A Bit of Optimism

Hello from Team Simon! We’re taking a few weeks off and will be back with brand-new episodes of A Bit of Optimism on Tuesday, October 27. Until then, we’re revisiting some of our favorite conversations, including this one with a longtime friend of Simon’s: Esther Perel. For most of history, we stayed in marriages and jobs because we had to. Happiness was a nice bonus. Today we get to choose who we love and where we work, so happiness has become the glue that holds it all together. Few people have watched that shift as closely as Esther Perel. For four decades, she’s seen how love, family and work have been reshaped by no-fault divorce, the internet, and now AI. Her conclusion hasn’t changed: the quality of our relationships determines the quality of our lives. It’s a line she first said out loud years ago, in a WHY Discovery session with Simon. Esther is a psychotherapist, the bestselling author of Mating in Captivity and The State of Affairs, and the host of the podcast Where Should We Begin? Her card game…

Team Simon here! A Bit of Optimism is on a short break, and brand-new episodes return October 27. Until then, we're revisiting a few conversations we keep coming back to. This week it's Arthur Brooks, a longtime friend of Simon's and one of his favorite people to talk to. Have you ever felt like you're falling behind? Everyone else seems to have a plan, a timeline and the next rung on the ladder lined up. Any detour, like a gap year, a pivot or a job that isn't quite right, feels like losing ground. Arthur Brooks thinks you're running the wrong race. Chasing a finish line is one of the surest ways to end up unhappy. He argues that happiness lives in the process, not the outcome. Arthur is a bestselling author and teaches one of the most popular classes at Harvard Business School: a whole course on happiness. He lives what he teaches, too. He played French horn professionally from 19 to 31 and then reinvented himself as a behavioral scientist. After that, he became president of a Washington think tank without…

Hello from Team Simon! We're taking a few weeks off and will be back with brand-new episodes of A Bit of Optimism on Tuesday, October 27. Until then, we're revisiting some of our favorite conversations, starting with one of the most fun we've ever had: Rob Lowe. Maybe you know the feeling: you've got an idea, a joke, a risk you want to take… and you talk yourself out of it before anyone else gets the chance. Rob Lowe has spent four decades doing the opposite. He calls it a healthy case of the "screw-its." It's how he survived an industry famous for chewing people up. He went from movies to The West Wing when movie stars didn't do TV, and from TV to hosting a game show when that was supposed to be career death. His secret isn't avoiding failure. It's never letting failure decide what he tries next. Rob is an actor, producer, and bestselling author whose career runs from The Outsiders and St. Elmo's Fire to The West Wing and Parks and Recreation. He hosts FOX's The Floor and the podcast Literally! with Rob…

Be honest: you've taken a mental health day that made you feel worse. You stayed in bed, you avoided the thing, and by evening it was still waiting for you—with less of the day left to face it. Amy Morin thinks the problem starts with the word. We treat mental health as something you either have or you don't… and framed that way, there's nothing to actually do on a bad day. Her work runs on the opposite premise: mental strength is a practice, and you build it like you'd build anything else. Amy is a psychotherapist, a clinical social worker, and the author of the bestseller 13 Things Mentally Strong People Don't Do and the new The Mental Strength Playbook. She became a therapist at 22 and lost her mother at 23. Three years later—to the day—her husband died, and the mental health agency where she worked gave her three days of bereavement leave. She built the practices that became her book in real time, from there. In this conversation, Amy walks through exactly what she did to get mentally fit. Not as theory,…

The internet is flooded with advice for dating in the smartphone age: know your type, trust the spark, watch for red flags, protect your peace, never settle. It sounds like self-respect, but relationship expert Amy Chan thinks it’s a big reason dating feels impossible right now. Her argument: we need to correct the lessons we’ve learned when it comes to dating. The person who’s great on a first date isn’t necessarily great at a relationship. Instant chemistry isn’t always a good sign. A red flag could just be an imperfection. And keeping our options open has made a lot of us genuinely bad at choosing someone. Amy is the founder of Renew Breakup Bootcamp and the author of Unsingle: How to Date Smarter and Create Love That Lasts. For nearly two decades she’s looked at dating through psychology and neuroscience — why we’re drawn to certain people, why relationships fall apart, and what actually predicts whether one lasts. She started her career helping people end relationships… Now, she teaches them how to…

