Midlife Circus

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. Links, resources, books mentioned:Join the Midlife Circus Community on Substack  Follow us: Instagram, LinkedIn, Facebook, YouTubeVisit Episode WebsiteThe 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.

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. Links, resources, books mentioned:Join the Midlife Circus Community on Substack  Follow us: Instagram, LinkedIn, Facebook, YouTubeVisit Episode WebsiteThe Let Them Theory - Mel Robbins(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: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.

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. Links, resources, books mentioned:Visit Episode WebsiteJoin the Midlife Circus Community on SubstackFollow us: Instagram, LinkedIn, Facebook, YouTubeTopics we are covering in this episode:Why fulfillment, purpose, and income don’t have to come from full-time workHow all-or-nothing thinking around your next great act limits career optionsConsulting as a common and flexible transition in midlifeSkill-based freelancing and gig work as a way to explore interestsThe difference between consulting and coaching—and the mindset each requiresWhy nonprofit and mission-driven work can offer meaningful rewardsThe identity shift that comes with stepping away from traditional titlesPractical ways to explore your next chapter, including learning from people already doing the work

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:Visit Episode WebsiteJoin the Midlife Circus Community on SubstackFollow us: Instagram, LinkedIn, Facebook, YouTubeTopics 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.

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. Links, resources, books mentioned:Visit Episode WebsiteJoin the Midlife Circus Community on SubstackFollow us: Instagram, LinkedIn, Facebook, YouTubeWhy We Sleep - Dr. Matthew WalkerEat 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.

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. Links, resources, books mentioned:Visit Episode WebsiteJoin the Midlife Circus Community on SubstackFollow us: Instagram, LinkedIn, Facebook, YouTubeTopics 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.

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. Links, resources, books mentioned:Visit Episode WebsiteJoin the Midlife Circus Community on SubstackFollow us: Instagram, LinkedIn, Facebook, YouTubeHow to Think Like Einstein - Scott D. ThorpeMoonwalking with Einstein - Joshua Foer(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: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.

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. Links, resources, books mentioned:Visit Episode WebsiteJoin the Midlife Circus Community on SubstackFollow us: Instagram, LinkedIn, Facebook, YouTubeThe Subtle Art of Not Giving a F*ck - Mark MansonCan’t Hurt Me - David GogginsNever Finished - David GogginsEthan 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 fearAI as a smarter alternative to traditional search and researchUsing AI as a thought partner to think more clearly and make better decisionsBuilding “virtual board of directors” with AI to evaluate ideas from multiple perspectivesUnderstanding bias, trust, and why AI shouldn’t be treated as gospelWhere AI helps—and where it hurts—creative authenticityReal-world examples of AI in action, from writing and planning to travel and content creationHow AI can help reframe challenges, reduce friction, and speed up learningWhy starting small (recipes, trips, simple questions) is a simple way to beginEmbracing AI as a tool that augments the human experience, not replaces it

In this episode of Midlife Circus, Brent and Rob unpack why adventures and experiences don’t last forever—and why waiting for the “right time” is often the biggest risk of all. From scratched bucket-list dreams and changing travel styles to family windows that close faster than we expect, they explore how health, relationships, and energy shape what’s still possible—and what’s already expired. This isn’t about drastic change or reckless decisions—it’s about awareness, choice, and action. Because the most expensive decision in midlife isn’t what you do—it’s what you keep postponing. Links, resources, books mentioned:Visit Episode WebsiteJoin the Midlife Circus Community on SubstackFollow us: Instagram, LinkedIn, Facebook, YouTubeTopics we are covering in this episode:Adventures can expire due to health, relationships, or interests.Seizing opportunities is crucial as life changes.Family dynamics affect the timing of adventures.Experiences with children have a finite window.Health impacts the ability to pursue adventures as we age.Writing down goals can help prioritize adventures.Sharing your goals with others can lead to support and accountability.It's important to embrace adventures before they expire.

