The Long Strange Trip: Why We Need a Different Conversation About Business, Retirement, and Death

The Problem Nobody Wants to Talk About

We spend more time planning our next vacation than we do thinking about the three biggest transitions we’ll ever face: how we show up in our businesses, what happens when we leave them, and how we deal with our own mortality.

And I get it. These aren’t exactly cocktail party topics.

But here’s what I’ve learned after years of working with business owners and going through my own transitions: the default path most of us follow is kind of a disaster. We work ourselves into the ground, wonder why our relationships are a mess, panic about retirement, and stick our heads in the sand about death until it’s staring us in the face.

There’s got to be a better way.

That’s what A Long Strange Trip is all about – creating a space where we can explore these three massive life phases together, as seekers rather than experts, and figure out how to do them differently than the conventional wisdom suggests.

The Business Problem: The 95/5 Split That’s Killing Us

Let me paint you a picture you’ve probably lived.

You’re building a business. You’re working 60, 70, maybe 80 hours a week. You tell yourself it’s temporary – just until you get the business established, just until you hit that revenue milestone, just until you can hire the right team.

Except “temporary” turns into years. Then decades.

Your family gets the leftover 5% of your energy. And when you do show up at home, you’re often bringing that same intense, demanding, results-driven energy that works in the boardroom but destroys connection at the dinner table.

I’ve watched business owners treat their eight-year-old like an underperforming employee. Heck, I’ve done this myself and more than once. I’ve missed countless school plays, family dinners, and quiet moments because there was always another deal to close, another fire to put out, another mountain to climb.

Here’s the brutal truth: you can build a successful business and still completely fail at the things that actually matter.

So how do we do it differently?

That’s one of the big questions we’re going to explore together. What does it look like to build something meaningful without sacrificing the relationships that make life worth living? How do you show up as a parent in a way that’s different from how you show up as a boss? Can you actually create boundaries that protect your family time without tanking your business?

I don’t have all the answers. But I know the current default setting isn’t working for most of us.

The Retirement Problem: Terror Disguised as Freedom

Now let’s talk about what happens when you actually succeed in business.

You sell. Or you step back. Or you hand things over to the next generation.

And suddenly you’re facing something terrifying: empty time.

Most business owners I know are absolutely terrified about retirement. Not because they’re worried about money – they often have that figured out. They’re terrified because they have no idea who they are without the business card, without the meetings, without the identity they’ve wrapped around themselves for 30 or 40 years.

The phone stops ringing. Not gradually. Immediately.

Your calendar goes from packed to empty overnight. The people who used to seek your advice stop calling. You’re no longer “the decision-maker” or “the boss” or “the entrepreneur.” You’re just… someone with a lot of free time and no idea what to do with it.

So what do most people do? They follow the script society hands them:

Travel. Play golf. Spend time with grandkids. Volunteer. Maybe do some consulting.

And for some people, that works. But for a lot of us? It feels like putting a Band-Aid on an existential crisis.

Because here’s what nobody tells you: retirement isn’t actually about having enough money or enough activities to fill your time. It’s about identity reconstruction. It’s about figuring out who you are when you’re not defined by what you do.

That’s hard work. And most of us are completely unprepared for it.

So how do we do retirement differently?

We’re going to explore questions like: What if retirement wasn’t about “stopping” but about transitioning to a different kind of contribution? What if you could use all that business wisdom and experience in ways that actually feel meaningful instead of just keeping busy? How do you rebuild your identity without going back to the same patterns that burnt you out in the first place?

What if retirement could be about integration rather than separation – bringing together all the phases of your life into something coherent instead of treating your working years as “real life” and everything after as the waiting room?

The Death Problem: Our Collective PTSD

And then there’s death.

Yeah, I went there.

Most of us have serious PTSD around this topic. We don’t want to think about it. We definitely don’t want to talk about it. And planning for it? That feels like inviting it to happen sooner.

So we avoid. We deflect. We change the subject.

Meanwhile, our lack of planning creates chaos for the people we love. Our unwillingness to face our mortality means we never have the conversations that matter. We never say the things that need to be said. We never make peace with the life we’ve actually lived instead of the one we thought we’d live.

I’m not talking about just writing a will or buying life insurance – though those things matter. I’m talking about the deeper work of actually facing our mortality while we’re still healthy enough to do something about it.

What does it mean to live differently when you acknowledge you’re going to die? How do you want to be remembered? What conversations need to happen now, not later? What does a “good death” even look like, and can we plan for it?

These aren’t morbid questions – they’re life-giving questions. Because when you get clear about death, you often get a lot clearer about life.

Why “Together” Matters

Here’s why this site is called A Long Strange Trip and not “Expert Advice on Business Transitions” or some other consultant-speak nonsense.

Because I’m not an expert who has it all figured out.

I’m a fellow traveler who’s navigating this stuff in real-time. I’ve made mistakes in business. I’m figuring out what my own transition looks like. I’m dealing with my own health challenges that have forced me to face mortality in ways I never expected.

And honestly? I think that makes this more valuable, not less.

The expert model assumes there’s one right way to do things. The seeker model acknowledges that we’re all figuring this out as we go, learning from each other’s experiences, asking better questions, and being honest about what we don’t know.

This site is a conversation, not a lecture.

It’s a place where we can admit that the conventional path isn’t working without pretending we’ve got all the alternatives figured out. Where we can share what we’re learning, what we’re struggling with, and what we’re discovering along the way.

What You’ll Find Here

We’re going to explore these three big transitions through real stories, honest conversations, and practical experiments.

You’ll find:

• Real experiences from business owners who are trying to do things differently with their families while still building something meaningful

• Honest talk about retirement transitions – the messy, complicated, scary parts nobody mentions in the financial planning brochures

• Thoughtful exploration of mortality that doesn’t shy away from the hard stuff but also doesn’t wallow in doom and gloom

• Questions that make you think rather than answers that shut down conversation

• Frameworks and ideas we can test together, not rigid systems we’re supposed to follow perfectly

This isn’t about getting it perfect. It’s about getting it different – and hopefully better – than the default path most of us stumble down.

Join the Journey

If you’re a business owner who’s tired of the 95/5 split and wondering how to actually show up for your family…

If you’re approaching retirement (or already there) and feeling that knot of anxiety about who you are without your business identity…

If you’re ready to face mortality in a way that’s honest and healthy rather than terrifying or avoidant…

Then this conversation is for you.

Let’s figure this out together.

Because life’s too short – and too long – to keep doing it the way everyone else says we’re supposed to.

Welcome to A Long Strange Trip.

It is what it is. But that doesn’t mean we can’t navigate it with more intention, more honesty, and a lot more humanity than the default path offers.