The Problems We're Investigating

About this Video:

The Long, Strange Trip: What Happens After the Handshake?

Have you ever noticed how everyone wants to talk about the “exit”—the deal, the number, the big celebration—but nobody wants to talk about the Tuesday morning after?

In this video, I’m breaking down what I call the “long, strange trip” of life once you step away from the business you built. Look, I’ve spent my career in wealth management and being a serial entrepreneur, so I’m supposed to have the “playbook” for this. But honestly? I’m right there in the trenches with you, trying to figure out why being “free” feels so much like being “lost.”

I’ve identified 18 specific problems across six major areas that most of us are too proud—or maybe just too tired—to talk about out loud:

• Work-Life Integration: How do you fill a calendar that used to be a weapon of productivity?

• The Retirement Identity Crisis: If I’m no longer the “business guy,” then who exactly is sitting in this chair?

• Mortality & Time: Realizing there’s “way less life going forward” than there is behind us.

• Resilience: Relearning how to take a hit when you don’t have a company structure to shield you.

• Wisdom Sharing: Finding a place for all that hard-earned knowledge when the office door is closed.

• Navigating Transitions: Managing the sheer complexity of moving through multiple life stages at once.

This isn’t about me giving you a “how-to” guide. It’s more of a map of the territory I’m currently wandering through myself. I’m hoping that by mapping out these challenges, we can stop the “navel-gazing” and start having a real conversation about what’s next.

Transcript

Here’s something I’ve been thinking about. When I sat down to map out the problems, we explored the long strange trip. I figured I’d come up with maybe a dozen, something manageable. Instead, I came up with 18 and I could have kept going. The list could have been 30, 40 problems. Maybe more. And here’s what that tells me.

We’re walking around with way more unresolved, completely unprepared for challenges than they’re willing to admit. You know, most business advice focuses on one or two problems at a time, nice and tidy. One problem or one solution. Move on, except that’s not how life actually works. When you’re navigating transition from business ownership to whatever comes next, you’re not dealing with one clean problem.

You’re dealing with identity reconstruction, with facing mortality, while adapting to health changes and trying to share wisdom in a culture where things are outdated.

So instead of the sanitized version, here’s what we’re actually investigating — six major areas and 18 significant problems. Let me walk you through them.

First: Work life integration. The just-till trap where temporary 80-hour weeks turn into years while your kids grow up without you.

Two: bringing boardroom energy home, treating your 8-year-old like an underperforming employee.

And three: the leftover 5% problem — your family gets whatever energy remains after the business demands are met.

Here’s the second area, retirement identity. Number one: the identity void — you have no idea who you are without your business card. Number two: the activity trap — golf and travel aren’t sufficient to replace the intellectual challenge you derive from business ownership or work. Number three: comparing new normal to old normal — constantly measuring your retirement life against your business life and finding your new life is seriously lacking.

Here’s the third area: mortality without PTSD, or how to have a good death. First: practical stuff nobody does — no updated wills, healthcare proxies, or clear instructions for end-of-life care. Number two: conversation avoidance — you’ve never actually talked with your spouse about what kind of medical interventions you’d want, and never facing your mortality, living like you have unlimited time, putting off what actually matters.

Fourth area: building resilience. This is where people often fight reality instead of working with it. Exhausting yourself, insisting your body should be different than it is. I tried that with skiing and it didn’t work very well. The grief — you’re not allowed. Trying to skip over loss and jump straight to acceptance. This is a big problem. We need to learn how to grieve and accept grieving. And finally in this area: catastrophizing about uncertain futures — your brain spiraling from “I’m tired today” to “what if this never gets better.”

Fifth area: sharing wisdom. A big one. Number one: making yourself irrelevant — telling stories like “back in my day” and wondering why nobody listens. Number two: ageism, internalization — holding back advice because you don’t want to be that old guy. Number three: the generational communications gap — the divide that makes wisdom sharing nearly impossible.

And here’s our final area: transition navigation. Number one: not knowing where you are — beating yourself up for not handling a transition better when you don’t even know what stage you’re in. Number two: finding the stage you’re in — trying to force certainty during anticipation or expecting to feel settled during the messy middle. Both are unrealistic ideas. Number three: the stack transitions problem — dealing with multiple transitions simultaneously, each affecting the other and each likely being at a different stage.

Here we have 18 problems in six areas. And here’s the thing — the list could have been longer, much longer, and that’s okay. These aren’t questions we’re going to answer definitively, though they’re real, messy, complicated challenges we’re exploring together with honest investigation, shared experiences, and the acknowledgment that we’re all figuring this out as we go.

That’s what the long, strange trip is actually about. What do you think of the 18 areas? Why don’t you let me know what I’ve missed and let’s figure this out together. Hey, this is Josh Patrick, you’re at the Long Strange Trip Videos. Thanks a lot for taking a look, and I hope to see you back here really soon.