Have you ever sat through a presentation and felt your attention just start to…drift? Chances are, it wasn't the content. It was the delivery. A year ago, Rob Willis was a corporate trainer with years of experience and a sharp eye for what makes people listen. He wondered if what he taught in workshops would resonate with a larger audience. So he started making short videos that break down what makes great speakers great: from their word choice, to structure, to the energy they brought to any room or conversation. Rob even made a video breaking down my method of public speaking. In his video, Rob dissects my signature opening line, and my friends couldn't stop sending it to me. One hundred videos in one hundred days later, Rob's videos are going viral on a regular basis, and a whole new audience is eager to learn from him. But what I find most interesting about Rob is where he actually learned all of this. Not in a classroom. He learned it by giving free walking tours in Berlin, where nobody pays up front…

This might sound familiar: you read a full page, get to the bottom, and realize you absorbed none of it. There's a stack of books beside your bed you fully intend to finish. And the only phone number you can remember is your own. Jim Kwik says none of that means something is wrong with our brains. It’s that we were taught what to learn, but rarely ever taught how to learn. Jim would know. A well-meaning teacher called him "the boy with the broken brain" when he was nine, and for years he believed it. He's spent the three decades since proving otherwise — as a top brain coach, a leading expert on memory and accelerated learning, and the bestselling author of Limitless. His new book, Limitless Daily, offers 366 daily upgrades to help you focus, remember, and think better. In this episode you'll learn: ➡️ Why reading faster can actually improve comprehension ➡️ The free technique that stops your mind wandering mid-page ➡️ How to prompt your own brain the way you prompt AI ➡️ What your "dominant question"…

Maybe this sounds familiar: you finally get the opportunity you've been waiting for, and the voice in your head says, "I'm not ready, I don't belong here." Now imagine hearing that voice with millions of people watching. Mary Holland Nader has lived it. She never dreamed of fame, but when Hulu's reality series Love Thy Nader came knocking, she traded her secure Wall Street job for the spotlight and put her new platform to work. It allowed her to launch Mary & Pip, a purpose-driven fintech company that takes a wellness approach to money, demystifying finance for those of us it usually makes feel dumb. She also brings that expertise to her new podcast, Growing Interest (where I was lucky to be among her first guests). On the show, Mary Holland lets us join every step of her founder’s journey… even when it’s messy. Because she never wanted to be famous, but now that she is, she’s realized fame is leverage. And Mary Holland's committed to using hers to help and inspire others. In this episode you'll learn: ➡️…

Maybe you know the feeling: everyone around you seems to be getting ahead, and every hour you spend on something "frivolous" — the hobby, the detour, the game on a Sunday afternoon — feels like falling behind. Brendan Hunt's career is proof those hours are never wasted. The detour turned out to be the path all along. Most of us know Brendan as Coach Beard and as the Emmy Award-winning co-creator of Ted Lasso. But before any of that, he was an unknown Chicago improv actor when the Amsterdam comedy institution Boom Chicago offered him something different. He moved to Amsterdam for a year… that turned into five… and he joined an alumni roster that now includes comedians like Seth Meyers, Jordan Peele, Amber Ruffin, and Jason Sudeikis. Brendan performed every night, fell head over heels for soccer ("a soccer missionary for all Americans," as he puts it), and struck up a friendship with Jason Sudeikis. Years later, all of it collided into one of the most beloved shows on television, Ted Lasso, which is back for…

Every lasting relationship has survived at least a few hard conversations. But most of us would still rather not have them... So we put them off and tell ourselves the tension will fade on its own. Instead it goes underground: into the stories we build about people, the resentments we quietly collect, and the side-texts we send about a colleague we won't talk to directly. But a hard conversation is a short burst of discomfort in exchange for something better on the other side: trust, collaboration, and a relationship strong enough to survive the next one. Feelings at Work is a special five-part series from A Bit of Optimism, where Simon Sinek and Alex Simon, founder of LifeShop, explore the human skills that shape how we work, lead, and build relationships. Together, they unpack the emotional challenges most of us face every day—from people pleasing and listening to giving feedback, taking accountability, and having difficult conversations. In this final episode, Simon and Alex take on hard conversations:…

