The Long Strange Trip: Business to
Retirement to Death
A journey through success, slowing down, and finding meaning at the end of the road
Most people spend decades grinding at work, treating family like employees, then panic when retirement hits and they don't know who they are without the business card. And death? We've got collective PTSD around that topic.
This isn't expert advice – it's a conversation between seekers figuring out how to navigate these three massive transitions differently. Real talk about businesses without sacrificing what matters, creating retirement that's about meaning not just filling time, and facing mortality honestly. No BS, no pat answers – just the messy truth about the journey from building something to stepping away to whatever comes next.
Our Areas of Interest
Doing Business Differently
Most business owners give 95% to work and 5% to family – then wonder why relationships suffer. We're exploring how to build meaningful businesses without sacrificing what actually matters. How do you show up differently at home than at work? Can you create real boundaries and still succeed?
Re-Inventing Retirement
Retirement isn't about having enough money or activities to kill time – it's about identity reconstruction when you're no longer "the business owner." We're exploring what it looks like to transition from business to whatever comes next in a way that feels meaningful rather than terrifying.
A New Look at Death
Many of us have PTSD around death and avoid it until forced to face it. We're exploring what it means to confront mortality while still healthy enough to act – having the conversations that matter, planning thoughtfully, and figuring out what a "good death" looks like before it's too late.
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Wisdom and Aegism
In a youth-obsessed culture, accumulated wisdom gets dismissed as "out of touch." We're exploring how to share decades of experience without being irrelevant – bridging generational gaps, positioning wisdom as valuable, and contributing meaningfully even when society thinks you're past your expiration date.
Transition Secrets
Life's biggest changes follow predictable patterns – stages of transition that help you navigate with clarity instead of panic. We're exploring frameworks that make sense of the messy middle when everything's changing, nothing feels certain, and you're suspended between what was and what will be.
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Resilience
Life throws curveballs – health challenges, losses, unexpected changes. We're exploring how to build genuine resilience that helps you adapt instead of break. Not the "power through" kind, but the flexible strength that lets you grieve what's lost, adjust to new realities, and keep moving forward when circumstances shift beyond your control.
FAQS ABOUT THE LONG STRANGE TRIP
Why The Long Strange Trip
I've spent 40+ years building businesses and advising owners, watching the default path destroy what matters most. Now, facing my own health challenges and transitions, I'm convinced there's a better way. I don't have all the answers – but I'm done pretending anyone does. Let's figure this out together.
Why do you talk about business - retirement - death?
These are the three massive transitions every business owner faces but rarely discusses honestly. We work ourselves to death, panic about retirement identity, and avoid mortality until forced to face it. They're connected – how you do business affects retirement, and facing death clarifies both.
Why the focus on transitions?
Understanding transition stages changes everything. When you can name where you are – anticipation, ending, passage, or new beginning – you stop fighting reality and start navigating with intention. These patterns repeat throughout life. Learn them once, and you've got a map for every major change ahead.
Where does wisdom fit into the work you're doing?
Business owners accumulate decades of hard-won wisdom, then retirement hits and suddenly that experience feels worthless in a youth-obsessed culture. We're exploring how to share what you've learned in ways that actually get heard – bridging generations, staying relevant, and contributing meaningfully beyond your business years.
Why we need to be resilient while we age.
Aging guarantees change – health shifts, capacity diminishes, limitations appear. Without resilience, these changes break us. We're exploring how to build the flexible strength that lets you adapt instead of shatter, grieve losses without getting stuck, and keep finding meaning even when your body won't cooperate.
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