Deep Questions with Cal Newport

Where to start with Deep Questions with Cal Newport

A Georgetown computer science professor arguing that attention is the scarce resource in knowledge work, followed by listener questions and a running check on what AI is actually doing to jobs.

Should you start at episode 1?

The show is close to 400 episodes in and has changed shape more than once. The early run predates Slow Productivity and everything Newport now says about AI. Each episode opens with a self-contained deep dive on a single question, so the useful sort order is by question, not by number.

Five episodes to start with

In order. If you only listen to one, make it the first.

1

Ep. 397: Is Deep Work Still Possible in 2026?

Newport revisits the four rules of Deep Work on the book's tenth anniversary and says what he would change now. The additions are a hybrid attention model that syncs a team's remote days so nobody schedules meetings on them, and a rule against letting AI write for you.

3

Am I Lazy or Overstimulated? | Monday Advice

A Georgetown psychologist dismantles the popular idea that you have a daily stimulation budget with one line: people in Times Square would be comatose by noon. The real cost is context switching, and that reframe changes what you actually do about it.

That's about 6 hours of listening

Which is the real problem with "where do I start" lists. Each episode above links to its summary on this site, free and without an account, so you can find out which of the five is worth your evening before committing to any of them.

What you can skip

The AI Reality Check segments are 20 to 35 minutes on the week's AI news, and episodes titled 'Did the LLM Job Apocalypse Begin Last Week?' age exactly as fast as that suggests. On the full episodes the deep dive sits at the front; the listener questions in the back half are more variable.

Frequently asked questions

Should I start Deep Questions with Cal Newport from episode 1?
The show is close to 400 episodes in and has changed shape more than once. The early run predates Slow Productivity and everything Newport now says about AI. Each episode opens with a self-contained deep dive on a single question, so the useful sort order is by question, not by number.
How long are Deep Questions with Cal Newport episodes?
Typically 60 to 85 minutes; the AI Reality Check segments run 20 to 35 minutes. The five starting points on this page come to roughly 6 hours in total. If that's more time than you have, PodSized produces a text summary of any episode in a couple of minutes so you can decide what deserves the full listen.
What should I skip?
The AI Reality Check segments are 20 to 35 minutes on the week's AI news, and episodes titled 'Did the LLM Job Apocalypse Begin Last Week?' age exactly as fast as that suggests. On the full episodes the deep dive sits at the front; the listener questions in the back half are more variable.
Can I read a summary instead of listening?
Yes. PodSized has 53 Deep Questions with Cal Newport episodes summarized, with timestamped chapter outlines and full transcripts. Every episode linked above opens a summary you can read here without an account. In the app, Premium ($4.99/month) adds a roughly five-minute narrated audio version of any episode.

Behind on more than one show?

The back-catalog problem is the same problem as the queue problem. Listening to summaries instead of full episodes and fitting long shows into a commute cover two other pieces of it.