Rich Conversations

Rich returns to the combine during harvest season in rural Wisconsin, beginning with five minutes of breathing and gratitude. Fresh off the Milwaukee Brewers' World Series championship, he reflects on the excitement of winning, the pride of belonging to a community, and how shared victories can bring people closer together.

From getting stuck in muddy fields to navigating obstacles in life, Rich explores the importance of asking for help, overcoming inconvenience, and creating meaningful memories. He considers why certain experiences mean so much to us even when others may not understand their significance, and how stepping away from a problem can sometimes reveal the solution.

The session concludes with reflections on the power of our thoughts, curiosity, perseverance, and the fundamentals of sustained success. What happens when we refuse to give up? How can small, consistent actions lead to extraordinary outcomes? And how can we become more intentional about the thoughts we allow to shape our lives?

A reflection on gratitude, community, resilience, meaningful memories, constructive thinking, and the joy of achieving something worth pursuing.

Questions in this Session:

1. What are we grateful for?

2. When was a time we got stuck in life, literally or metaphorically? What was the experience like, how difficult did it become, and how did we get out of it?

3. What's a moment when we felt proud and connected to our community, city, region, or country?

4. How did that experience of collective pride and connection make us feel afterward? Did it inspire us to change or grow individually?

5. When was the last time we celebrated collectively?

6. What's something that meant a great deal to us personally but might seem insignificant to others?

7. What's a meaningful memory we're grateful to have because we overcame an inconvenience to experience it?

8. What's something in our life that needs resolving? How might stepping back and taking a more holistic view help us find a solution?

9. What recurring thoughts have been on our mind recently? Are they constructive and helpful, or are they holding us back? How can we improve them?

10. What are we curious about recently?

11. What are we energized for in the upcoming week? 

Rich welcomes longtime friend Shawn McCormick back to the podcast for an in-person conversation from the farm shed in rural Wisconsin. Surrounded by tractors and the sounds of harvest season, they explore Shawn's experiences working at Case and as a pipefitter, the enormous Microsoft data center under construction in Mount Pleasant, and his growing interest in farming, business, and a possible career change.

Their conversation turns philosophical with the ancient story of the Sword of Damocles, exploring the responsibilities that accompany power, leadership, and financial success. Rich and Shawn consider how easily individuals in society envy the circumstances of others without understanding the pressures they face, and the importance of clearing our minds, finding perspective, and appreciating the present moment.

The discussion becomes especially personal as Rich remembers his late cousin Frank, who recorded his final podcast appearance in the same shed. Together, they reflect on grief, friendship, meaningful conversations, and the importance of finding closure with the people we love. The episode concludes with gratitude for modern life, the experiences we share with others, and excitement surrounding the Milwaukee Brewers' World Series appearance.

Rich takes us into the soybean fields of rural Wisconsin during autumn harvest season. Recording from the combine on a beautiful October afternoon, he begins with five minutes of breathing before exploring gratitude, seasonal traditions, and the satisfaction that comes from working toward something with focus and purpose.

From viewing farming as a form of agricultural art to finding clarity during solitary walks in nature, Rich reflects on the beauty of everyday experiences and the importance of making room for personal growth. He considers what impresses us about the world, from the resilience of vegetation to the remarkable movement of people through cities like New York and Chicago.

The session concludes with reflections on curiosity, recognizing our strengths, and applying successful principles from one area of life to another. Along the way, Rich explores how sounds, environments, and seasonal rituals become connected to our memories, making certain moments especially meaningful.

Questions in this session:

1. What are we grateful for?

2. What's something we look forward to annually or twice a year? Something that brings focus, excitement, or a sense of community.

3. What's something we do that we consider art, even if it isn't traditionally viewed as art?

4. What's something we love doing during the fall?

5. When was the last time we intentionally spent time alone in nature? What did we feel, think about, or take away from the experience?

6. What's an area of our life we could improve?

7. What's something we're genuinely impressed by? Something in nature, society, or everyday life that we find remarkable.

8. What are we curious about recently?

9. What's something we're good at, and how can we apply the principles behind that success to other areas of life?

10. What are we energized for in the upcoming week?

11. What's a memorable moment or experience that stands out because of its environment, sounds, or seasonal significance?

Rich explores gratitude, personal identity, creativity, and the importance of making deliberate choices that bring greater meaning to everyday life. Beginning with five minutes of breathing, he celebrates the Milwaukee Brewers' World Series excitement before reflecting on personal aesthetics, simplifying decisions, and appreciating the small details that make life beautiful.

