Midlife Circus: Gen X Reinvention
- Episodes
- 42
- Released
- every two weeks
- Latest episode
- Nov 4, 2026
About the podcast
Midlife isn't the end — it's the evolution. 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 career changes and empty nests to money, relationships, health, and second-act adventures, Rob and Brent explore the unpredictable, messy, and meaningful middle of life with humor, honesty, and a touch of rebellion. It's a show for Gen X and anyone reinventing what comes next. Pull up a seat under the tent — and get ready to laugh, reflect, and rediscover what's possible in Your Next Great Act.
Contributors
Episodes 42
Where to Live in Midlife: Is It Time to Move?
Message the ShowMost of us picked where we live because of a job or our kids’ schools, and midlife is usually the first time that choice is really ours. Rob, who has moved eight times, and Brent, who has lived …
Show notes
Most of us picked where we live because of a job or our kids’ schools, and midlife is usually the first time that choice is really ours. Rob, who has moved eight times, and Brent, who has lived in the same mountain town for 14 years, look at how where you live shapes your daily habits and the people around you, and why so many people stay put long after their original reasons for being there have changed. If you’re weighing a move, you’ll come away with a practical way to think it through, from sorting your must-haves from your nice-to-haves to spending real time in a place before you commit.
Links, resources, books mentioned:
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10 Things We Got Completely Wrong About Midlife
Message the ShowWhen Rob and Brent were 25, they were sure they'd have it all sorted by 50: the body, the diet, the friends, the whole point of it. This episode is a Letterman-style countdown of ten things …
Show notes
When Rob and Brent were 25, they were sure they'd have it all sorted by 50: the body, the diet, the friends, the whole point of it. This episode is a Letterman-style countdown of ten things they got completely wrong, from the belief that mac and cheese was a permanent food group to the assumption that leaving work would be the easy part. It's mostly a laugh at their own expense, but somewhere around the bottom of the list it turns into something real about drifting friendships, losing an identity built on work, and still not knowing what you actually want. If you're in midlife and quietly winging it, you're in good company.
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We Set 5 Big Summer Goals, Only Some Survived
Message the ShowThree months ago, with plenty of open time ahead of them, Rob and Brent gave themselves five challenges for the summer, one for each ring of the Midlife Circus: finances, relationships, health …
Show notes
Three months ago, with plenty of open time ahead of them, Rob and Brent gave themselves five challenges for the summer, one for each ring of the Midlife Circus: finances, relationships, health, purpose, and adventure. This episode is where they find out how it actually went, and some of the results are nowhere near what either of them planned. Along the way there's an accidental diet science experiment, plus the particular comedy of watching real life quietly rearrange your best intentions. If you've ever started a stretch of time full of ambition and ended up somewhere completely different, this one will land, and probably make you feel better about your own list.
Links, resources, books mentioned:
- Visit Episode Website (https://midlifecircus.fm/episodes/episode-39-we-set-5-big-summer-goals-only-some-survived)
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Losing a Parent: Sudden Loss and the Long Goodbye
Message the ShowSomewhere in midlife, losing a parent stops being a distant idea and starts happening to people around you. It's one of the few certainties waiting for everyone, and it rarely arrives the …
Show notes
Somewhere in midlife, losing a parent stops being a distant idea and starts happening to people around you. It's one of the few certainties waiting for everyone, and it rarely arrives the way you expect. This episode sits with two very different versions of it: Brent's sudden loss of his father, a massive stroke that took him within 48 hours, and the slow decline of his mother twelve years later, seven months from a cancer diagnosis to her death. One came with no warning at all. The other came with a timeline. Rob and Brent talk through what each one asked of the family, from the roles siblings quietly fall into, to the humor that keeps everyone upright, to the grief that got buried for years before professional help finally surfaced it. They close on the conversations and the paperwork worth handling while your parents are still here.
