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  1. Ep. 367: What if AI Doesn’t Get Much Better Than This?

    In recent years, it’s been hard not to react to the possibilities of generative AI without a mixture of euphoria or dread. But after OpenAI’s lackluster GPT-5 launch, a new, almost heretical-seeming question has emerged: what if progress on

  2. Ep. 366: How to Reinvent Your Life in 4 Months (Classic Episode from August, 2023)

    In this replay of one of the more popular episodes from the Deep Questions archives, originally aired in August ,2023, Cal explores some of his early strategies for cultivating a deeper life. Below are the questions covered in today's episo

  3. Ep. 365: What Technology Wants (and How to Push Back)

    Why do we end up entangled with tools that don’t have our best interests in mind? How can we fix this situation? In this episode, Cal dives deep into the difference between additive and extractive technologies, telling a story that weaves o

  4. Ep. 364: Metrics 101

    When Cal recently returned home from his time spent up in New England he set up a whole new set of daily metrics to track in the fall to keep him pointed toward the deep life. And they failed. Hard. In this episode, Cal dissects why metrics

  5. Ep. 363: Escaping the Digital Doldrums

    What does Walt Disney’s malaise in the 1940s have to do with our current struggles with our screens? In this episode, Cal uses a little-known story from Disney’s midlife to identify an effective strategy for escaping the nerve-deadening, du

  6. Ep. 362: The Texting Dilemma

    When we think about unhealthy phone usage, we think about the flashing apps, like TikTok and Instagram, in which billions of dollars have been spent to grab our attention. In this episode, Cal points to an unassuming culprit that may be jus

  7. Ep. 361: Do You Need an App Blocker?

    Are you worried that you’re using your phone too much? An app blocker might make sense. But how do they work, and which one is right for you? In this episode, Cal goes deep into the motivation, technology, and ultimate end game of this dist

  8. Ep. 360: One-Page Productivity

    Trying to stick to complicated time management systems without any breaks can eventually lead to burn out. But if you stop organizational efforts altogether, your life can become a stressful mess. In this episode, Cal taps the wisdom of an

  9. Ep. 359: Should We Fear Cognitive Debt?

    A blockbuster new study out of MIT takes a closer look at the impact of writing with the help of AI. In today’s episode, Cal breaks down this paper with the help of author Brad Stulberg (who made waves online recently with his reaction to i

  10. Ep. 358: Are Parents (Finally) Ready to Fight Smartphones?

    Back in 2023, Cal gave a detailed deep dive that described the three phases of scientific understanding of smartphones, social media, and kids. In today’s episode, Cal argues that we’ve entered a fourth phase; one that will finally lead to

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