From finding a flow state while working on his "Ads in New York" photography book to reconnecting with friends during a beautiful autumn day in Chicago, Rich considers what makes a truly great day. He revisits unforgettable experiences traveling through Barcelona and Valencia, Spain, and reflects on how the simplest moments can become some of our most meaningful memories.

The session concludes with the power of taking action. Inspired by advice from a close friend—“If you don't book it, you won't go”—Rich explores why we must actively pursue the experiences, relationships, and ambitions we desire rather than waiting for life to happen to us.

A reflection on gratitude, friendship, beautiful moments, curiosity, and creating a life filled with experiences worth remembering.

Questions in this session:

1. What are we grateful for?

2. If we could only choose five colors to wear for the foreseeable future, what would they be? What is our personal aesthetic, and how do we approach the way we dress?

3. What's a small thing we appreciate? Something simple, subtle, or easily overlooked that brings us joy.

4. When was the last time we experienced a flow state? What were we doing, and what made us feel completely present?

5. What's a current project we're working on that gives us energy?

6. Do we consistently make deliberate time to spend with friends?

7. When was the last time we had a truly great day? What were we doing, and what made that day so memorable?

8. What's a beautiful moment we've experienced in life?

9. What's a piece of wisdom or a meaningful quote someone close to us has shared? Something that has stayed with us and influenced how we approach life.

10. What are we energized for in the next week?

11. What are we curious about recently? What interests or ideas could we explore further?

Rich returns to his farmhouse studio in rural Wisconsin to explore the power of clarity, intentional living, and understanding what we truly want from life. Beginning with five minutes of breathing, he reflects on gratitude, personal aesthetics, and how knowing ourselves better can simplify decisions and bring greater purpose to our everyday actions.

From vintage furniture and the latest Rich Edition Classics release of Wuthering Heights to the importance of patience and long-term thinking, Rich considers how much unnecessary anxiety comes from focusing on immediate circumstances rather than the bigger picture. He explores the value of recognizing personal progress, finding new sources of energy, and appreciating how much we can change in just four months.

The session concludes with reflections on curiosity and the art of letting go. Sometimes, the more tightly we hold on to something, the more we prevent it from growing. What might happen if we stopped forcing outcomes, trusted the process, and gave things room to develop naturally?

A reflection on clarity, individuality, patience, personal growth, and the freedom that comes from knowing when to hold on—and when to let go.

Questions in this session:

Rich records from a small park in New York’s West Village, beginning with five minutes of breathing before exploring gratitude, curiosity, technology, routines, and the tension between reason and feeling.

While distributing books through Little Free Libraries and photographing advertisements for his Ads in New York project, Rich reflects on the unexpected things we collect, the rules we continually break, and whether every new app or technological convenience actually improves our lives.

The session closes by examining morning and nighttime routines, the value of following curiosity, and what we have to look forward to in the week ahead. From unexpected books to dive-bar conversations and a Harry Styles concert at Madison Square Garden, it’s a reflection on staying open to the information, experiences, and possibilities happening around us.

Questions from this session:

1. What are we grateful for?

2. What does our environment smell like right now? What smells from our past bring back memories?

3. What books are we energized to read? What is currently on our to-be-read list?

4. What personal rule or philosophy do we know is reasonable, but continually ignore or break? And relatedly, are we leaning more toward our head or our heart right now?

5. What is a recent app we downloaded, and why did we download it? What problem is it solving, what are we hoping to gain, and is it worth the additional data, information, and friction it introduces?

6. What is something in our recent use of technology that worked really well? What is something that didn’t work well?

7. What does our morning routine look like right now? Is it effective? Do we enjoy it? What would we change?

8. What does our nighttime routine look like? How well have we been executing it?

9. What are we curious about this week?

10. What are we energized for in the next week?

In this Rich Reflections session, Rich steps into the energy of New York City for an experiment in presence: can you find stillness in one of the most stimulating places in the world?

Recording from a park near Hudson Yards, Rich begins with five minutes of breathing before moving through a series of questions designed to create greater clarity about our lives. Against the sounds and movement of Manhattan, he reflects on gratitude, observation, curiosity, hope, travel, and the seemingly insignificant details that can reveal something larger about ourselves and the world around us.

Recorded on the 25th anniversary of September 11th, Rich remembers experiencing the attacks as a seventh grader in rural Wisconsin and considers how his perspective has changed over time. He reflects on the sense of national unity he remembers from the aftermath and asks listeners to consider their own memories—or, for younger listeners, what September 11th means to them today.

From there, the session follows curiosity wherever it leads: Thomas Jefferson, the history of coffee, walking through New York, travel, and Rich’s new Ads in New York book project. He explores advertising as a cultural time capsule and considers the value of becoming a better observer—noticing the overlooked details that tell us something about the larger human story.

