Figure Out What's Next

Test-Drive Your Dream Job

alfred gingold career change entrepreneurship Apr 25, 2009
Vocation Vacations

by Alfred Gingold

photo by Asad Photo Maldives

Years of dreaming about a career change led Brian Kurth to his perfect job

The Oregon entrepreneur helps clients take a trial run at their own dreams.

The notion popped into my head while I was breathing exhaust on the Kennedy Expressway in Chicago, halfway through my daily twenty-two-mile, one-and-a-half-hour, one-way commute. I didn’t think of it as a job or a business; it was simply a wish list—a list of all the jobs I wished I could do instead of the one I was actually doing. It was 1999 and I was 33 years old; I was feeling and looking older than my years, gaining weight and losing my hair. With a hard-earned master’s degree in international relations, I was spending most of my waking hours plugging numbers into sales and marketing projection spreadsheets for Ameritech, the Midwest’s major phone company. The phone company! I was a living, breathing Dilbert! It wasn’t that I hated my job; I didn’t. I had a great boss. I was making great money. In the last decade I had learned a ton about management and business. But in the end, making the world better through broadband technology just didn’t set me on fire. Many Friday nights my partner, Doug, and I would get together with friends—two were architects, one was a TV station’s programming director, and another was starting his own technology-marketing business. They’d talk about their jobs and their faces would light up. They loved what they were doing. Then I’d say something about the latest data network initiative we had launched and in seconds their eyes would glaze over and their heads would hit their spaghetti plates. My job was boring. They were bored listening to it; I was bored doing it!


So every day I spent my commute fantasizing about all the things I’d rather do. Some days I imagined being a dog trainer, walking through the park, a dutiful chocolate Labrador at my side. Other days I saw myself taste-testing wine in a cool, dark cellar in Sonoma County. Still others I saw myself leading groups of tourists through the cobbled streets of Budapest or Buenos Aires interpreting the local culture. With all that fantasy you’d think the commute would have passed quickly—but it didn’t. Ninety minutes in Chicago traffic is ninety minutes, no matter where your head is.

One evening I was staring out at the chain of rain-glazed brake lights in front of me, having just called home to tell Doug that, once again, I’d be late for dinner. As I clicked off the phone I thought, why am I just fantasizing about these jobs? There must be a company that arranges short-term internships so people like me can try out their dream jobs. That night I went online, but to my surprise I couldn’t find one. Guess I wasn’t going to be able to do it after all, I thought. But then a second later I had a brainstorm: If no one else has done it, maybe I could do it! I even knew what I would call such a company: VocationVacations, because the company would offer vacations that let you test-drive your dream vocation.

A Layoff, September 11, and a Stock Market ‘Correction’

That was the last serious thought I gave to VocationVacations for almost two years. I was too devoted to making money to think seriously about starting a business—especially one for which there was no precedent. I liked my benefits, I liked my lifestyle, and I liked the nest egg I was building. Sure, my job was boring and I envied friends who loved their work. But it wasn’t that boring and I didn’t envy them so much that I was willing to risk my security for a “great idea.' I just wanted to do my own little vocation vacation. I didn’t want to create the whole company.

That was over eight years ago. It took me two years, a corporate merger and acquisition, a layoff, September 11, and a stock market “correction' before I realized that working for a corporation was not as secure as I had imagined and I began to take the idea of starting a business seriously. But finally, after I’d left my phone company job, and the “make a million' job I’d taken at a dot-com start-up had imploded, and my hard-earned savings had nose-dived with the stock market, something clicked and I realized there was no point in waiting. Doug and I pulled up stakes and drove cross-country looking for the perfect place to live. Along the way I asked everybody who was standing still if they would want to test drive their dream job if they had a chance. The answer was a resounding yes!

So I figured I was onto something.

But it still took me a long time to get around to acting on it. We had settled in Portland, Oregon (indifferent to the fact that it was suffering its worst recession in decades), and I wanted to get to know the terrain. My head argued that I better get a job—a real job—and make as much money as I could, but my heart kept me ambling around the city, checking out neighborhoods and coffeehouses, driving down the Oregon coast, touring the pinot noir vineyards of the Willamette Valley, meeting people, and talking about my idea. When reality hit and I realized I needed to make money, instead of looking for another corporate job I went for a dream job of my own—working at a small family wine distributor for a fraction of what I’d been making in Chicago, selling wine out of a white Chevy Tahoe and loving it.

But all the while, VocationVacations was brewing. I asked all the people I met what their dream jobs were, how far they would travel and how much they would pay to try one, and what they would expect in a dream job vacation. By six months into my wine job I was calling businesses in popular industries, looking for people who were passionate about their jobs and would be genuinely interested in sharing them with others. Four months later, I had 10 mentors lined up—in everything from inn keeping and beer brewing to horse training and auto raceway management—who had agreed to take in vocationers' for one to three days for total-immersion, hands-on learning. Now all I needed was customers. Build it, I told myself, and they will come.

I asked my friend Berit McClure to help me write a press release describing the company and we sent it out to 15 West Coast newspapers. Nothing happened. Not a single one picked it up. The wine job was starting to look more like a career. And then two months after I sent out the release, Outside magazine saw it and did a story—and everything exploded. The Associated Press picked it up and the next thing I knew VocationVacations was in 250 papers. My home phone (the official VocationVacations telephone) began ringing off the hook, and in March 2004, Gail Haskett bought the very first VocationVacations package—a brewmaster package at Full Sail Brewing in Hood River, Oregon—as a birthday present for her husband, Steve.

That same month I realized two things: first, if I didn’t hustle my buns off and get more than 10 mentors I would never be able to meet the demand; and, second, if I didn’t grab the momentum while I had it, I might as well kiss the opportunity good-bye. So on March 15, I handed in my resignation at the wine distributor; on April 1, I became the first employee of VocationVacations. I took it as a good sign that it was April Fools’ Day.



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