Links, resources, books mentioned:
- Join the Midlife Circus Community on Substack
- Follow us: Instagram, LinkedIn, Facebook, YouTube
- Visit Episode Website
- Everything Happens for a Reason and the Other Lies I've Loved by Kate Bowler
Topics we are covering in this episode:
- The difference between sudden loss and a long terminal decline
- Why advance directives and a will are a gift to the people you leave behind
- The place of humor in getting a family through
- Burying grief versus seeking professional help
- Supporting the spouses and children who are grieving too
- The conversations to have with parents while they're still alive
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Sudden Money: How a Windfall Changes You and Everyone Around You
Message the ShowAt some point in midlife a financial windfall may show up: a business sale, an inheritance, a severance package, a bonus bigger than expected. Rob and Brent walk through what actually happens …
Show notes
At some point in midlife a financial windfall may show up: a business sale, an inheritance, a severance package, a bonus bigger than expected. Rob and Brent walk through what actually happens next, using the five rings of the Midlife Circus to look past the dollar amount at the parts nobody plans for. They get into how a windfall changes your relationships, why 75% of business owners regret selling within a year, the grief that can come attached to an inheritance, and the number one financial mistake that quietly drains it all away.
Links, resources, books mentioned:
- Join the Midlife Circus Community on Substack
- Follow us: Instagram, LinkedIn, Facebook, YouTube
- Visit Episode Website
Topics we are covering in this episode:
- Expected vs unexpected windfalls and why the difference matters
- How sudden money amplifies whatever was already there
- The money conversation to have with your spouse before it arrives
- When an inheritance brings grief instead of a gain
- How a financial windfall changes friends, family, and you
- Why 75% of business owners regret selling their company
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Navigating Health Scares in Midlife: The Visible and the Invisible
Message the ShowHealth scares in midlife come in two forms: the visible ones you feel, like a back that goes out and won't recover, and the invisible ones you can't, like a cholesterol number that …
Show notes
Health scares in midlife come in two forms: the visible ones you feel, like a back that goes out and won't recover, and the invisible ones you can't, like a cholesterol number that flags a problem you'd never have noticed on your own. In this episode, Brent and Rob each put a real one on the table. Brent walks through the lower back injury that sidelined him for three months and the month he wasted letting AI tell him what he wanted to hear. Rob shares his long history with elevated cholesterol, the heart testing that followed, and what his sports cardiologist actually told him about navigating it. It's a real look at how you respond when your body sends a signal, and why how you navigate it matters more than the scare itself. Plus a colonoscopy prep story that has to be heard to be believed.
Links, resources, books mentioned:
- Join the Midlife Circus Community on Substack
- Follow us: Instagram, LinkedIn, Facebook, YouTube
- Visit Episode Website
Topics we are covering in this episode:
- The difference between visible and invisible health scares
- A four-level framework for how people respond to a diagnosis
- Why relying on AI for self-diagnosis can make things worse
- The role of alternative therapy in injury recovery
- What heart and cardiovascular testing can reveal that you can't feel
- Balancing the things that keep you healthy against the things you love
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Connection, Health, and Renewal: A Midlife Adventure in Costa Rica
Message the ShowThis 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 …
Show notes
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 through the lens of the five rings of midlife: adventure, purpose, finance, relationships, and health. Rob makes the case for treating a trip like this as an investment rather than an expense, and both Brent and Rob get into what changed over a week when everyone disconnected from their lives back at home.
Links, resources, books mentioned:
- Join the Midlife Circus Community on Substack
- Follow us: Instagram, LinkedIn, Facebook, YouTube
- Visit Episode Website
- Surf Synergy (surfsynergy.com) — the all-inclusive surf and wellness retreat in Jacó, Costa Rica where this episode was recorded. Surf Synergy is offering Midlife Circus listeners 10% off with the code “circus” when you book your trip. Book by the end of August 2026; your trip can be scheduled for any available dates after that.
Topics we are covering in this episode:
- Recording an episode outside in the rainforest between surf sessions
- Learning to surf in your 50s, and what five days in the water actually teaches you
- A reminder on the regenerative power of slowing down
- Reframing an expensive trip as an investment in your family
- A week of healthy meals where three-year-olds and fifty-year-olds ate together
- Cold plunges, breath work, and holding your breath longer than you thought you could
- What happens to a group when nobody picks up their phone for a week
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The Stuff We Keep: Why Letting Go in Midlife Creates Room for What's Next
Message the ShowRob 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 …
Show notes
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 expensive stuff held hostage by sunk cost, and the things that just need to go — and dig into the fear and identity underneath why we hang on. The point isn't minimalism. It's making room for the version of yourself you're becoming instead of storing the one you left behind.