Everyone says they want more accountability at work… yet few of us think we're the ones who need to learn how to be more accountable. Most of us believe we already know how to own a mistake. We've all said sorry and truly meant it. But meaning it and doing it well are two very different things. And when we’re the first to apologize, we model to everyone around us how cathartic accountability can be. Feelings at Work is a special five-part series from A Bit of Optimism, where Simon Sinek and Alex Simon, founder of LifeShop, explore the human skills that shape how we work, lead, and build relationships. Together, they unpack the emotional challenges most of us face every day—from people pleasing and listening to giving feedback, taking accountability, and having difficult conversations. In this episode, Simon and Alex take on accountability: why owning a mistake can feel like losing, why taking credit and dodging blame come from the same place, and what a real repair actually looks like. You'll discover why…

Giving and receiving feedback is one of the hardest things we do at work and most of us just... avoid it. But avoiding feedback has a cost. Everything you need to grow is already in the room and it's just sitting in your blind spot. Your colleagues can see it. Your boss can see it. And nobody will tell you, unless you learn to ask. Feelings at Work is a special five-part series from A Bit of Optimism, where Simon Sinek and Alex Simon, founder of LifeShop, explore the human skills that shape how we work, lead, and build relationships. Together, they unpack the emotional challenges most of us face every day—from people pleasing and listening to giving feedback, taking accountability, and having difficult conversations. In this episode, Alex and Simon take on feedback: how to give it, how to take it, and how to ask for it. You’ll discover ways to give feedback people can actually hear, receive criticism without taking it personally, and build a feedback culture on any team. Alex and Simon share practical…

The fastest way to improve your relationships isn't talking. It's listening. Most of us hear what's being said. Very few of us know how to make someone feel heard. Feelings at Work is a special five-part series from A Bit of Optimism, where Simon Sinek and Alex Simon, founder of LifeShop, explore the human skills that shape how we work, lead, and build relationships. Together, they unpack the emotional challenges most of us face every day—from people pleasing and listening to giving feedback, taking accountability, and having difficult conversations. In this episode, they explore one of the most important communication skills we can develop: listening. Together, they share practical techniques to improve your listening skills, build trust, navigate difficult conversations, and create better outcomes at work and at home. You'll learn why people often ask for one thing but actually need another, how to stop jumping into fix-it mode, and Alex's simple Four-Second Rule for becoming a better listener. When people…

Welcome to Feelings at Work, a special series from A Bit of Optimism with Simon Sinek. Work isn't just about deadlines, meetings, and getting things done. It's also where we experience frustration, excitement, trust, anxiety, belonging, conflict, and joy. If we want to build healthier teams and better workplaces, we have to get better at understanding the emotions that shape how we work together. That's what this series is about. In each episode, Simon Sinek sits down with Yale professor and Lifeshop founder Alex Simon to explore one emotional challenge that affects how we work, lead, and relate to one another. Together, they unpack the emotional skills most of us were never taught—but use every single day. This episode is about saying yes. Have you ever agreed to something... and immediately regretted it? Maybe you didn't want to disappoint someone. Maybe you thought, I'll figure it out somehow. Maybe your calendar is packed, your to-do list never gets shorter, and somehow you're still worried you're…

Maybe this sounds familiar: you fall hard for someone, and over a year later you're fighting about the very things that drew you to them in the first place. And you can't figure out how the person who felt so right suddenly feels so wrong. Dr. Harville Hendrix has spent 50 years studying love. And he’s also lived through its hardest challenges: one divorce, two near-misses in his current marriage, and a couple’s therapist who fired him and his wife, calling them "the couple from hell." That marriage is now 45 years strong. Harville is a couples therapist, and alongside his wife and creative partner Dr. Helen LaKelly Hunt, they creator Imago Relationship Therapy. They’ve also written 10 books, including the bestseller Getting the Love You Want, the book that made him a fixture on Oprah for nearly two decades. Harville’s theory is this: we don't consciously choose who we fall for, rather our unconscious does. And it has an agenda. In this episode you'll learn: ➡️ Why you keep falling for the same person ➡️…

