A Bit of Optimism

My career is an accident. It started when I set out to rediscover my passion and reignite a spark I’d lost — and that journey led me to the work I do now. If you know me from my books or my speaking, you know I’m fascinated by why people do what they do. What makes someone find joy and meaning in their life, or pursue something far greater than themselves? I started A Bit of Optimism to explore those ideas and expand my own perspective. This podcast is a trove of honest conversations, with people who challenge me, teach me, or simply help me see things in a different way. Some guests are household names, and others you may be meeting for the first time. But each one of them has something to share that can help all of us grow. So if you’re looking for a spark — some insight, inspiration, or just a reminder that good things are possible — join me on A Bit of Optimism. Let’s grow together.

What if this podcast turned into a baking show? For Christina Tosi’s third visit to A Bit of Optimism, we decided to find out. So we headed to Milk Bar to make compost cookies from things in my own pantry and my favorite beer bread from scratch! Christina’s not just my best friend—she’s the founder of Milk Bar, host of Bake Squad on Netflix, a cookbook author, and a fan favorite on this podcast. She lives by one simple question: what if? In this experimental episode, we dug into some big ideas about creativity, uncertainty, and the magic of trying something new. Recipes below! This...is A Bit of Optimism. You can watch the video version of this episode on YouTube here. For more on Christina and her work, check out: christinatosi.com ---------------------------- Simon's Compost Cookie Recipe (makes 15-20 cookies): For the full step-by-step recipe, visit Milk Bar's website! Beer Bread Recipe: Mix ingredients slowly together Bake at 350 for 45-60 mins until baked through ---------------------------- This episode is brought to you by True Classic! I really love True Classic T-shirts, so we called them up and asked if they wanted to work together. And they said yes! Check out their clothes at: trueclassictees.com

We're taking some time off to bring you even more episodes of A Bit of Optimism that you're going to love! In the meantime, we're revisiting some of our favorite episodes, like this one with couples counselor Shawn McBride. Relationships are hard. No matter how much we like, respect, or love someone, conflict seems inevitable. But even as we fight and disagree, we can also learn the skills we need to resolve our problems. For over two decades, Shawn McBride has helped thousands of couples do the work to strengthen their relationships. And he has tons of practical advice. Shawn sat down with me to discuss the three biggest problems couples face, why I'm a huge fan of his Instagram, and how love can keep relationships afloat, but it's often not enough. This...is A Bit of Optimism. For more on Shawn and his work, check out: @couples_counseling_center @shawnmcbridespeaks and couplescounselingcenter.org

We're taking some time off to bring you even more episodes of A Bit of Optimism that you're going to love! In the meantime, we're revisiting some of our favorite episodes, like this one with Harvard professor Robert Waldinger. We all want to live a happy life. But what does the research say about how to achieve it? For more than 86 years, researchers at Harvard University have been trying to figure out how humans can live happier lives. In one of the longest-running and most comprehensive studies of human happiness, Harvard tracked 724 teenagers through every stage of their adult lives since 1938. Some of them are still alive today and the findings are clear: lasting happiness isn’t about wealth or fame—it’s about something much deeper. Robert Waldinger, a professor and psychiatrist, has directed the study for over 20 years. His TED Talk about it went viral with nearly 50 million views, and in 2023, he wrote a book about it - The Good Life: Lessons from the World's Longest Scientific Study of Happiness.I asked Robert to share what the study has revealed about happiness over the decades, how its insights have shaped his own life, and the one essential ingredient for a joyful, meaningful existence. This…is A Bit of Optimism. To learn more about Robert and his work, check out: The Harvard Study of Adult Development robertwaldinger.com

Sometimes in life, we must stop and ask ourselves, “Where am I you going next?” Other times, it’s more fun to do a podcast takeover. No one has ever interviewed me quite like Cal Fussman. Cal has a gift – he pulls things out of you that you didn’t even know were there. A prolific Writer At Large for Esquire, Cal has interviewed legends like Muhammad Ali and Mikhail Gorbachev, and he’s the host of the podcast Big Questions. So, to mark 15 years since writing Start With Why, I invited Cal to take over my podcast and ask me the questions I don’t usually get asked. Cal did get me to open up in this conversation, but not in the way you might expect. We talk about where I’ve been, where I’m going, the infinite game, creativity in AI…and why I’ve become so obsessed with friendship lately. This…is A Bit of Optimism For more on Cal and his work, check out: Big Questions with Cal Fussman

Sometimes in life, we choose the wrong path. When we feel like we're living a lie, it's hard to know what to do next. That’s where Suzy Welch comes in. She’s obsessed with helping people create lives worth living. A professor at NYU’s Stern School of Business, Suzy teaches a popular class called “Becoming You,” where she takes students down a brutal, but liberating, journey to live as their authentic selves. According to Suzy’s research, purpose is the key to unlocking the real you, but finding that purpose is often trickier than we imagine.I had a blast talking, and debating, with Suzy about what it means to craft a purpose-driven life. In this conversation, she shares with me the difference between passion and aptitude, the reason luck is overrated, and why so many people struggle to know their own values. To learn more about Suzy and her work, check out: her book, Becoming You and The Becoming You Podcast with Suzy Welch

