Midlife Circus: Gen X Reinvention

Message the Show This one is a field trip. Brent and Rob recorded it on location at Surf Synergy, a surf camp in Jacó, Costa Rica, where they brought their own families along with a group of friends and theirs, ages ranging from 3 to 55, for a week of surfing, yoga, and a lot of healthy eating. Recorded outside on a deck in the rainforest, the conversation explores the experiences of the week thro...

Message the Show Rob and Brent each did a room-by-room walkthrough of their own houses and came back with the evidence: a 90-year-old silk top hat, a custom motorcycle jacket from the Harley days, a bin of coaxial cables, gold-toed bowling shoes, and three corporate suits that have not been worn in years. In this episode they sort it all into three categories — the memories worth keeping, the expe...

Message the Show Ezra Vancil got signed to a music label as a teenager and spent the years that followed living the life of a rock star. By 21 his label had dropped him with no plan B, and the next two decades were a collapse into addiction and isolation that nearly cost him his life more than once. The night he hit bottom at 40, he woke up on the kitchen floor to the realization that his life had...

Message the Show Rob and Brent walked into this episode with no idea what the other was about to commit to. They each named 5 personal challenges for the next 90 days, one for every ring of midlife: finance, relationship, health, purpose, and adventure, and shared them live. The list includes losing twenty pounds, getting back to real planned date nights, joining a Friday golf group of strangers,...

Message the Show Almost everyone has a creative thing they've been thinking about for years but never started. Rob wants to shoot action videos. Brent wants to restore old cars. Other people have pottery, photography, or a book idea sitting in the back of their head. In this episode, Brent and Rob get specific about what it takes to move a creative hobby into a real business in midlife, inclu...

Message the Show What does it actually take to start consulting in midlife? Rob and Brent go a layer deeper than their earlier conversation on earning income in your next chapter, breaking down the foundational work most people skip — purpose, product, and market — and the six practical steps to launch your own consulting, advisory, or coaching practice. Drawing from Brent's 20+ years as a co...

Message the Show What if retirement isn't really just a finance problem? Finance is the part most people plan for. It's the four others — relationships, health, purpose, and adventure — that quietly reshape everything. Rob and Brent walk through all five: test-driving your spending before the leap, inventorying the relationships that will and won't survive, building health habits wh...

Message the Show At 52, Sarah Hager stepped away from a 30-year corporate career to take a midlife sabbatical she never planned for. Rob and Brent sit down with Sarah to talk about the events that pushed her to walk away, what she learned in two years of travel, rest, and creative exploration, and how she eventually came back to work on her own terms. It's a grounded, honest look at what a mi...

Message the Show What does it take to push past your own limits in midlife — and why does it matter? Brent and Rob unpack their own versions of Epic, from Rob’s 250-mile Cocodona race and his breakthrough at mile 170, to Brent’s 18-hour Grand Canyon Rim to Rim to Rim and the clarity it brought during a hard season of life. Everybody’s Epic looks different. This one is about why taking on something...

Message the Show What happens when the paycheck stops and you need to start funding life from what you’ve built? Brent and Rob explore the emotional and financial side of retirement distribution planning, including the 4% rule, bucket strategies, annuities, taxes, and the value of working with a professional to navigate the options.   Links, resources, books mentioned: Join the Midlife Circus Comm...

Message the Show What happens when the college drop-off is over and the house gets quiet? Rob and Brent talk honestly about kids leaving for college, the emotions that come with the empty nest, and how this transition can reshape family life, identity, and what comes next.   Links, resources, books mentioned: Join the Midlife Circus Community on Substack   Follow us: Instagram , LinkedIn , Faceboo...

Message the Show In this episode, Brent and Rob sit down with Dr. Dennis Lipton to break down the longevity fundamentals that matter in midlife. They cover the habits that compound over time—sleep, exercise, nutrition, metabolic health, and community—plus how to think about biomarkers and prevention without getting overwhelmed. It’s practical, grounded, and full of real-world perspective on how to...