We tell ourselves the reason we never chase the big dream is that we're not ready, not brave enough, doomed to fail. Nelly Attar would tell you she felt all of that too… but she chased them anyway. Nelly is a psychologist turned extreme athlete and mountaineer. She built Saudi Arabia's first dance studio, MOVE, at a time when women couldn't train publicly by sneaking classes into a warehouse and office building after hours. She's the first Lebanese person to climb the five highest peaks in the world, like Everest. And she also became the first Arab to summit K2, the world’s second highest peak that’s so dangerous that one in four people who attempt it survive. But what makes Nelly remarkable aren’t the summits and heights she reaches. It's that she's found a way to turn individual acts of accomplishment into acts of service: for the women she shows what's possible and for the team that climbs beside her. In this episode you'll learn: ➡️ The difference between fear that protects you and fear that holds you…

Sixteen years ago, an unknown CEO running a manufacturing company in the Midwest saw my TED Talk and recognized something in it. He sent me a letter and we made plans to meet. What started as a one-hour lunch turned into three, then four days touring factories together across the Midwest, and an idea I had only imagined turned out to already exist in reality. That CEO was Bob Chapman. Over five decades, Bob grew an unassuming manufacturing company in the Midwest into a global proof point that leadership grounded in humanity can scale and outperform. Bob saw the people in his company as human beings in his care, people he felt responsible to help become healthy, fulfilled, and whole. His belief was simple and profound: when people are cared for at work, they build happier families, stronger communities, and a better world. He called it Truly Human Leadership. In the years that followed, Bob became something more: a mentor, a close friend, the central figure in my book Leaders Eat Last, and one of the people…

Be honest: AI makes you a little nervous. Maybe you're afraid it'll take your job. Maybe you're overwhelmed by all the advice about prompts and agents and which chatbot to use. Or maybe you're just quietly hoping it'll all slow down. Ethan Mollick says we're underestimating our own agency in the age of AI. Instead of worrying about what AI will do to us, we should focus on what we choose to do with it. Ethan is a Wharton professor, the author of the bestseller Co-Intelligence: Living and Working with AI, and the writer behind “One Useful Thing,” one of the most popular newsletters on AI, work, and education. He's spent twenty years studying how people actually use technology, and he's become the go-to voice for making sense of AI without the hype or the doom. And in his new book, Co-Existence: The Next Phase of AI, he explores what comes next as AI moves from a tool we prompt to a presence we live and work alongside. In this conversation, Ethan shares the practical playbook most of us are missing and makes…

Most of us are so certain about, well, everything. We think we can predict what's coming, what that off-hand comment really meant, what that look was about, what's going to go wrong. And according to Dr. Ellen Langer, that certainty is making us miserable… and possibly making us sick. Dr. Langer is a psychologist, Harvard professor, and the "Mother of Mindfulness." In her book The Mindful Body, she makes the case that the way we think directly shapes the way we heal, age, stress, and recover. Her conclusion: the mind and the body were never two separate things to begin with. And we have far more agency over both than we've been led to believe In this episode you'll learn: ➡️ What mindfulness (and mindlessness) really is ➡️ The one question that can dissolve stress almost instantly ➡️ Why the story you tell yourself is more powerful than what actually happened ➡️ The study that proved people lost weight without changing their diet or exercise ➡️ The difference between nervousness and excitement (and why it…

In a world of job-hopping, side hustles, and an endless LinkedIn feed, Tim Harris did something almost no one does anymore. He stayed put. Few executives spend an entire career helping build a dynasty. Tim Harris spent 35 years with the Los Angeles Lakers, rising to President of Business Operations and helping transform the franchise into a global brand. Through championship eras, iconic athletes like Kobe Bryant and LeBron James, and decades of change in professional sports, Tim's influence was felt not on the hardwood, but in the culture, leadership, and business excellence that powered one of the NBA's most storied organizations. In this episode you'll learn: ➡️ Why clarity of role is the most underrated tool in any leader's arsenal ➡️ The three unspoken words that silently destroy any team ➡️ What Kobe Bryant taught Tim about mindset (+ why it matters off the court) ➡️ How the Lakers built one of the most powerful brands in sports ➡️ What elite athletes do differently + how it translates directly to…

