Hello Monday with Jessi Hempel

Latest Episodes:

Malcolm Gladwell and Kenya Barris on The Unusual Suspects, Improbable Careers, and Why Curiosity Wins Nov 02, 2026

Show notes

According to Malcolm Gladwell and Kenya Barris, curiosity is what they have most in common. Malcolm is a bestselling author and journalist, known for his books The Tipping Point, Outliers and more. Kenya is a Hollywood writer, producer, and actor known for creating the TV series Black-ish, Mixed-ish, Grown-ish and Black AF.

Together, they host the Audible Original show The Unusual Suspects, now in its second season, where they bring that curiosity to conversations with extraordinary and influential figures. They join Jessi in the studio to talk about what changes when two people interview one guest, what they’ve learned from their collaboration and their advice for others pursuing improbable careers.

In this episode, Jessi, Malcolm and Kenya discuss:

How Kenya introduced himself to Malcolm at a restaurant, and why he hasn’t let him go
Why Malcolm challenges the idea of an “unlikely pairing,” and what his parents’ marriage taught him about what people have in common
Kenya’s orchestra metaphor: why a hundred musicians playing slightly off is what makes the music beautiful
What changes when two people interview one guest, from an Amy Sherald conversation neither could have had alone to the Dr. Dre moment where Kenya and Dre traded LA bus routes
What every guest has in common: someone who set out to do something hard and did it well
Why Malcolm was drawn to Ursula Burns, and the self-possessed women he grew up around
Why interviewing powerful people is more fun than meeting them, from Adam Silver to Sue Bird
Where the fun comes from, and why two people with careers moving fast in other directions made a second season
“Hamlet was wrong”: why Malcolm thinks uncertainty is what frees you
Malcolm’s filter for saying yes or no: is it fun?
Kenya’s advice for anyone chasing an improbable career: dream about it, then put in the time alone doing the work

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A Video Game Designer on What Keeps People Coming Back Oct 26, 2026

Show notes

Bing Gordon spent a decade as chief creative officer of Electronic Arts, the publisher behind many of your favorite video games, like The Sims, Need for Speed, FIFA and Battlefield. His daughter Chloe grew up gaming before doing her homework, and landed her first job at age four testing gameplay for EA.

Together they wrote Everybody Wins: What Games Teach Us About Making Products People Love, and they join Jessi in the studio to talk about what great games know about human motivation: why people come back tomorrow, how to build a “wow” moment and why the number one driver of engagement is the people you play with.

In this episode, Jessi, Bing and Chloe discuss:

Why people fall in love with some products and not others, and how you can tell
The two things that bring players back tomorrow: social connection and personal mastery
Art vs. craft: how to iterate until a wow moment lands the way you intended
The one-to-ten test: how to count your good days and design for more of them
Social loops: why five small exchanges a day dramatically increase the odds someone returns
Magic numbers: the thresholds, like 15 friends on Facebook or a 30-day streak on Duolingo, where people stick around
Why “quantify everything” only works if you’re measuring the right thing, and what SNL’s music slot has to do with it
Why short-term metrics are poor long-term predictors, and how to build a “golden gut”
Growing up in a house where video games came before homework
A game designer’s playbook for the AI future: build your guild, open closed doors and find quick wins

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Building a Career for a 100-Year Life Oct 19, 2026

Show notes

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.

London Business School professor Lynda Gratton joins Jessi to offer a model for the arc of a long career. After selling a million copies of The 100-Year Life, which makes the economic case for longer lives, Lynda found readers were hungry for an actionable plan. Her new book, Living the 100-Year Life, is the answer.

In this episode, Jessi and Lynda discuss:

Why the career ladder is disappearing, and what to replace it with
The weave vs. the ladder: how thinking of your life as something you’re actively crafting changes everything
The eight threads that hold a long life together: four for staying productive, four for nurturing yourself
Why your employer is not your parent, and what it means to move to an adult-to-adult relationship with work
The three questions to ask yourself during any transition: who am I, where am I now and what promises can I make to my future self?
Why understanding your heritage is one of the most useful things you can do for your career
How a seven-minute conversation can begin to strengthen the thread of friendship
What’s worth mastering in an age of AI, and why finding an adjacency is almost always smarter than starting over
Why identity is the hardest part of reinvention, and how to explore your possible selves without losing yourself
Why pessimism is a bad psychological place to be right now, and how to choose optimism as an act of agency

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Brené Brown on Leading with Courage and Vulnerability Oct 12, 2026

Show notes

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.

