional weight of opinion overload: the pressure to react, post, and declare where we stand before we’ve even had a chance to feel what we feel. Together, they explore what it means to live in a world where silence is suspect, nuance is suspicious, and uncertainty is quietly taboo. What do we lose when we’re expected to be explainable at all times? A soft spiral into the exhaustion of constant takes, the grief of unspoken thoughts, and the quiet rebellion of saying “I don’t know yet.” 

- 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 a hard copy of Amanda's book The Age of Magical Overthinking: Notes on Modern Irrationality, or listen to the audiobook.

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How much of who you are is really you—and how much is habit, circumstance, or a story you started telling yourself a long time ago? This week, host Amanda Montell (@amanda_montell) is joined by journalist and author Olga Khazan (@olganator) to explore the strange, sticky concept of personality: where it comes from, why it feels so permanent, and whether we can actually change it. We touch on the appeal of personality frameworks like Myers-Briggs and the Enneagram, but zoom out to ask deeper questions: Do people ever really change, or do we just learn how to act differently? What happens when we no longer feel like the person we’re known to be? A quiet spiral about identity, adaptability, and the mysterious choreography of who we become.Further Reading: Me, But Better: The Science and Promise of Personality Change by Olga Khazan 

- 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 a hard copy of Amanda's book The Age of Magical Overthinking: Notes on Modern Irrationality, or listen to the audiobook.

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Why do we, against all logic, evidence, and bank account balances, still kind of believe that billionaires earned it? This week on Magical Overthinkers, host Amanda Montell (@amanda_montell) sits down with writer and cultural critic Dasia Sade (@dasiadoesit) to unravel the glittery, gaslight-y spell of billionaire worship in America: how it started, who profits from it, and what it’s doing to our collective sense of possibility (and sanity). From Calvinism to Musk, we trace how a stew of religious guilt, PR manipulation, and celebrity obsession shaped a culture where having a billion dollars feels aspirational instead of deeply dystopian. Plus: why most of us can’t actually comprehend how much a billion is, what billionaires are really doing with all that money, and what it might take to finally break the spell (spoiler: it’s not another Forbes profile).

- 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 a hard copy of Amanda's book The Age of Magical Overthinking: Notes on Modern Irrationality, or listen to the audiobook.

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What even is laziness? A moral failing? A personality flaw? Or just capitalism talking? In a culture obsessed with productivity and grindset mentality, the fear of being perceived as “lazy” runs deep—and it’s often weaponized against people who are overwhelmed, burnt out, or simply existing outside the hustle.
To help us rethink laziness from a more philosophical (and compassionate) perspective, host Amanda Montell (@amanda_montell) is joined by Ellie Anderson (@ellieanderphd), philosopher, college professor, and co-host of the podcast Overthink. Together, they explore where our cultural obsession with busyness comes from, how laziness intersects with class and race, and why doing nothing might just be the most radical act of all.
Further listening: Overthink podcast with Ellie Anderson and David Peña-Guzmán.

- 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 a hard copy of Amanda's book The Age of Magical Overthinking: Notes on Modern Irrationality, or listen to the audiobook.

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Is intuition just a fancy word for guesswork, or is it a real, reliable tool we can actually trust? And if it is real, how do we tell the difference between genuine gut feelings and anxiety disguised as instinct? For a phenomenon that’s supposed to be effortless, intuition can spark a lot of magical overthinking. To help untangle it all, host Amanda Montell (@amanda_montell) is joined by journalist and author Elizabeth Greenwood (@lizgreenwood4u), whose new book Everyday Intuition explores the science, psychology, and everyday magic of tuning into your inner voice. Together, they dive into how intuition really works, why it's often misunderstood, and how to cultivate it without spiraling into self-doubt.
Further reading: Elizabeth Greenwood’s Everyday Intuition (available May 6th!). 

- 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 a hard copy of Amanda's book The Age of Magical Overthinking: Notes on Modern Irrationality, or listen to the audiobook.

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The decision to cut someone out of your life—whether a parent, a sibling, or a once-close friend—can feel both deeply necessary and impossibly fraught. But why does going no contact inspire so much shame, confusion, and second-guessing, especially when it’s often a tool for self-preservation? What does it really mean to choose absence over obligation?

In this episode, host Amanda Montell (@amanda_montell) is joined by Jeanette Tran, a professor at Drake University who explores the complexities of estrangement through an unexpected lens: Shakespeare. Drawing from centuries-old drama, Jeanette helps us parse why going no contact still feels so taboo, how literature mirrors (and sometimes distorts) our ideas of family and forgiveness, and why choosing peace can be the most radical act of all.

Further reading: Jeanette Tran’s essay “As more Americans go ‘no contact’ with their parents, they live out a dilemma at the heart of Shakespeare’s ‘King Lear’” in The Conversation.  

- 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 a hard copy of Amanda's book The Age of Magical Overthinking: Notes on Modern Irrationality, or listen to the audiobook.

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