Modern-Day Troubadour

Modern-Day Troubadour

Kicking convention to the curb, Woodrow Landfair travels the country and works on novels.

Holding down a Monday through Friday, nine-to-five job isn't for everyone. Or, at least, not for Woodrow Landfair.

When he graduated from the University of Texas with a degree in creative writing last year, Landfair decided to take a different path into the working world.

"I read a bunch of books about land travel, had a degree in creative writing and thought 'Well, this will be my life,'" said Landfair. "'I’ll go on an adventure and spend my life writing stories.'"

After selling all his worldly possessions, including a car a friend gave him, Landfair bought a Suzuki Intruder 800 motorcycle, taught himself how to ride and took off to the eastern part of the country. Up to that point, he had never been on a motorcycle before. He had $3,000 in his pocket, two backpacks filled with clothes, his laptop, a digital camera and a sleeping bag.

"I didn't really put a whole lot of thought into where I was going at first, I just figured I'd go east to Florida at first and then north to Canada," he said. "My sister was having a baby and I thought it was important to be home for that and then I had a family reunion in Michigan. Before I realized it, it was the cold part of winter and I had made this zigzag path."

Landfair spent the early part of 2007 in New York City, living in a homeless shelter and working odd jobs to raise some money to continue his trip. Stuck in one place for a long stretch of time, he decided to put some thought into the remainder of his journey and plotted a course from New York City to New Orleans, west through Texas to California, back east through the prairies and ending in Maine at the end of July.

True to his craft, Landfair said he's been collecting stories from people in small towns and big cities along the way, using them as fodder for the open-mic night appearances he makes to promote his Web site and for the three books he's writing.

At the same time, Landfair has one set goal in mind for the end of his trip: He plans to give away $3,000 to someone, anyone, who submits an idea for what he or she would do with the money, pursuing his or her own dream. Landfair plans to select this person at the end of his trip.

"I had a dream. I just needed the capital to get started and I got it," he said at one of his early stops in New York, according to his Web site, "Now I want to offer you the same opportunity to change not only your life but also the lives of everyone you meet."

In the meantime, Landfair sees himself as an old-fashioned troubadour, traveling from town to town, telling stories and raising enough money to get to the next destination.

"The whole thing has been a huge confidence builder," he said.

FROM BEING EXPOSED to the elements on a nightly basis — he sleeps mostly on the side of the road, out in the open to avoid problems with police — to the realization that he had to be larger than himself in order to complete his journey, Landfair said he's been transformed by the trip.

"It’s allowed me to grow so much more. It’s been my experience that there could be some correlation between how much satisfaction you get out of life and how much time you spend out of comfort zone," he said. Landfair said if he finds himself getting too comfortable, he starts looking for ways to give himself a new challenge, a new way out of his comfort zone to keep things exciting.

He's met a wide variety of people on his travels, but finds that regardless of the location, people can be both incredibly kind and generous, or quick to complain and blame others for their hardships.

"Most people who are well-off like to believe they made their wealth themselves, but so many of them are among the [whiniest] people I've ever met," he said. "At the same time, I've met a lot of poor people who will admit if they did something to cause their hardships, but there's others who are convinced that everything is someone else's fault."

Other than a bad snowstorm that elongated the trip from New York to New Orleans by a couple weeks, Landfair said his trip and been relatively easy during the day. At night, when he falls asleep in a park or field, he's had a few run-ins with local police who think he may be a drunk driver or wanderer.

"I’ve learn to accept and understand this is someone doing their job," Landfair said in a very matter-of-fact tone. "For the most part, it's 'Thank you sir, I'll leave right away' and I'll stop someplace a little further down the road."

One night he fell asleep in the grassy yard of a small church and woke up to find the preacher trying to buy him breakfast and bring him into the faith.

"He thought I was some woebegone traveler who needed the Lord in his life," Landfair laughed. "I felt bad because he felt bad for me … I wanted him to understand that I have goals and an education and this whole trip has been well thought out."

Sherri Landfair said she's not surprised her son, the youngest of her three children, decided to take this path after graduation.

"He's full of adventure," she said. "The only part of it that worried me was the motorcycle, that's a little scary."

Sherri Landfair said between checking her son's MySpace account and Web site and the weekly phone calls, she has a good handle on how he's faring on his trip. His friendly, outgoing nature makes him easy to get along with, so she's not too concerned about anyone hurting him along the way.

"I liked when he was living in New Orleans because he was in one place for a while," she said. "I probably think about him and what might happen on that bike a few times a day. He's very good about touching base with me a few times a week."

While she doesn't plan on meeting Landfair in Maine at the end of his trip, she hopes he'll come home for a little while before starting off again.

"When he was little, he and his friends always talked about doing a cross-country road trip," Sherri Landfair said. The childhood best friend got married and the dream shifted for her son, she said, and this trip is essentially the one he's been planning his entire life.

"He enjoys this drifting," she said. "He gets antsy when he's been in one place too long. And he's an adult, you have to let him do what he feels is best."

WOODROW LANDFAIR'S grandfather, Johnny Sherman, said he used to hitchhike from his college in St. Paul, Minn., home to Washington, D.C., in his younger days, so the thrill of traveling is nothing new to his family.

"If I were a few years younger, I would consider joining him," Sherman said. "He's always done something that is probably different than I would ever have expected."

Sherman, who describes himself as a full-time volunteer for a handful of groups across Fairfax County, said he thinks his grandson is a good storyteller who will make his way just fine.

"He's got to get on the track of where he's going with the rest of his life and how would he get started on his career track," Sherman said.

When the trip ends in July, Landfair says he'll sell his motorcycle, give away the $3,000 to another lucky traveler and set about writing his books. There's nothing set in stone for him and he likes it that way.

"My sister, who's very motherly, thought of this as me taking time off, but that's not how I view this at all," he said. "I'm entering this new field, this is a new path for myself. I'm not out to get a job somewhere, I want to work this out and figure out how to make money doing this and live hand to mouth in the meantime."

Landfair says his only guidance right now is to "shoot from the hip and be an author." Everything else, he'll figure out along the way.