The Real Reason Young People Don't Have 'The Hunger' for Work (And What Leaders Need to Hear) with Generations Expert Dr. Eliza Filby

Admit it, you've complained about at least one other generation. Boomers, Gen X, Millennials, Gen Z—somehow, they all end up with reputations built around what's wrong with them. Dr. Eliza Filby has a different suggestion: stop asking what's wrong with them. And start questioning what world they were handed. Eliza is a contemporary historian, generations expert, and the author of Sunday Times bestseller: Inheritocracy. And with more generations in the workplace than at any point in history, she is precisely the person we need to show us a new way to win… together.  In this conversation, Eliza makes connections about how generational change is reshaping work, wealth, and modern life that I’d never thought to connect. She might just change how you see the world (and people) around you. In this episode you'll learn: ➡️ Why calling Gen Z "entitled" is the wrong diagnosis (and what's really driving the behavior leaders complain about most)  ➡️ How retirement planning and eldercare became the new midlife crisis ➡️ How the economy changed after 2008 + quietly rewrote the rulebook for every generation that followed  ➡️ Why belonging is becoming increasingly rare (even though we need it) ➡️ Why Millennials + Gen Z are more likely become homeowners by being loyal to their parents than by being loyal to their jobs ➡️ 3 things no AI will replace in the workplace… ➡️ What’s driving hyper-individualism + how do we fix it We all may have strong opinions about one another, but it’s time to focus on building greater understanding. This conversation is a good place to start. This… is A Bit of Optimism. + + + To buy a copy of Dr. Eliza Filby’s bestselling book Inheritocracy: It’s Time to Talk About the Bank of Mum and Dad, head to: https://www.elizafilby.com/books  Want to hear more from Eliza? Check out her It’s All Relative Newsletter: https://www.elizafilby.com/newsletter  + + + Chapters 00:00:00 Rethinking the Generational Divide at Work 00:01:35 How Dr. Filby Became a Generations Expert 00:04:33 Defining Generations: Why They're Getting Shorter 00:08:42 The Fragmentation of Shared Experience 00:14:29 Conspiracy Culture Infiltrates the Workplace 00:16:16 The End of Job Security and the Rise of the Solopreneur 00:18:02 What Leaders Must Offer in the Age of Uncertainty 00:20:31 The Bank of Mom and Dad: Living in an Inheritocracy 00:28:23 Why Young People Don't Have 'The Hunger' for Work 00:31:35 The Changing Life Cycle: Delayed Adulthood and Pressured Midlife 00:41:45 Rising Individualism and the Loss of 'We' at Work 00:47:02 Gen AI: The Next Generation in the Workplace 00:50:44 The Solution: Let Humans Do What Can't Be Counted 01:00:42 Disrupting the Path to Mastery and Nurturing Human Skills 01:03:02 How the Generations Can Come Together + + + Simon is an unshakable optimist. He believes in a bright future and our ability to build it together. Described as “a visionary thinker with a rare intellect,” Simon has devoted his professional life to help advance a vision of the world that does not yet exist; a world in which the vast majority of people wake up every single morning inspired, feel safe wherever they are and end the day fulfilled by the work that they do. Simon is the author of multiple best-selling books including Start With Why, Leaders Eat Last, Together is Better, and The Infinite Game. + + + Website: http://simonsinek.com/ Live Online Classes: https://simonsinek.com/classes/ Podcast: http://apple.co/simonsinek Instagram: https://instagram.com/simonsinek/ Linkedin: https://linkedin.com/in/simonsinek/ Twitter: https://twitter.com/simonsinek Facebook: https://www.facebook.com/simonsinek

