5 Challenges We Got Ourselves Into

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 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:Visit Episode Website

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 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.

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, 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)

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 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 SubstackFollow us: Instagram, LinkedIn, Facebook, YouTubeVisit Episode WebsiteEverything Happens for a Reason and the Other Lies I've Loved by Kate BowlerTopics we are covering in this episode:The difference between sudden loss and a long terminal declineWhy advance directives and a will are a gift to the people you leave behindThe place of humor in getting a family throughBurying grief versus seeking professional helpSupporting the spouses and children who are grieving tooThe conversations to have with parents while they're still alive

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 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 SubstackFollow us: Instagram, LinkedIn, Facebook, YouTubeVisit Episode WebsiteTopics we are covering in this episode:Expected vs unexpected windfalls and why the difference mattersHow sudden money amplifies whatever was already thereThe money conversation to have with your spouse before it arrivesWhen an inheritance brings grief instead of a gainHow a financial windfall changes friends, family, and youWhy 75% of business owners regret selling their company

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 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 SubstackFollow us: Instagram, LinkedIn, Facebook, YouTubeVisit Episode WebsiteTopics we are covering in this episode:The difference between visible and invisible health scaresA four-level framework for how people respond to a diagnosisWhy relying on AI for self-diagnosis can make things worseThe role of alternative therapy in injury recoveryWhat heart and cardiovascular testing can reveal that you can't feelBalancing the things that keep you healthy against the things you love

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, 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

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 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

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 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

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, 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