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
33 episodes
5 Challenges We Got Ourselves Into
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 sha...
Launching a Creative Business in Midlife
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...
A Guide to Earning Money as a Consultant in Midlife
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 mark...
Before You Retire: 5 Things We Wish We'd Done First
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-...
The Midlife Sabbatical: Taking a Career Break in Your 50s with Sarah Hager
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...
Find Your Epic: Why Big Challenges Matter in Midlife
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 ...
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...
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,...
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...
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...
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...
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...
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...
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...
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...
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...
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...
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 ...
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...
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...
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 ...
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...
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...
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 ...
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...