Links, resources, books mentioned:
- Join the Midlife Circus Community on Substack
- Follow us: Instagram, LinkedIn, Facebook, YouTube
- Visit Episode Website
Topics we are covering in this episode:
- A room-by-room inventory of the stuff we keep
- The three categories: sentimental keepers, expensive maybe-somedays, and things to let go
- Why old suits and ties carry the fear of going back to work
- The sunk cost trap of expensive purchases
- How giving things away can feel better than keeping them
- Replacing old stuff with items that fit your future self
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Acceptance as Strength: Recovery and Rebuilding with Musician Ezra Vancil
Message the ShowEzra 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 …
Show notes
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 to change. This conversation is the story of what happened next: how Ezra stopped running long enough to do the work of acceptance, and how that recovery became his next great act. During this episode, he picks up his mandolin and plays a brand-new song live, written with this conversation in mind.
Links, resources, books mentioned:
- Join the Midlife Circus Community on Substack
- Follow us: Instagram, LinkedIn, Facebook, YouTube
- Visit Episode Website
- Follow Ezra Vancil - https://ezravancil.com (shop, book, vinyl, music), Instagram @ezravancil, search "Ezra Vancil" for his music on all streaming platforms
Topics we are covering in this episode:
- Growing up in a traveling gospel band
- Getting signed to a record label as a teenager
- Twenty years of addiction and the slow collapse
- The kitchen-floor moment at 40 that changed everything
- Why Ezra calls acceptance a strength
- Walking away from a new record deal to choose family
- Making music with his daughter and building a business with his son
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5 Challenges We Got Ourselves Into
Message the ShowRob 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 …
Show notes
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, learning to ride a unicycle, and tracking every meal for ninety days. A working definition of growth in midlife, with the receipts due at the end.
Links, resources, books mentioned:
- Join the Midlife Circus Community on Substack
- Follow us: Instagram, LinkedIn, Facebook, YouTube
- Visit Episode Website
Topics we are covering in this episode:
- The 5 rings of midlife as a framework for growth
- 10 personal challenges put on the record
- The case against the easy-button challenge
- A 90-day window for real growth in midlife
- The case for public commitments and accountability
- An invitation for listeners to pick their own challenges
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Launching a Creative Business in Midlife
Message the ShowAlmost 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 …
Show notes
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, including the three categories of creative work, a passion-product-marketplace framework, and why most creators undercharge themselves out of the gate. If you've got a creative idea you keep coming back to, this episode is where you find out what to actually do with it.
Links, resources, books mentioned:
- Join the Midlife Circus Community on Substack
- Follow us: Instagram, LinkedIn, Facebook, YouTube
- Visit Episode Website
- Mountain Mud Ceramics (creative business mentioned)
Topics we are covering in this episode:
- The difference between a creative hobby and a creative business
- Three categories of creative work: physical goods, creative content, and creative services
- How to apply passion, product, and marketplace as a starting framework
- Why most creators underprice themselves out of the gate
- Choosing the right platform without spreading across too many
- Starting small with a minimum viable product
- Playing the long game and resisting the comparison trap
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A Guide to Earning Money as a Consultant in Midlife
Message the ShowWhat 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 …
Show notes
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 consultant and Rob's recent experience building his advisory business, they cover billing rates, marketing, entity structure, and the core mindset shift that changes everything: you are the product.
Links, resources, books mentioned:
- Join the Midlife Circus Community on Substack
- Follow us: Instagram, LinkedIn, Facebook, YouTube
- Visit Episode Website
Topics we are covering in this episode:
- The mindset shift from employee to consultant
- The difference between consulting, coaching, and advisory work
- How to define purpose, product, and market
- Path selection — independent, platform, or consulting firm
- How to set billing rates and avoid underselling yourself
- Marketing materials and digital presence that actually work
- Why your first client matters more than the perfect setup
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Before You Retire: 5 Things We Wish We'd Done First
Message the ShowWhat 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 …
Show notes
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 while you still have structure, giving yourself room to find purpose again, and writing the adventure lists you've been putting off. The episode they wish someone had handed them before they walked out the door.
Links, resources, books mentioned:
- Join the Midlife Circus Community on Substack
- Follow us: Instagram, LinkedIn, Facebook, YouTube
- Visit Episode Website
Topics we are covering in this episode:
- Test-driving your retirement lifestyle before you leave
- Why work relationships disappear overnight
- Building health habits before the paycheck stops
- The identity shift and the case for a real break
- Why adventure lists are a transition plan in disguise
- Plan Z as the fallback that frees you up
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The Midlife Sabbatical: Taking a Career Break in Your 50s with Sarah Hager
Message the ShowAt 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 …
Show notes
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 midlife career break can actually look like — the emotional side, the financial bridge, and the quiet confidence that comes from finding yourself again.
