Hello Monday with Jessi Hempel

Lessons From a Year of Letting AI Do Everything

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 [https://joannastern.com/], 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 [https://www.linkedin.com/in/jessihempel/] and Joanna Stern [https://www.linkedin.com/in/joannastern/] on LinkedIn.

Jenny Hagel on How to Build a Creative Career When the Odds Are Against You

Comedy writer Jenny Hagel has six Emmy nominations. The other week, she wrote 20 jokes. One made it to television. She doesn’t see this as failure, though. It’s the nature of the job. And it might offer the most useful career lesson you'll hear all year. Jenny is a writer on Late Night with Seth Meyers, where she also regularly appears on camera in the popular segment Jokes Seth Can’t Tell. She is also the author of a new book of essays called Advice No One Asked For. In this episode, Jessi Hempel sits down with Jenny to talk about the arc of her non-traditional career, and what it actually takes to keep going in the face of failure. In this episode, Jessi and Jenny discuss: * The live advice show Jenny built during the writer's strike, and how a room full of strangers asking earnest questions accidentally became the most community-building thing she's ever done * How humor acts as a spoonful of sugar that lets us endure the heavy stuff a little longer * The 411 call that landed Jenny a grad school internship * Why the find-yourself period matters, and what gets lost when young people skip it * The writing advice Jenny gives everyone: the part where you create and the part where you judge have to be two completely separate steps * How growing up queer in the '80s and '90s inadvertently became a blueprint for every out-the-box decision she's made since * Why a creative career isn't all-or-nothing, and what the middle actually looks like Find Advice No One Asked For [https://www.simonandschuster.com/books/Advice-No-One-Asked-For/Jenny-Hagel/9781668079614] wherever books are sold, and follow Jessi Hempel [https://www.linkedin.com/in/jessihempel/] on LinkedIn.

Bonus: Lesbian Bars and the Secret Formula for Belonging

Lesbian bars aren’t just nightlife, they’re evolving spaces of community and chosen family, and they have a special place in Jessi Hempel’s heart. On this bonus episode, Jessi sits down with one of Hello Monday’s own producers,  Rachel Karp, to talk about her new book The Lesbian Bar Chronicles: The Living History and Hopeful Future of America's Dyke Dives and Sapphic Spaces.  Rachel’s journey started as a passion project: a documentary podcast in which the Cruising podcast team went on a road trip to visit every lesbian bar in the US. Their goal was to tell the history of lesbian bars and stories of the people who go to them. Now, those stories– and the lessons we can learn from them about how to create real-life community spaces–are in a book. In this episode: * Why Rachel and the Cruising podcast team went on their road trip * Why lesbian bars have endured, even as culture, technology, and rights have shifted * What makes physical spaces of belonging different from digital communities * The role of leadership in shaping inclusive, values-driven spaces * What “chosen family” looks like in practice, and why it matters * What anyone (queer or not) can learn from lesbian bars Follow Jessi Hempel [https://www.linkedin.com/in/jessihempel/]and Rachel Karp [https://www.linkedin.com/in/rachel-karp/]on LinkedIn.

How to Build a Career You Actually Believe In

We're trained to climb ladders and chase titles, but what if the real metric of career success was the positive impact you have on the world? In this episode from the Hello Monday archives, host Jessi Hempel sits down with Rutger Bregman to explore moral ambition—a framework for building a career based on what positive impact you can have on the world.  Rutger's groundbreaking book, Moral Ambition: How to Stop Wasting Your Talent and Start Making a Difference [https://www.moralambition.org/book], is a wake-up call for anyone who's felt something was missing from their work. Whether you're early in your career, questioning your path, or rebuilding after a layoff, this conversation offers a practical roadmap for pivoting toward meaningful work. In this episode, Jessi and Rutger explore: * What moral ambition is, and why it's the antidote to burnout * Why "follow your passion" is the wrong advice for building a sustainable career * How to shift from success-driven to service-driven work * Which industries funnel talented people into unfulfilling roles, and how to break free * Real-world examples of people solving humanity's biggest problems * How to build coalitions and find collaborators aligned with your values * The hidden cost of prestige, and how to redefine what winning looks like This episode is a call to action for anyone who wants to do good—and do it well. Follow Rutger Bregman [https://www.linkedin.com/in/rutgerbregman/] and Jessi Hempel [https://www.linkedin.com/in/jessihempel/] on LinkedIn

We're Lonelier Than Ever. Ritual Is the Answer.

Rituals work. They help us make meaning, process transition, and connect with each other. That’s why we’ve been doing them for more than 300,000 years. So why, in this century, have we largely abandoned them?  This week, bestselling author, repeat Hello Monday guest, and longtime friend Bruce Feiler joins us in the studio to talk about his new book, A Time to Gather: How Ritual Created the World and How It Can Save Us [https://www.brucefeiler.com/books-articles/a-time-to-gather/]. Bruce traveled to 16 countries on six continents to explore why ritual matters and identify how we can bring it back into our everyday lives. In this episode: * Why ritual is the original human algorithm and why we've abandoned it * The difference between self-care and group care, and why the latter matters so much * The rise of new rituals: cancer-versaries, sober-versaries, infertility ceremonies, and divorce parties * Why funerals are disappearing, and what we're losing when they do * A live ritual design class: Bruce walks Jessi through building one for her daughter's preschool graduation * The three things every ritual needs: a beginning, a middle, and an end * From "rites of passage" to "bites of passage": why small, frequent moments of connection matter as much as the big ones * Virtual vs. ritual: why 2026 feels like the year we're choosing to come back together in person Follow Jessi Hempel [https://www.linkedin.com/in/jessihempel/] and Bruce Feiler [https://www.linkedin.com/in/brucefeiler/] on LinkedIn. And let us know how you’re incorporating ritual into your own life.