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.

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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 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

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