The Long Strange Trip Podcast

About this Episode: This episode on  The Long Strange Trip , Josh talks with Lisa Woodruff, founder of Organize 365, about the often-overlooked work of preparing our lives for those we love. Together they explore why organizing becomes more complex with age, how to manage the growing burden of paperwork and digital assets, and why sharing your plans with family is one of the most caring gifts you...

In this episode, I sit down with my friend Glenna Crooks to explore something we rarely think deeply about: the networks of people that quietly shape our lives, our resilience, and even our wisdom. Glenna’s had an extraordinary career, from advising Ronald Reagan on healthcare to helping build Merck’s vaccine division but this conversation goes somewhere much more personal. We talk about burnout,...

In this episode, I sit down with Anna Melikian, who’s faced multiple cancer diagnoses, to explore what resilience actually looks like when life gets very real. Anna shares the shock of her diagnosis, how she moved from denial into action, and why having a plan gave her something to hold onto. We also talk about the reality of treatment—the parts doctors don’t fully prepare you for—and how staying...

Who’s Driving Your Bus? Navigating the Internal Family System Have you ever felt like there’s a literal argument going on inside your head ? One part of you is ready to conquer the world, while another is whispering that you’re a fraud, and a third just wants to hide under the covers with a bag of Hershey’s kisses. I’ve been there. In fact, I’m 73, and I’m still figuring out who’s actually behind...

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 Deat...

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 understoo...

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...

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 onesel...

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. Th...

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 signific...

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 d...

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...

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....

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 ill...

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...

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 t...

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 c...

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 eventuall...

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 i...

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...

Podcast Summary Picture 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 hi...

Podcast Summary Retirement 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...

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 d...