Hello from Team Simon! We're taking a quick break this week and will be back with brand-new episodes of A Bit of Optimism next Tuesday. Until then, we're revisiting one of our favorite episodes — when bestselling novelist Fredrik Backman joined the show to talk about the thing he's spent his whole career writing about: the quiet, radical power of showing up for people. And Fredrik says great friendships aren't found by luck. They're built deliberately, repeatedly, and, sometimes, inconveniently by people who choose to do the work. Fredrik is the internationally bestselling author of A Man Called Ove (adapted into the film A Man Called Otto), Anxious People, and the Beartown series. His book, My Friends, is a love letter to the relationships that quietly shape who we become. In this conversation, Fredrik opens up about his best friend of over 30 years and what 30 years of real friendship actually requires. His words will have you thinking hard about the friends you might be taking for granted. In this episode…

Maybe this sounds familiar: you leave a party and spend the rest of the night convinced everyone was upset with you. Or you replay something you said in a meeting for days and second-guess every last word. Vanessa Van Edwards has been there. As a self-proclaimed "recovering awkward person," she’s spent two decades decoding the hidden dynamics of human interaction to make those skills teachable for introverts and extroverts alike. Vanessa is a behavioral researcher, bestselling author, and founder of Science of People. In her book, Conversation: How to Be Instantly Likeable in Any Interaction, she makes the case that social skills aren't a personality type, they're learnable. And she believes we are living in the most critical moment in history to start learning them. In this episode you'll learn: ➡️ Why "just be yourself" is unhelpful advice + potentially cruel ➡️ The important everyday interactions technology + AI replaced ➡️ Where to stand at a party so someone always talks to you ➡️ How to have better…

We often comfort ourselves with the idea that things happen for a reason, or define our struggles as a test of strength. Tom Nash might ask you to reconsider. Tom is a speaker, former DJ, and globe-trotting advocate for agency, anti-fragility, and the radical idea that your worst moment might be your greatest asset — as he argued in his TED Talk, "The Perks of Being a Pirate.” He’s also the mind behind Last Meal with Tom Nash where he asks his guests what their last meal would be if the world ended tomorrow, and then actually cooks it for them. In our conversation, Tom shares how, at 19, a rare bacterial infection left him a quadruple amputee with a 2% chance of survival. And he'll tell you it's the best thing that ever happened to him. This isn’t just another conversation about resilience. It’s a deep dive into agency and the difference between a life that happens to you and one you actually choose. In this episode, we explore: ➡️ Why the story you tell yourself about your own life is the most powerful…

If at some point, you've looked at your life—your job, your relationships, your achievements—and thought: “is this it?” This episode is for you. Mike Posner had that moment at 30. His life, by every external measure, was extraordinary: he had hit songs, Grammy nominations, millions in the bank. He was a pop star… And he was miserable. What followed was one of the most honest reckonings we've ever heard on this show. Mike walked across America, survived a rattlesnake bite, climbed Everest, and came out the other side with something no amount of success had ever given him: peace. Mike Posner is a multi-platinum, Grammy-nominated recording artist, songwriter, and producer. But the reason you should listen to this conversation has nothing to do with any of that. It has everything to do with where he was and his incredibly human journey getting to somewhere better, more peaceful, and more meaningful. He even wrote a song about it—a follow up to his hit song “I Took a Pill in Ibiza” called “I Went Back To Ibiza.”…

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 ➡️…

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…

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…

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…

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…

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…

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…

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…

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…

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…

It’s often true that the most challenging conversations are often the ones most worth having. Conversations that bring up strong feelings, different experiences, and questions without easy answers. Policing, and how we can make it better, is one of those conversations. San Leandro Police Chief Angela Averiett has spent nearly three decades in law enforcement, navigating the profession’s challenges while advocating for a healthier path forward. I met Angela through The Curve, my organization focused on helping policing evolve to meet the needs of a modern world. She’s a powerful example of forward-thinking leadership, exploring how culture, mindset, and psychological safety shape the way officers show up for each other and for the communities they serve. In this episode, Angela and I unpack why cynicism is so common among officers, how strong leadership creates healthier team cultures, and why rebuilding trust in policing starts from the inside out. Angela shares stories from her career that reveal a…

