Ep. 27: Inside My Planning Discipline, the Joys and Sorrows of Slack, and Finding Depth Among Shallow Friends | DEEP QUESTIONS

Ep. 27: Inside My Planning Discipline, the Joys and Sorrows of Slack, and Finding Depth Among Shallow Friends | DEEP QUESTIONS

In this episode of Deep Questions I answer reader questions about what’s on my weekly plan at the moment, the complicated impact of Slack, and pursuing depth among friends more interested in fun.I will be sending out a new request for text questions to my mailing list soon. You can sign up for my mailing list at calnewport.com. You can submit audio questions at https://www.speakpipe.com/CalNewportPlease consider subscribing (which helps iTunes rankings) and leaving a review or rating (which helps new listeners decide to try the show).Here’s the full list of topics tackled in today’s episode along with the timestamps:WORK QUESTIONS* Is monthly planning necessary? (Bonus: A look at my current plans) [2:12] * Breaking up time blocks [10:03]* Debunking writer’s blocks [11:28]* Favoritism versus career capital [17:56]* When to stop studying [27:35]* Getting back up when struggling in your work [30:19]QUESTION ROULETTE [34:58]TECHNOLOGY QUESTIONS* The productivity apps I use [42:49]* Do academics need good digital presences? [43:37]* Leaving social media when you can’t leave the house [45:13]* The mixed impact of the rise of Slack [50:53]BACKSTAGE PASS [57:41]DEEP LIFE QUESTIONS* Finding a calling when you’re interesting in many things [1:01:57]* Sticking to the deep life when you’re friends are deeply into the fun life (Bonus: tales from my one day as a Dartmouth frat brother) [1:07:14]Thanks to listener Jay Kerstens for the intro music. Learn more about your ad choices. Visit podcastchoices.com/adchoices

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Is AI Trending Up or Down in 2026? | AI Reality Check

Is AI Trending Up or Down in 2026? | AI Reality Check

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Do I Need More Discipline? | Monday Advice

Do I Need More Discipline? | Monday Advice

Is developing discipline one of the most effective bulwarks against the constant flood of distraction we face daily? And if so, what’s the best way to accomplish this goal? In this Monday Advice episo...

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Is Claude Mythos “Terrifying”? | AI Reality Check

Is Claude Mythos “Terrifying”? | AI Reality Check

Cal Newport takes a critical look at recent AI News. Today's episode on YouTube: youtube.com/calnewportmedia 0:00 What’s Really Going on with Mythos?  10:09 Security systems 21:27 Conclusion ...

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Ep. 400: Should I Embrace “Slow Technology”?

Ep. 400: Should I Embrace “Slow Technology”?

Ep. 400: Should I Embrace “Slow Technology”? If there was one word to describe modern digital tools, it would be “fast.” But not everyone thinks this is better. In today’s episode, Cal explores the c...

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AI Reality Check: Is AI Stealing Entry-Level Jobs?

AI Reality Check: Is AI Stealing Entry-Level Jobs?

AI Reality Check: Is AI Stealing Entry-Level Jobs? Cal Newport takes a critical look at recent AI News. Video from today’s episode: youtube.com/calnewportmedia OPENING: Is AI stealing entry-level j...

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Ep. 399: Is Deep Work Still Possible in 2026?

Ep. 399: Is Deep Work Still Possible in 2026?

It’s been a decade since the original publication of DEEP WORK. Do its ideas still hold in 2026? This is the question Cal tackles in today’s episode: reviewing the four major “rules” from his book, re...

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AI Reality Check: Can LLMs “Scheme”?

AI Reality Check: Can LLMs “Scheme”?

Cal Newport takes a critical look at recent AI News. Video from today’s episode: youtube.com/calnewportmedia ACT #1: Look Closer at the Article [1:20] ACT #2: A Closer Look at the Paper [3:21] ACT...

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Ep. 398: How Do I Find Purpose in a Distracted World? (w/ Arthur Brooks)

Ep. 398: How Do I Find Purpose in a Distracted World? (w/ Arthur Brooks)

Here’s a key question: Did technology like smartphones make us miserable, or were we already miserable and smartphones made it worse? To help figure out this answer, I talked to Arthur Brooks, the #1 ...

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