The most successful leaders, coaches, and teams in history share one counterintuitive secret: their main focus wasn’t winning. And yet… they won more than everyone else.  My guest, Don Yaeger, learned this lesson from his mentor: legendary college basketball coach John Wooden. Don is one of my favorite master storytellers, a top business leadership coach, author of 44 books, 13 of them New York Times bestsellers, and a former Associate Editor at Sports Illustrated. Don has worked alongside the greatest athletes of our generation: Michael Jordan, Serena Williams, Michael Phelps. But no relationship shaped him more than the 12 years he spent as Coach Wooden's mentee. Whether or not you're a sports fan, I promise you: the lessons Don shares are as universal as it gets. We explore what it really means to win in business and in life. The greatest leaders in history already figured this out. The question is why the rest of us aren't following their lead. In this episode you'll learn:  ➡️ Why the winningest coach in college basketball history never talked about winning (and what he focused on instead) ➡️ The Bill Walton story that reveals how great leaders hold standards without exceptions (even for their best people)  ➡️ How one conversation with John Wooden transformed Don's marriage & the weekly habit he's kept for 16+ years  ➡️ What Delta CEO Ed Bastian's "virtuous cycle" can teach any leader about putting people before results  ➡️ What a great mentor actually look like and how to know when you’ve found one If you've ever chased the short-term win at the cost of the long game… this episode is the reset you didn't know you needed.  This… is A Bit of Optimism. + + + If you want to read a free chapter from Don's upcoming book The Business of Storytelling, head to: https://www.donyaeger.com/chapter/ Join the Leaderful app! Listeners can use promo code: STORY30 when you download the app or sign up at simonsinek.com. + + + Chapters Chapters 00:00:00 The Power of Appreciation: What You Look For, You Find 00:02:02 From Delivering Newspapers to Sports Illustrated: Don's Journey to Journalism 00:04:21 Don’s 12-Year Mentorship with Coach John Wooden 00:06:50 Coach Wooden's Philosophy: Pyramid of Success 00:09:00 The Bill Walton Haircut Story: How Wooden Managed Ego and Held Everyone to the Same Standards 00:10:33 Building Better Humans, Not Just Better Players 00:14:36 The Love Letters That Changed Don's Marriage 00:19:35 Looking for Things to Love: The Mindset That Changes Everything 00:22:23 Leading with Employee Care Over Customer-First Mentality 00:33:55 What True Mentorship Really Means: It's Not Transactional 00:47:07 Why Aren't More Leaders Following Coach Wooden's Example? 00:53:17 The Best Storytelling Advice: Know Your Audience + + + Simon is an unshakable optimist. He believes in a bright future and our ability to build it together. Described as “a visionary thinker with a rare intellect,” Simon has devoted his professional life to help advance a vision of the world that does not yet exist; a world in which the vast majority of people wake up every single morning inspired, feel safe wherever they are and end the day fulfilled by the work that they do. Simon is the author of multiple best-selling books including Start With Why, Leaders Eat Last, Together is Better, and The Infinite Game. + + + Website: http://simonsinek.com/ Live Online Classes: https://simonsinek.com/classes/ Podcast: http://apple.co/simonsinek Instagram: https://instagram.com/simonsinek/ Linkedin: https://linkedin.com/in/simonsinek/ Twitter: https://twitter.com/simonsinek Facebook: https://www.facebook.com/simonsinek + + + Photo/Video credits for this episode: https://tinyurl.com/ycxdw52s

We talk a lot about building successful things. But what does it actually take to build something people love? Jesse Cole has built an entirely new genre of entertainment: The Savannah Bananas and the Banana Ball League. They’re a viral sensation, selling out stadiums across the country, and have over 4.2 million fans on their  ticket waitlist. On the surface, Banana Ball looks like a wild and entertaining version of baseball. But underneath it all is something much more disciplined: an obsession with the fan experience.  Jesse calls his approach Fans First and it’s more than a slogan and the title of his book… It’s a standard. Every minute of the two-hour games are crammed with attention grabbing spectacle. It’s a full-blown live experience designed for every seat in the stadium: players dance, fans are part of the show, trick plays defy the laws of physics, there are multiple sing-alongs… all during an actual baseball game.  In this conversation, we talk about building something new for others, from embracing years of failure (including selling just two tickets in the first three months), to creating experiences that make people feel included, joyful, and valued. We also discuss how he took inspiration from Disney and PT Barnum, the importance of affordable in-person experiences, and how his team reviews every single detail after every show to get better the next day. Because what Jesse’s building goes beyond just entertainment. It’s a place where people can feel seen for generations to come. And in a world that often moves too fast to build things with care… Those human details might be what matter most. This… is A Bit of Optimism. --------------------------- To learn more about the Banana Ball League or sign up for the ticket waitlist, check out: https://bananaball.com/  Or if you want all things Savannah Bananas, head to: https://thesavannahbananas.com/  ---------------------------

We live in a world that pushes us to simplify everything: right or wrong, good or bad, this or that. It makes things and our place in the world easier to understand. But the truth is rarely simple… in fact, it’s often messy and deeply human. For 50 years, Ken Burns has mastered his craft, becoming one of the most prolific and respected documentary filmmakers. His documentaries notably resist easy answers. From The Civil War to The Vietnam War to Baseball, Ken has shaped how we understand American identity, political memory, and our shared history. His latest project, The American Revolution, is a six-part PBS series that tells the story of America’s founding. He revisits the revolution through multiple human perspectives, which reveals new complexity to a familiar story. Ken’s guiding principle is simple: “it’s complicated.” And that philosophy shows up in everything he does. Because the most honest stories hold opposing truths at the same time. In this conversation, Ken and I explore why storytelling matters more than arguments, how simplifying the world can help us understand it—but also distort it—and why empathy lives in the space between what’s included in a story and what’s left out. We also dive into why human behavior hasn’t changed much over time, what mistakes humans keep repeating, how embracing complexity might help us better understand each other, and what history can teach us about who we are and who we’re still becoming. If you’ve ever struggled to make sense of a complicated world, or felt frustrated by how quickly we reduce people to labels, this episode is a powerful reminder: understanding lives in our ability to see the whole story. This… is A Bit of Optimism. --------------------------- If you want to watch “American Revolution” the six-part, 12-hour documentary directed by Ken Burns, Sarah Botstein, and David Schmidt on PBS, head to: https://www.pbs.org/kenburns/the-american-revolution ---------------------------

