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:

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

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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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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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