Episode (200)
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Ep. 373: The Internet’s Best Advice for Reinventing Your Life
Oct 06, 2025In 2023, I published an episode about resetting your life that became one of my most popular. In the years since, multiple major podcasters and YouTubers have done their own videos on the same theme. ...
Ep. 372: Decoding TikTok’s Algorithm
Sep 29, 2025Last week, it was announced that Oracle would take over operation of TikTok in the US. One of the primary reasons proposed for this deal is that it was in national interests for us to take over contro...
IN-DEPTH: Focus like a Nobel Prize Winner (w/ Brian Keating)
Sep 25, 2025In this episode of IN-DEPTH, Cal is joined by Dr. Brian Keating, the Chancellor’s Distinguished Professor of Physics at UCSD, and one of the most prolific popularizers of science around (you may have ...
Ep. 371: Is it Finally Time to Leave Social Media?
Sep 22, 2025We seem to be stuck in a purgatory when it comes to the worst of the social media platforms. We know they’re not great, but it’s hard to muster enough motivation to bother to leave. In today’s episode...
Ep. 370: Deep Work in the Age of AI
Sep 15, 2025A recent study called into question a core assumption about the generative AI revolution: that these tools, at the very least, will make us more productive. In this episode, Cal dives deep into the st...
Ep. 369: Why Are We Getting Dumber? A Debate.
Sep 08, 2025IQ scores had been steadily rising since WWII. But, more recently, this phenomenon has stopped. Since 2010, we’ve actually been getting dumber. In this episode, Cal gets into the common theories for ...
IN-DEPTH: The Game of Life (w/ Tim Ferriss)
Sep 04, 2025In this episode of IN-DEPTH, Cal is joined by bestselling author and podcaster, Tim Ferriss. Tim rocketed to prominence with his 2007 book, “The Four Hour WorkWeek” which basically redefined a generat...
Ep. 368: I Want Work-Life Balance. Am I Doomed to Mediocrity?
Sep 01, 2025A 22-year-old made a splash recently when he published a Wall Street Journal op-ed claiming that work-life balance makes you mediocre. He went on to brag about how sleeping less than 4 hours a night a...
Ep. 367: What if AI Doesn’t Get Much Better Than This?
Aug 25, 2025In 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 q...
Ep. 366: How to Reinvent Your Life in 4 Months (Classic Episode from August, 2023)
Aug 18, 2025In 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 ar...