Out of Left Field

Walt Disney was once fired from a newspaper for “lacking imagination” and “having no original ideas.”

That’s ironic in hindsight, but it also highlights an interesting truth: the path to success isn’t always linear.. and what seems random often makes perfect sense in retrospect.

Some journeys unfold predictably.
A sales leader builds a startup to solve a problem he faced firsthand.
A nurse launches a healthcare staffing firm after living through the pain of the system himself.

Those stories follow a certain logic.

But then there are the outliers, the people who leap from one world to another and somehow make it work.

My friend and mentor Josh Linkner began his career as a jazz guitarist before becoming a serial entrepreneur and investor focused on creativity and innovation. On the surface, that pivot might seem extreme. But jazz and entrepreneurship share the same fundamentals; improvisation, collaboration, and relentless pursuit of creativity.

What looks like a left turn is often just applying old skills to a new stage.

Howard Schultz, the long-tenured CEO of Starbucks, offers another example.
Before joining Starbucks, he worked for Hammarplast, a Swedish housewares company, where he managed sales of coffee makers and kitchen products. That role introduced him to a small Seattle coffee retailer that happened to be one of his clients.

His leap from selling kitchen goods to building a global coffee empire seems wild, until you notice the through-line. Schultz followed his curiosity about how people connect over coffee, and turned that curiosity into culture.

My wife and I get asked about this jump with Glenlore Trails, the immersive night walk we put together six years ago. From the outside, it seems like a rather sudden detour from our day jobs. But for those who know us, it’s a natural extension of everything we do; creating environments that connect people and making them smile.

What I like about these “out of left field” stories is that once you find the through line, you realize success rarely happens by accident. The dots always connect when you look back.

The trick is getting comfortable enough with uncertainty to start looking for those dots while you’re still moving forward.

“Innovation is seeing what everybody has seen and thinking what nobody has thought.” – Dr. Albert Szent-Györgyi

So when something feels random or out of place, don’t dismiss it.
Lean into it. Follow the thread to see where it’s been, and where it might lead next.

Once you understand how the dots connect, you stop looking for clarity in the rearview, and start seeing opportunity on the road ahead.

With a bit of practice, who knows, maybe the next “out of left field” story people tell… will be yours.