The Long Strange Trip Podcast

In this episode, we’re asking a question that most of us spend our lives trying to outrun: What does it actually mean to have a "good death"? It’s a heavy topic, and I’ll be the first to admit that exploring this territory can feel very disconcerting. Today, I’m sitting down with Rose Zeeland, who looks at the end of life through a unique, dual lens as both a Certified Financial Planner and a Death Doula. We aren't just talking about the clinical or the legal "stuff" here. We’re digging into the emotional and logistical challenges that start to feel much more real for those of us in our 40s and 50s. I’ve often found myself thinking about the "way less life going forward" part of the journey, and Rose offers a perspective that’s grounded in both professional expertise and deep human care. In this episode, we explore:The Transition: Why Rose believes midlife is the critical time to start these honest investigations. The Family Table: How to have those necessary discussions with the people you love without it feeling morbid. Logistics vs. Legacy: Navigating the complex financial wealth management side while holding space for the emotional weight of loss. Being the Support: What it looks like to walk alongside a client or loved one through their final transition. I’ll be honest—I teach this kind of stuff, and I still find it difficult to apply to my own life sometimes. Rose is a fellow traveler who provides more than just a checklist; she provides a way to navigate the uncertainty with a bit more grace. Whether you're a business owner in transition or just someone trying to figure out how to support a parent, I think you’ll find this conversation as helpful as I did. How are you handling the "un-talkable" conversations in your own life?

In this episode of The Long Strange Trip, Josh sits down with long-time friend and transition expert Susan Bradley, founder of the Sudden Money Institute. Together, they explore why we’re so afraid of the "in-between" and how we can learn to embrace it as a vital part of our personal evolution.In this conversation, we dive into:The Threshold: Why liminal space is universal but rarely understood or celebrated in Western culture.Pilots and Navigators: A new way to look at professional help—where you fly the plane, and your advisor helps you read the map.Throwing Out Anchors: Practical tools like the "quadrant exercise" and "anchoring" to help you stabilize when the weather gets rough.The Power of the Question: Why "What do you want to protect?" might be the most important thing you ask yourself today.Whether you’re selling a business, navigating a loss, or just feeling a bit "stuck" in the transition, this episode offers a warm, reflective look at how to find your way when the path forward isn't clear.

In this episode of the Long Strange Trip, I sat down with Adam Hansen to explore what it really means to become wise. What started as a simple question—“How do you actually become wise?”, quickly turned into a deeper conversation about curiosity, self-awareness, and personal growth.This isn’t a step-by-step guide. It’s an honest exploration.We talk about: Why wisdom is more about asking better questions than having the right answers  How curiosity shapes the way we grow and understand the world  Why experience alone isn’t enough without reflection  The trap of confusing your perspective with reality  And why grace for yourself and others matters more than being right We also unpack the idea of “metabolizing experience” , learning from life in real time instead of just going through it.No conclusions. No perfect answers. Just a conversation.If you’re interested in mindset, self-awareness, and real personal development, this episode will make you think.So here’s the question: How do you define wisdom?🌐 Learn more: thelongstrangetrip.com 💬 Share your thoughts. I’d love to hear your perspective 📩 [email protected]

In this insightful interview, Susan Schramm discusses the nature of risk, change, and resilience in launching initiatives and personal growth. She shares practical strategies for managing risk, overcoming fear of failure, and building resilient teams to succeed in innovative endeavors.

In this episode of the Long Strange Trip podcast, Josh Patrick interviews Michelle Glass, an IFS practitioner and psilocybin guide. They explore the intricacies of psilocybin guided journeys, including the preparation, the journey experience, and the integration of Internal Family Systems (IFS) therapy. Michelle explains how the journey can facilitate healing by accessing different parts of oneself, particularly in the context of mental health issues like PTSD. The conversation also covers the training required for psilocybin guides and the diverse motivations individuals have for embarking on these journeys.

In this episode of the Long Strange Trip podcast, Josh Patrick and Mike Holbrook discuss the concept of Elder Life Planning, which focuses on helping clients navigate the complexities of late life and end-of-life decisions. They explore the importance of family conversations around death, the role of healthcare in these discussions, and the significance of having a healthcare power of attorney. The conversation also highlights the Five Wishes framework for planning end-of-life care and the necessity of empowering families to make informed decisions. Mike shares personal experiences and insights on how financial planners can play a crucial role in reducing elder abuse and ensuring that clients' wishes are honored.