Fanbases are some of the most powerful forces on the planet. They show up. They buy the tickets. They travel across countries and time zones. They memorize lyrics, study interviews, hunt for Easter eggs, and turn the smallest detail into an entire universe of meaning. They collaborate, they organize, and they care deeply. Fan communities are savvy. They are smart. And when they are invited in, they create extraordinary momentum. Adam Met, best known as the “A” of indie-pop band AJR, believes that this kind of energy can extend far beyond concerts or comment sections. He is asking a bigger question. What if we harnessed that same passion, creativity, imagination, and sense of belonging to improve the communities we live in? Adam has spent years studying how to move people from curiosity to action. He’s also a climate activist, the founder of the nonprofit Planet Reimagined, an adjunct professor at Columbia University, and the author of the bestselling book Amplify: How to Use the Power of Connection to…

We’re often told that the secret to success is grit - more discipline, more perseverance, more individual effort. And grit does matter. But what if it’s only half the story? In today’s world, we’ve become experts at tracking achievement, yet novices at nurturing belonging - and the cost of that imbalance is showing up everywhere from burnout to loneliness. Few people are better equipped to help me make sense of that tension than today’s guest, Angela Duckworth. Angela is a professor of psychology at the University of Pennsylvania, a MacArthur “Genius” Award winner, and the bestselling author of Grit: The Power of Passion and Perseverance. Angela is one of those people I could talk to for hours and we cover a lot of ground, but our conversation isn’t just about grit or performance. It’s about something deeper: why belonging gives achievement meaning and why human beings are actually wired to thrive together. In this episode, Angela and I explore how a culture obsessed with individual success quietly erodes…

In a world defined by constant change, reinvention isn’t optional - it’s essential. We often assume reinvention comes from bold leaps or lucky breaks, but actor and author Matthew McConaughey’s story suggests a quieter approach can be far more powerful. In this episode, Matthew joins me to explore the inner practices that have shaped both his life and his legendary career in Hollywood. From stepping away from romantic comedies at the height of his success to sitting with uncertainty when there were no guarantees on the other side, Matthew shares how learning to get comfortable with discomfort empowered the most meaningful reinventions of his life. At the center of our conversation is curiosity - self-curiosity. Matthew reflects on decades of journaling as a way to notice patterns, stay honest, and make sense of moments that feel unclear. Rather than avoiding discomfort, he learned to treat it as information to study, learn from, and eventually act on. We talk about what it takes to stay relevant without…

Hello from Team Simon! We’ll be back next week—January 27, 2026—with brand-new episodes of A Bit of Optimism. We’re excited to bring you new guests, conversations, and opportunities to learn. Until then, we’re diving back into the archives to revisit one of our favorite episodes from 2024, when comedian Trevor Noah joined the show… to get as serious as possible. Most Americans know Trevor as the former host of The Daily Show, a bestselling author, and a stand-up comedian. But his brand of humor isn’t just a barrel of laughs— it’s raw, witty, thought-provoking, and often makes you see the world in a whole new way. In this conversation, Simon and Trevor ditched the small talk (mostly) and went deep into the paradox of choice, the public's response to the murder of United HealthCare's CEO, and why the human experience might be defined by constraint. It will make you chuckle, think, and probably question everything all at once. This… is A Bit of Optimism. --------------------------- For more on Trevor and his…

Team Simon here! We’re revisiting some of our favorite episodes from 2025. But we'll be back in just two weeks with brand-new episodes of A Bit of Optimism on January 27, 2026. We think you’re going to love them! Today, we’re going back to January of last year when Dr. Becky Kennedy joined us to discuss the hardest job in the world—parenting. It turns out, it’s also one of the best training grounds for leadership. Dr. Becky Kennedy, aka the “Millennial Parent Whisperer,” became an essential voice for caretakers by offering practical, actionable parenting advice that resonated with millions during the pandemic. As a clinical psychologist and founder of Good Inside, she’s now helping parents build sturdy leadership skills that not only transform their homes but also their work lives. In this conversation, Dr. Becky shares how understanding boundaries, emotional triggers, and big feelings can help us become more effective leaders. Whether you’re a parent or a manager (or both!), her insights will help you lead…

