エピソード

  • How to Make a Career Pivot When You Don’t Know What You Want

    How to Make a Career Pivot When You Don’t Know What You Want
    2026/11/09
    Molly Graham was the person founders called to bring big ideas to life. She worked at Google and Facebook, was COO at Quip and VP of operations at the Chan Zuckerberg Initiative. Then, at what she thought would be the pinnacle of her career, she wanted out. Today Molly hosts WorkLife, the TED podcast Adam Grant used to host, and runs Glue Club, a community for operators and builders. She’s joining Jessi, a friend of over 15 years, to discuss what it’s like to reinvent a career when you don’t know what comes next. In this episode, Jessi and Molly talk about: What it’s like to get the job you thought you wanted and realize it isn’t the hill you want to climb Why people who don’t know you well will always offer you the last job on your résumé, and who to talk to instead The “Molly-shaped holes”: how the people who know you best can see where you belong Jessi’s struggle at Wired, and the photo she took of herself crying on a Monday Two versions of the same stuck feeling: leaving a career you’ve built and watching it fall away around you Why it’s easier to know what you don’t want, and why giving yourself a three-month deadline to find an answer doesn’t work Career emergence: the idea from YouTuber Mark Rober that a career can take shape the way a beehive or a flock of starlings does, with clear principles and one next step at a time How Molly gave up on building “the McKinsey for tech” and founded Glue Club by accident How to respond to “what do you do?” when you don’t have an answer yet Why you aren’t your title, and the exercise of rating every meeting on your calendar from one to ten for energy Jessi’s thesis on separating work from a job, and why careers twist and change What Molly has learned taking over WorkLife from Adam Grant, and why the answer is “the next right thing” Follow Molly Graham and Jessi Hempel on LinkedIn.
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    30 分
  • Malcolm Gladwell and Kenya Barris on The Unusual Suspects, Improbable Careers, and Why Curiosity Wins

    Malcolm Gladwell and Kenya Barris on The Unusual Suspects, Improbable Careers, and Why Curiosity Wins
    2026/11/02
    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 Follow Malcolm Gladwell and Jessi Hempel on LinkedIn Join us for Office Hours this Wednesday at 3pm EST, live from Jessi Hempel’s LinkedIn page
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    27 分
  • A Video Game Designer on What Keeps People Coming Back

    A Video Game Designer on What Keeps People Coming Back
    2026/10/26
    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 Follow Bing Gordon, Chloe Gordon and Jessi Hempel on LinkedIn. Join us for Office Hours this week, live on Jessi’s LinkedIn page, on Wednesday at 3pm EST.
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    26 分
  • Building a Career for a 100-Year Life

    Building a Career for a 100-Year Life
    2026/10/19
    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 Follow Lynda Gratton and Jessi Hempel on LinkedIn. Continue the conversation with us at Hello Monday Office Hours! Join us Wednesday at 3 PM ET, live on Jessi’s page
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    30 分
  • Brené Brown on Leading with Courage and Vulnerability

    Brené Brown on Leading with Courage and Vulnerability
    2026/10/12
    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 Follow Brené Brown and Jessi Hempel on LinkedIn Continue the conversation with us at Hello Monday Office Hours! Join us Wednesday at 3 PM ET, live on Jessi’s page Want more? LinkedIn Premium members can watch an extended version of this interview.
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    28 分
  • When Perseverance Becomes Self-Sabotage

    When Perseverance Becomes Self-Sabotage
    2026/10/05
    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 Follow Lindsay Crouse and Jessi Hempel on LinkedIn.
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    29 分
  • What Four Decades of Building Great Restaurants Taught Danny Meyer About Culture

    What Four Decades of Building Great Restaurants Taught Danny Meyer About Culture
    2026/09/28
    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 Follow Danny Meyer and Jessi Hempel on LinkedIn. 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.
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    29 分
  • Angela Duckworth on Why Grit Isn’t Always Enough

    Angela Duckworth on Why Grit Isn’t Always Enough
    2026/09/21
    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 Follow Angela Duckworth and Jessi Hempel on LinkedIn. This conversation was recorded live and broadcast to LinkedIn Premium members. Premium members can watch the extended version here.
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    29 分