Techno-philosopher Eliezer Yudkowsky recently went on Ezra Klein's podcast to argue that if we continue on our path toward superintelligent AI, these machines will destroy humanity. In this episode, Cal responds to Yudkowsky’s argument point by point, concluding with a more general claim that these general styles of discussions suffer from what he calls “the philosopher’s fallacy,” and are distracting us from real problems with AI that are actually afflicting us right now. He then answers listener questions about AI, responds to listener comments from an earlier AI episode, and ends by discussing Alpha schools, which claim to use AI to 2x the speed of education.

OpenAI has been making waves recently with their release of their Sora 2 video generation model, which they have launched alongside a TikTok-style social media sharing app. The internet is usually pretty excited about AI innovations, but this one has people unsettled. In today’s episode, Cal looks at one implication of Sora 2 in particular that is both important but currently overcooked: the impact of AI content generation on the existing social media giants. He then answers listener questions on AI and social media and reacts to a new Sam Altman tweet that signals bad news for OpenAI.

It’s hard to cultivate a deep life when you cannot go more than a few minutes without checking your phone. In this episode, Cal looks closer at the precise neural mechanisms at play that make the physical act of looking at your phone irresistible. Then armed with this knowledge, he explains why many popular remedies fail, and which specific responses are most likely to succeed. He then answers listener questions and discusses the five old-fashioned analog books (!) that he read last month.

In 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. In today’s episode, I extract the best ideas from five such recent videos to create an all-star reset strategy. I connect this to my work on technology and its impacts, by noting that taking control of your life can be the most important first step toward taking control of your devices.

Last 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 control of TikTok’s fabled “algorithm.” But what is this algorithm? How does it work? To what extent can it be controlled? In today’s episode, Cal looks deeper at these questions and arrives at a broader philosophical point about the role these services, in general, should play in our civic culture. He then answers listener questions on the same topic and reacts to the three recent news articles about TikTok’s influence on our culture.

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, motivated by the assassination of Charlie Kirk, Cal puts on his technology critic hat and offers a step-by-step technical explanation for why these platforms are strictly and incessantly making your life worse and why the only reasonable response is to quit them. He then answers listener questions on the topic and reacts to some recent news about the US Congress getting involved.

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 study and argues that when it comes to efforts that require deep work, AI can sometimes make things worse. He then answers listener questions and then takes a closer look at an article claiming that the lack of Wi-Fi in a West Virginia school is making their students dumber. 

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 why this is true before offering his own take, which leads to some practical takeaways to help you thrive in an increasingly stupider world. He then answers listener questions and talks about something he read recently.

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 and gaining 80 pounds helped him become a millionaire. In this episode, Cal wades into the furious debate this article sparked. He argues that once you look past the author’s dorm bro bravado, the kid does actually ask a good question. It’s just that his answers are lacking. Cal then tackles listener questions and reviews the books he read in August.

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 AI is stalled well short of the wild predictions we were promised? In today’s episode, Cal draws from reporting on his recent New Yorker article to go deep into this question. What is going on with AI? How did we get here? What does it mean for our personal quest to live deeper lives? He then answers listener questions and ends by discussing his recent brush with literary acclaim.

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.

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 matter, why they’re easy to mess up (including the mistakes he made), and how to use them correctly (including how he corrected his own setup). He then answers listener questions and discusses a recent AI article that got him all hot and bothered.

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, dull state created by spending more and more of your professional and personal life on screens. He then answers listener questions (with an unusual level of spiciness), tries to calm himself with a reprise of the SLOW PRODUCTIVITY CORNER theme music, and concludes with a discussion of a recent essay he wrote about how no one really knows anything about AI.

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 just as responsible: simple messaging apps. He explores research that connects the social stress of pending messages to phone addiction, and explores ways to free yourself from constant messaging without having to isolate yourself socially. He then answers listener questions and discusses what he’s been reading.

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 distraction fighting technology. He then answers listener questions and discusses some intriguing comments he’s been seeing about limits to AI’s ability to code.

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 elite running coach to devise what he calls one-page productivity: a minimum time management system, meant to be run for limited periods to help you recharge, but that also maintains just enough organization that you can avoid disaster. He argues such maintenance modes should be an important part of any time management practice. Cal then answers listener questions and concludes by reviewing the books he read in June 2025.

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 its findings), picking apart the role of AI in deep work activities. Cal then answers listeners questions, and presents a twist on his typical final segment in which he now describes what he is not reading this week, which provides him a thinly-concealed excuse to rant about AI coverage.