Happy New Year from Team Simon! We’re so excited to bring you more new episodes of A Bit of Optimism when we return on January 27, 2026. With your support, we’ll make 2026 an incredible year together. In the meantime, we’re revisiting some of our favorite episodes from last year. We kicked off 2025 with a guest most podcast enthusiasts probably have heard of—Mel Robbins. This insightful conversation answers an important question: how do we push through the days where life can feel overwhelming? Especially when we're too drained to even get out of bed. For Mel Robbins, facing this very question turned her life around. Struggling with $800,000 in debt and at rock bottom, she became obsessed with finding practical ways to regain control. Fast forward to today, and Mel is a bestselling author and podcast host who has helped millions transform their lives. In her latest book, The Let Them Theory, she reveals how shedding the weight of others' expectations can help us live more authentically. Simon sat down with…

Team Simon is revisiting some of the episodes you helped make our favorites of the year until A Bit of Optimism returns on January 27, 2026, with brand-new episodes. We’re rewinding back to August, when talented polymath Elle Cordova joined the show and unpacked how we’re all wired to chase the next spark. We scroll, swipe, refresh, and repeat—but some of our brightest ideas sneak in when we stop chasing, let boredom settle in, and give our minds room to wander. Elle knows the power of that pause. When the pandemic hit pause on her life as a touring musician, she stumbled into new creative territory—making offbeat comedy videos about delightfully nerdy topics like particle physics, grammar, and fonts. Those sketches went viral, and suddenly she was thriving as a social media creator with a devoted following. In this episode, Simon and Elle talk about finding what truly lights you up, pushing through writer’s block, working with anxiety—and yes, Star Wars makes an appearance (because of course it does). Plus,…

Team Simon here! As the year comes to a close, A Bit of Optimism is pressing pause for a short winter break. The show will return on January 27, 2026 and we can’t wait to be back with you. But before we go, we want to say thank you. Truly. This show exists because of you—the listeners who show up every week, share episodes and clips, leave thoughtful comments, start conversations, and carry these ideas into your own lives and workplaces. Your support, curiosity, and generosity are what give this podcast its momentum. It wouldn’t be what it is without this community. While we’re away, we’ll be revisiting some of our favorite episodes from the past year—conversations you helped turn into something special. We also invite you to explore the archive and revisit the episodes you loved most, the ones you shared, commented on, and helped make a success. We’re taking all of that energy with us into the break as we prepare for the year ahead. More meaningful conversations, more inspiring guests, and more moments we…

Team Simon here! Thank you for being part of such an incredible year—and for helping us grow the podcast through your support, sharing it with others, and showing up week after week. We love seeing your comments and hearing what resonates with you. A Bit of Optimism returns on January 27, 2026, with brand-new episodes we think you’re really going to enjoy. Until then, we’re revisiting a few of our favorite moments from the past year. We’re kicking things off with one of our most popular episodes—the conversation we filmed in London with Mo Gawdat. As a “Happiness Expert,” Mo teaches us that happiness is a choice, even if it’s not always an easy choice to make. Mo had to face an impossible choice. Before he was a bestselling author and podcast host, Mo worked a lucrative career as Chief Business Officer at Google X. He reached the heights of business influence and amassed a fortune by 29. And yet, he was miserable. It was only after the tragic death of his 21-year-old son Ali that Mo was forced to confront…

Often the biggest transformations we undergo don’t arrive as lightning bolts, but as quiet shifts we’ve been preparing for all along. For John Fox, the transformation from a 25-year career in high finance to becoming a chaplain wasn’t sudden at all. It was a slow burn—shaped by loss, reflection, community, and a deep desire to live a more meaningful life. John’s successful finance career spanned decades. To the world, he was thriving, but internally he yearned for fulfillment no paycheck could give him. After losing his mother, questioning the purpose of work, and rediscovering his spiritual roots, he began to sense that his life was preparing him for a very different kind of service. That path eventually led him to the Peace Corps, seminary, and finally chaplaincy—where he now spends his days sitting with people in hospitals, jails, shelters, and hospice care. In this conversation, John shares how you can slowly build a new life, why most of us struggle to talk about things we can’t fix, and the human need…

