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 middle of retirement, why curiosity and experimentation can help you find your way forward, and why waiting for clarity can keep you stuck. Josh and Fritz also explore the idea of treating life like a hand of cards: pick up new ones, put down the ones that no longer fit, and keep reinventing yourself. At the heart of the conversation is a question Josh has wrestled with himself: Who am I if I don't own a business anymore?

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 of who we are when our old identity no longer fits. They talk about asking for help, owning mistakes, removing toxic people from your life, and using small experiments to navigate uncertain transitions. At the heart of the conversation is a question that applies to all of us: Who can I be now within this reality? Joy and Josh explore how resilience isn't about simply pushing harder, but about finding new ways to move forward when life doesn't go according to plan.

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 can force us into the messy middle of becoming someone new. Josh and Joe also explore why wealth managers often focus on accumulating money instead of helping people use their wealth to create better lives and meaningful legacies. From retirement and reinvention to health, resilience, and personal growth, this conversation asks a bigger question: who are you becoming, and what kind of life are you trying to create?

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, and how silence around wealth can create chaos and conflict between generations. Tom also shares what he’s learned from his three books about building families that work well after we’re gone, passing wisdom not just wealth to our children, and creating a plan that protects both our assets and our relationships.

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 peace. Ron and Josh also talk about retirement, purpose, community, and the difference between simply getting older and actually growing as we age. If you're navigating a major life transition or wondering how to approach aging with more wisdom, flexibility, resilience, and intention, this conversation is for you.

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 debating beliefs, they ask thoughtful questions about consciousness, connectedness, and what it means to live fully while accepting mortality.

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 an identity crisis if you’re not prepared for it.

We explore:

• Why many retirees underspend—even when they have more than enough
• The emotional shift from earning a paycheck to living off your savings
• Why retirement should be about purpose, not escape
• The importance of asking better questions instead of rushing to answers
• How vulnerability and honest conversations help us navigate life's biggest transitions

This isn’t really a conversation about money. It’s about building a life you actually want to wake up to after work is no longer the center of your identity.

We’re all just trying to figure this out together.

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.

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.

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.