A Bit of Optimism

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

Parenting is the hardest job in the world—and 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 with more intention, connection, and confidence. This… is A Bit of Optimism. Check out Dr. Becky's work: https://www.goodinside.com/

When the wildfires struck Los Angeles, turmoil quickly consumed the city. People were desperate for clear, reliable information—unsure of evacuation routes or how to track the fires as they spread in a history-making wind storm. Then, we found Watch Duty. This intuitive app became our lifeline. The visionary behind the app is John Mills, a seasoned tech entrepreneur who created Watch Duty out of necessity after his own community in Northern California was repeatedly threatened by deadly wildfires. But John didn’t just build an app—he reimagined how business and philanthropy can intersect to solve real-world problems. Watch Duty is a not-for-profit initiative that harnesses the power of technology and human talent, relying on volunteers to gather critical data from fire scanners and reporters to save lives. Despite its explosive growth, John has no plans to sell the app, because for him, the value isn’t in making money—it’s in using his skills to help others. In a world where many focus on getting rich, John is challenging us to rethink how we can use our talents to serve the greater good. This...is A Bit of Optimism. For more on John and his work, check out: Watch Duty

Life can feel overwhelming, especially when we're too drained to even get out of bed. So, how do we push through those days? 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. I sat down with Mel to dive into how we can take action when we're emotionally spent, why our need for control ties us to other people's opinions, and how giving others the freedom to be themselves allows us to align with our true values. This…is A Bit of Optimism. For more on Mel and her work, check out: The Mel Robbins Podcast and her book, The Let Them Theory

Loneliness has reached epidemic proportions. Where do we go to feel like we belong? As the Surgeon General of the United States, Dr. Vivek Murthy has been a leading voice in bringing the loneliness crisis to light, stressing its devastating impact on public health. As his second term nears its end, he leaves behind a powerful reflection in his letter, My Parting Prescription for America and the World. In an insightful conversation with Dr. Murthy, we delve into what it truly means to be healthy—not just physically, but emotionally and socially—and discuss why the pursuit of fame, wealth, and power often leads us further from what we really need. This…is A Bit of Optimism. To read the letter, visit this link: My Parting Prescription for America and the World To learn more about Dr. Murthy, click here: vivekmurthy.com

It’s our last episode of 2024, so I decided to invite comedian Trevor Noah on…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, we 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. P.S. Come back and see us on January 7, 2025 for an all new episode. Until then, take care of yourself and each other. For more on Trevor and his work, check out: trevornoah.com

They say business and pleasure don’t mix. But what about business and friends? My dear friend Will Guidara is the perfect person to dive into this question because we're actively trying to get into business together. And, let's just say, it requires a lot of effort. In addition to being someone I love, Will is a renowned restaurateur, known for owning and operating Eleven Madison Park, once named the best restaurant in the world. He’s also the author of the brilliant book Unreasonable Hospitality and a co-producer of the HBO television series The Bear. Will and I have worked together before, so I was excited to chat with him about turning friends into colleagues, the reality of friendship breakups at work, and why sometimes showing respect means we have to change the way we treat a friend. This…is A Bit of Optimism For more on Will and his work, check out: Unreasonable Hospitality The Art of Creating Fiercely Loyal Customers

We all want to live a happy life, but what does research say about how to actually achieve it? For more than 86 years, researchers at Harvard University have been trying to answer that question. 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

Finding love is a journey. We might take some wrong turns along the way. Matthew Hussey helps people find love, and sometimes, redefine their relationship with love. Matthew is a dating coach who balances practical advice about the art of attraction with the importance of centering our own sense of self in our search for love. Starting as a teenager and working primarily with women, he’s helped thousands of people find romance and create relationships built on values which feel right for them. I sat down with Matthew to ask him everything he’s learned about love after decades as a dating coach. He shares with me the most common mistakes people make when looking for a partner, what we ought to be looking for, and why our own happiness is ultimately our own responsibility, not anyone else’s. This…is A Bit of Optimism. To learn more about Matthew and his work, check out: his new book, Love Life his YouTube channel matthewhussey.com

Close friends are the best thing for your health. Friendship, it turns out, is one of life’s best medicines. If you don’t believe me, believe Dr. Mark Hyman. Mark is one of the leading voices in the functional medicine movement, which is all about taking a holistic approach to our health for natural healing and preventing disease. The smallest changes in our daily lifestyle habits, or what we eat and drink, or our positive social interactions can have huge impacts on our long-term health. I sat down with Mark to talk about my most recent obsession – friendship. I was eager to get a physician’s perspective on all the ways friendship is beneficial for our health. In this conversation, we discuss the biological benefits of talking to a good friend and why you’re only as healthy as your five closest friends. This…is A Bit of Optimism For more on Mark Hyman and his work, check out: The Doctor’s Farmacy podcast Function Health drhyman.com

In 2020, Reddit co-founder Alexis Ohanian resigned from his own company in protest. After 15 years building Reddit into a social media juggernaut, why leave? The answer is values. Alexis is the kind of entrepreneur and investor who believes that integrity and long term profits go hand in hand. It’s the reason he started his new company 776, allowing him to invest in startups that are trying to make the world a better place. And it’s the reason he resigned from Reddit after George Floyd was killed, requesting the board replace him with a Black director. In this conversation, Alexis shares with me his thoughts on the future of entrepreneurship, the race for AGI, climate change, and the principles that guide the way he leads. It turns out, building a business with values is the best thing for long term greed. This...is A Bit of Optimism For more on Alexis and his work, check out: 776 alexisohanian.com