The Context Window with David Deming Podcast
Oct 28, 2026 · 29 min · 11 segments
Today’s topic is A.I. in the classroom, and it's a personal one for David. As Dean of Harvard College, he's been thinking and writing and talking with students a lot about A.I.: how it’s changed…
My very first speech as dean in the fall of 2025 was about this moment we are in now, where AI appears to be threatening established career ladders at big consulting, finance, and tech firms, the kinds of jobs that students at schools like Harvard have typically been able to obtain.
I said that while I understand their concerns and sympathize with them, I also think there's opportunity in the job market disruption that is coming.
History tells us that periods of technological disruption and economic distress are actually windows of opportunity for talented, ambitious young people to join or start something new because they aren't wedded to old ways of doing things.
And I shared data in that speech suggesting that many of today's top companies were founded during recessions or in the quantum foam of technological breakthroughs like the personal computer and the internet or the railroads or electricity if you want to go way back.
I told them that if you graduated from Harvard in the mid-1990s, when the internet was really taking off, the safe jobs would be at corporate giants like ExxonMobil, Coca-Cola, Bank of America.
And some of the founders or early employees at the top companies of 2050 are probably freshmen at Harvard right now.
And although I didn't know it at the time, it was like a bat signal for Harvard freshmen who were interested in AI.
And so I spent most of the fall 2025 semester talking with students who were interested in AI and how it was going to change the world.
One thing I heard over and over was how much AI was changing the academic experience for our students in high school and at Harvard.
I heard over and over again that it felt like the Wild West out there, with some professors taking AI really seriously and doing innovative, interesting things, but many not fully aware of how much it was affecting students' daily experiences.
And after I completed my first term in the fall and I had a moment to breathe over winter break, I decided that I needed to understand more.
And the result was an essay I published on my Substack with a somewhat lengthy and honestly maybe a bit pretentious title, Using Generative AI to Learn is Like Odysseus Untying Himself from the Mast.
My very first speech as dean in the fall of 2025 was about this moment we are in now, where AI appears to be threatening established career ladders at big consulting, finance, and tech firms, the kinds of jobs that students at schools like Harvard have typically been able to obtain.
I said that while I understand their concerns and sympathize with them, I also think there's opportunity in the job market disruption that is coming.
History tells us that periods of technological disruption and economic distress are actually windows of opportunity for talented, ambitious young people to join or start something new because they aren't wedded to old ways of doing things.
And I shared data in that speech suggesting that many of today's top companies were founded during recessions or in the quantum foam of technological breakthroughs like the personal computer and the internet or the railroads or electricity if you want to go way back.
I told them that if you graduated from Harvard in the mid-1990s, when the internet was really taking off, the safe jobs would be at corporate giants like ExxonMobil, Coca-Cola, Bank of America.
And some of the founders or early employees at the top companies of 2050 are probably freshmen at Harvard right now.
And although I didn't know it at the time, it was like a bat signal for Harvard freshmen who were interested in AI.
And so I spent most of the fall 2025 semester talking with students who were interested in AI and how it was going to change the world.
One thing I heard over and over was how much AI was changing the academic experience for our students in high school and at Harvard.
I heard over and over again that it felt like the Wild West out there, with some professors taking AI really seriously and doing innovative, interesting things, but many not fully aware of how much it was affecting students' daily experiences.
And after I completed my first term in the fall and I had a moment to breathe over winter break, I decided that I needed to understand more.
And the result was an essay I published on my Substack with a somewhat lengthy and honestly maybe a bit pretentious title, Using Generative AI to Learn is Like Odysseus Untying Himself from the Mast.
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