*Please note: At 9:01, Simon and Cory have a discussion about suicide. What happens after we attain success and glory? Where do you go when there's nowhere left to run from yourself? In Part 2 of my conversation with Cory Richards, Cory explains why reaching the summit of Everest marked the beginning of a long, painful fall from grace. After his tumultuous decision to retire from climbing, Cory found himself lost and confused about his true identity. At the same time, he was forced to grapple with multiple life-shattering events at once -- some of his own making. In this episode, we discuss the difference between identity and purpose, the skills Cory learned to cope with multiple tragedies, and why the more we ignore life’s harshest lessons, the louder they become. Listen to Part 1 here or watch it on YouTube. This…is A Bit of Optimism. For more on Cory Richards and his work, check out: coryrichards.com

What happens when we reach the top? There’s only one place to go. Cory Richards has scaled the world’s highest peaks and fallen to life’s lowest lows. An acclaimed mountain climber, photographer, and filmmaker, Cory has literally reached the top of the world. He climbed Mount Everest with no supplemental oxygen, became the first American to summit an 8,000-meter mountain, and narrowly survived an avalanche, after which he skyrocketed to fame when his photos graced the cover of National Geographic. And yet, after all that success, Cory felt like an emotional wreck. As his mental health deteriorated, his volatile behavior damaged his career and his relationships. Without the identity of “climber” to give him validation, Cory was forced to confront who he really is.I n Part 1 of this conversation, Cory shares with me head-spinning stories from climbing the Himalayas, his struggles with mental health as a teen, and the difference between survival and resilience. This…is A Bit of Optimism. For more on Cory Richards and his work, check out: coryrichards.com

Change happens to all of us whether we choose it or not. What’s the best way to go through transition, especially when it’s something we didn’t want? Melinda French Gates has seen her fair share of big transitions. A philanthropist, author, and champion for female empowerment, she spent decades building the Gates Foundation into one of the mightiest charitable organizations in the world. But after 25 years, she decided it was time for a change. Leaving the Foundation and her marriage to Bill Gates behind, she struck out on her own for a new decade of philanthropy. I was delighted to sit down with Melinda to talk about how we can successfully navigate the big changes in life, and why finding your allies during tough transitions is the best way to start a new chapter. This…is A Bit of Optimism. For more on Melinda French Gates and her work, check out: her book, The Next Day: Transitions, Change, and Moving Forward her investment and philanthropy organization, Pivotal Ventures

We often define ourselves by what we do or who we are to other people. But at our core, who we are is often something much deeper, and sometimes wildly different, from the version that the world sees -- or projects onto you. 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 my best friend. We talked about how we became each other’s “8-minute friends,” the quiet questions that shape us, and her 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. This…is A Bit of Optimism. For more on Maria Shriver, check out: her book, I Am Maria mariashriver.com

Self-love is never as easy as we think. Is it possible to fall in love with ourselves the way we fall for other people? Lewis Howes knows that learning to like yourself, let alone love yourself, can take decades. After surviving a traumatic childhood, Lewis spent years working on himself to try and understand what it takes for human beings to achieve greatness. He overcame learning disabilities, insecurity, and self-loathing to become who he is today. Lewis is a New York Times bestselling author, a former pro athlete, and host of the popular podcast The School of Greatness. After appearing several times on Lewis’s show, I was excited to finally have Lewis join me on A Bit of Optimism. Together, we unpack our insecurities, talk through our money trauma, and discuss why the first step to liking yourself is to find a little courage. This…is A Bit of Optimism. For more on Lewis and his work, check out: his book, Make Money Easy his podcast, The School of Greatness

A Bit of Optimism is on hiatus this week, so we’re revisiting one of our favorite conversations! In this episode, Simon talks with psychologist Ty Tashiro about social awkwardness and why being awkward can actually be a superpower. ***** Awkwardness gets a bad rap. But being awkward is often an indicator that someone has extraordinary. Psychologist and author Ty Tashiro has spent a great deal of time studying (and living!) social awkwardness. He's fascinated by how the same traits that cause us social embarrassment can also drive exceptional accomplishment. As a fellow awkward person, I was delighted to sit down with Ty and discuss the competitive advantages of social awkwardness, and how sometimes what society labels a weakness turns out to be our greatest strength. This...is A Bit of Optimism. For more on Ty and his work check out: his book, AWKWARD: The Science of Why We're Socially Awkward and Why That's Awesome tytashiro.com

