Hello Monday with Jessi Hempel

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.

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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Join us for Office Hours this Wednesday at 3pm EST, live from Jessi Hempel’s LinkedIn page

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.

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

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