Midlife Circus
Midlife isn’t the end — it’s the evolution of Gen X. Hosted by Brent Drever and Rob Espenel, Midlife Circus is where real conversations meet reinvention. Like any good circus, midlife is part chaos, part wonder — a stage for learning new acts. From careers and relationships to purpose and adventure, Rob and Brent explore the unpredictable, messy, and meaningful middle of life with humor, honesty, and a touch of rebellion. Pull up a seat under the tent — and get ready to laugh, reflect, and rediscover what’s possible in Your Next Great Act.
Episodes
27 episodes
No More Paycheck: How to Pay Yourself in Retirement
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, annui...
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Episode 26
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55:43
Kids Leaving for College: Facing the Empty Nest
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,...
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Episode 25
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52:03
Longevity Fundamentals with Dr. Dennis Lipton
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—p...
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Episode 24
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42:06
Micro-Adventures Matter
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 relati...
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Episode 23
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50:33
How to Give Back in Midlife
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 th...
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Episode 22
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40:58
Getting Honest With Your Money — So You Have More Options
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 c...
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Episode 21
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57:58
The 10-Year Letter to Yourself: Relationships, Health, and What Matters Most
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 relati...
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Episode 20
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1:00:45
Work That Fits Your Life Now: 5 Flexible Ways to Earn in Your Next Chapter
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 st...
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Episode 19
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56:26
Why Not Now? Your Next Great Act Is Waiting
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 wh...
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Episode 18
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43:51
Built to Last: The "Big Three" for Midlife Healthspan
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: exerci...
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Episode 17
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53:04
The Solo Retreat: Alone With Your Thoughts
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 h...
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Episode 16
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51:41
Starting Law School at 50: Proof It’s Not Too Late, with our Guest Ron Mayer
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 ...
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Episode 15
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48:47
Midlife Meets AI
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 d...
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Episode 14
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52:05
Someday Is a Lie: Adventures Expire
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 styl...
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Episode 13
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42:47
Setting Goals for the Year Ahead
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 ...
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Episode 12
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54:33
New Habits, New Year, New You
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...
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Episode 11
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48:22
Holiday Traditions
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 adven...
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Episode 10
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32:19
Repurposed NOT Retired
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 ...
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Episode 9
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52:17
Hiring a Financial Advisor? Listen To This First
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 persona...
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Episode 8
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53:50
Your Life Needs a Quest—Even a Small One
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, ...
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Episode 7
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49:48
Navigating Loneliness in Midlife
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 v...
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Episode 6
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57:50
Being Bad at Something, On Purpose
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 experi...
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Episode 5
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52:39
The Two Numbers Between You and Retirement Freedom
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 fr...
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Episode 4
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49:50
Deal Friends vs. Real Friends—The Midlife Sort
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 'rea...
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Episode 3
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46:41