In this episode, Rob and Brent discuss their intentions and goals for 2026, focusing on themes of health, balance, and personal growth. They reflect on the past year, share their adventures planned for the upcoming year, and emphasize the importance of building a community through the Midlife Circus podcast. The conversation highlights the significance of setting intentions, being flexible with goals, and fostering relationships. Links, resources, books mentioned:Visit Episode Website Join the Midlife Circus Community on SubstackFollow us: Instagram, LinkedIn, Facebook, YouTubeThe One Word That’ll Change Your Life - John Gordon, Dan Britton, and Jimmy Page(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:Reflecting on the past year helps set intentions for the new year.Choosing a one-word theme can guide personal growth.Health encompasses physical, mental, and relationship aspects.Setting goals should be flexible and adaptable.Quality time with loved ones enhances relationship health.Adventures can be both personal and shared experiences.Building a community can provide support and connection.Intentions for the year can be documented and revisited.Creating a balance between work and personal life is essential.

In this conversation, Brent and Rob explore the significance of habits, particularly in the context of sleep, transitions in life, and midlife changes. They discuss the importance of understanding and improving sleep habits, navigating the anxiety of transitions, and the value of slowing down to create space in life. The discussion also emphasizes the need for self-reflection during midlife, envisioning changes before they occur, and the process of building new habits through cues and rewards. Ultimately, they highlight the journey of habit formation and the importance of creating healthy habits for a fulfilling life. Links, resources, books mentioned:Visit Episode WebsiteJoin the Midlife Circus Community on SubstackFollow us: Instagram, LinkedIn, Facebook, YouTubeThe Power of Habit - Charles Duhigg(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:Navigating transitions can create anxiety, but it's important to find a new pace.Creating space in life allows for better enjoyment of activities and reduces stress.Midlife is a time for reflection and reassessment of habits and priorities.Envisioning changes before they happen can help ease transitions.Practicing new habits in advance increases the likelihood of success.Understanding the cues and rewards associated with habits can facilitate change.It's essential to identify habits that serve you well and those that don't.Sleep is a crucial habit that can significantly impact productivity and well-being.Midlife offers an opportunity to create a new version of yourself through healthy habits.

In this festive conversation, Brent and Rob explore their cherished Christmas traditions, childhood memories of Santa, and the nostalgia that surrounds the holiday season. They share humorous anecdotes about family Christmas tree adventures, unique traditions, and the significance of ornaments. The discussion also touches on the experience of celebrating Christmas in warmer climates, the joy of holiday music and movies, and the meaning of Christmas in their lives today. Ultimately, they emphasize the importance of family and friends during the holiday season. Links, resources, books mentioned:Visit Episode WebsiteNewsletter Sign UpFollow us: Instagram, LinkedIn, Facebook, YouTubeTopics we are covering in this episode:Christmas traditions evoke nostalgia and create lasting memories.Family adventures in finding Christmas trees can be humorous.Unique family traditions can evolve over time.Ornaments can hold sentimental value and represent memories.Celebrating Christmas in warm climates can feel different.Holiday music sets the tone for the Christmas season.Movies play a significant role in holiday traditions.The meaning of Christmas shifts as families grow and change.Quality time with loved ones is the essence of the holidays.

In this conversation, Brent shares his experiences and challenges faced after retirement, particularly around identity and purpose. He discusses the awkwardness of answering the question 'What do you do?' and the discomfort that comes with losing a professional identity. The dialogue explores the journey of finding new opportunities, the importance of experimentation, and the need to create a balanced portfolio of skills and activities that bring joy and fulfillment. Both Rob and Brent reflect on their transitions and the significance of taking time to discover their next great act after a long career. Links, resources, books mentioned:Visit Episode Website Newsletter Sign UpFollow us: Instagram, LinkedIn, Facebook, YouTubeTopics we are covering in this episode:The question 'What do you do?' can be challenging post-retirement.Finding purpose after retirement is a common struggle.Exploring new opportunities can lead to unexpected paths.It's important to balance activities and not overcommit.Experimentation is key in discovering new passions.Creating a portfolio of skills can provide fulfillment.It's okay to take time to figure out what's next.Lingering in discomfort can lead to personal growth.

