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.

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• 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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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.

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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

Be sure to follow Midlife Circus wherever you get your podcasts — Midlife Circus is available on all major podcast platforms.

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.

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• 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

Be sure to follow Midlife Circus wherever you get your podcasts — Midlife Circus is available on all major podcast platforms.

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.

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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

Be sure to follow Midlife Circus wherever you get your podcasts — Midlife Circus is available on all major podcast platforms.

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.

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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

Be sure to follow Midlife Circus wherever you get your podcasts — Midlife Circus is available on all major podcast platforms.

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.

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• 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

• Going back to work on your own terms — pay cut and all

• Advice for anyone considering a midlife career break

Be sure to follow Midlife Circus wherever you get your podcasts — Midlife Circus is available on all major podcast platforms.

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.

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• Join the Midlife Circus Community on Substack

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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

Be sure to follow Midlife Circus wherever you get your podcasts — Midlife Circus is available on all major podcast platforms.

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.

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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

Be sure to follow Midlife Circus wherever you get your podcasts — Midlife Circus is available on all major podcast platforms.

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.

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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

Be sure to follow Midlife Circus wherever you get your podcasts — Midlife Circus is available on all major podcast platforms.

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.

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• 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

Be sure to follow Midlife Circus wherever you get your podcasts — Midlife Circus is available on all major podcast platforms.

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.

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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

Be sure to follow Midlife Circus wherever you get your podcasts — Midlife Circus is available on all major podcast platforms.

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.

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• 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

Be sure to follow Midlife Circus wherever you get your podcasts — Midlife Circus is available on all major podcast platforms.

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.

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• 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.

Be sure to follow Midlife Circus wherever you get your podcasts — Midlife Circus is available on all major podcast platforms.

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.

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• View Episode Transcript

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• The Let Them Theory - Mel Robbins

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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.

Be sure to follow Midlife Circus wherever you get your podcasts — Midlife Circus is available on all major podcast platforms.

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.

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• View Episode Transcript

• Join the Midlife Circus Community on Substack

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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

Be sure to follow Midlife Circus wherever you get your podcasts — Midlife Circus is available on all major podcast platforms.

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:

• View Episode Transcript

• Join the Midlife Circus Community on Substack

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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.

Be sure to follow Midlife Circus wherever you get your podcasts — Midlife Circus is available on all major podcast platforms.

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.

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• View Episode Transcript

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• 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.Be sure to follow Midlife Circus wherever you get your podcasts — Midlife Circus is available on all major podcast platforms.

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.

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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.

Be sure to follow Midlife Circus wherever you get your podcasts — Midlife Circus is available on all major podcast platforms.

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.

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• How to Think Like Einstein - Scott D. Thorpe

• Moonwalking with Einstein - Joshua Foer

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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.

Be sure to follow Midlife Circus wherever you get your podcasts — Midlife Circus is available on all major podcast platforms.

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.

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• View Episode Transcript

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• 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

Be sure to follow Midlife Circus wherever you get your podcasts — Midlife Circus is available on all major podcast platforms.