The Long Strange Trip Podcast

Passing wisdom from one generation to the next sounds simple until you realize that people rarely want to be lectured by the people who raised them.  In this episode, Josh Patrick talks with Steve Legler, a family facilitator who works with wealthy families, about the difficult work of helping generations communicate, repair relationships, and make decisions together. They explore why wisdom is be...

Life doesn't move from one stable chapter to another as neatly as we like to think. Sometimes we're navigating several transitions at once, each at a different stage, with no clear line between where one ends and another begins. In this week's episode, Josh Patrick talks with Rebecca Southerns, a transition coach and author of the forthcoming book In Between Is All the Time , about why the messy m...

Retirement isn't just about replacing your paycheck. It's about figuring out what replaces everything else that work gave you. In this episode, Josh Patrick talks with Fritz Gilbert, author of The Keys to a Successful Retirement and creator of The Retirement Manifesto, about identity, relationships, purpose, structure, and the sense of accomplishment we often get from work. They dig into the messy...

What happens when life forces you to become someone you never expected to be?  Josh Patrick talks with Joy Selak, PhD, about resilience, identity, and the messy middle of major life transitions. Joy shares her journey through chronic illness, disability, divorce, career changes, and rebuilding her sense of purpose, while Josh reflects on his own experiences with business, cancer, and the question...

What happens when experiences aren't enough anymore? In this episode Josh sat down with Joe Pine, co-author of The Experience Economy and author of The Transformation Economy , about the next step in how we create value: helping people transform. They dig into why transformation is really about identity change, why retirement can be one of the biggest transformations of our lives, and how trauma c...

Wisdom isn’t just about what we know. It’s about what we’re willing to question, explore, and pass on. In this episode of The Long Strange Trip , Josh sits down with Tom Deans to talk about wisdom, family wealth, inheritance, and the conversations most families avoid until it’s too late. They explore why so many people avoid talking about death, why estate planning is about much more than money, a...

In this episode of The Long Strange Trip, Josh sits down with Ron Pevny, an author, educator, and pioneer in conscious aging, to talk about resilience, curiosity, aging, and the inner work that helps us navigate life's inevitable transitions. They explore why curiosity can keep us growing, how discomfort can become a doorway to personal growth, and why letting go of expectations can create more pe...

Can curiosity replace fear when we think about death? In this episode of The Long Strange Trip, Josh Patrick welcomes Michele Asch for one of the most personal conversations on The Long Strange Trip . Together they explore guided psilocybin experiences, messages from loved ones who have passed, the role of mediums, and how spiritual curiosity can change the way we approach life. Rather than debati...

In this episode, I sat down with financial advisor Russ Thornton to explore a question that has very little to do with investments and everything to do with how we live: What are you retiring to? We talk about why so many successful people struggle to spend the money they’ve spent decades saving, why financial scarcity often has more to do with psychology than math, and how retirement can become a...

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...