Episode 24: Why Getting Organized Becomes More Important as You Age | Lisa Woodruff

Episode 24: Why Getting Organized Becomes More Important as You Age | Lisa Woodruff

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 can give. This thoughtful conversation is a reminder that getting organized isn’t about perfection, it’s about intention, peace of mind, and making the future a little easier for the people who matter most.

Episode 23: The Hidden Network That Shapes Your Life with Glenna Crooks

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, the uncomfortable space of “unknowing,” and why wisdom often comes from sitting with hard questions longer than we’d like. We explore: *  Why relationships act like a hidden operating system in our lives  *  The difference between shallow connection and meaningful community  *  How “ghost networks”  people from our past still influence us today  *  Why wisdom comes from patterns, reflection, and lived experience  *  The tension between being a generalist and a specialist in a complex world  This is one of those conversations that may change the way you think about the people you surround yourself with—and the person you’re becoming because of them. We’re all just trying to figure this out together.

Episode 22: Cancer, Resilience & Reinvention with Ana Melikian

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 connected to her work helped her maintain a sense of normalcy. We explored: * Why resilience isn’t something you force—it’s something you grow into * The importance of support and being open instead of going it alone * How to take things one step at a time when the future feels overwhelming This is an honest conversation about uncertainty, mortality, and what it means to keep going when you don’t know how things will turn out. We’re all just trying to figure this out together.

Episode 21: The Hidden Voices Running Your Life Explained (IFS Therapy) with Tammy Sollenberger

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 the wheel.  In this episode of The Long Strange Trip, I sit down with Tammy Sollenberger, a gifted Internal Family Systems (IFS) therapist, to talk about why we do the "stupid" things we do—and how to stop vilifying ourselves for it. We dive deep into the "multiplicity of the mind" and why "No Bad Parts" isn't just a catchy book title, but a way to find actual internal peace. We explore: * The Internal Family: Why your mind is less like a single person and more like a crowded dinner party (and yes, sometimes it’s rowdy). * Managers vs. Firefighters: How our protective parts try to keep us "likable" or "numb" to avoid the pain of our inner exiles. * The "C" Qualities: How to access your Authentic Self—that core of calm, curiosity, and compassion that’s often buried under the noise. * The Skiing Dilemma: A personal look at my own struggle with aging and the conflicting voices that crop up when life forces a transition. If you’ve ever felt "stuck," "ineffective," or just plain curious about why your brain works the way it does, this conversation is for you. We aren't just talking psychology; we're talking about how to become a more integrated, self-led human

Episode 20: Redefining a Good Death: Insights from a Death Doula Rose Zealand

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?