Daniel Pink is a seven-time New York Times bestselling author, a three-time Hello Monday guest, and one of the most trusted voices on motivation and performance. This week, he joins Jessi in the studio to talk about productivity and regret: how to actually get meaningful work done, how to protect your time and attention in an age of infinite distraction, and how to use the things you wish you'd done differently as a map for what you actually care about. 

Jessi and Dan discuss:

• Why productivity shouldn’t be measured in units of output, it should be measured in meaningfulness
• The MIT method: why Daniel writes his single most important task at the top of his to-do list before anything else
• How to design your environment for deep focus instead of trying to willpower your way there
• The to-don't list: how to treat the things that drain your time with the same seriousness as the things you need to do
• Why you probably overestimate how disappointed people will be when you say no, and how to say it cleanly
• The SNL rule for shipping work: "We don't go on because we're ready. We go on because it's 11:30."
• What to do when your boss keeps changing the priorities
• The Pomodoro technique: whether it still holds up, and Dan thanked its inventor in the acknowledgments of one of his books
• Why regret is one of the most misunderstood and underused emotions we have
• The four core regrets that show up across 26,000 people in 130 countries, and what they reveal about what we actually value

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

Follow Daniel Pink and Jessi Hempel on LinkedIn.

Most of us approach a long break from work with some anxiety. Whether it’s a layoff, parental leave, or a season of caregiving, there’s tension around if and when we’ll return to work and how we’ll explain the gap on our résumé.

DJ DiDonna, senior lecturer at Harvard Business School and author of the new book Big Time Off, wants to change that. This week, he joins Jessi to make the case that stepping away from routine work — for whatever reason, for however long — is one of the most strategic things you can do for your career and your life. 

Jessi and DJ discuss:

• What a sabbatical actually is, and why two-thirds of them happen because of a negative catalyst, not a choice
• Why immediately job-searching after a layoff is like grocery shopping while hungry
• The difference between a vacation, a corporate "sabbatical," and the real thing, and why it takes six to eight weeks just to feel like yourself again
• What DJ calls "fertile emptiness," and why most of us never let ourselves get there
• How to use a sabbatical to run experiments on possible future versions of yourself
• The story of a CTO who went to Norway, built a text-to-speech app, and redesigned his entire relationship with work and money
• Why functional workaholism is the thing most of us are living with
• What AI has to do with the case for stepping back, and why learning from a place of fear versus curiosity makes all the difference
• How Jessi's own three-month hiatus from the workplace, during which she wrote a book and raised a newborn, turned out to be a sabbatical she didn't know she was taking
• How to start planning for a sabbatical five years from now, even if taking one today feels impossible

Follow DJ DiDonna and Jessi Hempel on LinkedIn.

You can't lead a team through a hard moment if you can't manage yourself first. That's the core of Dr. Becky Kennedy's work. The clinical psychologist and founder of Good Inside built a global movement teaching parents how to navigate the hardest moments with their kids. It turns out those same skills are exactly what the modern workplace needs. This week, Dr. Becky joins Jessi in the studio to translate her parenting playbook for managers, leaders, and anyone who's ever had to deliver hard news, hold a line they didn't fully believe in, or hold it together when someone on their team fell apart. 

In this episode, Jessi and Dr. Becky discuss:

• Why conviction matters more than confidence, and how to tell if you actually have it before walking into a hard meeting
• The AVP method (acknowledge, validate, permit) for regulating your own emotions before they spill into the room
• Why self-regulation isn't a two-minute fix, and what Dr. Becky calls "the road to reactivity"
• How to separate behavior from identity when giving feedback, and why conflating the two is what makes hard conversations go wrong
• Why sturdiness is the key to managing a team through uncertainty and layoffs
• The sentence structure to use when you don't have all the answers but still need to show up as a leader
• Why empathy requires boundaries, and a tennis court visualization that keeps other people's feelings on their side of the net
• What anger is actually telling you, and how to use it productively instead of letting it drive the conversation
• Why Dr. Becky is skeptical of the feedback sandwich, and a feedback method to use instead
• A simple question managers can ask every week to make upward feedback feel safe and specific

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

Follow Dr. Becky Kennedy and Jessi Hempel on LinkedIn.

Most of us think of negotiation as something reserved for high-stakes boardrooms—or even hostage situations. But Christopher Voss, former FBI lead hostage negotiator and bestselling author of Never Split the Difference, says negotiation is everywhere: in salary talks, in team meetings, even in conversations with your kids. 

In this episode from the Hello Monday archives, Jessi Hempel sits down with Chris to explore how we can all become better negotiators by focusing on empathy, collaboration, and trust. Drawing on decades of experience, Chris shares practical tools you can use to move conversations forward—whether you’re asking for a raise, dealing with a difficult boss, or navigating conflict at home.

Chris and Jessi discuss:

• Why negotiation is really about collaboration and long-term relationships
• How to shift from seeking control to building influence
• The power of labeling emotions to build trust and lower defenses
• Why “no” is often more powerful than “yes”
• How to recognize when a negotiation is over—or when it’s time to walk away
• Strategies to reframe salary conversations and show your value

This episode was recorded live in-studio. For an extended, behind-the-scenes version, watch on LinkedIn Premium.

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.

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 and Rachel Karp on LinkedIn.

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, 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 and Jessi Hempel on LinkedIn