In this engaging conversation, Josh Patrick and Jennifer Hough explore the concepts of resilience and flourishing, discussing how individuals can navigate life's challenges with presence and wisdom. They delve into the importance of accepting circumstances, the journey from mere survival to thriving, and the role of vulnerability and support in personal growth. The dialogue emphasizes the significance of being present and the transformative power of asking the right questions to foster resilience and create a fulfilling life.

In this episode, I’m sitting down with Jeffrey Deckman, a death doula, to poke around a topic most of us spend our entire lives avoiding. We dive into the world of death doulas and the kind of compassionate, human support they provide outside the cold machinery of the "medical industrial complex". Jeffrey shares the personal journey that led him to this work and why it’s so vital to start seeing death as a natural part of life rather than a problem to be solved. We also get into a pretty honest critique of our current medical system, the strange liminal space between living and dying, and how near-death experiences can completely flip your perception of what it means to go.

In this episode of the Long Strange Trip podcast, host Josh Patrick engages in a profound discussion with Amy Bruce and Betsy Walkerman from Patient Choices Vermont about medical aid in dying. They explore the history of Act 39, the importance of understanding end-of-life options, and the challenges faced in discussing these topics within the medical community. The conversation emphasizes the need for better training for healthcare professionals, the personal nature of end-of-life decisions, and the integration of hospice and palliative care. The episode also highlights the resources available for patients and families navigating these difficult conversations.

In this special episode of The Long Strange Trip Podcast, host Josh Patrick sits down with his son, Sam Patrick, a recently retired Special Operations veteran and campus coordinator at The Honor Foundation. Together, they explore the emotional and practical challenges of transitioning from military to civilian life from losing a sense of identity and purpose to rebuilding community and direction.Sam shares his powerful journey after 20+ years of service, offering honest insights into the realities of retirement, mental health, and reinvention. He also explains how The Honor Foundation helps special operations members prepare for life beyond service — focusing on self-discovery, resilience, and purpose.

In this episode of the Long Strange Trip podcast, host Josh Patrick engages in a deep conversation with Matthew Kimberly, exploring the concept of wisdom and how it is developed over time. Matthew reflects on his journey from youthful arrogance to a more nuanced understanding of life, shaped by personal experiences such as parenting and the loss of his father. He shares poignant anecdotes that illustrate how wisdom often comes from self-awareness and the recognition of one's limitations. The discussion also touches on the importance of curiosity and the dangers of speaking in absolutes, emphasizing that true wisdom involves acknowledging the complexity of life and the need for continuous learning.As the conversation unfolds, both Josh and Matthew delve into the challenges of parenting, the generational impact of upbringing, and the balance between being present for one's children while also allowing them the space to grow independently. They reflect on the societal pressures surrounding parenting and the importance of fostering open communication with children. The episode concludes with Matthew sharing insights on his work with Book Yourself Solid and his unique approach to marketing and self-employment, encouraging listeners to embrace their own journeys of self-discovery and wisdom.

In this episode, Josh Patrick speaks with Paul Bond, a cancer survivor and CEO of Bond Safety. They discuss their experiences with cancer treatment while managing their businesses, the importance of family support, and the positive impact of sharing their journeys publicly. Paul shares valuable advice for those facing similar challenges, emphasizing the significance of embracing the experience and the support that comes from being open about one's struggles. The conversation highlights the resilience and personal growth that can emerge from such life-altering events.

So, what happens after you finally hand over the keys?In this episode of the Long Strange Trip, Paul Cronin and I dive into the messy, often uncomfortable reality of transitions—specifically that nagging sense of seller’s remorse so many of us feel but rarely talk about. Paul gets real about his own walk through the corporate world and the emotional gut-punch that comes when you leave a career that’s defined you for decades.We’re not just talking about money here; we’re looking at the hard work of finding purpose and meaning when your old identity is gone. It’s a challenge, right? You lose the built-in social life of the office and suddenly realize you need to reinvent who you are from the ground up. We explore why building a new social network and a fresh identity isn't just a "nice to have"—it’s a late-life necessity if you want to actually enjoy the trip.

In this episode of the Long Strange Trip podcast, Josh Patrick interviews Rick Kahler, a seasoned wealth manager turned financial therapist. They explore the concept of financial therapy, which merges the emotional aspects of money with financial planning. Rick discusses the importance of understanding the emotional drivers behind financial decisions and how Internal Family Systems (IFS) therapy can help individuals navigate their financial behaviors. The conversation also delves into the challenges of business succession, the need for resilience during transitions, and the role of coaches in supporting individuals through these processes. Rick shares personal experiences and insights, emphasizing that money problems are often rooted in deeper emotional issues.

