Podcast Episodes

Ep. 371: Is it Finally Time to Leave Social Media?

Episode 371

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 episod…

Published on 8 hours ago

Ep. 370: Deep Work in the Age of AI

Episode 370

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 s…

Published on 1 week ago

Ep. 369: Why Are We Getting Dumber? A Debate.

Episode 369

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…

Published on 2 weeks ago

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 genera…

Published on 2 weeks, 4 days ago

Ep. 368: I Want Work-Life Balance. Am I Doomed to Mediocrity?

Episode 368

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 …

Published on 3 weeks ago

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

Episode 367

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 …

Published on 4 weeks ago

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

Episode 366

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…

Published on 1 month ago

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

Episode 365

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 te…

Published on 1 month, 1 week ago

Ep. 364: Metrics 101

Episode 364

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. …

Published on 1 month, 2 weeks ago

Ep. 363: Escaping the Digital Doldrums

Episode 363

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 stra…

Published on 1 month, 3 weeks ago