Episode Details

Cal Callahan was a successful financial trader who retired at 41, appearing to have won the game of life. But as he reveals in this intimate conversation, checking all the boxes (wealth, fitness, status) left him feeling unfulfilled and trapped in a script he hadn't written.

In this episode, Cal opens up about the terrifying moment during the Route 91 Harvest Festival shooting that became his catalyst for awakening, realizing that all his accumulated success couldn't save him. He discusses his profound journey of unlearning the societal programming of achievement and how he moved from a black-and-white world into the gray zone of curiosity and endless possibility.

Corissa and Cal dive deep into the power of unlearning, specifically why true success isn't about the outcome but about the freedom to show up authentically without masks. Cal explains how he redefined his approach to investing and relationships, prioritizing connection and alignment over ROI, and why "clear is kind" is his new mantra for navigating endings.

In this episode, we cover:

• The Route 91 Awakening: How a near-death experience forced Cal to surrender and realize his strategy for success was useless in the face of mortality.
• The Winning the Game Trap: Why achieving traditional success often leads to a "is this it?" moment, and why Cal encourages people to win the game anyway just to learn that lesson.
• Community as a Mirror: The vital importance of surrounding yourself with curious people who challenge your worldview, and Cal's intentional approach to men's groups.
• Redefining Investment: How Cal shifted from "fear of missing out" investing to "who is this person?" investing, focusing on the journey rather than just the exit.
• The Courage to be Disliked: Navigating the discomfort of shedding old identities (like "the fit guy" or "the trader") to embrace a more fluid, authentic self.

Notable Quotes:

• "I tried so hard and I played the game and I won the game, but it wasn't the game." — Cal Callahan
• "I realized that if I didn't make it out alive, that I would be really disappointed that this is how my life turned out." — Cal Callahan
• "Success is to be able to show up as you, truly you, and just let the kind of chips fall where they may." — Cal Callahan

Resources & Links:

• Podcast: https://podcasts.apple.com/us/podcast/the-great-unlearn/id1492460338
• Website: https://www.thegreatunlearn.com
• Instagram: https://www.instagram.com/cal.callahan
• Youtube: https://www.youtube.com/channel/UCneI0an6qiL7t-7sne9TjhQ
• Facebook: https://www.facebook.com/thegreatunlearn
• Twitter: https://twitter.com/TGUpodcast

Connect with Corissa:

• Explore the Advisory. https://corissasaintlaurent.com/advisory
• Inquire for Keynotes. https://corissasaintlaurent.com/speaking

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Thanks for tuning in!