The future is always bright…if you know where to look. Join me each week for A Bit of Optimism! I talk to inspiring people who teach me more about life, leaders...
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 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
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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 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
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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 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
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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 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
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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 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/
The future is always bright…if you know where to look. Join me each week for A Bit of Optimism! I talk to inspiring people who teach me more about life, leadership and general interesting things.
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