Hello Monday with Jessi Hempel

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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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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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:

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Why the career ladder is disappearing, and what to replace it with

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The weave vs. the ladder: how thinking of your life as something you’re actively crafting changes everything

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The eight threads that hold a long life together: four for staying productive, four for nurturing yourself

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Why your employer is not your parent, and what it means to move to an adult-to-adult relationship with work

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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?

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Why understanding your heritage is one of the most useful things you can do for your career

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How a seven-minute conversation can begin to strengthen the thread of friendship

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What’s worth mastering in an age of AI, and why finding an adjacency is almost always smarter than starting over

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Why identity is the hardest part of reinvention, and how to explore your possible selves without losing yourself

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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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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.

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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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.

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.

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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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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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

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

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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

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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

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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

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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.

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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

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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.

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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.

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“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

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