Links, resources, books mentioned:
- Join the Midlife Circus Community on Substack
- Follow us: Instagram, LinkedIn, Facebook, YouTube
- Visit Episode Website
- Sarah’s Etsy Shop – Hernage Creek Design
Topics we are covering in this episode:
- What prompted Sarah to step away from a 30-year career at 52
- The emotional side of taking a midlife sabbatical
- How to bridge the financial gap between working and full retirement
- Rediscovering yourself in the quiet after stepping away
- Unlocking creativity through a print-on-demand Etsy business
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Find Your Epic: Why Big Challenges Matter in Midlife
Message the ShowWhat 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 …
Show notes
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 hard — a race, a trip, a business, a book — might be exactly what this chapter of life is asking you to do.
Links, resources, books mentioned:
- Join the Midlife Circus Community on Substack
- Follow us: Instagram, LinkedIn, Facebook, YouTube
- Visit Episode Website
Topics we are covering in this episode:
- What “Epic” really means in midlife
- Why big challenges give you what ordinary life can’t
- Rob’s breakthrough at mile 170 of Cocodona
- The shift from accomplishment to meaning
- How community makes the hard things possible
- Travel, adventure, and learning to trust the guide
- Finding the version of Epic that fits your life
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No More Paycheck: How to Pay Yourself in Retirement
Message the ShowWhat 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 …
Show notes
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 Community on Substack
- Follow us: Instagram, LinkedIn, Facebook, YouTube
- Visit Episode Website
Topics we are covering in this episode:
- The emotional side of no longer receiving a paycheck
- How withdrawal planning works in retirement
- The pros and cons of the 4% rule, bucket strategy, and annuities
- Why professional guidance can matter in retirement planning
- How taxes and withdrawal timing can shape your retirement income
Kids Leaving for College: Facing the Empty Nest
Message the ShowWhat 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 …
Show notes
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, Facebook, YouTube
- Visit Episode Website
Topics we are covering in this episode:
- The empty nest transition
- Kids leaving for college
- College drop-off and the emotions that follow
- Changing parent-child communication
- Family identity and shifting household rhythms
Longevity Fundamentals with Dr. Dennis Lipton
Message the ShowIn 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 …
Show notes
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 stay strong, sharp, and independent for the long haul.
Links, resources, books mentioned:
- Join the Midlife Circus Community on Substack
- Follow us: Instagram, LinkedIn, Facebook, YouTube
- Visit Episode Website
- Dr. Dennis Lipton (Website)
Topics we are covering in this episode:
- Why longevity fundamentals matter in midlife
- How sleep supports long-term health and recovery
- How strength training helps preserve muscle and independence as we age
- How nutrition choices can improve health span and metabolic health
- How biomarkers can guide smarter prevention and earlier action
- Why community and purpose play a real role in aging well
Micro-Adventures Matter
Message the ShowExplore 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 …
Show notes
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, this conversation shows how small adventures and personal exploration can lead to real personal growth. If you’ve been feeling stuck in routine, this episode offers practical inspiration to help you rediscover spontaneity, connection, and the joy of trying something new.
Links, resources, books mentioned:
- Join the Midlife Circus Community on Substack
- Follow us: Instagram, LinkedIn, Facebook, YouTube
- Visit Episode Website
Topics we are covering in this episode:
- Why spontaneity matters in micro-adventures
- How to find and plan micro-adventures close to home
- How local exploration can spark growth and strengthen relationships
- Using local insight to uncover hidden gems
- Ideas for half-day, single-day, and overnight adventures
How to Give Back in Midlife
Message the ShowWhat 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 …
Show notes
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.
Links, resources, books mentioned:
- Join the Midlife Circus Community on Substack
- Follow us: Instagram, LinkedIn, Facebook, YouTube
- Visit Episode Website
- The Cycle Effect
- Podcast-a-thon
Topics we are covering in this episode:
- Midlife philanthropy and the shift from achievement to contribution
- Time, experience, relationships, and resources as ways to give back
- Volunteering and using professional expertise to support nonprofits
- Donor-advised funds and strategic charitable giving
- The power of local community impact
- The Cycle Effect and its work supporting girls through mountain biking
Getting Honest With Your Money — So You Have More Options
Message the ShowIn 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 …
Show notes
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:
- Join the Midlife Circus Community on Substack
- Follow us: Instagram, LinkedIn, Facebook, YouTube
- Visit Episode Website
- The Psychology of Money — Morgan Housel
(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:
- The gap between what you think you spend and what you actually spend can be meaningful — and that gap shapes what you believe is possible.
