Hello Monday with Jessi Hempel

Latest Episodes:

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

Follow Laura Vanderkam and Jessi Hempel on LinkedIn.

Join Laura’s time-tracking challenge here

Join us for Office Hours, Wednesday at 3pm EST

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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Join us for Office Hours, Wednesday at 3pm EST

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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Join us for Hello Monday Office Hours, Wednesday at 3pm EST

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

How to Make the Most of the Time You Have Aug 24, 2026

Show notes

We spend a lot of energy trying to optimize our time, but what happens when we're forced to surrender to it? Writer, meditation teacher and lifetime student of Buddhism Sebene Selassie has been living with cancer for more than twenty years. In that time, she's learned something most of us spend a lifetime avoiding: how little control we actually have, and how to find joy anyway. This is the third and final episode in our month-long series on time. We’ve discussed how we spend our minutes, our days, our months and our years. Today you’ll hear about how we make the most of all of it..

In this episode, Jessi and Sebene discuss:

Why a cancer diagnosis at 34 became the entry point to a deeper spiritual life, and eventually, to teaching
The tight relationship between fear and control, and how Sebene has spent twenty years slowly loosening her grip on both
What Sebene’s ticking clock has taught her about the present moment
The difference between joy and happiness, and why joy is available even in the hardest moments
Why meditation isn't about feeling better, and what the saccharine corporate version gets wrong
The paradox at the heart of Sebene’s book You Belong: A Call for Connection
How grasping for time is often just grasping for control, and what we miss when we do this
What it means to show up to life openhearted, fully as yourself

Follow Sebene Selassie and Jessi Hempel on LinkedIn.

Join us this Wednesday at 3pm EST for the return of Office Hours!

The Case for Working Slower with Cal Newport Aug 17, 2026

Show notes

Being busy and being productive are not the same thing. Cal Newport, computer science professor at Georgetown and author of Slow Productivity: The Lost Art of Accomplishment Without Burnout, has spent years making that case. This is the second of three episodes from the archive that we're revisiting this month on the subject of time. In it, Cal joins Jessi to zoom out and ask: what does it really mean to get meaningful work done over the course of our weeks, our months, and even our years?

In this episode, Jessi and Cal discuss:

Why "pseudo-productivity" — using visible activity as a proxy for real work — was always a bad idea, and why mobile computing made it unsustainable
How the pandemic pushed knowledge work past a breaking point
The administrative overhead trap: why agreeing to too many things at once is slowing you down
How to say no to new work without actually saying no, and why transparency is the key
Why boredom is essential
What your phone has to do with short-circuiting the most human productivity tool we have
Cal's rule for his kids on smartphones and social media, and the age he thinks unrestricted internet access becomes safe
Why doing fewer things at once will get you to the finish line faster
What AI tools like ChatGPT are actually good for, and what Cal is waiting for them to do instead
The difference between technology that helps you do things faster and technology that takes things off your plate entirely

Follow Jessi Hempel on LinkedIn.

You Have More Time Than You Think. Here's How to Use It. Aug 10, 2026

Show notes

Most of us are convinced we don't have enough time. Laura Vanderkam argues that we have enough time, we just aren’t using it with enough intention. This month, we're revisiting our series of episodes on time, and how we make the most of it. We’re starting here, with the bestselling author of numerous books on time management and the host of the daily four-minute podcast Before Breakfast.

In this episode, Jessi and Laura discuss:

Why 5 PM on Thursday is actually the exact midpoint of your week, and what that reveals about the time you're losing
How Laura has tracked every half hour of her life since April 2015, and what nine years of data taught her
The biggest time waster of all (it's not email or your phone)
Effortful fun versus effortless fun, and why doing a little of the first before the second changes everything
Why you should give yourself a bedtime, and how most adults are already getting more sleep than they think
The case for moving for 10 minutes by 3 PM every day
Why busy people need a hobby
The Friday punch list: how batching your small tasks protects your best hours for the work that actually matters

Follow Laura Vanderkam and Jessi Hempel on LinkedIn.

Why Baratunde Thurston Fired ChatGPT—and What he Learned Aug 03, 2026

Show notes

Baratunde Thurston fired ChatGPT. And ChatGPT helped him do it. This week, the Emmy-nominated storyteller, writer and host of Life with Machines joins Jessi in the studio to talk about what it actually means to have agency in a moment when we’re still figuring out the rules and norms of AI.

In this episode, Jessi and Baratunde discuss:

Why Baratunde fired ChatGPT and what the chat bot taught him on his way out
What he means when he says we're not using a tool, we're entering a relationship
The "direction, not perfection" principle for navigating an imperfect landscape of AI companies and choices
Why switching platforms is itself a practice of agency, and proof that you can leave
What AI tools reveal about you that you didn't know you were sharing
The two people living inside every employee at an AI all-hands: the one on-program, and the one who's scared and skeptical
What the kids opting out of AI are trying to tell us
What the internet could look like if we treated it as a public utility instead of a commercial space
Why token-maxing is a "flagrant foul" in an era of climate change
What executives get wrong when rolling out AI, and the questions they should be asking their teams instead

Follow Baratunde Thurston and Jessi Hempel on LinkedIn.

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