When he was in university, 22-year-old Jason Paul only ever used Craigslist to get rid of furniture and find apartments. But post-graduation, he was jobless and decided to give the online classifieds site another chance. In an unusual social experiment, the Washington, D.C. native vowed to devote nine months of his life to a three-city journey in the United States – completely executed through Craigslist.
He started out with his car, just one bag of clothes and food staples, a phone, a computer and $2,500. Everything else – jobs, housing, friends, leisure activities – he had to find through the popular classifieds community. And there was one more rub: He restricted himself from interacting with anyone new unless contact was initiated online.
Mr. Paul is now more than halfway through his expedition, which began in Oakland, Calif. (where he made cash by street canvassing) and has taken him to Denver (where he’s working at a Denny’s restaurant).
He’s been documenting it all at livingcraigslist.com. He’s scored a free Thanksgiving dinner with strangers, found a friend he meets weekly for crochet lessons, and experienced the highs and lows of searching for roommates online. But with each passing week, he’s had more difficulty defining his role – is he an interloper running an experiment, or a legitimate member of the Craigslist community? And, as Mr. Paul told The Globe and Mail in a phone interview, this has led to some tough questions about how honest he should be with the people on the other end of the Craigslist ads.
Tell me what your goal is in all of this. Is this the equivalent to a post-grad backpacking trip through Europe?
I often say some people do Greenpeace, I do Craigslist. … I’m sort of in search of the story of what is possible with Craigslist. If I failed at doing this experiment, I hadn’t really failed because the worst that could happen is I go back to my parents’ basement and I start applying for jobs again. … I did this because I have a bunch of blog-book ideas, and eventually I see myself going into publishing of some sort.
You’d had the experience of using Craigslist to find apartments, get rid of furniture, but in this project you were using it for everything from finding food to finding friends. So what have you had the most trouble tracking down through this?
It’s ironic, actually, because Craigslist is one of those things that is very instantaneous. If you want to buy a couch, you can buy a couch within two hours. But if you want to find someone to go to the movies with that you feel comfortable with, it’s a different story. Whereas in my normal life I could just pick up the phone and call a friend, looking on Craigslist and scanning those ads or posting myself to find that person became a whole different ball game.

One of the jobs Jason Paul picked up on Craigslist was that of a live-in nanny. Mr. Paul says he felt as though he became a part of a family, at times even feeling like an older brother to 5-year-old Tessa.
Where have you gone on the site to find friends?
The Community section has a few listings of events, activities. They have groups and I like to go to as many events as I can. … For example, I went to underwater hockey; I went to trampoline dodgeball. It’s part juggling act between finding the story and experiencing the existence of living off of Craigslist. … The people I live with now, I went to a movie with one of them, and after my housing situation fell through they invited me to live at their house. That was someone I met through the Strictly Platonic section.