In this episode from the Hello Monday archives, Jessi Hempel sits down with Brené to talk about what it really takes to lead today and why developing human skills like courage and empathy matters more than ever.

Jessi and Brené discuss:

Why we’ve been “building on dysfunction” at work, and how to stop
How to embrace paradox instead of rushing toward certainty
Why grounded confidence is a stronger foundation than bravado
What leaders get wrong about vulnerability
How values clarify choices and protect against resentment
Practical ways to set boundaries and build trust
Why human skills are the real core muscles of work today

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Want more? LinkedIn Premium members can watch an extended version of this interview.

When Perseverance Becomes Self-Sabotage Oct 05, 2026

Show notes

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.

The four-time Emmy Award winner, four-time Oscar nominee and author of the new book The Case for Quitting spent 15 years at the New York Times covering endurance sports before walking away. This week she joins Jessi in the studio to make the case that sometimes stopping is the most courageous thing you can do, and that knowing when to quit is an essential skill.

In this episode, Jessi and Lindsay discuss:

Why quitting on time almost always feels too early
The moment when perseverance flips into self-sabotage, and how to catch it before you crash
Why the decision to continue always has costs, we just can't see them as clearly as the costs of quitting
What Lindsay's own running career taught her about the difference between stopping and giving up
Why women in particular are conditioned to override their instincts and keep going, and what it costs us
The spotlight illusion: why we overestimate how much anyone notices when we leave
Jessi on quitting Wired too late, and what it took from her before she finally walked away
The five-to-ten year question: a simple way to know whether it's time to start building an off-ramp
What Lindsay's 15 years at the New York Times taught her about identity, and why leaving felt like both nothing and everything
How writing a book about quitting transformed her
What’s next for Lindsay Crouse

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What Four Decades of Building Great Restaurants Taught Danny Meyer About Culture Sep 28, 2026

Show notes

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.

His new book, What Could Possibly Go Right, is about a common obstacle in business. How do you grow without losing the thing that made people love you in the first place? Danny joins Jessi in the studio to talk about everything he’s learned in four decades of building businesses around hospitality, including how to scale a feeling.

In this episode, Jessi and Danny discuss:

The assumption Danny held at 30 that he has since debunked
Why culture is what happens when you're not in the room, and how to build it so it endures
The 49/51 rule: why the job is only half of what Danny is actually hiring for
The six emotional skills that make up a high HQ (hospitality quotient), and why "soft skills" is one of Danny's least favorite phrases
The interview questions Danny uses to reveal character, including one that stops almost everyone cold
The jigsaw puzzle theory: why the worst hiring mistakes happen when you keep jiggling a piece that doesn't fit
Why Danny's biggest leadership mistakes came from hanging on too long: to people, to businesses, to deals
How to get to "no" faster, and why a quick, honest no is kinder than a slow one
The five-year, no-tipping experiment at Union Square Hospitality Group: what worked, what didn't, why the pandemic ended it and what Danny replaced it with
What Danny is still learning, and why he looks to younger people to teach it to him

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RSVP here for a special edition of Office Hours this Wednesday at 3pm EST. We’ll be discussing how we might be able to get what we need from work if jobs disappear, inspired by this micro-documentary from the Hello Monday team.

Angela Duckworth on Why Grit Isn’t Always Enough Sep 21, 2026

Show notes

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.

In this episode, Jessi and Angela discuss:

Why grit isn't enough and what Angela has learned in the decade since she wrote her first book
The three-box model: how your situation shapes your thoughts, and your thoughts shape your behavior
Why changing your situation feels like giving up and why Angela calls it an act of heroism instead
Status quo bias: the psychological reason we cling to circumstances we know aren't working
The difference between quitting and job crafting and how to make smaller career moves before the big one
What Taylor Swift moving to Nashville at 14 has to do with your next career decision
Microfriction: the surprisingly small physical changes that do what willpower can't
The Pygmalion Effect: why so much of what we believe about ourselves is borrowed from the people around us
Three kinds of mentors everyone needs: mentors for a reason, a season and a lifetime
The curiosity conversation: how Oprah got Maya Angelou to be her mentor, and how you can apply the same approach
Why Y Combinator funds in batches and what that tells us about trying to go it alone

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

Where You’re Losing Time and How to Get It Back Sep 14, 2026

Show notes

Laura Vanderkam tracks her time in 30-minute increments and has been for over a decade. That’s 336 half-hour blocks over the course of a week. After reviewing thousands of people’s schedules, she finds, again and again, that most of us are sitting on more time than we think. We just have to shift our mindset to believe it. The time management expert and author of the new book Big Time: A Simple Path to Time Abundance returns to Hello Monday to talk about what it actually takes to move from time scarcity to abundance.

