Hello Monday with Jessi Hempel

We tend to talk about AI and the future of work as a young person's game. Dr. Myechia Minter-Jordan, CEO of AARP, is here to challenge that notion. A physician turned healthcare executive turned nonprofit leader, she joins Jessi in the studio to talk about ageism, AI, and what it means to not just stay relevant, but to move ahead, in the second half of a working life. 

In this episode, Jessi and Dr. Minter-Jordan discuss:

How the fifty-plus workforce is upskilling faster than other generations

How to reframe experience as an asset in a job search, and why soft skills are having a moment

The move Dr. Minter-Jordan made that surprised everyone: going back to business school in her thirties, while practicing medicine

Why mentorship is one of the most powerful tools an older worker has for demonstrating value, and why stepping back from it is a mistake

How Dr. Minter-Jordan got her current job as CEO of AARP

What the trillion-dollar caregiving economy means for employers, and why the policies aren't keeping up

How to approach AI without feeling overwhelmed: start small, stay consistent, and focus on what's relevant to your field

Whether you should de-age your résumé

How to be strategic about timing a career pivot, especially when you have real responsibilities

What Dr. Minter-Jordan would tell a thirty-five-year-old building a career for the long arc

This episode was originally recorded live and broadcast to LinkedIn Premium members. Premium members can watch the extended version here.

Follow Dr. Myechia Minter-Jordan and Jessi Hempel on LinkedIn.

“It’s not your fault.” This is the message Alissa Quart has spent over a decade trying to get people to believe when it comes to economic hardship. Right now, it feels harder than ever to embrace.

Alissa Quart is the executive director of the Economic Hardship Reporting Project, the nonprofit Barbara Ehrenreich built after writing her groundbreaking exposé Nickel and Dimed. A journalist herself, Alissa is the author of seven books, including Squeezed: Why Our Families Can’t Afford America and Bootstrapped: Liberating Ourselves from the American Dream. She's spent over a decade reporting on class, caregiving, and economic precarity.

In this episode, Jessi and Alissa discuss:

Why "insecurity" is a more honest and unifying framework than "affordability," and how it builds solidarity across class lines

The data behind it: 52% of US families are now financially insecure by one measure, and nearly half of workers lack confidence they could find a job they'd want

"Apocalyptic insecurity": the new framework Alissa and economist Lynn Parramore developed to describe how employers use AI dread to manipulate workers

The Frederick Taylor parallel: how AI is repeating the logic of scientific management, a century later

"AI brain fry": the exhaustion of performing enthusiasm for AI at work while feeling something very different about it personally

Why losing the narrative of generational progress is its own kind of psychological injury

The AI dividend, universal basic income, and what a modern New Deal could look like

Why naming the problem matters: how failing to recognize insecurity as systemic — rather than personal failure — can curdle into self-blame and even disordered coping

What Alissa tells her own daughter about finding agency in an uncertain future

Follow Alissa Quart and Jessi Hempel on LinkedIn.

We've built an economy that rewards destroying value. Eric Ries wants to know how we got here, and whether we can build our way out.

Eric wrote The Lean Startup in 2011 and helped define a generation of entrepreneurs. Since then, he's watched promising, mission-driven companies get hollowed out, and he thinks he knows exactly why. His new book, Incorruptible: How Good Companies Go Bad and How Great Companies Stay Great, is his attempt to name what's happening, explain how we got here, and lay out a blueprint for building something better. 

In this episode, Jessi and Eric discuss:

What Eric calls "financial gravity": the systemic force that pulls organizations away from their mission and toward extraction

Why shareholder primacy isn't ancient law; it's a 1980s invention that was never voted on by anyone

The private equity problem: how you can taste the cost-cutting in your food when private equity buys your favorite restaurant

Why today's best practices are actually value-destroying, and what the data says about the alternative

The Public Benefit Corporation filing: a two-page form that could change what your company is legally obligated to do

Why "it's always too early until it's too late," and how founders miss their window to protect their mission

The AI layoff glee: why Eric thinks companies racing to replace people with robots is slow-motion suicide

How to find opportunity in this moment, even if you've been laid off, and why trust is the most underrated asset in business today

Follow Eric Ries and Jessi Hempel on LinkedIn.

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.

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 wherever books are sold, and follow Jessi Hempel on LinkedIn.