Change happens to all of us whether we choose it or not. What’s the best way to go through transition, especially when it’s something we didn’t want? Melinda French Gates has seen her fair share of big transitions. A philanthropist, author, and champion for female empowerment, she spent decades building the Gates Foundation into one of the mightiest charitable organizations in the world. But after 25 years, she decided it was time for a change. Leaving the Foundation and her marriage to Bill Gates behind, she struck out on her own for a new decade of philanthropy. I was delighted to sit down with Melinda to talk about how we can successfully navigate the big changes in life, and why finding your allies during tough transitions is the best way to start a new chapter. This…is A Bit of Optimism. For more on Melinda French Gates and her work, check out: her book, The Next Day: Transitions, Change, and Moving Forward her investment and philanthropy organization, Pivotal Ventures

Is there such a thing as female leadership? Or is gender not a factor? DeDe Halfhill would say yes and no. A retired Air Force colonel, Dede spent 20 years in the military, where she advised some of the military’s most powerful leaders during the War in Iraq. She was often the only woman in the room for weeks on end. And while DeDe found the principles of leadership to be universal, there was no denying her experience as a woman leader was different from the men. DeDe is an old friend of mine, and I was excited to talk with her about what she learned during her time in the Air Force. She explained to me why people react differently to male versus female leaders, why loneliness often shows up as exhaustion, and how the ability to do emotional labor makes all leaders great, regardless of gender. This...is A Bit of Optimism. For more on DeDe and her work, check out: dedehalfhill.com

We turn to ancient philosophies to help us cope with the stress of modern life. But what if ancient wisdom could use some help from the modern world? Jay Shetty has made it his life’s work to make wisdom, peace, and purpose available to everyone. After living as a monk for 3 years, he left his monastic lifestyle with the hope of spreading what he learned to as many people as possible. Today, he’s the host of the On Purpose podcast, a #1 New York Times bestselling author, a life coach, and an entrepreneur who has helped millions of people find clarity in their lives. I was excited to talk with Jay about the balance between ancient practices and modern life. He shared with me the three biggest lessons he learned as a monk, what people get wrong about meditation, and how we can slow down and reflect amid the bustle of modern society. For more on Jay and his work, check out: On Purpose Live Tour jayshetty.me

To recognize your own talent takes time and self-awareness. But to find the courage to pursue it? That often requires a spark of inspiration from someone else. For Hasan Minhaj, that spark came from an unexpected trio—a teacher, a roommate, and Napster. A former correspondent on The Daily Show, Hasan’s natural gift of gab allowed him to build a wide-ranging career which spans standup, acting, Netflix shows, and, most recently, his podcast, Hasan Minhaj Doesn’t Know. I had the pleasure of sitting down with Hasan to discuss his journey—why gifted people crave external validation, why kids are braver than adults, and where comedians truly rank in the artistic hierarchy. This… is A Bit of Optimism. For more on Hasan and his work check out: hasanminhaj.com

Most people believe the only way to lead is to become the best at something. But what if great leadership means admitting you’re not the best at anything? Jocko Willink believes the secret to his greatest achievements come down to one thing – humility. A retired Navy SEAL commander, Jocko served 20 years in the U.S. military, leading one of the most decorated special operations units through combat in the Iraq War. A New York Times bestselling author, podcast host, and entrepreneur, he now teaches those in the civilian world the skills he learned from his time in the SEAL Teams. This was my first time meeting Jocko Willink, and we discussed why new leaders should never try to prove their own competence and the difference between tyrannical and open-minded leaders. This…is A Bit of Optimism. For more on Jocko and his work, check out: jocko.com

Death is a word we like to avoid. 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. When I sat down with Alua, I was prepared for a grim conversation. Instead, I was pleasantly surprised by her candor and good humor about dying. She shares with me how she made a career pivot from lawyer to death dula, the most interesting stories she’s heard from people on their death bed, and why thinking about our deaths is the key to living the way we wish to live. This…is A Bit of Optimism. For more on Alua and her work, check out: Going With Grace

People aren’t born great leaders. They learn to become great leaders. For Brian Chesky, the learning never stops. As the co-founder of Airbnb, he had to transition from an impassioned entrepreneur with a brilliant idea into a CEO responsible for thousands of employees. To make the hard decisions necessary for Airbnb to survive the COVID pandemic, a cataclysmic event for the travel industry, Brian had to lean into the skills and thinking he’d learned and practiced for over a decade of leadership. I’ve watched Brian grow as a leader for years, and so I was delighted to sit down with him for a conversation on what people get wrong about great leadership. He shares with me the difference between micromanagement and “eyes on” leadership, why leaders should fight the instinct to be liked, and why an existential crisis is the best thing to put a company’s values to the test. This…is A Bit of Optimism. For more on Brian and his work, check out: airbnb.com

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 brilliant songwriter and musician, he’s known for transforming his live audiences into massive three-part choirs, making music with the very people who attend his concerts. 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." I sat down with him in a music studio a few days before the Grammys, surrounded by multiple pianos, and it was a joy to hear him play. Jacob’s approach to music—blending structure with spontaneity—offers insights into creativity that are as inspiring as his sound. This…is A Bit of Optimism. For more on Jacob, check out: jacobcollier.com