A Bit of Optimism
Simon Sinek hosts a podcast exploring what makes people find joy and meaning in life. Through honest conversations with a variety of guests, he seeks to expand his own perspective and inspire listeners. The show covers topics like leadership, purpose, and optimism, featuring both well-known figures and lesser-known individuals with valuable insights.
Episodes
How to Tell If Fear Is Protecting You or Holding You Back with Extreme Athlete Nelly Attar
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
Remembering Bob Chapman: The Mentor Who Changed My Life
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 de
The AI Skills Nobody is Teaching (And Everyone Needs) with AI Expert Ethan Mollick
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
How to Stop Letting Your Own Thoughts Make You Sick, Stressed, and Stuck with Dr. Ellen Langer
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, sh
What Happens When You Stop Optimizing and Start Committing with Former LA Lakers President Tim Harris
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
Revisited: Choose Your Seven Humans Wisely with Author Fredrik Backman
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
How to Stop Being Socially Awkward (According to Science) with Behavioral Scientist Vanessa Van Edwards
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
Stop Telling Us Everything Happens for a Reason with Anti-Victim Tom Nash
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 b
The Real Reason You Feel Empty (Even When Life Looks Good) with Musician Mike Posner
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
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 best
The Leadership Advice Nobody Follows (But Everyone Should) with Top Leadership Expert Don Yaeger
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 Ti
Why This Baseball Team Has a 4.2 Million Person Waitlist With Savannah Bananas Founder Jesse Cole
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 en
Ken Burns and the Art of Telling the Whole Story
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
What Happens When You’re Naive Enough to Try with KIND Founder Daniel Lubetzky
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
AI Can Do Everything… Except This (Why Humans Still Win) With Restaurateur Will Guidara
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 t
Revisited: What Dying Teaches Us About Living with Death Doula Alua Arthur
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 bein
Revisited: The Kennedy Family and the Search for Self with Journalist Maria Shriver
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 bo
Revisited: How to Turn Stress Into Creativity With Grammy-Winner Jacob Collier
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
The Confidence Conversation We Need to Have with Scott Galloway
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, bestsellin
28 Years on the Force: Chief Angela Averiett on What It Really Takes to Change Police Culture
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
When Pop Fandom Becomes a Force for Good with AJR’s Adam Met
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, the
What Grit Really Teaches Us About Happiness with Professor Angela Duckworth
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
Matthew McConaughey on How to Fall Back in Love with Your Life
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 steppi
Revisited: Trevor Noah Makes My Brain Hurt
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 f
Revisited: Kids (And Employees) Know More Than You Think with Dr. Becky Kennedy
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 ground
Revisited: The First Steps To Reducing Your Anxiety with Author Mel Robbins
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 conversati
Revisited: The Beautiful Brilliance of Boredom with Creative Polymath Elle Cordova
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
A Bit of Optimism Will Return in the New Year
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
Revisited: Your Unhappy Brain Needs Some Assistance with Happiness Expert Mo Gawdat
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
Prepare for the Life You’re Meant to Live With Chaplain John Fox
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 d
How Losing Everything Taught Her to Help Everyone: Joan Howard’s Story
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 w
A Rebel With a Cause (and a Cone) with Jeni’s Ice Cream Founder Jeni Britton
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 playb
The Culture That Converts Even the Biggest Cynics with former WD-40 CEO Garry Ridge
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 r
Choose Your Seven Humans Wisely with author Fredrik Backman
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 fr
The Smartest Way To Be Stupid with comedian Matthew Broussard
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 ana
The Man Who Proved Me Right with CEO Bob Chapman and the Barry-Wehmiller Team
I’ve long imagined a world where people wake each morning inspired, feel safe wherever they work, and return home fulfilled by what they’ve created. That vision once felt like a dream - until I met Bob Chapman, CEO of Barry-Wehmiller, who quietly built it into reality. Over five decades, Bob has grown a humble Midwestern manufacturing company into a global business success story, proving that lead
Rob Lowe Names Names: The Power of ‘Screw It’
We don’t usually look to Hollywood for lessons in career longevity. But it might be the perfect place to study it. Few industries move faster or cast people aside more quickly, and yet Rob Lowe has spent more than four decades defying those odds. His story isn’t just about surviving fame—it’s about overcoming adversity, finding joy in the work, and proving that authenticity is the only path to a c
The Future You Avoid Is Riskier Than the One You Face with LinkedIn co-founder Reid Hoffman
The future is something we create, not just something that happens. To guide progress toward real good, we need bold, optimistic visions of what society can become.
