HeyJaredMidlife 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.
- Indexed episodes, last 90 days
- 5
- Latest publication
- Sep 2, 2026
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- Earliest in this view
- Jul 8, 2026
Latest episodes
We Set 5 Big Summer Goals, Only Some Survived (opens the original)
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Message the Show 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 b...
Losing a Parent: Sudden Loss and the Long Goodbye (opens the original)
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Message the Show 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 a...
Sudden Money: How a Windfall Changes You and Everyone Around You (opens the original)
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Message the Show 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 num...
Navigating Health Scares in Midlife: The Visible and the Invisible (opens the original)
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Message the Show 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 e...
Connection, Health, and Renewal: A Midlife Adventure in Costa Rica (opens the original)
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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...
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