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 stepping away from romantic comedies at the height of his success to sitting with uncertainty when there were no guarantees on the other side, Matthew shares how learning to get comfortable with discomfort empowered the most meaningful reinventions of his life.

At the center of our conversation is curiosity - self-curiosity. Matthew reflects on decades of journaling as a way to notice patterns, stay honest, and make sense of moments that feel unclear. Rather than avoiding discomfort, he learned to treat it as information to study, learn from, and eventually act on.

We talk about what it takes to stay relevant without losing yourself, why reinvention often requires carrying the risk before anyone else believes in the outcome, and how self-curiosity can become a compass when the path forward isn’t obvious.

Matthew also shares how these ideas come to life in his newest book, Poems & Prayers - a collection of reflections shaped by presence, patience, and the courage to keep asking better questions.

If you’re navigating change, questioning your direction, or looking to grow while remaining true to yourself, this conversation offers a grounded and thoughtful path forward.

This is… A Bit of Optimism.

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To check out Matthew’s new book Poems & Prayers, head to: http://www.poemsprayers.com

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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 former host of The Daily Show, a bestselling author, and a stand-up comedian. But his brand of humor isn’t just a barrel of laughs— it’s raw, witty, thought-provoking, and often makes you see the world in a whole new way.

In this conversation, Simon and Trevor ditched the small talk (mostly) and went deep into the paradox of choice, the public's response to the murder of United HealthCare's CEO, and why the human experience might be defined by constraint.

It will make you chuckle, think, and probably question everything all at once.

This… is A Bit of Optimism.

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For more on Trevor and his work, check out: https://www.trevornoah.com/

Team Simon here! We’re revisiting some of our favorite episodes from 2025. But we'll be back in just two weeks with brand-new episodes of A Bit of Optimism on January 27, 2026. We think you’re going to love them!

Today, we’re going back to January of last year when Dr. Becky Kennedy joined us to discuss the hardest job in the world—parenting. 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.

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Check out Dr. Becky’s work: https://www.goodinside.com/