A Bit of Optimism

Latest Episodes:

The Cure for Nihilism with professor Suzy Welch May 06, 2025

Show notes

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 authentic selves.

According to Suzy’s research, purpose is the key to unlocking the real you, but finding that purpose is often trickier than we imagine.I had a blast talking, and debating, with Suzy about what it means to craft a purpose-driven life. In this conversation, she shares with me the difference between passion and aptitude, the reason luck is overrated, and why so many people struggle to know their own values.

To learn more about Suzy and her work, check out:

her book, Becoming You

and The Becoming You Podcast with Suzy Welch

(PART 2) The Climb Out of Pain is Taller Than Everest with National Geographic photographer Cory Richards Apr 29, 2025

Show notes

*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 found himself lost and confused about his true identity. At the same time, he was forced to grapple with multiple life-shattering events at once -- some of his own making.
In this episode, we discuss the difference between identity and purpose, the skills Cory learned to cope with multiple tragedies, and why the more we ignore life’s harshest lessons, the louder they become.
Listen to Part 1 here or watch it on YouTube.
This…is A Bit of Optimism.
For more on Cory Richards and his work, check out:
coryrichards.com

(PART 1) The Climb Out of Pain is Taller Than Everest with National Geographic photographer Cory Richards Apr 22, 2025

Show notes

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 avalanche, after which he skyrocketed to fame when his photos graced the cover of National Geographic.

And yet, after all that success, Cory felt like an emotional wreck. As his mental health deteriorated, his volatile behavior damaged his career and his relationships. Without the identity of “climber” to give him validation, Cory was forced to confront who he really is.I

n Part 1 of this conversation, Cory shares with me head-spinning stories from climbing the Himalayas, his struggles with mental health as a teen, and the difference between survival and resilience.

This…is A Bit of Optimism.

For more on Cory Richards and his work, check out:

coryrichards.com

Find Your Allies Fast with philanthropist Melinda French Gates Apr 15, 2025

Show notes

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

Who Are You, Really? with journalist Maria Shriver Apr 08, 2025

Show notes

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 start, the world had ideas about who she should be. But after decades as a journalist, years as California’s First Lady, and raising four amazing kids, Maria has been on a lifelong journey to peel back the layers and ask Who am I now?—and answer it for herself.

Maria also happens to be my best friend. We talked about how we became each other’s “8-minute friends,” the quiet questions that shape us, and her beautiful new book of poetry—which she reads from in this episode. It’s all about identity, self-reflection, and finding your voice in a world that keeps trying to define it for you.
This…is A Bit of Optimism.
For more on Maria Shriver, check out:
her book, I Am Maria
mariashriver.com

The Search for Self-Love with podcaster Lewis Howes Apr 01, 2025

Show notes

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

Revisited: Why Awkward Is Awesome with psychologist Ty Tashiro Mar 25, 2025

Show notes

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

Does Gender Change How We Lead? with Retired Colonel DeDe Halfhill Mar 18, 2025

Show notes

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

The Myth of the Perfect Meditator with podcaster Jay Shetty Mar 11, 2025

Show notes

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

When Your 'Flaw' Becomes Your Edge with Comedian Hasan Minhaj Mar 04, 2025

Show notes

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

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