Ep. 371: Is it Finally Time to Leave Social Media?
We 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...
22 Sep 20251h 25min
Ep. 370: Deep Work in the Age of AI
A 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...
15 Sep 20251h 10min
Ep. 369: Why Are We Getting Dumber? A Debate.
IQ 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 ...
8 Sep 20251h 33min
IN-DEPTH: The Game of Life (w/ Tim Ferriss)
In 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...
4 Sep 20251h 57min
Ep. 368: I Want Work-Life Balance. Am I Doomed to Mediocrity?
A 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...
1 Sep 20251h 27min
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 q...
25 Aug 20251h 37min
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 ar...
18 Aug 20251h 17min
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 tec...
11 Aug 20251h 2min
