AI, Digital Nostalgia & Information Overload
What I learned with, from and by Jeremy Caplan of Wonder Tools & the Newmark School
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Earlier this week, I joined Jeremy Caplan, my friend of 25+ years, for a discussion on our analog past, digital present, and AI future. Jeremy, who was a Knight-Bagehot Fellow at Columbia Journalism School when I was a dean there, is Director of Teaching and Learning at CUNY's Newmark Graduate School of Journalism and author of the indispensable Wonder Tools newsletter (subscribe!).
We covered a lot of ground in our nearly 90-minute conversation, but here are a few clips that stand out.
In our largely (and relatively newly) digital lives, it’s easy to sort of forget about physical paper and the power it has to command one’s attention. It may seem obvious that trading a small box that allows you to access the breadth of Earthly knowledge for a book, newspaper or magazine is a big swing, but I don’t think we consider it enough.
Never underestimate the power of the physical world, even if it’s as simple as a piece of paper.
PARTNER MESSAGE
Hidden Brain Podcast & Shankar Vedantam Live in NYC March 25, Philly March 21!
Discover the unseen forces that shape your life as Hidden Brain, one of the world’s 20 most popular podcasts, returns to the stage for the “Perceptions” Live Tour in 2026. My friend Shankar Vedantam brings seven key insights from the first decade of Hidden Brain to the stage. Whether you’re new to the show or a longtime listener, this performance of science and storytelling will change how you think about yourself.
Philadelphia: Saturday, March 21 at 7:30 PM at the Miller Theater
New York: Wednesday, March 25 at 7:30 PM at The Town Hall
Portland, Maine: Friday, April 3 at 7:30 PM at the State Theatre [SOLD OUT!
Some AI Bits & Pieces
Jeremy and I discussed several AI tools for all sorts of things—editing, task management, research, and more—but we also got into the more existential aspects of what AI is, what it isn’t, and what it means for all of us.
Jeremy’s concept of a socialized AI, akin to a public library but for computing power, is an excellent idea.
I love this idea for countless reasons, but the main thing for me is how AI is exposing, yet again, the vast digital divide that exists all over the world, and especially in the US.
In the case of AI, the more traditional definition of “digital divide” is almost flipped on its head. Instead of people in poorer households not having access to devices or the internet, now these kids have the devices and AI is doing their homework. Children in wealthier households are largely not using AI in this way. This, via the Pew Research Center:
PARTNER MESSAGE
India Giving Day is March 13, with a new live show!
India Giving Day is back! IGD 2026, to be held on March 13, is the fourth annual national campaign to super-charge American philanthropy to India. A record 51 carefully-chosen, high-impact nonprofits will take part this year, working collaboratively to spur more, better, and more joyful giving to India.
And this year, join us for INDIA GIVING DAY LIVE!, a three-hour celebration of collective generosity hosted by Alex Counts of the India Philanthropy Alliance. You can watch live or later in multiple social platforms. You can set a reminder to watch via LinkedIn here.
The livestream will feature inspiring conversations with nonprofit leaders, philanthropists, India Giving Day ambassadors and youth leaders, and real-time giving updates and special announcements. Alex will be joined by co-hosts Manisha Bharti of Pratham USA, Neha Gupta of Teach For India and Sree Sreenivasan of Digimentors.
What I’m about to say won’t make me popular with students (or the younger me), but here goes: Homework is important, studying is important, and learning how to do research is important. Outsourcing this to a random free LLM may seem easy—it is easy—but failing to learn the crucial skills that homework teaches will only do more harm than good.
Another great tip: Use AI as in-house critic. It doesn’t need to be—and shouldn’t be—a so-called glaze machine that just acts as a sycophantic little helper.
Treating AI as an answer machine is irresponsible at best, but it’s great at pointing out things that are not clear or may not make sense. From another former student:
The power of AI isn’t that it gives you answers.
It’s that it forces you to ask better questions.
— Nina Dec, photographer & storyteller
Jeremy’s Substack is loaded with all sorts of tips for all sorts of things, some AI, some not. First, I am absolutely a calendar hawk. One of my mottos: Live by the 📆, die by the 📆. Meetings, calls, work, tasks, you name it—it’s all about time. Jeremy’s guide to timeboxing your days and weeks is absolutely a must-read for people who find themselves governed by their calendars.
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Second, teachers listen up! Jeremy put more than 200 educational tools through the wringer, and his guide is as useful as it is exhaustive.
These are just two examples of many. Follow Jeremy, use his tips, send him feedback—he’s as thoughtful as they come about these issues. Here’s the entire discussion:
Thank you, Jeremy. A long time ago, the student became the master!
— Sree / Twitter | IG | LinkedIn | FB | YouTube | Spread | TikTok
FYI: 17.1% of 2026 is already over. What will you do with the remaining 82.9%? LMK and I’ll understand you made it all the way down here.
Have suggestions for guests? Do you think you would make a good guest? Do you have a story to tell? Let’s collaborate! sree.sreenivasan1@gmail.com, and please connect w/ me: Twitter | IG | LinkedIn | FB | YouTube | Spread | TikTok
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