Reid Hoffman makes the case for better science fiction - stories that don’t just entertain, but illuminate the futures we can strive for. As a serial entrepreneur and cofounder of LinkedIn, Reid brings a unique perspective on how story
What Your Love Life Can Teach You About Work Relationships with psychotherapist Esther Perel
We’ve never had more freedom in our relationships—yet many of us feel more disconnected than ever. Marriage, family, and even the workplace have all been reshaped by shifting norms, new technologies, and rising expectations. Happiness, once a nice-to-have, is now the very glue that keeps both couples and teams together.
Few people understand these changes better than Esther Perel. For decades, she
Your Instincts Know What You Want with Author Arthur Brooks
Your instincts aren’t just whispers. They’re a compass pointing you toward the life you’re meant to live. But in a world obsessed with speed, metrics, and outcomes, most of us forget how to listen.
Arthur Brooks, bestselling author and Harvard Business School professor, teaches one of the most popular classes on happiness. But his insights come not just from research, but from a life of reinventio
The Power of Doing One Thing Exceptionally Well with Gymshark Founder and CEO Ben Francis
We’re often told to do more, move faster, and chase the next big trend—but some of the most remarkable successes come from narrowing your focus, obsessing over one thing, and truly understanding the people you’re serving.
Ben Francis knows this better than most.
He started Gymshark with nothing more than a sewing machine and a passion for making gym clothes that actually worked for him. From thos
Simon Goes Nuclear with nuclear energy influencer Isabelle Boemeke
“Nuclear” might make you wince—but the real problem isn’t the energy, it’s the branding. Safe, low-carbon, and scalable, nuclear could be a climate hero—if only we told the story right.
Isabelle Boemeke is on a mission to change how we think about nuclear energy. A Brazilian model turned the world’s first nuclear influencer, she created her alter ego, Isodope, to show a new generation the benefits
The Brilliance of Boredom with creative polymath Elle Cordova
We’re wired to chase the next spark - scrolling, swiping, refreshing - but some of our brightest ideas sneak in when we stop chasing, let boredom settle in and give our minds room to wander.
Elle Cordova 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 topic
The Privilege of Bad Experiences with NASA astronaut Jonny Kim
This was the most epic Zoom call we’ve ever been a part of — an incredible conversation with NASA astronaut Jonny Kim, live from the International Space Station, with sunrise on Earth as a stunningly causal site behind him as they barreled at 17,000 mph in orbit. Thanks to the amazing team at Johnson Space Center, Jonny was able to join us to share insights from a life that defies limits, showing
The Business Case for Good Manners with etiquette coach William Hanson
Good manners aren’t just about being polite — they’re about making other people feel seen.
William Hanson is one of the world’s leading etiquette coaches. He’s advised royalty, CEOs, and television personalities on how to communicate with clarity, confidence, and grace. But his mission goes far beyond fine dining or proper handshakes.
In today’s fast-paced, informal world, William argues that etiq
Live Like You Have 2 Years Left with dancer and cancer survivor Angela Trimbur
You have two years left to live. What would you do?
That's a real question Angela Trimbur had to answer. In 2018, a breast cancer diagnosis forced her to get honest with herself. If Angela had only 2 years to live, what kind of life did she truly wish to live? Angela chose to start over. She sold everything she owned, moved to New York City, and became a dance teacher. Angela's irreverent teaching
The Quiet Power of the Empathetic Leader with Navy SEAL turned rowing coach Gordon Schmidt
When morale problems affect a team, some leaders choose to make a big, rousing speech. But quite often, it’s the quiet leader who leads with empathy that sees a better emotional solution.