This is an episode about getting out of our heads and back into the world. What gives us hope? When do we feel completely present? What obscure interests make us who we are? And what are we genuinely excited to experience next?

Because if you can sit still, breathe, and reflect in New York City, maybe you can do it anywhere.

Questions in this session:

1. What are we grateful for?

2. Where were we on September 11th, 2001? What do we think about it now? If you weren’t born or don’t remember it, what stands out to you about September 11th culturally, societally, or in relation to your family?

3. What—or who—have we been curious about learning about lately?

4. What is something most people would consider uninteresting that you find interesting?

5. What place would we like to experience next? What’s next on our travel or curiosity list—even if we experience it through film, YouTube, or learning rather than physically traveling?

6. When was the last time we felt completely present?

7. What gives us hope?

8. What is a small nuance in our life that others wouldn’t know about, but that is personally meaningful to us?

9. What are we curious about recently?

10. What are we energized for in the next week?

Rich reconnects with Timothy Hayden in Los Angeles for a wide-ranging morning conversation about work, discipline, freedom, gratitude, and what it actually means to improve yourself.

Timothy shares what he’s learning from his new job delivering for FedEx—from navigating unfamiliar streets and physically demanding days to discovering how quickly repetition can turn confusion into instinct. The experience has also pushed him to think more seriously about nutrition, exercise, recovery, and taking care of his body.

The conversation moves into Timothy’s life after incarceration and his desire to find the right balance between enjoying his freedom and remaining committed to the habits that helped shape his future. After nights at the beach, rock climbing, seeing friends, and simply experiencing life again, Timothy reflects on his need to recenter himself around reading, writing, learning, and building toward a larger mission.

Rich and Timothy also explore the extraordinary comforts of modern life. Reading classic literature has made Rich increasingly conscious of how commonplace disease and premature death once were, while Timothy compares that history with experiences of cold showers and limited resources in prison. Together, they consider whether modern comfort has made us less resilient—and how much of everyday life we simply forget to appreciate.

The episode closes with a spirited debate about David Goggins, physical endurance, excellence, and why we push ourselves in the first place. Is becoming stronger an end in itself, or should self-improvement ultimately enable us to contribute something greater to other people and society?

From rock climbing one step at a time to pushing the limits of mind and body, this is a conversation about freedom, resilience, gratitude—and making sure personal growth has somewhere meaningful to go.

Rich Reflections returns around a campfire.

After spending more time than he’d like in front of a computer, Rich heads outside, lights a fire, and creates space to breathe, think, and reconnect. Beginning with five minutes of intentional breathing, this session explores where we are right now—and where we might want to go next.

Rich reflects on the prevalence of self-doubt and anxiety he noticed during a recent trip to New York and asks how we can better understand our own relationship with uncertainty. From there, the conversation moves into gratitude—not only for what we have today, but for the decisions and work of our former selves that made our present lives possible.

Around the fire, Rich considers what history can teach us, drawing inspiration from the unusual devotion and independence of the Carthusian monks. He explores his own “full throttle or idle” approach to life, reflects on the summer that is coming to an end, and shares his excitement surrounding Blue Byron Books and the expanding Gate of Clouds universe.

The episode ultimately turns outward: How can we participate more in the world? How can we be useful to the people and communities around us? And instead of waiting for some distant transformation, what is one action we can take today to make life better?

A reflection on stillness and action, solitude and participation, gratitude and growth—and the value of occasionally sitting beside a fire and thinking about what it means to be alive.

Questions in this session:

Recored in May 2026, in this Rich Reflections session of Rich Conversations, Rich takes us into the tractor cab during planting season in rural Wisconsin for a conversation about growth, acceptance, collaboration, and living with intention.

After beginning with breathing, Rich looks at how life has changed from 2025 to 2026—from a year dominated by individual creation and isolation to one centered on collaboration and collective creation. He reflects on New Year’s resolutions, the importance of having something ahead of us to look forward to, and his upcoming trip to Miami as an opportunity to step away, zoom out, and see what might reveal itself.

Along the way, Rich considers a different approach to self-improvement: instead of constantly trying to eliminate our flaws, what if we better understood and accepted our individual nature? He explores finding joy through awareness, appreciating where we exist in the long continuum of human history, examining the media and creativity we consume, and asking what becomes possible when we work with other people toward something larger than ourselves.

The session ultimately turns toward curiosity and letting go. Sometimes progress doesn't require adding another task, ambition, or responsibility. Sometimes we gain more by doing less. And when we don't know where to go next, there is a simple compass: follow your curiosity.