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
• Outlive: The Science and Art of Longevity - Peter Attia

(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:

• 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.

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 Website
• Newsletter Sign Up
• Follow us: Instagram, LinkedIn, Facebook, YouTube

Topics 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 Up
• Follow us: Instagram, LinkedIn, Facebook, YouTube

Topics 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 Website
• Newsletter Sign Up
• Follow us: Instagram, LinkedIn, Facebook, YouTube
• BrokerCheck
• Investment Adviser Public Disclosure

Topics 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 Website
• Newsletter Sign Up
• Follow us: Instagram, LinkedIn, Facebook, YouTube

Topics 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 Up
• Follow us: Instagram, LinkedIn, Facebook, YouTube
• Quiet: 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 Up
• Follow us: Instagram, LinkedIn, Facebook, YouTube
• Living with a Seal - Jesse Itzler
• Living 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 Website
• Newsletter Sign Up
• Follow us: Instagram, LinkedIn, Facebook, YouTube

Topics 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.