Naiveté is one of the most powerful assets an entrepreneur can have. In fact, I think some of the most meaningful things in the world only exist because someone was naive enough to try. Daniel Lubetzky would know. In a crowded category and cutthroat industry, Daniel dared to build a company called KIND. He started with a simple question: how can we help people snack healthily without compromising their values? KIND Bars are now a household name and Daniel achieved his dream of building the culture behind the brand. A culture rooted in trust, long-term thinking, and social good. Essentially, a place where people loved to work and a company that thrived as a result. In this conversation, Daniel and I explore why entrepreneurship is less about ego and more about problem-solving, why brands are promises that must be kept, and how thinking in the short-term erodes trust in both business and society. Daniel’s story doesn’t stop at the wildly successful business he founded. The son of a Holocaust survivor, he grew up with a deep sense of responsibility to prevent hatred and division from taking root again. That calling first led him to create PeaceWorks, bringing people together through commerce, and now fuels his work with the Builders Movement. Builders is an effort to channel curiosity, compassion, and courage to reduce polarization and rebuild trust… together. Some important context, because this episode touches on peace building and polarization, is that it was recorded back in December 2025 and before recent developments in the Middle East. But this episode is about how kindness can be a competitive advantage, how optimism can be strategic, and how each of us has a role to play in building a future that’s more connected than divided. This… is A Bit of Optimism. --------------------------- If you want to learn more about the Daniel’s work with The Builders Movement, head to: https://buildersmovement.org Check out the products and work being done at KIND: https://www.kindsnacks.com ---------------------------

As businesses race toward faster systems, smarter tools, and total automation, something critical is getting lost: human connection. And ironically, the rise of AI is making that gap impossible to ignore. In this episode, I sit down with returning guest and close friend Will Guidara, former co-owner of Eleven Madison Park, to explore why humanity is becoming the ultimate competitive advantage in the age of AI. Will helped transform a restaurant into the best in the world, not by reinventing the food being served, but by reinventing the experience around it. He calls this philosophy "Unreasonable Hospitality," which is the practice of going beyond what’s expected or required to make someone feel genuinely seen, valued, and cared for to create a memorable human experience. He argues that in a world where people expect excellence, the real differentiator is care. And Will isn’t alone in this belief. His book Unreasonable Hospitality, which I’m the proud publisher of, is a global bestseller. And his follow up book, Unreasonable Hospitality: The Field Guide, comes out April 28, 2026. In this conversation, Will and I unpack why human value will continue to rise in an automated world, how the smallest moments of care can create lasting loyalty, how we can turn automation’s efficiency into better experiences, and why the things that matter most in our lives are the hardest to measure. And fair warning, Will and I do giggle our way through some of this conversation about why technology can’t replace human connection, the hidden cost of achievement, and a story about how a single piece of Basque cheesecake delivered to a hotel room is a gesture thoughtful enough to make someone feel seen. That’s just the kind of friendship we have. So if you’re wondering how to stand out and live a more meaningful life in a world increasingly shaped by AI… and share a laugh with us… this is a conversation for you. This… is A Bit of Optimism. --------------------------- To stay in the loop with Will or purchase his best-selling book Unreasonable Hospitality, head to: https://www.unreasonablehospitality.com/ If you’d like to pre-order Unreasonable Hospitality: The Field Guide, out April 28, 2026, check out: https://uhthefieldguide.com/ ---------------------------

Team Simon here! While A Bit of Optimism is on a short break, we’re revisiting a few episodes you helped make some of our favorites. We’ll be back with brand-new conversations next week, on March 24th, 2026. In the meantime, we’re bringing back an episode that explores a word most people like to avoid: death. We dance around the subject or use vague euphemisms to not hurt anybody. But what if being open about our deaths meant we could live happier lives? That’s where Alua Arthur comes in. Alua is one of the most prominent death doulas in the country, which means it’s her job to help people die. She offers support to her clients and their families as they embark on their dying journey, tackling everything from financial planning and insurance policy to emotional support and grief. Before this work, Alua was a lawyer, but after a life-changing encounter that forced her to confront mortality in a new way, she shifted her path entirely. Now she has dedicated her career to helping others prepare for the end of life with clarity, compassion, and even a bit of humor. In this conversation, Simon and Alua talk about why our culture struggles to talk honestly about death, what she’s learned from the people she’s accompanied in their final days, and why remembering that life is finite can help us live with more presence, gratitude, and intention. This… is A Bit of Optimism. --------------------------- For more on Alua and her work, check out: https://goingwithgrace.com/ & @GoingwithGrace‬  ---------------------------

