Midlife Circus: Gen X Reinvention

Brent Drever & Rob Espenel
  • 4.8 (53)
  • Self-Improvement
  • Updated Biweekly

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.

  1. 18h ago ·  Video

    Connection, Health, and Renewal: A Midlife Adventure in Costa Rica

    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 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 SubstackFollow us: Instagram, LinkedIn, Facebook, YouTubeVisit Episode WebsiteSurf 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 sessionsLearning to surf in your 50s, and what five days in the water actually teaches youA reminder on the regenerative power of slowing downReframing an expensive trip as an investment in your familyA week of healthy meals where three-year-olds and fifty-year-olds ate togetherCold plunges, breath work, and holding your breath longer than you thought you couldWhat happens to a group when nobody picks up their phone for a week

    41 min

  2. Jun 24 ·  Video

    The Stuff We Keep: Why Letting Go in Midlife Creates Room for What's Next

    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 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 SubstackFollow us: Instagram, LinkedIn, Facebook, YouTubeVisit Episode WebsiteTopics we are covering in this episode: A room-by-room inventory of the stuff we keepThe three categories: sentimental keepers, expensive maybe-somedays, and things to let goWhy old suits and ties carry the fear of going back to workThe sunk cost trap of expensive purchasesHow giving things away can feel better than keeping themReplacing old stuff with items that fit your future self

    1h 2m

  3. Jun 10 ·  Video

    Acceptance as Strength: Recovery and Rebuilding with Musician Ezra Vancil

    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 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, YouTubeVisit Episode WebsiteFollow Ezra Vancil - https://ezravancil.com (shop, book, vinyl, music), Instagram @ezravancil, search "Ezra Vancil" for his music on all streaming platformsTopics we are covering in this episode: Growing up in a traveling gospel bandGetting signed to a record label as a teenagerTwenty years of addiction and the slow collapseThe kitchen-floor moment at 40 that changed everythingWhy Ezra calls acceptance a strengthWalking away from a new record deal to choose familyMaking music with his daughter and building a business with his son

    1h 14m

  4. May 27 ·  Video

    5 Challenges We Got Ourselves Into

    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, 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, YouTubeVisit Episode Website Topics we are covering in this episode: The 5 rings of midlife as a framework for growth10 personal challenges put on the recordThe case against the easy-button challengeA 90-day window for real growth in midlifeThe case for public commitments and accountabilityAn invitation for listeners to pick their own challenges

    52 min

  5. May 20 ·  Video

    Launching a Creative Business in Midlife

    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, 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, YouTubeVisit Episode WebsiteMountain Mud Ceramics (creative business mentioned) Topics we are covering in this episode: The difference between a creative hobby and a creative businessThree categories of creative work: physical goods, creative content, and creative servicesHow to apply passion, product, and marketplace as a starting frameworkWhy most creators underprice themselves out of the gateChoosing the right platform without spreading across too manyStarting small with a minimum viable productPlaying the long game and resisting the comparison trap

    55 min

  6. May 13

    A Guide to Earning Money as a Consultant in Midlife

    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 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, YouTubeVisit Episode WebsiteTopics we are covering in this episode: The mindset shift from employee to consultantThe difference between consulting, coaching, and advisory workHow to define purpose, product, and marketPath selection — independent, platform, or consulting firmHow to set billing rates and avoid underselling yourselfMarketing materials and digital presence that actually workWhy your first client matters more than the perfect setup

    1h 12m

  7. May 6

    Before You Retire: 5 Things We Wish We'd Done First

    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 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, YouTubeVisit Episode WebsiteTopics we are covering in this episode: Test-driving your retirement lifestyle before you leaveWhy work relationships disappear overnightBuilding health habits before the paycheck stopsThe identity shift and the case for a real breakWhy adventure lists are a transition plan in disguisePlan Z as the fallback that frees you up

    59 min

  8. Apr 29

    The Midlife Sabbatical: Taking a Career Break in Your 50s with Sarah Hager

    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 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, YouTubeVisit Episode WebsiteSarah’s Etsy Shop – Hernage Creek DesignTopics we are covering in this episode: What prompted Sarah to step away from a 30-year career at 52The emotional side of taking a midlife sabbaticalHow to bridge the financial gap between working and full retirementRediscovering yourself in the quiet after stepping awayUnlocking creativity through a print-on-demand Etsy business

    55 min
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4.8
out of 5
53 Ratings

About

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.

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