Hello Monday with Jessi Hempel

Lessons From a Year of Letting AI Do Everything

Hello Monday with Jessi Hempel

Show Notes

Joanna Stern spent a year using AI to do (almost) everything: write her emails, analyze her medical records, text her wife, drive her around, and even fold her laundry. The result is her new book, I Am Not a Robot, which documents what she learned testing AI as a journalist, a parent, and a newly independent founder.

Joanna spent over a decade as a tech reporter at The Wall Street Journal before leaving to launch her own media outlet, New Things. She brought the same approach that's defined her career — hands-on, consumer-first testing of the technology itself — to her year-long experiment in living with AI.What she found was more nuanced than the hype: some of it works, some of it really doesn't, and some of it needs guardrails.

In this episode, Jessi and Joanna discuss:

Why the same AI technology that's transforming cancer detection is also upselling you at the dentist

The data privacy moves everyone should make right now, including the settings most people never touch

What happened when Joanna tried to let AI handle all her communications

Why robots are bad at folding clothes

How AI gave Joanna the confidence to leave a staff job and start a business

The emotional difference between work you make yourself and work a machine makes for you

What it means to raise kids in a world where the struggle of figuring things yourself might disappear entirely

Follow Jessi Hempel and Joanna Stern on LinkedIn.

More from Hello Monday with Jessi Hempel

Oct 19, 2026

We plan our careers like life is short. Go to school, climb the career ladder, retire. But as we live longer, the model doesn’t hold up.

Oct 12, 2026

After more than two decades exploring courage, vulnerability and leadership, Brené Brown’s work has helped millions of people and changed how we talk about shame and belonging. In her latest book, Strong Ground, Brené introduces the idea of “grounded confidence,” a practice of leading with consistency, clarity and courage instead of bravado.

Oct 5, 2026

How do you know when it’s time to stop? Most high achievers would say never. We keep going because quitting feels like failure. But Lindsay Crouse argues that sometimes the bigger failure is continuing past the point you should have.

Sep 28, 2026

Danny Meyer has built some of the most beloved and enduring restaurants in the US. The “secret sauce” behind Union Square Cafe, Gramercy Tavern, The Modern, Shake Shack, and more? How diners feel when they walk in the door.

Sep 21, 2026

Ten years ago, Angela Duckworth wrote the book on grit. Now she's back with the advice you need to keep moving forward. The MacArthur genius fellow, University of Pennsylvania professor and bestselling author joins Jessi in the studio to make the case that individual effort only takes you as far as your situation allows and that changing your situation is one of the most powerful tools you have. Her new book is called Situated: Find the People and Places That Bring Out Your Best.

See all episodes →