Gordon Schmidt is a retired Navy SEAL with enough combat experience to understand that empathy is an operational advantage, not a weakness. After 20 years of military service, he started his second act as a high
Your Unhappy Brain Needs Some Assistance with happiness expert Mo Gawdat
Happiness is a choice. But it’s not always an easy choice to make.
Mo Gawdat 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
We All Get Cancelled One Day with Somebody Feed Phil’s Phil Rosenthal
🚨 Chomp Alert! 🚨
We saw your comments — loud and crunchy. Turns out not everyone wants front-row seats to mouth sounds. Who knew?
Skip to 29:29 to dodge most of the chewing. We promise, after that it’s just a few graceful nibbles of Basque cheesecake. 🧀🍰😅
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We turned the studio into a restaurant for the day—because when Phil Rosenthal’s in the house, you don’t
The Extraordinary Magic of Ordinary People with author Brad Meltzer
Magic moments do happen in real life. If you ask Brad Meltzer, magic happens when ordinary people choose to do the extraordinary.
Brad is a prolific writer and bestselling author. He’s published over 70 books in nearly every genre you can think of—thriller novels, biographies, children’s books, film and television. He’s written comic books for iconic superheroes like Spider-Man, Superman, and Bat
This Is... 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 th
Ask Yourself "What If?" with Milk Bar Founder Christina Tosi
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.
Revisited: Love Is Not Enough with couples therapist Shawn McBride
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
Revisited: The Secret to Happiness with Harvard professor Robert Waldinger
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 figur
Where Is Simon Going? with journalist Cal Fussman
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 Cure for Nihilism with professor Suzy Welch
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 authen
(PART 2) The Climb Out of Pain is Taller Than Everest with National Geographic photographer Cory Richards
*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 f
(PART 1) The Climb Out of Pain is Taller Than Everest with National Geographic photographer Cory Richards
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
Find Your Allies Fast with philanthropist Melinda French Gates
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
Who Are You, Really? with journalist Maria Shriver
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 s
The Search for Self-Love with podcaster Lewis Howes
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, i
Revisited: Why Awkward Is Awesome with psychologist Ty Tashiro
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.
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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 t
Does Gender Change How We Lead? with Retired Colonel DeDe Halfhill
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 d
The Myth of the Perfect Meditator with podcaster Jay Shetty
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
When Your 'Flaw' Becomes Your Edge with Comedian Hasan Minhaj
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, Netf
Humble Leaders Lead Better Teams with Retired Navy SEAL Jocko Willink
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 comba
A Sweet Conversation About Dying with Death Doula Alua Arthur
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 thei
The Secret Art of Micromanagement with Airbnb CEO Brian Chesky
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
You Are More Like Grammy-Winner Jacob Collier Than You Think
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 Yea
Kids (And Employees) Know More Than You Think with Dr. Becky Kennedy
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
Spite Is The Greatest Motivator with Watch Duty founder John Mills
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 n
The First Steps to Reducing Your Anxiety with author Mel Robbins
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 m
The Cure for Loneliness with U.S. Surgeon General Vivek Murthy
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 Wo
Trevor Noah Makes My Brain Hurt
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 th
Should You Work With Your Friends? with my friend Will Guidara
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 Secret to Happiness with Harvard professor Robert Waldinger
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 t
The First Steps to Find Love with Matthew Hussey
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 th
Dr. Mark Hyman: To Live Longer You Need...
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
Alexis Ohanian: Why I Left Reddit and Why Greed Can Inspire Good
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 mak
What can we learn from a rural school in Kenya? with principal Carol Moraa
Kenya's Maasai Mara is rugged, beautiful, and tough. Values are everything for the people who live in this rural countryside,
On a trip to Kenya, I had the opportunity to visit The Mara. The intelligence and grit of the young people there blew me away! I met incredibly driven young women determined to uplift their families from poverty. Carol Moraa is giving them that opportunity. She's the foun
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