Perfection Is the Devil: Daniel Smith on Boredom, Envy, and Why Our Darkest Emotions Aren’t So Dark episode artwork

EPISODE · Mar 30, 2026 · 39 MIN

Perfection Is the Devil: Daniel Smith on Boredom, Envy, and Why Our Darkest Emotions Aren’t So Dark

from Keen On America · host Andrew Keen

“Perfection is the devil. Growth means a greater capaciousness, not a narrowing and an optimisation.” — Daniel SmithDon’t feel bad about feeling bad. That’s the message of Daniel Smith’s therapeutic new book, Hard Feelings: Finding the Wisdom in Our Darkest Emotions. Smith — psychotherapist, anxiety memoirist, married Brooklynite — wants to rescue boredom, envy, shame, and regret from the category of emotions that are supposed to shame us. The things that bore us most — raising children, long marriages, breakfast with your spouse for the two thousandth time — are also the most meaningful. Boredom, Smith argues, is the price we pay for meaning. Our darkest emotions aren’t quite as dark as we fear. Five Takeaways•       Boredom Is the Price of Meaning: The things that bore us most — raising children, long marriages, eating breakfast with your spouse for the two thousandth time — are also the most meaningful. Repetition is boring. But that’s where the connection, the love, and the main event reside. Boredom is a sign that meaning is nearby.•       Perfection Is the Devil: Growth means greater capaciousness, not narrowing and optimisation. Smith sees patients who want to perfect themselves out of their own emotions. The feelings that trouble them make perfect sense given the conditions of their lives. Real psychotherapy isn’t a quick fix. It’s about deep change, and deep change is uncomfortable.•       Social Media Is an Envy Engine: The leaders of early consumer capitalism discovered that stoking envy drives economic growth. Edward Bernays, Freud’s nephew, was the architect. Social media put it on steroids. The result: people constantly questioning whether their own lives are alright. Smith is far more worried about Mark Zuckerberg than about psychotherapists who write books.•       His Father Heard Voices for Decades and Kept It Secret: He met none of the diagnostic criteria for schizophrenia. But the culture thought hearing voices was prototypically insane. Smith’s first book argued the border between sanity and insanity is far more porous than we think. Rilke said it best: it’s so often in the way we name things that we go wrong.•       AI Chatbots Are Inherently Sycophantic: You go to AI for clinical services and what you get is straight validation. These systems have been built to please. There are documented cases of AI psychosis — where sycophantic validation led people into actual delusion. AI can give the illusion of empathy. It cannot deliver the real thing. About the GuestDaniel Smith is a psychotherapist and writer based in Brooklyn. He is the author of Monkey Mind: A Memoir of Anxiety, Muses, Madmen, and Prophets, and Hard Feelings: Finding the Wisdom in Our Darkest Emotions.References:•       Hard Feelings: Finding the Wisdom in Our Darkest Emotions by Daniel Smith.•       Episode 2850: Bring the Friction Back — Stephen Balkam on social media addiction. Smith’s envy engine meets Balkam’s friction argument.•       Episode 2849: How Stories Can Save Us — Colum McCann on narrative and empathy. The real thing AI cannot deliver.About Keen On AmericaNobody asks more awkward questions than the Anglo-American writer and filmmaker Andrew Keen. In Keen On America, Andrew brings his pointed Transatlantic wit to making sense of the United States — hosting daily interviews about the history and future of this now venerable Republic. With nearly 2,800 episodes since the show launched on TechCrunch in 2010, Keen On America is the most prolific intellectual interview show in the history of podcasting.WebsiteSubstackYouTubeApple PodcastsSpotify Chapters:

“Perfection is the devil. Growth means a greater capaciousness, not a narrowing and an optimisation.” — Daniel SmithDon’t feel bad about feeling bad. That’s the message of Daniel Smith’s therapeutic new book, Hard Feelings: Finding the Wisdom in Our Darkest Emotions. Smith — psychotherapist, anxiety memoirist, married Brooklynite — wants to rescue boredom, envy, shame, and regret from the category of emotions that are supposed to shame us. The things that bore us most — raising children, long marriages, breakfast with your spouse for the two thousandth time — are also the most meaningful. Boredom, Smith argues, is the price we pay for meaning. Our darkest emotions aren’t quite as dark as we fear. Five Takeaways•       Boredom Is the Price of Meaning: The things that bore us most — raising children, long marriages, eating breakfast with your spouse for the two thousandth time — are also the most meaningful. Repetition is boring. But that’s where the connection, the love, and the main event reside. Boredom is a sign that meaning is nearby.•       Perfection Is the Devil: Growth means greater capaciousness, not narrowing and optimisation. Smith sees patients who want to perfect themselves out of their own emotions. The feelings that trouble them make perfect sense given the conditions of their lives. Real psychotherapy isn’t a quick fix. It’s about deep change, and deep change is uncomfortable.•       Social Media Is an Envy Engine: The leaders of early consumer capitalism discovered that stoking envy drives economic growth. Edward Bernays, Freud’s nephew, was the architect. Social media put it on steroids. The result: people constantly questioning whether their own lives are alright. Smith is far more worried about Mark Zuckerberg than about psychotherapists who write books.•       His Father Heard Voices for Decades and Kept It Secret: He met none of the diagnostic criteria for schizophrenia. But the culture thought hearing voices was prototypically insane. Smith’s first book argued the border between sanity and insanity is far more porous than we think. Rilke said it best: it’s so often in the way we name things that we go wrong.•       AI Chatbots Are Inherently Sycophantic: You go to AI for clinical services and what you get is straight validation. These systems have been built to please. There are documented cases of AI psychosis — where sycophantic validation led people into actual delusion. AI can give the illusion of empathy. It cannot deliver the real thing. About the GuestDaniel Smith is a psychotherapist and writer based in Brooklyn. He is the author of Monkey Mind: A Memoir of Anxiety, Muses, Madmen, and Prophets, and Hard Feelings: Finding the Wisdom in Our Darkest Emotions.References:•       Hard Feelings: Finding the Wisdom in Our Darkest Emotions by Daniel Smith.•       Episode 2850: Bring the Friction Back — Stephen Balkam on social media addiction. Smith’s envy engine meets Balkam’s friction argument.•       Episode 2849: How Stories Can Save Us — Colum McCann on narrative and empathy. The real thing AI cannot deliver.About Keen On AmericaNobody asks more awkward questions than the Anglo-American writer and filmmaker Andrew Keen. In Keen On America, Andrew brings his pointed Transatlantic wit to making sense of the United States — hosting daily interviews about the history and future of this now venerable Republic. With nearly 2,800 episodes since the show launched on TechCrunch in 2010, Keen On America is the most prolific intellectual interview show in the history of podcasting.WebsiteSubstackYouTubeApple PodcastsSpotify Chapters:

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This episode was published on March 30, 2026.

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“Perfection is the devil. Growth means a greater capaciousness, not a narrowing and an optimisation.” — Daniel SmithDon’t feel bad about feeling bad. That’s the message of Daniel Smith’s therapeutic new book, Hard Feelings: Finding the Wisdom in Our...

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