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Is This Working?!: Daily Summaries Delivered
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.
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- 2 days ago44 min
Is Everything at Work Really an Emergency? – Former Bomb Tech Devan Trammel
Devan Trammel used to walk toward live bombs for a living. Literally. That was his job on a US Air Force bomb squad, which he joined at 19. From there, he helped start a technology incubator at the Pentagon before getting an MBA at Stanford. After all that, he has a very short list of what counts as risk at work: "someone dying, or you're going to bankrupt the entire business, or you're going to really hurt people." Everything else, he says, is "really just management." Connor and Devan get into: the question he asks in front of a live bomb: "What is the worst thing that could absolutely happen in this scenario, and what actions would I have to take to make that happen?" why he hid his mistakes from his team, and the commander whose one story made him call everyone who had ever worked for him to apologize why his team took three minutes to write down what they thought before anyone said a word, so nobody would just agree with the boss the crochet snail he pulled out in the middle of the test that decided whether he'd lead a bomb team the movie soundtrack he listens to on the way to a bomb If everything at work feels like a live bomb, or you've been hiding your mistakes from your team, start here. Chapters 00:00:00 Intro 00:01:33 Why he joined the bomb squad at 19 00:03:59 What the job actually is 00:06:27 The leaking package in England 00:09:15 The 250-pound bomb in Charleston 00:13:50 Staying calm in front of a live bomb 00:15:11 Why he stopped pretending to be perfect 00:20:18 Why the leader talks last 00:22:51 Why attitude is non-negotiable 00:24:16 Humor in the field 00:28:22 Why harder work needs more humor 00:30:35 Volunteering for Thanksgiving week in Appalachia 00:32:20 Treating the food crew like Michelin chefs 00:34:00 Leaving the military 00:37:29 Should leaders think more about death? 00:39:10 Most risk isn't really risk 00:40:53 What he's still working on 00:42:44 The billboard
- 2 weeks ago50 min
Should My Kid Still Go to College? – WGU President Scott Pulsipher
Scott Pulsipher isn't scared of what AI will do to education. Which is strange, given that he runs Western Governors University, the largest university in the country: nonprofit, online, nearly 200,000 students. A lot of other university leaders are scared, and he says they probably should be. He doesn't believe anyone can predict the future of work, so WGU looks 12 to 36 months out at how jobs are actually changing and works backward into what students learn. He'd also like to shrink the four-year degree to one or two years, with the rest earned on the job. So Connor asks him the question everybody actually wants answered: should my kid go to college? They get into: his answer, from the person with the most to lose from saying no why job skills now expire faster than a four-year degree can teach them his "yes and no" on whether college is still the path to the American dream the question he uses to test whether a college remembers who it's for: "what does the world lose if you don't exist?" the week at Amazon when twenty-six of his peers told him to his face how he actually made them feel, and the sentence from his boss that put him back together the three things that have to be true before anyone can change Plus: a rocket scientist uncle who shook satellites until the parts fell off, how he went from twenty years in tech to a university he'd never heard of, and six kids, four grandkids, and a wife who took one look at him that Friday night and asked what happened. If you're trying to work out whether college is still worth it, for your kid or for yourself, start here.