- “One-off” expenses rarely stay one-off — they’re part of the rhythm of life.
- Avoidance is what makes personal finances feel heavy and complicated. Clarity simplifies the story.
- This isn’t about budgeting. It’s about truth.
- Simplifying your accounts — both expenses and assets — can give you a clearer, calmer view of your financial picture.
- The money stories you carry quietly influence how you earn, save, and spend.
- When you know your numbers, you stop guessing — and that’s where optionality begins.
The 10-Year Letter to Yourself: Relationships, Health, and What Matters Most
Message the ShowWhat 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 …
Show notes
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:
- Join the Midlife Circus Community on Substack
- Follow us: Instagram, LinkedIn, Facebook, YouTube
- Visit Episode Website
- The Let Them Theory - Mel Robbins
(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:
- Writing a letter from your future self is a powerful way to get clear on what actually matters now.
- Midlife isn’t a crisis—it’s a transition, and how you show up determines what the next decade looks like.
- Health works best as a filter for decisions, not a short-term goal or catchphrase.
- Strong relationships evolve when you stay present, let go of control, and make room for change.
- You don’t need to eliminate risk—just approach it with intention and preparation.
- Vulnerability, especially when shared with someone you trust, deepens connection and self-awareness.
- While we can’t control the future, the choices we make today have more influence than we think.
Work That Fits Your Life Now: 5 Flexible Ways to Earn in Your Next Chapter
Message the ShowIn 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 …
Show notes
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.
Links, resources, books mentioned:
- Visit Episode Website
- Join the Midlife Circus Community on Substack
- Follow us: Instagram, LinkedIn, Facebook, YouTube
Topics we are covering in this episode:
- Why fulfillment, purpose, and income don’t have to come from full-time work
- How all-or-nothing thinking around your next great act limits career options
- Consulting as a common and flexible transition in midlife
- Skill-based freelancing and gig work as a way to explore interests
- The difference between consulting and coaching—and the mindset each requires
- Why nonprofit and mission-driven work can offer meaningful rewards
- The identity shift that comes with stepping away from traditional titles
- Practical ways to explore your next chapter, including learning from people already doing the work
Why Not Now? Your Next Great Act Is Waiting
Message the ShowIn 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 …
Show notes
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?
Links, resources, books mentioned:
- Visit Episode Website
- Join the Midlife Circus Community on Substack
- Follow us: Instagram, LinkedIn, Facebook, YouTube
Topics we are covering in this episode:
- Retirement doesn’t have to mean slowing down—it can be an active and intentional next chapter.
- The traditional idea of retiring at a set age no longer reflects how people want to live today.
- Waiting for the “right time” often becomes the biggest obstacle to change.
- Trusting yourself is essential when navigating major life transitions.
- Financial clarity creates flexibility and opens more options.
- Simplifying life through downsizing can free up time, energy, and experiences.
- Sabbaticals can offer valuable space to explore what’s next without full commitment.
Built to Last: The "Big Three" for Midlife Healthspan
Message the ShowIn 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 …
Show notes
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:
- Visit Episode Website
- Join the Midlife Circus Community on Substack
- Follow us: Instagram, LinkedIn, Facebook, YouTube
- Why We Sleep - Dr. Matthew Walker
- Eat Right Now - Referenced as a tool focused on the psychology and habits of eating.
- ProLon - Referenced in the context of a planned 5-day fasting reset.
- Oura Ring - Mentioned as a long-term sleep tracking tool used to improve sleep quality.
(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:
- Health isn’t three separate goals—it’s one system. Exercise, diet, and sleep rise and fall together. Ignoring one eventually undermines the others.
- Your future self is already paying the bill. The question isn’t if today’s choices matter—it’s what you’re willing to trade now for 10 good years later.
- Diet debates miss the point. The “best” diet is the one you can sustain—and that actually makes you feel better, not just morally right.
- Alcohol doesn’t just cost you the night—it borrows from tomorrow. Poor sleep quietly compounds into worse workouts, worse food choices, and lower energy.
- Sleep is the multiplier. When sleep improves, everything else gets easier—from discipline to decision-making.
The Solo Retreat: Alone With Your Thoughts
Message the ShowIn 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 …
Show notes
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.
