A Bit of Optimism

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,...

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 o...

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...

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 wi...

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...

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...

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 frie...

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...

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...

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...

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 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...

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 ent...

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...

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...

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...

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...

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...

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...

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...

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...

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...

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...

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...

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...