In this conversation, Rob and Brent explore the often-overlooked topic of loneliness, particularly as it relates to midlife transitions. They share personal experiences of navigating loneliness after career changes, the importance of vulnerability, and the value of seeking help through therapy. The discussion also delves into the evolution of friendships, distinguishing between 'real friends' and 'deal friends,' and the difference between solitude and loneliness. Ultimately, they emphasize the importance of connection and the proactive steps one can take to foster relationships and combat feelings of isolation.
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In this conversation, Brent and Rob explore the significance of learning new skills, especially in midlife. They discuss childhood hobbies, the importance of having a learning list in midlife, and the challenges of embracing new experiences. Rob shares his journey of learning to bake bread, riding a unicycle, and his ambitious list of 50 things to learn in his fifties. The conversation emphasizes the value of curiosity, the joy of learning, and the importance of maintaining mental stimulation as we age.
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In this conversation, Brent and Rob explore the emotional and mathematical aspects of retirement planning. They discuss the importance of understanding one's relationship with money, the two critical numbers that determine financial freedom, and the emotional challenges faced when transitioning from a working life to retirement. The discussion emphasizes the need to evaluate spending habits, predict future expenses, and consider the trade-offs between income and health. Ultimately, the conversation encourages listeners to take control of their financial future while also prioritizing their well-being.
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In this conversation, Rob and Brent discuss Brent's upcoming triathlon and the challenges of training for it. They then transition into a deeper discussion about friendships, particularly the differences between 'deal friends' and 'real friends' as Brent reflects on his experiences after leaving his last company. The conversation highlights the loneliness that can accompany such transitions and offers insights on rekindling connections and the importance of maintaining relationships beyond work.
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In this episode of Midlife Circus, Brent and Rob crack open the Choose Your Own Adventure theme of midlife—where you get to decide what comes next. They explore what it means to rewrite the script, embrace curiosity, and step off autopilot to direct your next great act.
From motorcycles and model cars to 3D printing and solo adventures, this conversation blends humor, nostalgia, and introspection to show that midlife isn’t a crisis—it’s a creative rewrite. Rob and Brent share personal stories, lessons learned, and the joy of rediscovering hands-on passions while reimagining purpose beyond the career grind.
Whether you’re rebuilding, reinventing, or just wondering what’s next, this episode will remind you that it’s never too late to choose your own adventure.
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In this episode, Rob and Brent explore the transition into semi-retirement, discussing the challenges and surprises that come with leaving behind a long career. They reflect on the impact of the inner critic, the importance of finding meaning beyond money, and the need to build new relationships. The conversation emphasizes the significance of time abundance and the journey of creating a fulfilling life portfolio. They aim to share their experiences and insights to help others navigate this transformative stage of life.
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In this short trailer, Rob and Brent introduce Midlife Circus—a podcast for anyone navigating the glorious chaos of midlife.
Somewhere along the way, they realized they were officially in it: backs that ache for no reason, playlists stuck in the ‘90s, and kids wearing T-shirts from their favorite bands. But instead of calling it a crisis, they’re calling it what it really is—a circus.
Each week, they’ll dive into the unpredictable world of midlife—talking about reinvention, curiosity, purpose, health, finance, and relationships—with honesty, humor, and the occasional wipeout.
Midlife Circus isn’t about having it all figured out. It’s about dropping the script, laughing at the chaos, and realizing this might just be your next great act.
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