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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

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, 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

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, 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

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, 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

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, 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

Message the Show

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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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

Message the Show

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