Last month, Derek Thompson published an intriguing essay that made waves in technology criticism circles. It was titled: “Everything is Television.” In today’s episode, Cal takes a closer look at this essay, unpacking and expanding Thompson’s arguments, and ultimately concluding with a series of predictions about what to expect next from the internet. He then answers listener questions and discusses the five books he read in November 2025.

In today’s episode, Cal reviews some of his favorite advice from legendary writers (plus a bonus piece of advice from his own craft). Within each suggestion, he finds a general idea that can apply to anyone looking to build a deep life in an increasingly distracted world. He then answers listener questions and responds to comments about last week’s episode.

There has been a lot of loose talk online recently about the capabilities of existing AI tools. In this episode, Cal reacts to a specific recent clip from the Joe Rogan podcast in which the guest argues that language models are like a child’s brain, and may already be conscious. Cal puts on his (always stylish) computer scientist had to explain why this cannot be true. He then answers listener questions and reacts to feedback on his recent episode about using a notebook to enhance long thinking.

When companies began instituting return-to-office plans after the pandemic, a disproportionate number of women chose instead to leave the workforce. Why? The obvious answer is that they wanted the flexibility of remote work. But in this episode, Cal draws on a recent New York Times op-ed that offers a deeper explanation – one that affects all knowledge workers. He then explores solutions to the problem, answers listener questions, and (God help him) respond to comments on his recent Superintelligence episode.

We often talk on this show about how digital devices undermine our ability to consume more complicated and meaningful ideas. But what about our ability to produce such ideas from scratch? In this episode, Cal identifies a key productive skill –  long thinking – that we’re increasingly losing. He argues that it’s critical for living a deep life and provides a simple strategy to help regain the skill. He then answers listener questions and discusses the books he read in October 2025.

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.

How do you escape a world where constant digital distractions and darkness threatens to pull you down? Maybe take a page out of Abraham Lincoln’s life. In this episode, Cal argues that Lincoln faced analog versions of many of the same issues we face in our contemporary digital world, and by studying how he escaped we can learn a method to accomplish something similar. He then answers listener questions on this theme and revisits the comments from a 2008 essay where he first introduced some of these questions.

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.