In this episode of the Long Strange Trip podcast, host Josh Patrick speaks with Jenny Bellinger, a marketer and transitions expert. They discuss Jenny's unique upbringing as an Air Force child, the challenges of moving frequently, and how these experiences shaped her resilience. Jenny shares her journey from being a middle school teacher to entering the world of multi-level marketing and eventually becoming a coach. The conversation highlights the importance of adaptability, emotional processing, and the interconnectedness of personal and professional lives.

In this episode of the Long Strange Trip podcast, Josh Patrick interviews Troy E. Jones, founder of Access Financial Resources. They discuss Troy's unique approach to financial planning, focusing on building meaningful relationships with clients and prioritizing employee welfare. Troy shares insights on transitioning clients into retirement, addressing the emotional challenges they face, and the importance of lifelong learning and curiosity in achieving wisdom. The conversation also touches on creative problem-solving techniques in financial planning and the significance of asking the right questions.

In this engaging conversation, Josh Patrick interviews Bruce Peters, who shares his unique approach to balancing family and work through the creation of a family business plan. Bruce discusses the genesis of this plan, its implementation, and how it has shaped his relationships with his family and grandchildren. He reflects on the importance of intentionality in both personal and professional life, the wisdom gained from his experiences, and the strategies he employed to foster meaningful connections with his loved ones. The discussion also touches on the challenges faced in the legal profession and the insights gained from his time with Vistage.

Podcast SummaryPicture a teenage boy strumming rhythm and blues in smoky bars, who then ascends the professional ladder to conquer the insurance field, only to transform into a healer within natural healthcare, and eventually earn degrees in psychotherapy. Richard, our remarkable guest on this episode of Long Strange Trip, embodies the art of reinvention at every stage of life. He now channels his journey into business coaching and classical music composition, offering a treasure trove of insights into managing life's unpredictable turns. Richard's story is a testament to the resilience needed to transition between careers and the courage to pursue one's true passions, no matter the age.As we explore the challenges faced by those in their mid-70s yearning to redefine their purpose, the episode casts a light on the often-unspoken struggles of retirement. Financially secure yet yearning for purpose, many retirees find themselves adrift without the anchor of a career. With my experience as a psychotherapist, I discuss how guided career assessments and imaginative exercises can reveal hidden interests and new paths. The conversation is a gentle reminder of the importance of seeking professional guidance from career-savvy therapists during this pivotal life transition.In a poignant segment, we share the inspiring journey of an octogenarian who found renewed purpose through memoir writing. Initially chronicling her own story, she evolved to write for others nearing the end of life, bringing solace and closure to families. Her journey highlights reinvention's transformative power, underlining the profound impact of hospice care in offering dignity and peace. We wrap up with an open invitation to our listeners to share their thoughts and consider joining us as guests on this ongoing exploration of life's unexpected paths. Your stories could be the next chapter in our Long Strange Trip.

Podcast SummaryRetirement isn't just an ending; it's a new beginning. Join me, Josh Patrick, as Alan Newman and I explore the winding paths of reinvention during life's later stages. Alan's journey from rural medicine to yacht timeshares and direct mail to manufacturing is anything but ordinary, marked by consistent reinvention. At 72, he faces the challenge of slowing down, grappling with brain fog, and reevaluating his priorities. Together, we reflect on how our relationship with work evolves over time, emphasizing the importance of community building and mental shifts as age brings new perspectives.We also venture into the emotional aftermath of leaving significant roles at Seventh Generation and Magic Hat, where the loss of a supportive community reshaped Alan's outlook. From planned transitions to the unexpected struggles during the pandemic, Alan's story reveals the continuous need for reinvention, even in retirement. As we navigate these experiences, we also share a captivating journey through the legacy of the Grateful Dead, inviting you to reflect and share your thoughts. Open dialogue enriches our collective journey, and your feedback is invaluable as we continue to explore these shared human experiences.

In this inaugural episode of the Long Strange Trip, host Josh Patrick introduces the podcast's mission to explore significant life transitions, including work-life integration, retirement as reinvention, and facing mortality. He emphasizes the importance of community and shared wisdom in navigating these challenges, positioning himself as a fellow traveler rather than an expert. The conversation delves into the lies we tell ourselves about work, retirement, and death, and sets the stage for a deeper exploration of these themes in future episodes.