A Year of Living With AI
21 Questions with Joanna Stern on AI, authorship, and the future of creative work
As a longtime personal tech columnist for The Wall Street Journal and now the founder of the media outlet New Things, Joanna Stern has become one of the sharpest and funniest voices covering how technology shapes daily life. She is a two-time Gerald Loeb Award winner, a Pulitzer Prize finalist, and the creator of the Emmy-winning 2021 documentary E-Ternal.
Her new book, I Am Not a Robot: My Year Using AI to Do (Almost) Everything, chronicles a year spent letting artificial intelligence into nearly every corner of her life, from work and decision-making to parenting and household chores.
In this edition of 21 Questions, Stern reflects on first drafts, AI, and why the hardest part of writing has nothing to do with the words themselves.
21 Questions with Joanna Stern
1. I couldn’t have written my last book without…
My back patio. I spent most of the summer of 2025 out there, writing day after day, with my dog, Browser. Also Gaby, my barista, who made me an iced latte every morning that summer. She's the first person named in the acknowledgments.
2. What’s the thing most people get wrong about being a writer?
It's not the writing that's hard. It's the thinking.
3. What’s your most common form of procrastination?
Checking social media.
4. Do you read your reviews?
Yes. Are there people who don’t?
5. Kiss, marry, kill: podcasts, newsletters, and speaking gigs.
Marry newsletters — they're the long-term relationship, the thing that actually compounds.
Kiss speaking gigs — thrilling, profitable, over quickly.
Kill podcasts — sorry, I love them but I’ve been on so many of them lately.
6. What’s a writing habit you’re embarrassingly superstitious about?
The first draft of anything important: Google Docs, Arial, 11pt. Any other font and it doesn't feel real.
7. What’s something you wish you’d started doing five years ago?
Building my own newsletter audience. For 12 years, I wrote for The Wall Street Journal. I learned a ton and built a great following, but I didn’t build a direct relationship with that audience that I personally owned. Everything I'm doing now at New Things—and launching my first book—would have been much easier if I'd focused on that in 2021.
8. Where do you find new ideas, and how do you keep track of them?
My mother-in-law asking me why her iPhone is doing "that thing." Other parents complaining to me at kids’ birthday parties. The gap between what tech companies promise and what we all actually experience. My best ideas come when I'm not looking at my phone or laptop. I keep track of them on a phone or a laptop.
9. What’s the best piece of professional advice you’ve ever received?
Find what you love to do and the money will come.
10. And the worst?
Find what you love to do and the money will come.
11. What’s on your nightstand right now?
Ice water and a Theragun. Launching a book has not been good for my back.
12. How did you find your agent?
Through trusted friends.
13. What’s a writing rule you’ve happily broken?
“Kill your darlings.” I keep mine. In fact, I feed them. If I wrote a joke I still laugh at on the fourth read, it’s staying, and my editor can (and will) fight me.
14. What tech tools (AI included) do you actually use—and which ones do you actively ignore?
This question could be a new book on its own. The short version: ChatGPT and Claude daily, for editing myself, brainstorming, fact-checking, and talking me out of bad ideas. Notion for to-do lists, meeting notes, and shared calendars with my team. Otter for transcripts. Google Docs for pretty much everything else.
15. What’s the best non-writing skill that’s helped your writing career?
My sense of humor and my reporting. I don’t consider myself a particularly good writer, but I know how to find a story and present it in a way that’s direct, clear, and occasionally makes someone laugh.
16. How many drafts before you show your editor?
My AI editor or my human editor? AI, one. Human, two.
17. Can you describe your ideal workday?
Up at 8. Coffee. Shoot some fun video in my studio or out in the world. Writing, scripting, brainstorming. Done by 6. Put the kids to bed. No email after 8.
18. How does that compare to your actual workday?
Meetings all morning. Lunch. More meetings. Begin writing or scripting. Break for dinner. Email until midnight.
19. If you could write one book in a totally different genre than you usually do, which would it be?
A children’s book! Working title: Goodnight iPad. But seriously, something like that!
20. What’s something about the writing life that still surprises you?
When I was really in the throes of writing the book, I was surprised by how torturous it was not to have a simple end-word count. As a columnist or newsletter writer, you know the length you need to hit, and that constraint makes you more thoughtful about every paragraph. With a book, the boundaries are a lot blurrier because some chapters or sections can be longer than others. It was freeing, but not always in a good way!
21. Fill in the blank: In five years, successful authors will _____
Allow AI to interact with our books in productive ways. I don’t want my book to be completely sucked up by a large language model, but what if people could use a large language model after buying the book to ask questions or go deeper into my source material?
If you enjoyed Joanna’s Q&A, you can learn more about her new book here: I Am Not a Robot.
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Until next time,
Panio Gianopoulos
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