Links, resources, books mentioned:
- Visit Episode Website
- Join the Midlife Circus Community on Substack
- Follow us: Instagram, LinkedIn, Facebook, YouTube
Topics we are covering in this episode:
- Solo retreats create space for thoughts and insights to surface without distraction.
- Stepping away from constant midlife chaos often brings clarity before answers.
- Reset time works best when it’s not focused on problem-solving or productivity.
- Simplicity matters—adding too many logistics can reduce the benefits early on.
- Quiet space can feel uncomfortable at first, especially when inner dialogue shows up.
- Learning to sit with that discomfort is part of the growth.
- The urge to document or explain the experience can pull attention away from being present.
- With practice, solo time becomes easier and more rewarding.
- Solo retreats are not selfish—they often lead to showing up better for others.
- Intentional space helps reconnect with perspective, creativity, and calm.
Starting Law School at 50: Proof It’s Not Too Late, with our Guest Ron Mayer
Message the ShowIn 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 …
Show notes
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:
- Visit Episode Website
- Join the Midlife Circus Community on Substack
- Follow us: Instagram, LinkedIn, Facebook, YouTube
- How to Think Like Einstein - Scott D. Thorpe
- Moonwalking with Einstein - Joshua Foer
(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:
- Life can go down many different paths.
- You can pivot at any point in life.
- Early experiences shape our willingness to explore new paths.
- It's important to move towards something meaningful.
- Managing doubt is crucial during transitions.
- Self-reflection helps in navigating career changes.
- Trust yourself and your decision-making process.
- Engaging with others can alleviate feelings of loneliness.
- Identifying limiting beliefs is key to personal growth.
- You have the power to write your own story.
Midlife Meets AI
Message the ShowIn 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 …
Show notes
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:
- Visit Episode Website
- Join the Midlife Circus Community on Substack
- Follow us: Instagram, LinkedIn, Facebook, YouTube
- The Subtle Art of Not Giving a F*ck - Mark Manson
- Can’t Hurt Me - David Goggins
- Never Finished - David Goggins
- Ethan Mollick – One Useful Thing (Substack)
- Reid Hoffman – Possible (podcast)
(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:
- How in midlife, we can use AI in practical, everyday ways—without hype or fear
- AI as a smarter alternative to traditional search and research
- Using AI as a thought partner to think more clearly and make better decisions
- Building “virtual board of directors” with AI to evaluate ideas from multiple perspectives
- Understanding bias, trust, and why AI shouldn’t be treated as gospel
- Where AI helps—and where it hurts—creative authenticity
- Real-world examples of AI in action, from writing and planning to travel and content creation
- How AI can help reframe challenges, reduce friction, and speed up learning
- Why starting small (recipes, trips, simple questions) is a simple way to begin
- Embracing AI as a tool that augments the human experience, not replaces it
Someday Is a Lie: Adventures Expire
Message the ShowIn 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 …
Show notes
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.
Links, resources, books mentioned:
- Visit Episode Website
- Join the Midlife Circus Community on Substack
- Follow us: Instagram, LinkedIn, Facebook, YouTube
Topics we are covering in this episode:
- Adventures can expire due to health, relationships, or interests.
- Seizing opportunities is crucial as life changes.
- Family dynamics affect the timing of adventures.
- Experiences with children have a finite window.
- Health impacts the ability to pursue adventures as we age.
- Writing down goals can help prioritize adventures.
- Sharing your goals with others can lead to support and accountability.
- It's important to embrace adventures before they expire.
Setting Goals for the Year Ahead
Message the ShowIn 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 …
Show notes
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.
Links, resources, books mentioned:
- Visit Episode Website
- Join the Midlife Circus Community on Substack
- Follow us: Instagram, LinkedIn, Facebook, YouTube
- The One Word That’ll Change Your Life - John Gordon, Dan Britton, and Jimmy Page
(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:
- Reflecting on the past year helps set intentions for the new year.
- Choosing a one-word theme can guide personal growth.
- Health encompasses physical, mental, and relationship aspects.
- Setting goals should be flexible and adaptable.
- Quality time with loved ones enhances relationship health.
- Adventures can be both personal and shared experiences.
- Building a community can provide support and connection.
- Intentions for the year can be documented and revisited.
- Creating a balance between work and personal life is essential.
These are the latest 40 of 42 episodes. You’ll find older episodes in the podcast’s feed.
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