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 Website
• Join the Midlife Circus Community on Substack
• Follow us: Instagram, LinkedIn, Facebook, YouTube

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.

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 Website
• Join the Midlife Circus Community on Substack
• Follow us: Instagram, LinkedIn, Facebook, YouTube
• 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.

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 Website
• Join the Midlife Circus Community on Substack
• Follow us: Instagram, LinkedIn, Facebook, YouTube

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.

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 Website
• Join the Midlife Circus Community on Substack
• Follow us: Instagram, LinkedIn, Facebook, YouTube
• How to Think Like Einstein - Scott D. Thorpe
• Moonwalking 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 Website
• Join the Midlife Circus Community on Substack
• Follow us: Instagram, LinkedIn, Facebook, YouTube
• 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

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 Website
• Join the Midlife Circus Community on Substack
• Follow us: Instagram, LinkedIn, Facebook, YouTube

Topics 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 Substack
• Follow us: Instagram, LinkedIn, Facebook, YouTube
• The 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 Website
• Join the Midlife Circus Community on Substack
• Follow us: Instagram, LinkedIn, Facebook, YouTube
• The 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.