Why does failure feel so much bigger than it actually is? This week, Amanda is joined by entrepreneur, author, and leadership coach Jane Marie Chen (@janemarie.chen) to spiral about failure: why we're so terrified of it, why we avoid it at all costs, and why it often hurts so much more than the thing that actually happened. Together, they explore perfectionism, rejection, burnout, imposter syndrome, and the childhood experiences that shape our relationship to failure long before we ever encounter it. And what if failure isn't evidence that we're unworthy? What if it's simply the price of catching bigger waves? A reflective spiral about risk, resilience, and learning to love yourself even when things don't go according to plan.

Further Reading: Like a Wave We Break by Jane Marie Chen

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No matter how old we get, there’s a decent chance a small part of us is still trying to impress, understand, forgive, rebel against, or be comforted by our mothers. This week, Amanda is joined by writer and editor Ashley Oerman (@ashleyoerman), author of Motherf*cked, to spiral about one of the most loaded relationships in the human experience: the one between mothers and their children. Together, they unpack the impossible expectations placed on mothers, the ways our earliest relationships shape our adult identities, and why "mommy issues" have become both a punchline and a profound psychological reality. A tender spiral about the stories we spend a lifetime trying to rewrite.

Further Reading: Motherf*cked: How to Stop Your Mothers Toxic Drama from Ruining Your Life by Ashley Oerman

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When we first aired this episode in 2024, burnout felt like the defining emotional state of modern life. Two years later… honestly, not much has improved. If anything, burnout has shape-shifted. The girlboss hustle era may be less aspirational than it once was, but it’s been replaced by new flavors of exhaustion: constant digital overwhelm, economic anxiety, doomscrolling, and the strange pressure to be “healing” productively at all times. So this week, we’re revisiting Amanda’s conversation with the brilliant Amelia Nagoski (@burnoutbookgroup), co-author of Burnout: The Secret to Unlocking the Stress Cycle, for a much-needed refresher on what burnout actually is. Together, they unpack what happens when our bodies get stuck in an incomplete stress response cycle, why modern life keeps us there, and what it actually takes to start feeling better. If you’re emotionally fried, physically depleted, or somehow both overstimulated and numb, this one’s for you. We’ll be back in two weeks with a brand new episode.
Further Reading: Burnout: The Secret to Unlocking the Stress Cycle by Emily Nagoski, PhD, and Amelia Nagoski, DMA

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What does “thinking critically” actually mean and why is everyone so convinced they’re already good at it? This week, Amanda is joined by psychologist and author of Radical Thinking, Peter Lamont to explore how all of our beliefs are shaped by a limited slice of what we notice and how we interpret it, which means disagreement is inevitable. Peter reframes critical thinking as something quieter and more uncomfortable: recognizing the limits of your own perspective and being willing to engage with people who see the world differently. From the role of the internet and social media to why curiosity might matter more than certainty, this episode is a grounded spiral about attention, interpretation, and learning to question your own thinking before anyone else’s.

Further Reading: Radical Thinking: How to See the Bigger Picture by Peter Lamont

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What does a healthy relationship actually look like, and who gets to decide? This week, Amanda is joined by relationship expert Dr. Sara Nasserzadeh (@dr.saranasserzadeh) to overthink "healthy" relationships. Together, they unpack why “healthy” can feel impossible to define, and why a more useful question might be: Does this relationship leave you feeling fulfilled? They explore how many people waste energy trying to fix the wrong things, and Sara breaks down the six ingredients she believes help relationships thrive. From situationships that feel surprisingly safe to whether healthy couples are “boring,” this episode is a grounded spiral about connection, boundaries, and giving yourself permission to believe you deserve the kind of love that feels steady.

Further Reading: Love by Design: 6 ingredients to build a lifetime of love by Dr. Sara

Further Viewing: The 6 Essential Ingredients of Loving Relationships 

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What if the antidote to insecurity isn’t looking inward, but reaching outward? This week, Amanda is joined by psychiatrist and attachment expert Dr. Amir Levine to overthink insecurity; where it comes from, why it can feel so consuming, and how it shapes the way we love. Together, they explore how healing happens in connection and how leaning on your support system and surrounding yourself with secure people can help reshape those patterns over time. From overanalyzing texts to fearing abandonment or pulling away entirely, this episode is a thoughtful spiral about connection, self-trust, and learning how to feel safe in community.

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“Do your own research.” It sounds empowering… so why does it so often lead us straight into confusion, conspiracy, or complete information overload? This week, Amanda is joined by pharmacist and science communicator Dr. Harini Bhat (@tilscience) to overthink what it really means to “do your own research” in the age of the internet. They unpack how a phrase rooted in curiosity became a cultural catchphrase for skepticism, distrust, and DIY fact finding. Why do we feel so confident after reading a few threads or watching a couple of videos? How do algorithms, bias, and the illusion of understanding shape what we think we “know”? And where’s the line between healthy questioning and going down the rabbit hole? A brain bending spiral about knowledge, misinformation, and why thinking critically might be harder (and more necessary) than ever.

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Why does flirting feel so natural for some people and completely impossible for the rest of us? This week, Amanda is joined by dating coach and relationship expert Francesca Hogi (@dearfranny) to overthink the art and anxiety of flirting. Together they unpack why flirting often gets misunderstood as manipulation or performance, how modern dating apps have scrambled our instincts, and why genuine curiosity might be the most underrated flirting skill of all. From the fear of coming on too strong to the panic of missing signals entirely, they explore the psychology behind attraction and the subtle ways we communicate interest. A playful spiral about eye contact, mixed signals, and why flirting might actually be less about being charming and more about being present.

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This week, host Amanda Montell takes the mic solo to overthink the creeping sense of doom that seems to hum beneath modern life. Drawing from her Esquire essay on “doomslang,” she unpacks the language we use to joke about collapse, catastrophe, and existential dread... and what those jokes might be revealing about how we’re actually coping. From ironic nihilism to memeified despair, Amanda explores why we’ve turned apocalypse into punchline, how constant crisis reshapes our nervous systems, and whether calling everything “doomed” is a defense mechanism… or a warning. A short spiral about dread, dark humor, and the strange comfort of saying the quiet part out loud.  

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

To learn more about how to support Minnesota’s immigrant communities, check out this MSP Mag article, which shares several ways to offer help or find support.

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This week, Amanda is joined by psychologist and bestselling author Guy Winch (@guywinch) to overthink workaholism. Why being “busy” feels virtuous, why burnout can masquerade as success, and how overworking often hides deeper emotional needs. Together, they unpack the psychology behind overwork and the quiet ways it can become a socially acceptable addiction. The conversation offers a new lens on why so many of our attempts at “work/life balance” leave us feeling even more depleted and what it might actually take to build a life that feels sustainable instead of performative. A reflective spiral about rest, self-worth, and learning that you are more than what you produce. 

- Join the "Magical Overthinkers Club" by following the pod on Instagram @magicaloverthinkers.

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

To learn more about how to support Minnesota’s immigrant communities, check out this MSP Mag article, which shares several ways to offer help or find support.

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