In this conversation, Brent and Rob discuss the critical aspects of hiring a financial advisor, emphasizing the importance of trust, understanding fiduciary responsibilities, and aligning values with financial goals. They share personal experiences and insights on navigating the complexities of financial planning, the significance of asking the right questions, and the necessity of building a strong advisor-client relationship. The discussion also highlights the generational shift in financial planning, where individuals are now responsible for their retirement savings and investment decisions, making the role of a financial advisor more crucial than ever. Links, resources, books mentioned:Visit Episode WebsiteNewsletter Sign UpFollow us: Instagram, LinkedIn, Facebook, YouTubeBrokerCheckInvestment Adviser Public DisclosureTopics we are covering in this episode:Hiring a financial advisor is a significant decision that requires careful consideration.Trust is the most important factor when choosing a financial advisor.Understanding the difference between fiduciaries and salespeople is crucial.Asking the right questions can help you evaluate potential advisors effectively.It's essential to align your financial advisor with your personal values.The timing of hiring a financial advisor can impact your financial future, especially before retirement.Regular communication with your advisor is key to a successful relationship.Newer advisors can be effective if they have a strong support team behind them.Understanding your relationship with money can guide your financial decisions.You should feel comfortable discussing your financial situation with your advisor. 

In this conversation, Brent and Rob explore the theme of adventures and personal growth, discussing their experiences with travel and the importance of stepping out of comfort zones. They share stories about climbing Colorado's 14ers, the challenges of planning big adventures like summiting Kilimanjaro, and the insights gained from cultural experiences. The discussion also emphasizes the value of micro-adventures and how small changes in routine can lead to significant personal growth. Links, resources, books mentioned:Visit Episode WebsiteNewsletter Sign UpFollow us: Instagram, LinkedIn, Facebook, YouTubeTopics we are covering in this episode:Adventures contribute significantly to personal growth.Planning for big adventures requires careful consideration and preparation.Cultural experiences can provide valuable insights into different lifestyles.Micro-adventures can be easily integrated into daily life.Traveling can change your perspective on abundance and happiness.It's important to embrace the unknown when traveling.Finding joy in simplicity can lead to personal transformation.Small changes in routine can enhance everyday experiences.Adventure is about stepping out of your comfort zone. 

In this conversation, Rob and Brent explore the often-overlooked topic of loneliness, particularly as it relates to midlife transitions. They share personal experiences of navigating loneliness after career changes, the importance of vulnerability, and the value of seeking help through therapy. The discussion also delves into the evolution of friendships, distinguishing between 'real friends' and 'deal friends,' and the difference between solitude and loneliness. Ultimately, they emphasize the importance of connection and the proactive steps one can take to foster relationships and combat feelings of isolation. Links, resources, books mentioned:Visit Episode Website Newsletter Sign UpFollow us: Instagram, LinkedIn, Facebook, YouTubeQuiet: The Power of Introverts in a World That Can’t Stop Talking - Susan Cain(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:Loneliness can creep in at different points in life, especially during transitions.Navigating loneliness can be challenging, particularly after leaving a career.Seeking help and being vulnerable is crucial in overcoming loneliness.Therapy can serve as a performance coach to help individuals navigate their feelings.It's important to recognize the difference between solitude and loneliness.Building and maintaining friendships requires effort and intention.Not all friendships will transition from work to personal life; some may fade.Embracing solitude can be healthy, but too much can lead to loneliness.Putting yourself out there is essential for building new connections.Change can be tough, but surrounding yourself with supportive people can ease the journey.

