Hey Optimists!

We’re taking a little hiatus, but exciting things are coming your way! We’ll be back on October 21 with some amazing new episodes that we can’t wait to share. In the meantime, take care of yourself, enjoy the little moments, and remember—good things are just around the corner.

See you soon!

- Team Simon

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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 career that lasts.

Across his career, Rob has navigated the highs of teen idol stardom, the lows of very public failures, and the challenge of reinventing himself again and again—all while staying relevant and true to himself. His secret? A willingness to take risks, embrace failure, and laugh at himself along the way.

Rob and I dive into Rob’s philosophy of resilience, authenticity, and joy. He shares how humiliations turned into lessons, why not taking yourself too seriously is a strength, and how authenticity has become the ultimate currency in today’s culture.

You can also see Rob hosting the fourth season of The Floor, airing September 24th on FOX.]

This is A Bit of Optimism.

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 storytelling shapes technology, society, and innovation. He argues that imagining optimistic futures is essential if we want to create them.

In this episode, we also explore how technology like AI is changing the way our brains work and how our faculties will evolve, why humanity has shifted from focusing on external threats to internal ones, and how optimism isn’t blind faith—it’s a clear-eyed strategy for shaping a better world.

This is... A Bit of Optimism.

Check out Reid’s new book here: https://www.superagency.ai/

SUPERAGENCY: What Could Possibly Go Right with Our AI Future

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’s helped us rethink intimacy, navigate conflict, and reimagine what a healthy connection looks like—at home and now at work with her new conversation inducing game of questions, Where Should We Begin? At Work.

Esther and I explore how our ideas of love and partnership have evolved, why friendships can be just as life-giving as romance, and why learning to “talk to strangers” may be the most important skill for the next generation. We also dive into the role of play, trust, and risk-taking in building lasting bonds.

If you care about creating relationships that are strong enough to withstand the pressures of modern life, this episode might just be for you.

This is A Bit of Optimism.

To learn more about Esther’s work, visit:

www.estherperel.com

And to check out Where Should We Begin? At Work here:

https://game.estherperel.com/products/where-should-we-begin-at-work?gad_source=1&gad_campaignid=21749016432&gbraid=0AAAAA93e13laOUsIrrGSZUodaliBNmZVP&gclid=CjwKCAjw_fnFBhB0EiwAH_MfZtrMmVTRj7QgBn4ER-_HF10aCifdOOpY1DLy9R4dt4K0Sbh2WKJDeRoC2XUQAvD_BwE