In this episode, Jessi and Laura discuss:

Why "I don't have enough time" is not just inaccurate, it's actively making things worse
The math that surprises everyone: what a full-time worker actually has left after work and sleep each week
Why we're bad narrators of our own experience and how to get better data
The biggest blind spots in a week: weekday evenings and weekends
How email and digital communication expand to fill all available space and what to do about it
The one-hour a week experiment that could change how you feel about your job
Why tiny tweaks beat lifestyle overhauls every time
How to carve out "play and possibility time"
The right way to think about learning something new at work, including AI
How to recast ambition when climbing the ladder no longer feels like enough
Laura's September time-tracking challenge and why she's been doing it every year since 2015

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We’re Terrible at Fighting. Here’s How to Get Better. Sep 07, 2026

Show notes

Most of us try to avoid conflict. But done right, fighting can be a path to stronger teams and healthier communities. On this episode of Hello Monday, Priya Parker makes the case for embracing “healthy heat” and learning how to navigate conflict with care.

Priya Parker is a conflict resolution facilitator and author of The Art of Fighting: The Transformative Power of Conflict. Drawing on her work with teams, organizations, communities and groups, she shares practical ways to face conflict effectively.

Jessi and Priya discuss:

Why conflict is often a sign of relevance, and why we tend to fight with the people and groups we care about most
The difference between healthy heat, unhealthy peace and destructive conflict
How healthy conflict can create connection, clarity, better decisions and stronger teams
Why our “fighting muscles” have atrophied, particularly after the pandemic
How digital communication can flatten or exacerbate conflict rather than help us hold productive tension
How to become an artful fighter by approaching conflict with curiosity instead of immediately trying to shut it down
How to identify “hairline fractures” before they grow into larger rifts within teams and communities
How to determine whether a conflict is worth facing
The role of an outside facilitator in helping teams navigate conflict and develop practical conflict-resolution skills
Why preparing your body for conflict matters, including breathing, grounding and learning to stay physically relaxed under pressure
How listening can transform conflict and why staying in the heat long enough to hear each other can create breakthroughs
A lesson from the Canlis restaurant team: how treating feedback as “an investment in you” can help people listen without becoming defensive
What the Seattle Seahawks can teach us about culture and hairline fractures
Why learning to gather and fight well is increasingly important as AI reshapes the workplace

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What Behavioral Science Says About Leading Under Pressure Aug 31, 2026

Show notes

For a lot of people, work feels especially chaotic right now.. Projects start and don't finish. Layoffs happen, then reorgs, then new strategies, and through all of it, managers are expected to have the answers. Caroline Webb spent 25 years coaching leaders through exactly this kind of turbulence. She's a behavioral scientist, a former economist and the author of the new book Leadership Intelligence: Science-Backed Strategies for Mastering 21 Everyday Management Challenges. This week she joins Jessi to talk about what the science of the human brain tells us about leading through uncertainty.

In this episode, Jessi and Caroline discuss:

Why the current moment hits a stress trifecta — demanding, uncontrollable and unpleasant — and what that does to your team's brains
The "know-be-do" framework: how to lead people through uncertainty when facts are in short supply
Why naming how you feel is one of the most powerful things a leader can do and what affect labeling actually does in the brain
What "measured authenticity" means, and why "terrified" is not a word you want your manager to use
How to be honest with your team when you know more than you can say
Why letting projects die quietly is one of the most demoralizing things a manager can do, and what to do instead
What Astro (Google X's moonshot factory) does when it kills a project, and why it works
The "when-then" method for taking the sting out of worst-case scenarios before they happen
"Compassionate clarity": what it means in practice when layoff season arrives
Why walking people out of the building immediately is almost never necessary and what a seasoned CHRO said about it

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Listen to Caroline’s previous Hello Monday episode on how to have a good day at a bad job

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