- Oct 7, 202648 min
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 second camp. He joined Bain Capital in its early years and became one of the most successful investors in the world. Then, in his late fifties, he went to work for the governor of Massachusetts, where he led 5,000 people and started the state's first cybersecurity department from scratch. And he spent his hour with Connor talking about what he doesn't know. About parenting, which he says he got "spectacularly wrong" in places and calls the best thing he ever did. About capitalism, which he still calls the winning model even though "we have not had the shared prosperity that we need." And about AI, where his read is that "we're looking at the movie in its first minutes," and everyone is already describing the final scene. They get into: why the companies we think are winning AI today probably won't be the ones that win why "follow your passion" needs an asterisk, and the evidence to look at instead what he would do with $100 million to do the most good, and why it starts with medicine thirty years of work on American education, and why it left him less hopeful and more determined the eulogy test, and the two decisions he ranks above everything else he did If you're making big calls right now without knowing how any of this ends, this one is for you. Chapters 00:00:00 Intro 00:01:09 From a preacher's kid to private equity 00:03:46 People can't know how much you know until they know how much you care 00:04:57 Leaving Bain for public service 00:06:43 Luck, and following your passion with an asterisk 00:10:29 Look at the pattern, and get comfortable failing 00:12:04 The eulogy test, marriage and fatherhood 00:15:37 Thirty years of education reform 00:20:45 Choosing possibility over catastrophe on AI 00:29:24 Capitalism and shared prosperity 00:32:11 "Just tell me it's going to be okay" 00:32:45 The $100 million question 00:35:25 Why today's AI winners won't stay the winners 00:38:36 Two handfuls of unelected people 00:39:56 A kid off the turnip truck from Kentucky 00:43:20 A year around the world with a small backpack 00:44:42 Intensely, neurotically calm 00:45:49 The next chapter
- Sep 23, 202659 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 in advance, or working as a design lead at IDEO and Nike, helping clients tackle problems differently, his work is always about one fundamental question: How do I earn the trust of everyone in this room? His answer? Surprise. Take the disaster of a video call he had with a team in Korea. Echo, feedback, nobody able to see anybody. Finally, after fifteen grueling minutes, they get it working, and Andrew clicks through to the agenda slide he'd built a week earlier. First item: 9:00 to 9:15, technical difficulties. Everybody laughed, and then everybody relaxed. "We're not behind on anything. This is right where we're supposed to be." That's the magic trick: let people think one thing, and when they realize it was something else entirely, they know they're in good hands. In this episode, Andrew and Connor get into why he treats a flop as a persona failure and not a personal one, the ten-second question to ask before you design anything for your colleagues, and why making his Zoom setup more professional made people trust him less. If you want your next pitch or offsite to bring some real joy instead of corporate cringe, this episode's for you. Chapters 00:00:00 The mutant magician who infected IDEO's DNA 00:00:53 The BDSM approach to opening a magic show 00:08:22 Technical difficulties: the slide deck joke that built trust 00:11:04 Consider the context: the hack for creating wonder 00:14:39 Casting clients as investors 00:16:13 Snapping people out of Zoom multitasking 00:18:13 The psychology of deception 00:25:34 Adult-like wonder vs childlike wonder 00:30:26 Be creative by standing on the backs of giants 00:36:00 Being liked: the persona vs the person 00:40:41 Purpose is a byproduct, not something you find 00:43:19 From roller coasters to the Magic Patio 00:46:32 Shake up your routines and add randomness 00:49:24 Let's do some magic
- Sep 9, 20261h 16m
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 Kardashian to build the coalition behind the First Step Act — the most substantial breakthrough in criminal justice in a generation, according to the New York Times. 53,000 people are home from federal prison because of that one bill. Near the end of this conversation, Connor asks her a simple question: after decades of this work, are you tired? "Yes, I'm very tired, Connor. I'm very tired. And I never experienced burnout before in my life." We recorded this a few months ago. Since then, Nisha has announced she's stepping down from her nearly seven-year tenure as CEO of Dream.org. What you're hearing is a leader thinking out loud, before the decision, about what fighting to the best of her ability looks like at 50, compared to when she was 21 and chained by the neck to six other activists in the center ring of a circus. Along the way, she walks Connor through how she actually gets things done: how she names what she won't trade before anyone else at the table speaks, when working with an opponent is strategy and when it's selling out, and the question she asks her own staff when a deal starts to feel like a betrayal — who are we doing this for? If you've ever wondered whether the work is worth what it's costing you, this one is for you. Chapters 00:00:00 Fake blood, arrests, and the woman who gets sh*t done 00:01:08 Growing up rebellious 00:06:05 Punk rock and straight-edge hardcore 00:08:54 The circus arrest 00:14:11 Myanmar prison and five years of hard labor 00:23:25 The elevator with Marjorie Taylor Greene 00:26:18 Finding common ground without selling out 00:28:32 The First Step Act — 53,000 people home from prison 00:39:18 Would young Nisha think you're a sellout? 00:55:58 Exhausted but optimistic — why she can't stop 00:59:50 The trap of working hard 01:14:41 Power, unlikely allies, and what comes next
