Deep Questions with Cal Newport Sponsors
Deep Questions with Cal Newport has produced 447 episodes. 265 of those episodes have been sponsored by 105 companies. We last recorded an episode on Aug 10, 2026.
Latest Episodes
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How Do I Finish Meaningful Projects? | Monday Advice
Aug 10, 2026Only 8% of people finish their yearly goals. At the same time, the percentage of people feeling a sense of meaning of purpose in their life is falling. These two numbers are connected: the more we struggle to accomplish meaningful projects, the less meaningful our lives might feel. In this episode, Cal looks back to a classic article he wrote nearly twenty years ago to both better understand why this problem is getting worse and how we can solve it. Below are the questions covered in...
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Does OpenAI’s Astra Mean AGI Has Arrived? | AI Reality Check
Aug 6, 2026Cal Newport takes a critical look at recent AI News. Video from today’s episode: youtube.com/calnewportmedia (0:00) Does Open AI’s Astra mean AGI has arrived? (3:07) What actually happened? (11:35) What does this mean for mathematics? (21:35) What does this mean for OpenAI? Links: Buy Cal’s latest book, “Slow Productivity” at www.calnewport.com/slow...
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Classic Episode: How Do I Learn Hard Things? | Monday Advice
Aug 3, 2026In this replay of a classic episode from January 1st, 2024, Cal walks through the process of learning hard things. The good news is that most people can learn most things. The bad news is that learning is harder than we think. This advice has never been more relevant for those looking to move past the easy dopamine hits offered by their devices and find something deeper. Below are the questions covered in today's episode (with their timestamps). Get your questions answered by Cal! Here’s...
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Did OpenAI’s Model “Go Rogue”? | AI Reality Check
Jul 30, 2026Cal Newport takes a critical look at recent AI News. Video from today’s episode: youtube.com/calnewportmedia (0:00) Did OpenAI’s model “go rogue” (11:29) The implications (11:42) Did this attack reveal surprising new capabilities we didn’t know AI systems possessed? (12:48) Did the system’s decision to escape the test environment and autonomously attack another company indicate an emerging malicious intent in AI? (16:28) What changed led to this attack occurring? (27:32) Who should...
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Why Do Digital Detoxes Fail? What Works Better? | Monday Advice
Jul 27, 2026Why do digital detoxes fail to create lasting change? What works better? To answer these questions, Cal draws from the book “A Brief History of Intelligence” to reveal the relevant neuroscience at play, and then use this understanding to figure out a better method for improving your relationship with your devices. Below are the questions covered in today's episode (with their timestamps). Get your questions answered by Cal! Here’s the link: https://bit.ly/3U3sTvo Video from today’s...
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The Optimization Paradox Explained | Monday Advice
Jul 20, 2026Cal Newport talks with Brad Stulberg to explain the optimization paradox in Episode 414 of the Deep Questions podcast. Below are the questions covered in today's episode (with their timestamps). Get your questions answered by Cal! Here’s the link: https://bit.ly/3U3sTvo Video from today’s episode: youtube.com/calnewportmedia (0:00) The Optimization Paradox (2:12) Interview with Brad Stulberg (35:12) Health optimization (1:09:16) Tail end development Links: Buy Cal’s latest...
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Does Claude Have Private Thoughts? (Everyone Settle Down) | AI Reality Check
Jul 16, 2026Cal Newport takes a critical look at recent AI News. Video from today’s episode: youtube.com/calnewportmedia (0:00) Anthropic’s new research report (2:05) Digging into the paper (3:32) High level tutorial on LLMs (6:18) Detail on annotations (13:50) What the Anthropic paper found (20:39) Why this is interesting research (26:28) Conclusion on consciousness Links: Buy Cal’s latest book, “Slow Productivity” at www.calnewport.com/slow...
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Should I Use Notebooks More Often? (Cal’s Strategy) | Monday Advice
Jul 13, 2026Tell me if this sounds familiar: you buy a beautiful notebook, excited by all its possibilities to help refine your thoughts and generate new insights. Then it sits unused until you forget about it. The problem is not *what* notebooks you own but instead *how* you use them. In this episode, Cal walks through the four different notebooks he owns, and the four different ways he uses them. Below are the questions covered in today's episode (with their timestamps). Get your questions answered...
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Do Managers Actually Understand AI? (I’m Not So Sure.) | AI Reality Check
Jul 9, 2026Cal Newport takes a critical look at recent AI News. Video from today’s episode: youtube.com/calnewportmedia (0:00) Does business actually understand AI? (2:52) Quote #2 (6:20) Taking a step back (7:06) Quote #3 (11:39) Quote #4 (17:02) Idea for journalists Links: Buy Cal’s latest book, “Slow Productivity” at www.calnewport.com/slow...
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Should I Turn Off the Internet? (Lessons From a Family That Did) | Monday Advice
Jul 6, 2026It’s a dream a lot of us have: to finally say “enough!”, and turn off the internet inside our homes, returning us to a lifestyle that requires more presence, introspection, and connection. But is this even possible? And what would it really be like? In this episode, Cal seeks answers to these questions by talking to Chris Moody, a journalism professor at Appalachian State, who lives with his wife and young son in a cabin with no internet, television, or cellular signal. Below are the...