Message the Show Explore the power of micro-adventures, backyard adventures, and simple travel with Rob and Brent. In this episode, they share how spontaneous outings, nearby day trips, and easy adventure planning can spark curiosity, strengthen relationships, and bring more excitement to everyday life. From childhood bike rides and underground forts to coffee shops, caves, and overnight getaways,...

Message the Show What does giving back look like in midlife? In this episode, Brent and Rob talk about how service often shifts from something we admire to something we feel called to do. They explore the different ways people can support nonprofits through time, experience, relationships, and financial resources, and why local community impact can feel especially powerful. As part of this year’s...

Message the Show In this episode, Brent and Rob explore one of the biggest hidden barriers to your next great act: truly understanding your personal expenses. From the “one-off” costs that somehow show up every year to the money stories we carry from childhood, they unpack why avoidance makes finances feel more complicated than they need to be. This isn’t about budgeting or restriction — it’s abou...

Message the Show What would your future-self want you to hear right now? In this episode, Rob and Brent write letters to themselves from ten years in the future—and then read them out loud. What follows is an honest, emotional conversation about relationships, health, risk, and the quiet shifts that happen in midlife. From evolving family dynamics to staying physically resilient and letting go of...

Message the Show In this episode, Brent and Rob dig into a question many people face in midlife: how to keep earning money while redesigning work to better fit who you are now. They explore the difference between productive stress and anxiety-driven stress, why so many of us get stuck in all-or-nothing thinking about careers, and what it really means to create a Second Act Paycheck that aligns wit...

Message the Show In this episode, Rob and Brent dig into why the traditional idea of retirement no longer fits—and why waiting for “someday” often keeps us stuck. They talk candidly about their own experiences, the fear and excitement of change, and what it really takes to trust yourself enough to make a bold move. From financial clarity and sabbaticals to real-life stories of people who’ve alread...

Message the Show In this episode, Rob and Brent ask a simple but uncomfortable question: what would your future self want you to change today? Looking back 20 years—and ahead 20 more—they break down the “Big Three” that quietly shape healthspan: exercise, diet, and sleep, and why treating them as separate is the biggest mistake most people make. This isn’t about perfection or biohacking. It’s abou...

Message the Show In this episode of Midlife Circus, Brent and Rob explore solo retreats and the value of intentionally stepping away from the noise of midlife. They share personal stories—from quick outdoor resets to multi-day retreats—and reflect on how creating space can unlock clarity, creativity, and perspective. The conversation also touches on the discomfort that can surface when distraction...

Message the Show In this episode, Brent and Rob sit down with longtime friend and guest Ron Mayer to explore what reinvention really looks like in midlife. Ron shares his remarkable journey—from college football and Division I basketball refereeing to financial services, building a successful barbershop business, and ultimately starting law school at age 50. Along the way, they talk openly about d...

Message the Show In this episode, Rob and Brent dig into what AI actually looks like in midlife—beyond the hype, fear, and sci-fi doom. They break down how they use AI in three practical ways: as a smarter search tool, as a thought partner for better decisions (including “virtual board of directors”), and as a creative engine for making things—from trip itineraries to short-form video experiments....

Message the Show In this episode of Midlife Circus, Brent and Rob unpack why adventures and experiences don’t last forever—and why waiting for the “right time” is often the biggest risk of all. From scratched bucket-list dreams and changing travel styles to family windows that close faster than we expect, they explore how health, relationships, and energy shape what’s still possible—and what’s alr...

Message the Show In this episode, Rob and Brent discuss their intentions and goals for 2026, focusing on themes of health, balance, and personal growth. They reflect on the past year, share their adventures planned for the upcoming year, and emphasize the importance of building a community through the Midlife Circus podcast. The conversation highlights the significance of setting intentions, being...

Message the Show In this conversation, Brent and Rob explore the significance of habits, particularly in the context of sleep, transitions in life, and midlife changes. They discuss the importance of understanding and improving sleep habits, navigating the anxiety of transitions, and the value of slowing down to create space in life. The discussion also emphasizes the need for self-reflection duri...