In this conversation, Brent and Rob explore the significance of learning new skills, especially in midlife. They discuss childhood hobbies, the importance of having a learning list in midlife, and the challenges of embracing new experiences. Rob shares his journey of learning to bake bread, riding a unicycle, and his ambitious list of 50 things to learn in his fifties. The conversation emphasizes the value of curiosity, the joy of learning, and the importance of maintaining mental stimulation as we age. Links, resources, books mentioned:Visit Episode Website Newsletter Sign UpFollow us: Instagram, LinkedIn, Facebook, YouTubeLiving with a Seal - Jesse ItzlerLiving with the Monks - Jesse Itzler(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:Learning new skills can bring joy and opportunity.Embracing challenges is essential for personal growth.Having a learning list can help fill time in midlife.Curiosity drives lifelong learning and exploration.It's okay to be a novice and embrace the learning process.Humor can help navigate the awkwardness of being a beginner.Setting achievable goals can motivate continued learning.Sharing experiences with others can enhance the learning journey.The journey of learning is as important as the outcome.

In this conversation, Brent and Rob explore the emotional and mathematical aspects of retirement planning. They discuss the importance of understanding one's relationship with money, the two critical numbers that determine financial freedom, and the emotional challenges faced when transitioning from a working life to retirement. The discussion emphasizes the need to evaluate spending habits, predict future expenses, and consider the trade-offs between income and health. Ultimately, the conversation encourages listeners to take control of their financial future while also prioritizing their well-being. Links, resources, books mentioned:Visit Episode WebsiteNewsletter Sign UpFollow us: Instagram, LinkedIn, Facebook, YouTubeTopics we are covering in this episode:Stop worrying about money immediately.There's only two numbers between you and retirement freedom.Understanding your relationship with money is crucial.The spend rate is a more important question than income.You can always go back to work if you have to.What would you trade for 10 extra healthy years?All choices have a cost associated with them.You can generate income in other ways after retirement.Living your best life should be a priority.Do the math to find peace of mind.

In this conversation, Rob and Brent discuss Brent's upcoming triathlon and the challenges of training for it. They then transition into a deeper discussion about friendships, particularly the differences between 'deal friends' and 'real friends' as Brent reflects on his experiences after leaving his last company. The conversation highlights the loneliness that can accompany such transitions and offers insights on rekindling connections and the importance of maintaining relationships beyond work.Links, resources, books mentioned:Visit Episode WebsiteNewsletter Sign UpFollow us: Instagram, LinkedIn, Facebook, YouTubeFrom Strength to Strength — Arthur C. Brooks (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:Training for a triathlon can be both challenging and enjoyable.Active recovery is essential for athletes during training.Friendships often change after leaving a work environment.'Deal friends' are often transactional, while 'real friends' are supportive without dependency.Loneliness can set in after retirement due to lack of daily interactions.Reaching out to old friends can rekindle valuable relationships.It's important to take inventory of your friendships as you transition in life.People are often more open to reconnecting than you might expect.Making an effort to connect can lead to rewarding relationships.Embrace the transition and be open to new friendships.

In this episode of Midlife Circus, Brent and Rob crack open the Choose Your Own Adventure theme of midlife—where you get to decide what comes next. They explore what it means to rewrite the script, embrace curiosity, and step off autopilot to direct your next great act. From motorcycles and model cars to 3D printing and solo adventures, this conversation blends humor, nostalgia, and introspection to show that midlife isn’t a crisis—it’s a creative rewrite. Rob and Brent share personal stories, lessons learned, and the joy of rediscovering hands-on passions while reimagining purpose beyond the career grind. Whether you’re rebuilding, reinventing, or just wondering what’s next, this episode will remind you that it’s never too late to choose your own adventure. Links and Resources:Visit Episode WebsiteNewsletter Sign UpFollow us: Instagram, LinkedIn, Facebook, YouTubeTopics we are covering in this episode:Midlife as an opportunity to rewrite your own script.How curiosity can replace the need for constant productivity.The difference between being scripted and unscripted in your 30s vs. 50s.Why small steps—like fixing an e-bike or learning 3D printing—can spark big change.Reclaiming hands-on creativity and joy from childhood passions.The balance between freedom, purpose, and reinvention.How Gen X is redefining midlife on its own terms.Simple ways to start crafting your next great act today.Midlife as a time to choose growth, not crisis.Becoming the director—and hero—of your own story.