- Aug 26, 202646 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. First, he lost. Then he won. Then he won again. And then he lost. After that second loss, DeWine came home to Ohio where everyone congratulated him on a great end to a great career. Well, almost everyone. His wife Fran, who he met in the first grade and has now been married to for fifty-nine years, said, "you're not done unless you tell yourself you’re done." DeWine wasn't done. Next, he ran for Attorney General of Ohio and won. Then, he became Ohio's Governor, a role he finishes this coming January. So Connor sat him down for an exit interview on topics including: whether the American Dream can survive the AI revolution why the worst thing a leader can be is the smartest person in the room DeWine's thirty-year history of humanitarian work in Haiti his secret to remaining stubbornly optimistic (hint: have eight kids) Plus: the box of chocolates in sixth grade and the line his whole career comes down to: "Work is the price we pay to achieve what we want. No shortcuts." If you're looking for hope from someone who's been in the trenches for the past fifty years driving actual change, this episode is for you. CHAPTERS: Chapters 00:00 The career nobody wins by accident 00:06:53 Learning to lose — The 2006 Senate defeat 00:10:03 Never be the smartest person in the room 00:13:31 59 years — The partnership that started in first grade 00:21:41 Is the American Dream dead? 00:26:55 AI, critical thinking, and muddling through disruption 00:31:48 30 years in Haiti — Why he keeps going back 00:36:47 Springfield and the eating dogs rumor 00:38:30 What's next — Leaving the governor's mansion 00:41:03 Work is the price we pay — Advice for the next generation
- Aug 12, 202633 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: figuring out how to explain to a four-year-old that a parent is in prison. Deciding whether Elmo wears a mask during the pandemic, knowing half the country will be furious either way. Spending three years with every autism organization in America building a single Muppet. Doing layoffs in the hardest year the place has ever had. And answering the question she can't get away from: how do you stay true to your values and remain a beacon without becoming a lightning rod? She ran a television network before this. She worked in the White House. She says this one is harder than both. "People are like, how hard could it be? You're hanging out with Muppets. Yeah, right." What nobody tells you about Sesame Street is that it's a research operation. They tried a storyline about divorce, tested it, found it was scaring kids, and killed it. When they built Julia, the first autistic Muppet, they got every autism organization in one room, groups that disagreed with each other on almost everything, and found the one thing they all agreed on. A mother wrote in afterward. She'd never been able to find the words to tell her five-year-old she had autism, until her daughter saw the Muppet Julia on Sesame Street. Her daughter's reaction: "So I'm amazing too, right?" Plus: Big Bird's actual age, why she hires for a sense of humor, and what a lot of adults could stand to learn from a show made for three-year-olds. CHAPTERS Chapters 00:00:00 Managing Big Bird is harder than running the White House 00:01:44 The hidden complexity of Sesame Street 00:06:21 Reaching 500 million children — The scope of Sesame's mission 00:10:26 Creating Julia, the first autistic Muppet 00:14:22 "So I'm amazing too, right?" 00:17:28 Staying nonpartisan when everything is political 00:23:06 Big Bird is six years old 00:27:01 The hardest part: downsizing and losing USAID funding 00:30:40 Screen time guilt
- Jul 29, 202651 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 bitch on wheels (Connor's favorite). The real story starts there: how does a journalist turned national icon become herself without losing the magic that got her there in the first place? Connor and Katie’s conversation went everywhere: fame and what it does to your head, loss and what actually lasts, getting older, the Sarah Palin interview she still feels "secondhand cringe" about, pickleball, breast milk, how she got completely fooled by AI, and her glorious give-no-fucks era. Katie fills out a report card for Connor at the end too. You'll want to stay for that. CHAPTERS Chapters 00:00:00 How fame f*cks with your head 00:02:51 What most interviewers mess up 00:06:27 The power of boredom and the hippocampus 00:08:05 Addicted to the grind 00:12:18 Going independent before the creator economy existed 00:15:42 The perky problem and clapbacks on Threads 00:18:09 Fighting to be taken seriously 00:27:17 Sarah Palin and the interview heard around the world 00:33:20 AI, income inequality, and the Jevons paradox 00:37:59 Your colon saved a lot of lives 00:41:40 Faith, God, and being a secular humanist 00:45:12 We're all terminal, how do you want to spend your time? 00:47:55 Nothing matters but your friends and your family 00:49:38 The Katie Couric report card
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About Is This Working?!
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.
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