Published in The Attention Architect, a newsletter on LinkedIn, May 3, 20 22

While it would be unheard of today, I walked to elementary school every day as a kid in the south. It was a long trek, about 35 minutes in total, through the old brick neighborhoods, then past the big steepled church, over the single lane bridge, and the modern supermarket just beyond the edge of main street.

The most exciting part of my journey was crossing the railroad tracks that cut our town in half. If my pals and I got the timing right, we could catch the Northfolk Southern Railway freight train come roaring across our path.

The sheer heft of the million-pound freight train—huffing and puffing its way past us—was a mighty sight for a young boy to behold. I wasn't sure what was in those train cars or where they were going with all that momentum, but whatever it was, it was important enough to put our busy little town on pause.

Some days, we'd have to wait 20–30 minutes for the train to finish its coupling and uncoupling performance before crossing the tracks. During these delays, my buddies and I would hang out in the adjacent field full of junk — abandoned cars, old tires, beer cans, and washing machines. In the background, we'd sometimes hear a group of dusty, oily men singing folk songs. These men were what locals in my town called "hobos," and — unlike today — nobody seemed to mind them being there.

They didn't bother us, and we didn't bother them.

The hobos would camp out in the field for a few days in makeshift tents, heating vittles of canned food over a small campfire. But then they'd be gone for a few weeks before we'd see them again.

A WAY OF LIFE

Hobos were different from the ordinary homeless people who lived in our town and panhandled on the streets during the day. They never asked for money. Nor do they seem to want anything from us townsfolk.

Unlike "tramps" who traveled but didn't like to work and "bums" who didn't want to work or travel, hobos were homeless by choice.

They chose the freedom and adventure of the traveling life, as they sought seasonal jobs all over the country.

Most of the hobos had a Marlboro Man's rough and tumble look, as if they’d been working in a coal mine instead of on horses. They wore distinctive traveling clothes — thick canvas jackets, derby caps, steel-tipped boots, and handkerchiefs hanging out of their jean pockets. Today, they might be models in ads for rugged jean-wear.

Many of the hobos were thinkers, poets, and musicians. They'd carry Jack Kerouac-type books and journals full of scribbled notes. We'd sometimes see them running at full speed to catch the train as it pulled away from town. But they had to be very strategic about getting beyond the rail officials' sight—what they called "bulls"—before they could jump inside one of the open boxcars.

TRAILER THE PHILOSOPHER

My buddies and I saw one particular hobo on and off for most of our elementary school education. His name was Trailer. Why they'd call him that, I don't know, but Trailer was always gracious to us and would dole out sage advice about life, learning, and the open road.

I often wondered where Trailer was from, where he was going, and what he'd seen during his travels. I figured he must have some fascinating stories in that notebook to tell.

Although I was only 11 years old, I had 72 pounds of curiosity to know more about him. One day, while waiting for the train to pass, I mustered up the courage to walk over to Trailer's campsite and ask him some probing questions about his life and wanderlust. We had a riveting conversation, but there was one thing he said that I've carried with me all my life.

"Mister Trailer," I asked, "there will be trains going by this field all week long, so how do you know which train is the right one for you to take?"

"I don't have a specific plan or method for it, son." Trailer said. "It's just a feeling I get. While hundreds of cars are going by me all day, somehow, I know when my boxcar has arrived. And when I see that boxcar, I run like hell to catch it. And I'll go wherever that train wants to take me, which always ends up being the right place for me."

"But you can't mess around debating which car to take or overanalyzing this decision," Trailer stressed.

"Once your boxcar arrives, you should be packed and ready to go. Do whatever you have to do to catch that car, and don't ever look back to second guess it."

Somehow I knew that Trailer was talking about much more than just catching a train ride, but life in general. And that concept of "waiting for your boxcar to arrive" stuck with me as a principle to live by my entire life, particularly when making major career decisions.

WAITING FOR YOUR CAREER OPPORTUNITY TO ARRIVE

People often asked me how I knew it was time to quit my good-paying job to risk starting a business. Although owning a business was my dream, I wasn't sure when or how it would happen. But just in case, I had all my stuff packed and was ready to run the moment my boxcar arrived.

And then one day, that boxcar did arrive.

Like Trailer, I traveled all over the country to meet with clients and work on projects for my employer. And I had been hanging out in the design and consulting field, learning everything I could about the business world. But I still hadn’t found what I was looking for. I wanted to be a part of something great and meaningful at least once in my life. And if I failed, so be it! I was too young to settle for an average life.

