I had the opportunity recently to interview Dr. Freelance, aka Jake Poinier, principal at Boomvang Creative Group, a Phoenix-based editorial services/advertising/marketing firm, and the erstwhile blogger on a variety of entrepreneurial topics at Jake’s Take. You can learn more about Dr. Freelance, ask him questions, and read his great advice at http://deardrfreelance.com/. Right now, take some time, sit back, and enjoy our conversation.

MSE: Could you tell us about your background? How did you get into freelancing? Do you have a specialty?
DF:
I had to answer the question, “What the heck are you going to do with an English degree?” somehow. I had done a bit of newspaper writing in high school and college, which I parlayed into an internship with the New York Times Magazine Group after graduating. I bounced through several two-year editing positions at a variety of magazine companies, as well as the longest 18 months of my life during a stint in public relations.

I’d been in corporate life for almost exactly 10 years when I started plotting my escape. During my time as an editor, I had come to recognize that there were a lot of freelance writers who were only marginally talented yet making a decent living and enjoying a darn good lifestyle. I figured I had the bullheadedness and background to make it a business. One day, I simply handed in my letter of resignation.

A lot of freelancers swear by having a specialty. I’m not one of them. I’m an omnivore, and if I don’t have exact experience in some topic or medium, I make it my job to figure it out. (Unless someone might get hurt or killed by my ignorance. For example, I wouldn’t accept an assignment to edit a repair manual for Space Shuttle engines!)

MSE: Is it harder for those who want to become freelancers today than it was for you? If so, why?
DF:
When I started out in 1999, I was on a tedious dial-up modem and had to mail a 9″x12″ envelope of physical samples when someone expressed interest. It was slow and expensive.

Freelancers today have a couple of advantages: better, faster tools and a much richer, deeper “content” environment, thanks to the web. There’s also a surplus of information on how to freelance successfully, without as much fly-by-night stigma.

That being said, there is arguably more competition today. Content mills aren’t slave labor, because people choose to do it anyway—but it’s close. And when new publishing tools enable DIYers to believe they can write, edit and design like a pro, you have to be able to prove that you’re a better bet.

MSE: How long does it take for a “newbie” to become successful in freelancing? Is this related to the economy?
DF:
The sharpest part of my learning curve was in the first three years. Year one was easy. Year two was a disaster—it was the economic dip that occurred in the summer right before 9/11.

Well, when my phone stopped ringing, I knew I had to do something—I was the sole wage earner with a wife, two kids under 5, and a mortgage. I’ve always thought that urgency played a role in building my business so quickly in year three. If I’d been doing it part time or had a spouse who was earning a big income, I think my progress wouldn’t have been as fast. The newbie who doesn’t want to starve or be a lifelong hobbyist needs to figure out what lights that competitive fire, regardless of the economy at large.

MSE: Is it imperative for those interested in freelancing to have a background in publishing?
DF:
I can only speak to my own experience, in which it was a huge help to know people, the lingo, how things work and to have a couple of client projects waiting in the wings. But it’s clearly not a prerequisite—you can come at it from any field as long as you have the writing/editing skill *and* the ability/desire to work the business side. If you think you can make it just on your skill with words, you’re like the 18-year-old girl who goes to Hollywood to get “discovered” as an actress while waiting tables.

MSE: Is there anything you know now that you wished you knew when you first started freelancing?
DF:
At the risk of dodging the question, I’m a serendipity lover—I enjoy not knowing what comes next. In fact, that might be my favorite aspect of freelancing. On the other hand, I would have sold all my stocks at the top of the tech bubble instead of riding them down, and I’d be driving a Ferrari right now.

MSE: Do you have any pearls of wisdom that you want to share?
DF:
Well, I just had a Dear Dr. Freelance reader comment that he really liked something I said the other day. “Don’t overthink it…you’ll get more confident as you (fill in the blank).” I had said it in regard to cold calling, but he thought that it made a pretty good all-purpose mantra.

The truth is, if you can ride out the bumpy patches—and trust me, they’ll be there—you’ll probably look back a decade from now and be amazed how far you’ve come.