Hello from Team Simon! We’re taking a short hiatus, but A Bit of Optimism will return with brand-new episodes March 24th. In the meantime, we’re revisiting some of our favorite episodes. Episodes that many of you who listened, shared them, and told us what resonated. This week, we’re bringing back Simon’s conversation with journalist, author, and longtime friend Maria Shriver. Maria Shriver was born into the legendary Kennedy and Shriver families, arriving with a script already written for her—an identity shaped by legacy and expectation. From the start, the world had ideas about who she should be. But after decades as a journalist, years as California’s First Lady, and raising four amazing kids, Maria has been on a lifelong journey to peel back the layers and ask Who am I now?—and answer it for herself. Maria also happens to be Simon’s best friend. They talked about how they became each other’s “8-minute friends,” the quiet questions that shape us, and Maria’s beautiful new book of poetry—which she reads from in this episode. It’s all about identity, self-reflection, and finding your voice in a world that keeps trying to define it for you. If you’ve ever wondered who you are beyond what you do or how to rediscover yourself after life changes, this conversation is a beautiful reminder that identity is something we can reclaim again and again. This… is A Bit of Optimism. --------------------------- For more on Maria Shriver, check out: her book: https://bookshop.org/p/books/i-am-mar... ---------------------------

Team Simon here! As we take a short hiatus, A Bit of Optimism will return with brand-new episodes on March 24, 2026. Until then, we’re revisiting some of the conversations you loved and we still think about long after the microphones turned off. This week, we’re rewinding to Simon’s conversation with the wildly creative and endlessly curious Jacob Collier. To create something truly original, do we build something new or break what came before? Perhaps the answer is both—simultaneously.  Jacob Collier does exactly that. A songwriter, multi-instrumentalist, and Grammy Award winner, Jacob has built a career on blending structure with spontaneity. He’s known for turning entire concert halls into three-part choirs, transforming audiences from spectators into collaborators. His album "Djesse Volume 4" was nominated for Album of the Year at the 2025 Grammy Awards, alongside icons like Beyoncé, Billie Eilish, and Taylor Swift. Although Beyoncé's "Cowboy Carter" won, Jacob snagged his seventh Grammy for his rendition of "Bridge Over Troubled Water." Simon sat down with Jacob in a music studio just days before the 2025 Grammys, surrounded by pianos and possibility. What unfolded was more than a conversation about music. It was a masterclass in creativity, about holding opposites at once, embracing imperfection, and having the courage to follow curiosity wherever it leads. If you’ve ever wondered how creativity really works or how to find your own voice without losing what came before—this one’s worth another listen. This… is A Bit of Optimism. --------------------------- For more on Jacob, check out:  http://jacobcollier.com   ‪@jacobcollier‬ ---------------------------

Scott Galloway and I don’t always see the world the same way, but our friendly debates almost always lead us back to common ground. It’s probably why we enjoy talking to each other as much as we do. If you haven’t heard my friend Scott’s name before, he’s known for being brilliant, provocative, and unapologetically himself. He’s a professor at NYU Stern School of Business, entrepreneur, bestselling author, and larger-than-life social commentator. In recent years, his work, which includes his new book Notes on Being a Man, has explored the challenges facing men today, from loneliness and dating to purpose and identity. Scott and I have different views on what “healthy masculinity” looks like. He’s not afraid to say things during this podcast that might ruffle some feathers. But inevitably, the conclusions we get to are introspective, vulnerable, and often universal. That’s certainly true for one revelation we share: confidence matters. Not the loud, performative kind. The real kind. The kind that helps people risk rejection, build meaningful relationships, and show up more generously in the world. In this episode, Scott and I talk about the “masculinity crisis,” why young people are struggling to connect, how purpose outlasts happiness, and why masculine and feminine traits are complementary rather than competing. We explore the need for good social risks like leaving the house, meeting people, pursuing relationships, and hearing “no,” and why confidence is less about ego and more about security, kindness, and connection. This is a conversation between two opposites who challenge each other, listen deeply, and ultimately agree that building real confidence may be one of the most important skills we can teach the next generation. This… is A Bit of Optimism. --------------------------- If you want to read Scott’s new book Notes on Being a Man, head to: https://www.simonandschuster.com/books/Notes-on-Being-a-Man Check out Scott’s podcast “The Prof G Pod”: https://www.youtube.com/c/TheProfGShow-ScottGalloway You can also watch his podcast “Pivot with Kara Swisher and Scott Galloway”: https://www.youtube.com/@pivot To stay up to date with all of Scott’s work, head over to: https://www.profgalloway.com/ ---------------------------