So per Trailer's advice, I waited on the sidelines for the right doors to open.

On the day my boss offered to put me on the partnership track, I quit my job and decided it was time to start a consulting practice with my new business partner. There was no logical rhyme or reason for why it had to be that day. But I saw an opening in the market for a new business model that combined the multiple disciplines of branding, social science, and design into one integrated approach. And just as Trailer said, that boxcar took me exactly where I needed to be in life.

That was over 30 years ago, and I rarely look back to think about how random and illogical that decision was.

For the first many years of my career, I was like a professional hobo, traveling all over the country and trying to find my place in it. I couldn't settle down, but I now live 2,732 miles away from my original campsite. However, if you had told that young boy walking to school every day in the South that someday he'd put down roots in the big metropolis of Los Angeles, I would've said not in a million years.

But I am so glad I jumped on the train when I did and let those tracks take me wherever they wanted to go. Although I didn't realize it, my timing was perfect for catching the wave of a new field of growth, and I am so grateful I had Trailer's words of wisdom to teach me to "wait for my boxcar to arrive," and the courage to run for it when I say my brief opening.

Now that the pandemic is becoming a thing of the past, I know many people wonder how to get their careers on the right track. Understandably, many worry about what's next. I get it, as I've been there several times myself. Sometimes life seems like it's passing us by. We feel stuck on the sidelines eating beanie weenies while others are going somewhere, but here's my advice to future entrepreneurs.

PACK LIGHT

If you have an entrepreneurial drive in you, don't get in too much debt, particularly when you're young, and don't buy too much stuff that you have to lug around and hire movers to carry it out for you, or worse, put in storage.

Stay light, flexible, nimble, agile, and ready to jump trains or tracks.

When I got out of college, I had a tiny room with a single mattress on the floor, 67 of the best books on life, and a few hangers of clothes, all of which could fit in one suitcase, except for the books I’d leave behind. 

I was ready and able to go at a moment's notice.

WAIT FOR IT

Get a job, work hard, learn as much as possible, but always be on the lookout for the right opportunity to come down the track. While a thousand train cars may pass you by, you'll know when the right one comes along if you listen to your gut.

Don't let anyone force you to take a job you don't want to do or go down a track you don't want to be on, no matter the money, title, or benefits.

Wait for that gut feeling and intuition that says, "Your boxcar has arrived."

Nobody will see it or understand it but you, and you won’t have to explain it to them because you’ll have to make your run for it.

Like Trailer said, though, you'll know the right opportunity when you see it.

EXPERIMENT

If the one train you jump on takes you to a place you don't want to be, don't sweat it because there's always another train coming down the tracks.

Sometimes you have to experiment with different types of jobs — e.g., big companies vs. small companies — to find what works for you. And sometimes, you might end up in a place you don't want to be, but that's all part of learning what you enjoy doing and what you don't want to do.

Be prepared to change your mind as you try on different career roles with different outfits. What you thought you might like — like being the manager of a giant company — might not feed your soul or inspire your creativity. The more you travel around to different jobs and stations, the more you'll discover where you'd like to land someday. I mean, I ended up in LA of all places, and love it! 

JUMP OFF

The worst thing you can do is stay on a train going nowhere, or, at least, nowhere you want to be. But far too many people get comfortable with jobs they hate, and they get afraid to jump off, especially when they've been on one career track for a long time.

But the longer you stay on that train on those dead-end tracks, the further you get away from where you need to be, and the more unfulfilled you’ll be with where your life is heading. 

Be bold, pack light, keep your eyes open, and make the jump when you see the right boxcar arrive.

WHERE'S TRAILER NOW?

When I returned to my hometown for a funeral many years later, I drove by that field where the hobos used to hang out. It's now a high-end shopping center.

When I asked one of my old classmates what happened to Trailer, he said the other hobos put him somewhere in New Mexico. They said he's writing novels now under a pseudonym. I look for Trailer's tracks and words in bookstores, train yards, and vacant fields, but I haven't found him yet. But wherever Trailer is today, I know it's where he wanted to be.

Trailer, if you read this, I want you to know your sage advice stuck with me forever. I waited for my boxcar to arrive, and it took me exactly where I needed to be in life, so thank you for giving me the courage to make a run for it.