Explore every episode of the podcast Midlife Circus
| Title | Pub. Date | Duration | |
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| Deal Friends vs. Real Friends—The Midlife Sort | 05 Nov 2025 | 00:46:42 | |
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. Links, resources, books mentioned:
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| Midlife: Choose your Own Adventure | 05 Nov 2025 | 00:53:56 | |
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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| Leaving the Grind: Now What? | 05 Nov 2025 | 00:44:18 | |
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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| Welcome to the Midlife Circus (Trailer) | 20 Oct 2025 | 00:02:38 | |
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. Links and Resources: | |||
| Being Bad at Something, On Purpose | 19 Nov 2025 | 00:52:40 | |
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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| The Two Numbers Between You and Retirement Freedom | 12 Nov 2025 | 00:49:51 | |
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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| Navigating Loneliness in Midlife | 26 Nov 2025 | 00:57:51 | |
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.
Links, resources, books mentioned:
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| Hiring a Financial Advisor? Listen To This First | 10 Dec 2025 | 00:53:51 | |
In this conversation, Brent and Rob discuss the critical aspects of hiring a financial advisor, emphasizing the importance of trust, understanding fiduciary responsibilities, and aligning values with financial goals. They share personal experiences and insights on navigating the complexities of financial planning, the significance of asking the right questions, and the necessity of building a strong advisor-client relationship. The discussion also highlights the generational shift in financial planning, where individuals are now responsible for their retirement savings and investment decisions, making the role of a financial advisor more crucial than ever.
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| Your Life Needs a Quest—Even a Small One | 03 Dec 2025 | 00:49:49 | |
In this conversation, Brent and Rob explore the theme of adventures and personal growth, discussing their experiences with travel and the importance of stepping out of comfort zones. They share stories about climbing Colorado's 14ers, the challenges of planning big adventures like summiting Kilimanjaro, and the insights gained from cultural experiences. The discussion also emphasizes the value of micro-adventures and how small changes in routine can lead to significant personal growth.
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| Repurposed NOT Retired | 17 Dec 2025 | 00:52:18 | |
In this conversation, Brent shares his experiences and challenges faced after retirement, particularly around identity and purpose. He discusses the awkwardness of answering the question 'What do you do?' and the discomfort that comes with losing a professional identity. The dialogue explores the journey of finding new opportunities, the importance of experimentation, and the need to create a balanced portfolio of skills and activities that bring joy and fulfillment. Both Rob and Brent reflect on their transitions and the significance of taking time to discover their next great act after a long career.
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| Holiday Traditions | 24 Dec 2025 | 00:32:20 | |
In this festive conversation, Brent and Rob explore their cherished Christmas traditions, childhood memories of Santa, and the nostalgia that surrounds the holiday season. They share humorous anecdotes about family Christmas tree adventures, unique traditions, and the significance of ornaments. The discussion also touches on the experience of celebrating Christmas in warmer climates, the joy of holiday music and movies, and the meaning of Christmas in their lives today. Ultimately, they emphasize the importance of family and friends during the holiday season.
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| New Habits, New Year, New You | 31 Dec 2025 | 00:48:23 | |
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 during midlife, envisioning changes before they occur, and the process of building new habits through cues and rewards. Ultimately, they highlight the journey of habit formation and the importance of creating healthy habits for a fulfilling life.
Links, resources, books mentioned:
(This post includes affiliate links. As an Amazon Associate, we may earn a small commission if you purchase through these links—at no extra cost to you.)
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| Setting Goals for the Year Ahead | 07 Jan 2026 | 00:54:34 | |
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 flexible with goals, and fostering relationships.
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(This post includes affiliate links. As an Amazon Associate, we may earn a small commission if you purchase through these links—at no extra cost to you.) Topics we are covering in this episode:
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| Someday Is a Lie: Adventures Expire | 14 Jan 2026 | 00:42:48 | |
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 already expired. This isn’t about drastic change or reckless decisions—it’s about awareness, choice, and action. Because the most expensive decision in midlife isn’t what you do—it’s what you keep postponing.
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| Midlife Meets AI | 21 Jan 2026 | 00:52:06 | |
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. Along the way, they talk about trust, bias, authenticity, and why AI should augment your life—not replace your voice.
Links, resources, books mentioned:
(This post includes affiliate links. As an Amazon Associate, we may earn a small commission if you purchase through these links—at no extra cost to you.)
Topics we are covering in this episode:
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| Starting Law School at 50: Proof It’s Not Too Late, with our Guest Ron Mayer | 28 Jan 2026 | 00:48:48 | |
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 doubt, identity shifts, and the courage it takes to move toward something meaningful rather than running away from what no longer fits. This conversation is for anyone wondering if it’s too late—and looking for proof that it’s not.
Links, resources, books mentioned:
(This post includes affiliate links. As an Amazon Associate, we may earn a small commission if you purchase through these links—at no extra cost to you.)
Topics we are covering in this episode:
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| The Solo Retreat: Alone With Your Thoughts | 04 Feb 2026 | 00:51:42 | |
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 distractions fade, and why learning to sit with it often leads to growth and calm. If midlife feels full or overwhelming, this episode offers a simple reminder: sometimes clarity comes from stepping back.
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| Built to Last: The "Big Three" for Midlife Healthspan | 11 Feb 2026 | 00:53:05 | |
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 about the small, repeatable habits that compound into either freedom—or limitation—later in life. If you want to keep doing the things you love not just longer, but better, this conversation is a reminder that health isn’t a side project—it’s the foundation.
Links, resources, books mentioned:
(This post includes affiliate links. As an Amazon Associate, we may earn a small commission if you purchase through these links—at no extra cost to you.)
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| Why Not Now? Your Next Great Act Is Waiting | 18 Feb 2026 | 00:43:52 | |
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 already taken the leap, the conversation challenges listeners to rethink timing, momentum, and what’s possible next. The question at the center of it all: if you’re feeling the pull… why not now?
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| Work That Fits Your Life Now: 5 Flexible Ways to Earn in Your Next Chapter | 25 Feb 2026 | 00:56:27 | |
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 with your life today. Along the way, they discuss flexible income paths—including consulting, freelancing, coaching, nonprofit work, and board member roles—and the identity shifts that often come with stepping away from traditional titles and routines. More than a list of options, this episode is about permission: to rethink work, question old assumptions, and take practical steps toward a next chapter that feels meaningful, sustainable, and true to you.
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| The 10-Year Letter to Yourself: Relationships, Health, and What Matters Most | 04 Mar 2026 | 01:00:46 | |
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 the need to control outcomes, this episode blends vulnerability, laughter, and practical insight into a simple reminder: while we can’t control the future, we can influence it by how we show up today.
Links, resources, books mentioned:
(This post includes affiliate links. As an Amazon Associate, we may earn a small commission if you purchase through these links—at no extra cost to you.)
Topics we are covering in this episode:
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| Getting Honest With Your Money — So You Have More Options | 11 Mar 2026 | 00:57:59 | |
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 about clarity. By revisiting the two numbers — what you spend and what you have — they explain how getting honest with your annual spending can simplify your financial life and create real optionality for what comes next.
Links, resources, books mentioned:
(This post includes affiliate links. As an Amazon Associate, we may earn a small commission if you purchase through these links—at no extra cost to you.)
Topics we are covering in this episode:
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| How to Give Back in Midlife | 18 Mar 2026 | 00:40:59 | |
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 global Podcast-a-thon, they also highlight The Cycle Effect, a Colorado nonprofit creating brighter futures for young women through mountain biking, mentorship, and access to the outdoors.
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