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Careers · Connor Diemand-Yauman

Is This Working?!

by Connor Diemand-Yauman

What if the most interesting thing about work isn’t what we do—but what it does to us? Is This Working?! dives into meaningful work and the messy humans who do it. As AI reshapes industries and upends old definitions of success, social entrepreneur and Stanford GSB lecturer Connor Diemand-Yauman talks with extraordinary people about both sides of the story: the outer work (what they built, how they pivoted, the tactics that actually worked) and the inner work(the therapy, the doubt, the failure) it took to get there. Because when the world is changing this fast, maybe these stories are the only way to know if any of this is actually working.

Latest episodes

Showing 20 · updated from the feed

Who Wins the AI Race? Probably Not Who You Think – Former Bain Capital Executive Mark Nunnelly

There are two types of hyper successful people. The ones who have an answer for everything, and the ones you actually want to talk to. Mark Nunnelly is squarely in the se

Oct 7
48 min

The Magician's Guide to Blowing Your Colleagues' Minds – Magic Patio Founder Andrew Evans

Andrew Evans is a magician, but his real job? Gaining people's trust. Whether he's headlining at The Magic Patio, the SF venue he created that now sells out three months

Sep 23
59 min

The Hardest Part Isn't Getting Sh*t Done. It's Knowing When to Stop — Dream.org CEO Nisha Anand

Nisha Anand might be the only person alive who's thrown fake blood on the White House and worked alongside Jared Kushner, Newt Gingrich, the Koch network, and Kim Kardash

Sep 9
1 h 16 min

The Secret to a 50-Year Career Is Being Willing to Lose It – Ohio Governor Mike DeWine

"You have to be willing to fail." That's Mike DeWine, the man who's held just about every role in Ohio politics, including US Senator, a job he ran for four times. Firs

Aug 26
46 min

Running Sesame Street Is Harder Than Working in the White House: Sesame Workshop CEO, Sherrie Westin

Everyone loves Sesame Street. Now imagine being in charge of it. That's Sherrie Westin's job. As CEO and President of Sesame Workshop, Westin's day-to-day includes: figur

Aug 12
33 min

No One Knows Katie Couric Like This

You think you’ve known Katie Couric your whole life. You have no idea. Yes, the press called her America's Sweetheart. They also called her a diva, an ice queen, and a b

Jul 29
51 min

How to Make Yourself AI-Proof, According to One of the World's Top VCs - Ann Miura-Ko

When the VC Forbes once called “the most powerful woman in startups” says there's a way to make yourself AI-proof, it's worth listening. Ann Miura-Ko spent the last two

Jul 8
57 min

How to Actually Change Your Behavior (No, It's Not Willpower) — Behavioral Scientist Kristen Berman

Kristen Berman is one of the world's foremost experts on getting people to do what they say they want to do. She also routinely has a hard time following her own advice,

Jun 24
41 min

Why Real Leadership Feels Like Crap — Farmgirl Flowers Founder Christina Stembel

Christina Stembel started Farmgirl Flowers in 2010 with $49,000 in her bank account, no college degree, and no VC funding. Sixteen years later, it’s a $35-million-a-year

May 27
49 min

Don’t Follow Your Passion — Do This Instead | Crankstart Foundation's CEO Missy Narula

Most people in philanthropy wouldn't call themselves a "safety-net capitalist." Most people aren't Missy Narula. Missy’s made a career being comfortable in contradiction

May 13
49 min

Winning AI *Without* Losing The American Dream — Fmr US Commerce Secretary Gina Raimondo

AI is here. The layoffs have started. Does anyone have a plan? Gina Raimondo does. Two-term Governor of Rhode Island, former U.S. Commerce Secretary, the person who shep

Apr 29
49 min

The Slowest Career Change In History | Magician David Gerard

Is there a version of you that feels unattainable? For David Gerard, it was becoming a full-time magician. So he did it slowly. Twelve years slowly. VP at Sequoia-backed

Apr 8
1 h 07 min

Why She Took the Hardest CEO Job in America | PG&E's Patti Poppe

84 counts of involuntary manslaughter. A worker dying every 90 days. An empty C-suite. That's what Patti Poppe signed up for when she became CEO of PG&E. In this episode

Mar 25
47 min

The Overachiever’s Guide To Effective Communication - Stanford's Matt Abrahams

Matt Abrahams teaches Stanford’s Essentials of Strategic Communication, the university’s most popular communication course. His “Think Fast. Talk Smart” talks and podcast

Mar 11
39 min

Jin Ha (Hamilton, Only Murders In The Building): Stop Performing and Start Breathing

"Are you breathing?" Jin Ha's acting teacher used to interrupt class with that one question. It became a running joke among the students. It also changed how Jin Ha move

Feb 25
50 min

We've Built Cities for 20,000 Years. Why Did We Stop? — California Forever's Jan Sramek

"Am I wasting some of the best years of my life?" Jan Sramek asked himself that question for years while working on one of the most audacious development projects in a g

Feb 11
56 min

AI Won't Erase Jobs. Here’s Why — Cognizant CEO Ravi Kumar

Ravi Kumar is one of the clearest voices on why AI will create more jobs than it replaces—which is surprising, because he's the CEO of a $35 billion company where machine

Jan 27
43 min

You Can Change a Lot More Than You Think — Somatic Coach Harley Frank

How much can people actually change? According to renowned somatic coach Harley Frank, a whole lot more than you might think. Once a startup executive living with chroni

Dec 17 2025
1 h 00 min

Want to Keep Fighting? Stay Optimistic — ACLU's Anthony Romero

Anthony Romero has led the ACLU for nearly a quarter century—through four presidents, constitutional showdowns, and a political landscape that feels more chaotic every da

Dec 3 2025
33 min

Follow the Laughter, Find the Truth — Comedian Sarah Cooper

Sarah Cooper went viral for lip-syncing Donald Trump on TikTok — and suddenly, the world knew her face. From there came a Netflix special, a memoir, acting alongside Jerr

Nov 12 2025
59 min

Chart trend

Position in the Careers chart (US), last 90 days.

#24
all-time peak
4
days in the top 50 since Apr 2026

Chart positions

Where Is This Working?! ranks today in each Apple Podcasts chart (US, Oct 12, 2026).

#198 NEW Careers US

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