Life can change in an instant. One day you’re shopping at Saks Fifth Avenue, and the next you’re sitting in your car with everything you own, and everyone you love, wondering what happens now. Joan Howard grew up in Beverly Hills with every advantage until a series of crises left her homeless and living in her car with her mother and three dogs. What helped her rebuild wasn't luck or charity. It was kindness, consistency, and one simple weekly practice of being in service to others. Today, Joan is a long-time volunteer for Food on Foot, the very organization that helped her decades ago. Food on Foot is more than a meal line—it’s a community built on dignity, kindness, and practical support for people experiencing homelessness in Los Angeles. Their model helps people find work, save money, build confidence, and move forward with independence. In this episode, we talk about what homelessness actually looks like, why service can be transformative, and how organizations like Food on Foot help people not just get…

What if a great business was built like a handmade mixtape? A lovingly crafted experience that is as much a love letter from its founder as it is custom-tailored to its audience. Before Jeni’s Splendid Ice Creams became a household name, Jeni Britton was a 22-year-old art school dropout scooping her ice cream creations at a farmers market in Ohio. She didn’t have investors, connections, or a playbook. What she did have was a vision - not just for ice cream, but for connection. Jeni believed her bold ice cream could be a conduit for something bigger: a place where people feel seen, conversations happen naturally, and strangers become community. Over the next two decades, she bootstrapped her way from a small counter to a nationally recognized brand by doing everything the slow, hard, old-fashioned way — one customer, one flavor, and one act of service at a time. She refused shortcuts. She prioritized people. And she built her company like a handmade mixtape — crafted with intention, risk, rebellion, and love.…

Who would’ve guessed that one of the world’s best company cultures was hiding behind a can of WD-40? Of all the places to find a leadership masterclass, the blue-and-yellow can in your garage probably wasn’t on your list - but it’s time to put it there. Garry Ridge - an Australian who brought his charm and curiosity across the Pacific - joined WD-40 Company in the late ’80s and rose through the ranks, eventually serving as CEO for 25 years. But he didn’t start out as the culture-building expert he’s known as today. Early in his career, he lived by the old mantra: “be brilliant, be brief, be gone.” He had to unlearn that mindset and rebuild himself into a leader who centers people, learning, and belonging - an evolution that reshaped WD-40 from the inside out. His new book, Any Dumb Ass Can Do It, captures that journey. In this episode, we break down how Garry built a company where people genuinely love coming to work - even through recessions, pandemics, and all the external chaos leaders can’t control. We…

What if great friendships aren’t found by luck but built through effort? Bestselling novelist Fredrik Backman, the mind behind A Man Called Ove (adapted into the Tom Hanks film A Man Called Otto), Anxious People, and the beloved Beartown series, has spent his career writing about the quiet power of ordinary people. But in his real life, he learned one of his most important lessons from his best friend of 30 years: meaningful friendship is a skill you develop, not a lottery you win. Despite being a self-described introvert, Fredrik discovered that you don’t need hundreds of friends. You only get a few humans who truly shape your life. His newest book, My Friends, is a tribute to those relationships and the daily work of showing up for the people who matter most. In this candid and inspiring conversation, Fredrik and I talk about the healing power of friendship, why differences make relationships stronger, the value of having friends who edit us, and the joy of being genuinely happy for someone else. If you…

If you feel stupid while learning something new, you’re doing it right. But if you keep doing the same thing over and over hoping it’ll suddenly make sense - that’s on you. The trick isn’t to push harder; it’s to find a new teacher, a new explanation, a new way in. That’s exactly how Matthew Broussard approaches comedy - and everything else. A stand-up comedian, math nerd, and former financial analyst, Matthew is obsessed with learning and cracking the formula behind how things work. He treats every joke like an equation, testing, refining, and solving for laughter. He’s the creator of Monday Punday, a puzzle webcomic and app, and has been featured on The Tonight Show with Jimmy Fallon, Conan and Comedy Central’s Roast Battle. He’s also made appearances on The Marvelous Mrs. Maisel and The Mindy Project. His storytelling, including his viral tales about his mother-in-law, proves that logic and vulnerability can live in the same sentence. In this episode, we explore the overlap between comedy and…