Many of us choose a freelance career because the full-time job doesn't work for us. On the other hand, plenty of freelancers hope to turn their gigs into full-time jobs. It can seem like an impossible task, though, competing for spots with other candidates who have been in the full-time jobforce much longer, or finding a position that would fit the skills of a full-time freelancer. You know you'd make a great editor, but would HR believe you based on the last ten years of writing?

I found two freelancers who managed to make the transition, and turned their freelancing careers into full-time jobs.

"I recently got hired at the New York Daily News after nine years full-time freelancing for other publications and a recent non-fiction book," says Caitlin Kelly. It helped that she had connections and was good at keeping in touch: "I knew the editor-in-chief (who has since quit) from working together in 1988, but I still had to pass muster with two other top execs and enter a roomful of Pulitzer and Neiman winners."

More after the break.

Caitlin Kelly has made this transition before, though. "It's the second time I've gone from freelance to full-time at a major paper. I graduated college in 1979 and freelanced full-time from 1979 to 1984 and then was hired at the Globe and Mail (having freelanced for them for 8 years but with no daily experience.)" Doing that, she learned a major lesson about waiting to be offered a full-time job: don't hold your breath. "I was full-time freelance in New York from 1995 onward-- but did NOT work only for one publication (although some people do, which I think is insane and heartbreaking because they're so SURE they'll eventually get a staff job -- and often never do. It's like dating a married man. Enjoy it while it works for you but never rely on it turning into something real and permanent. Like dating, it's only once you've made yourself a hot(tish) property elsewhere and gotten good offers and/or bolstered your resume through awards, books,
fellowships (all of which I have) that I think you can -- possibly --- blast in the door. I also think it's very different going freelance to full-time staff in the magazine world (where editors get it because many of them have done both) versus TV or newspapers.

If it seems that you are developing a good, long-lasting relationship with an editor, it can't hurt to mention that you'd love to work for them full-time. Matt Kelly (no relation to Caitlin) almost missed his full-time job because his freelancing career was so good. "I'd been freelancing for ComplianceWeek for 18 months when the managing editor job opened up. In fact, at first the editor presumed I wouldn't be interested because I had a lucrative freelance practice. I learned about it when an assistant editor mentioned it to me, and then the editor followed up with me once I expressed interest."

While images of benefits and time off dance in your head, the actual daily grind can be a shock for some freelancers. "Was it hard to make the transition back to freelance? Yes and no," says Matt Kelly. "The editorial responsibilities and routines came back to me almost immediately, and I have a great boss and team working with me. The real transition, to my thinking, is getting accustomed to the personal changes that happen once you no longer work for yourself from home any more-- planning your errands around your workday rather than vice-versa, figuring out how a 9-to-5 job changes other obligations in your life or even the things you do (my grocery bill fell 40 percent, but my spending money to buy lunches soared). That sort of stuff is what I'm still trying to learn."

Caitlin says, "Some freelancers find the transition back to an office job with set hours, colleagues and office politics a real shock. Other freelancers, as I did, grow weary of having no set hours, working nights and weekends and having no paid sick days or holidays. It's great to have some smart, helpful colleagues after years working in isolation. On your own, you're forced to absorb health insurance rates that jump 15% every year while freelance rates remain stagnant or falling. I think the transition back to an office is less stressful if you're clear why you want to go back, if you can find a corporate culture you feel comfortable in, and in which you still produce satisfying work. People who have never freelanced tend to really glamorize it and can't imagine why you'd give it up. Sometimes it's the right choice."

Like Caitlin, Matt Kelly also advises survival above wishing and hoping for that full-time job to open up. "I think anyone who hopes to make a living in this profession needs to know how to survive long-term as a freelancer, and how to move between both worlds as necessary."

How can you groom a promising relationship with an editor into one that might pay off more down the line? Hook up with people whose last name is Kelly. No wait. Caitlin Kelly did, though: "I read Keith Kelly's media ink column in the NY Post -- as I'm sure every ambitious New York reporter does. He kept saying Mike Cooke was coming to the Daily News, even a year before Cooke did and kept on denying it. So I emailed Cooke at the Sun-Times, where he was Editor-in-Chief at the time, and said if he DID ever head to New York for the Editor-in-Chief job I'd love to come and work for him again. He had good memories of me from our work together at the Montreal Gazette and I had certainly well-filled my resume since then, so it was not asking a favor but re-connecting with a colleague. He at least had the loyalty to meet me very shortly after he arrived and
brought me in for interviews. You need 1) a good track record 2) loyalty 3) someone to be your in-house rabbi 4) something impressive to push you apart from the pack of freelancers.

Meanwhile, while you're at it, why cultivate one good relationship with an editor when you can develop several at one publication? "I freelanced 8 years (ages 18 to 26) for all sections of the paper -- sports, travel, dance, books, news, foreign -- before the Globe and Mail hired me," says Caitlin Kelly of the first time she went from freelance to full-time. "By the time they did, many editors knew me and my work and my skills and my personality. You are, to some degree by then, a known and proven quantity."