Real Stories of the Normal 40

I never know who I’m going to meet every time I hit “Join Meeting.”

Today, let's meet Dan.

For the last two years, I’ve opened my calendar to people who never thought they’d be here—elite performers, executives, entrepreneurs, career military, physicians. High achievers who have built success but now feel restless, frustrated, called to something more, but unable to move.

I’ve met with more than 1000 of them on the Normal 40 Highway. Each of them has left a mark on me -- each of them with a story to tell.

These are their stories.

It was May 16, 2023. A Tuesday. One of those days where the calendar was full, but something about this conversation felt different before we even started. Dan showed up like a guy who had spent years pushing forward but wasn’t sure where “forward” was anymore. There was an energy about him—not hesitation, but something close. Like a man who had climbed every mountain he was supposed to climb and suddenly realized he didn’t care about the view.

He got right to it. No small talk. No wasted words.

“I don’t want to waste the next five years,” he said.

I knew exactly what he meant.

Dan grew up in a place where work wasn’t optional—it was survival. His dad drove a truck for decades, hauling freight across highways that stretched longer than Dan could ever imagine as a kid. His dad didn’t talk much about what he wanted out of life. That wasn’t the kind of thing men like him did. You worked. You provided. You did what needed to be done.

Dan saw it all. The early mornings, the late nights, the way exhaustion lived in his dad’s bones, how the smell of diesel clung to his jacket like a second skin. There were no sick days. No vacations. No retirement plan beyond working until you couldn’t.

And for a long time, Dan told himself he was different.

He wasn’t going to punch a clock. He wasn’t going to spend his life waiting for the next payday. He was going to build something for himself, something bigger. Sales became his way out. He knew how to talk, how to read people, how to outwork the next guy. And it worked.

IBM. A startup. Then Salesforce. Then Box. The money followed. The titles followed. The success, the stability—everything he had set out to build was suddenly there. He had made it.

But then, life threw its first punch.

Dan’s dad got sick.

Looking back, instead of stopping to process it, he kept going. He pushed harder and climbed higher. It didn’t occur to him to slow down. Maybe he thought there would be time later. Maybe he thought working harder was the answer to grief.

Then, three years later, it happened again. This time there was no ignoring it. No masking it, hiding from it, or outworking it.

He was at Dreamforce, his largest industry event of the year. He had been standing in the middle of it all—clients, deals, the very thing that had defined his career—when his phone rang. His mom was going into surgery. His sister told him to come home.

And for the first time, Dan made a different choice.

He walked away. He left Dreamforce. Left the meetings. Left the money. Because in that moment, none of it mattered.

Shortly after that call, she was gone.

And suddenly, he was out of people to make proud. Out of reasons to keep proving himself. Out of distractions big enough to hide behind.

So he did something terrifying.

He started asking himself questions that didn’t have easy answers. What am I doing? How much more am I willing to trade for a job that doesn’t fulfill me? What happens if I never stop?

This is when he called me.

“I’ve spent my whole life building this,” he told me. “And I know I can keep going. I can keep making more. But at what cost?”

I stopped him.

“Dan, the goalpost is always going to move. You know that. The real question is, are you willing to trade more years of your life for it?”

He sat with that. And I could see it happening—the moment the truth hit him, the moment he realized that leaving to chase a dream wasn't irresponsible, but...

Never finding out if it was possible was.

Dan wasn't looking for an easy way out. He’s never been that guy. But for the first time, he was choosing a different kind of work. The work of building something that matters. The work of betting on himself. The work of making sure that when he looks back, he doesn’t see regret staring back at him.

It was 2023, and Dan was about to be up to something ...

And that’s exactly what he did.

2025 Update:

Today, Dan has his own company and his own team, and he's chasing the dream on?his?terms. He’s working fewer hours but making a bigger impact. He replaced his income—not by grinding harder, but by designing a life that works for him.

He talks with a huge smile on his face, and when we catch up, I don’t just see a guy who made a leap—I see a guy who landed.

Sometimes I call Dan for advice now, and every time I do, I leave the conversation feeling like I should have paid for it. The dude is a gem.

I need you to believe me--The life you want to try next is out there.

Finding it won’t be easy, obvious, or free.

It will be a trade.

The Trade of a Lifetime.

Dan is up to something, and ...

I am a fan.

If you ever think a #ramble might be for you, find me here: https://linktr.ee/lon.stroschein