The Sustainable Business

The Sustainable Business Join us on our journey as we explore six areas of interest on The Long Strange Trip.

09/09/2026

That question can hit harder than retirement itself.
For decades, your identity may have been tied to being the owner, the leader, the person everyone needed.

Then you retire—and suddenly “I’m retired” doesn’t feel like a real answer.
In this conversation with Joe Pine, we talk about why retirement isn’t just about leaving work. It’s an identity transformation—and figuring out who you are beyond the business.

Sometimes the hardest part of retirement isn’t having more free time.
It’s discovering who you are when the thing that defined you is gone.

🎙️ This conversation is from The Long Strange Trip podcast.

Watch the full episode on YouTube here:
https://youtu.be/HT-bKt8c7iQ?si=j-Gw3Tm5_yHBNfPh

or Learn more by visiting our website : https://thelongstrangetrip.com/post/thelongstrangetrip-episode29

09/07/2026

Sometimes the lesson you’ve been teaching everyone else is the one you’re failing to follow yourself.

I spent years telling people around me to take a break.

I genuinely believed I was doing the right thing.

What I didn't realize was that I had built an entire story around why I was the exception.

Looking back, the logic was pretty convincing.

There was always a customer who needed me.

A problem that couldn't wait.

A reason I couldn't be away for very long.

The uncomfortable part wasn't discovering that I needed a vacation.

It was realizing how good I had become at explaining to myself why I didn't.

There's a particular kind of self-awareness that only arrives when someone puts the evidence right in front of you.

Mine came in the form of a spreadsheet.

And I really, really didn't like what it told me.

🎧 Listen to the full episode: https://thelongstrangetrip.com/post/importance-of-rest-two-week-vacation-mindset

📺 Watch the full conversation on YouTube: https://youtu.be/D5rPbKspEQo

09/04/2026

Apparently, talking about death can make you die.

Okay… can you hear how absurd that sounds?

And yet, we laugh at superstition while quietly practicing a lot of it ourselves.

One example?

There are 125 million Americans who don’t have a will.

Why?

Because somewhere in the back of their minds is this idea:

“If I make a will, I’m just asking for trouble.”

So we leave death alone, hoping death will leave us alone.

But that’s not really how this works.

Maybe talking about death doesn’t make us die.

Maybe it just helps us live with a little less fear—and a little more preparation.

🎧 Listen to the full episode: https://thelongstrangetrip.com/post/thelongstrangetrip-episode28

📺 Watch the full conversation on YouTube:
https://youtu.be/OSCsP3BIkZo

09/03/2026

What if the hardest part of retirement isn't figuring out what to do with your time...

but figuring out who you are when nobody needs you anymore?

That's something I underestimated for a long time.

We spend decades building businesses, solving problems, making decisions, and becoming the person everyone turns to.

Then we step away.

And suddenly, the thing that filled your days—and maybe a much bigger part of your identity than you realized—is gone.

I thought knowing how transitions worked would make me immune to this.

I was wrong.

There's a side of retirement nobody puts into the financial plan.

And I think we need to talk about it a lot more.

🎧 Listen to the full episode: https://thelongstrangetrip.com/post/life-after-selling-business-identity-purpose

📺 Watch the full conversation on YouTube:
https://youtu.be/ez2LcKCSM4A

09/02/2026

Most people think estate planning is about what happens after you die. I think we’ve got that backwards.

Sure, a will answers the question, “Who gets my stuff when I’m gone?”

But estate planning is also about what happens while you’re still here.

A power of attorney for finances.
A power of attorney for healthcare.

Those documents give your family direction when you can’t make decisions for yourself.

That’s not really about death.

That’s about living and making sure the people you love aren’t left guessing when something happens to you.

🎧 Listen to the full episode:
https://thelongstrangetrip.com/post/thelongstrangetrip-episode28

📺 Watch the full conversation on YouTube:
https://youtu.be/OSCsP3BIkZo

08/24/2026

What happens when you sell your company and suddenly realize nobody needs you anymore?

I recently sat down with Paul Cronin from Touchstone Advisors to talk about the part of selling a business that rarely gets discussed: what happens to your identity after the deal closes.

Paul shared a story about a CEO who sold his software company for eight figures and went from having people bring him coffee to being, in Paul’s words, “seventh in line at the coffee shop.”

The money was there. The status was gone.
And suddenly, so was the sense of purpose.

That’s the part of business succession nobody prepares you for.

A successful exit isn’t just about getting the deal done. It’s about figuring out who you’re becoming when the business is no longer who you are.

🎧 Listen to the full episode:
https://thelongstrangetrip.com/post/life-after-selling-business-identity-purpose

📺 Watch the full conversation on YouTube:
https://youtu.be/ez2LcKCSM4A

08/21/2026

What if going with the flow is something you can actually learn?

We tend to think resilience means pushing harder, holding on tighter, and fighting through whatever life throws at us.

Ron Pevny sees it differently.

A big part of resilience is learning to let go of our attachment to how we think things should unfold.

That takes practice. And the earlier we start doing the inner work, the better.

🎥 Watch the full conversation with Ron Pevny:
https://youtu.be/RN8dqvm1dpQ

Learn more about the episode:
https://thelongstrangetrip.com/post/thelongstrangetrip-episode27

08/20/2026

I used to think experience automatically made me wiser.

It doesn’t.

You can spend decades becoming really good at knowing your field—and still miss what’s happening right in front of you.

For me, wisdom started showing up when I became less interested in proving I had the answer and more interested in understanding the question.

That shift changed the way I look at business, relationships, and life.

🎧 Listen to the full conversation:
https://thelongstrangetrip.com/post/knowledge-vs-wisdom-leadership-lessons

📺 Watch the full episode on YouTube:
https://youtu.be/BpRds35-hYI

08/18/2026

Sometimes life forces you through a doorway you never would have chosen.

A loss. A major change. A health crisis. Something that shakes your sense of who you are and how the world works.

Ron Pevny calls these moments a kind of “doorway in.”

We don't always get to choose what happens to us. But sometimes the things we would never choose are exactly what force us to look at life differently.

🎥 Watch the full conversation with Ron Pevny:
https://youtu.be/RN8dqvm1dpQ

Learn more about the episode:
https://thelongstrangetrip.com/post/thelongstrangetrip-episode27

08/17/2026

Being smart nearly became one of my biggest career mistakes.

For years, I thought having the answers meant I was wise.

I had decades of business knowledge, frameworks, strategies, and expertise. But I eventually realized something:

Knowledge tells you what you know. Wisdom helps you discern what actually matters.

I was going miles deep in my specialty while missing the bigger picture.

And that's when I started seeing business owners who had all the technical knowledge they needed—but were still completely stuck.

The difference between being knowledgeable and being wise can change everything.

Learn more: https://thelongstrangetrip.com/post/knowledge-vs-wisdom-leadership-lessons

📺 Watch the full conversation on YouTube: https://youtu.be/BpRds35-hYI

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