Hello Monday with Jessi Hempel

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

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.

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.

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.

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.