At first sleeping outside, he worked as a manual laborer, eventually crossing all forty-eight contiguous states. During his time on the road, he legally changed his name to "Woodrow", stayed in two New York City homeless shelters, worked for cash with illegal immigrants, and spent over a month living within the Anarchist group Common Ground Collective in New Orleans's Lower Ninth Ward after Hurricane Katrina. Among other odd jobs, he worked as a day laborer, a swimming pool lifeguard, a bouncer, a truck driver, a door-to-door salesman, a beverage delivery man, a stagehand, and a waiter for an Italian restaurant with ownership ties to the Gambino crime family. Landfair used the jobs as material for oral stories. Between traveling and working, he began self-promoting in roadside bars and coffee shops where he talked about his hoboing experiences. He developed a storytelling act, eventually appearing in theaters and on regional and nationwide television.