Another dip into the Writer’s Mailbag. Blogger Sean Brereton asked me some good questions the other day about freelance writing: How do you first get into freelance writing? Where can you find jobs? Does it take a lot of crappy jobs to get jobs you enjoy?

The answers:
a) It’s a long story
b) everywhere
c) yes

Here’s the long answer to the first question:

Originally, I got into freelance writing because I wanted to write for magazines. I took some journalism classes in college and got the writing bug, but wasn’t satisfied covering events for my college newspaper. I wanted a “real” byline. So I went about it the old-fashioned way, sending query letters to various magazines describing articles I could write for them. I ended up getting published in a couple of small magazines you’ve never heard of and which no longer exist. I made about $75 in freelance money from those articles. Total.

Eventually I became the editor of the college magazine, which was printed at a local print shop. The print shop was experimenting with a creative services division, which meant they would no longer just print their customers’ newsletters and brochures, but design and (potentially) write them as well. They knew me from the college mag. They knew I could write. They knew I was a college student who might work for peanuts. So they asked me if I’d be willing to write for some of their customers as a freelancer.

And I said yes. That’s how I got started. For the next year, I wrote profiles of supermarket employees for a regional chain’s employee newsletter. I edited newsletters for a local retirement home. I wrote some ad headlines and body copy for a locally based risk management company. I wrote brochures. I learned how to write a news release. I even ghost-wrote letters from the CEO of a local bank, explaining something to his customers (I forget what it was).

I got paid for all of it.

Eventually those freelance assignments turned into a full-time job for the print shop. I kept doing the small, unimpressive stuff while working toward bigger writing jobs, and within a few years I’d begun writing for national magazines and even getting some books published.

Freelance writing can be a glamorous thing, involving travel and bylines and national publicity. (I’ve gotten a small taste of that with a few TV appearances and radio interviews and writing assignments that have taken me to Nicaragua and the Dominican Republic.) But it can also be an unglamorous thing, too. A lot of my writing doesn’t even have my name attached to it. It’s corporate stuff, or ghostwriting, or content production for websites. But in many cases this kind of writing pays better — and takes less time — than writing on assignment for magazines. So guess what? I’ve found a humble measure of success writing for legitimate publication, but I still do a lot of freelance copywriting for companies you’ve never heard of and for ad campaigns and brochures and newsletters you’ll probably never see.

I do it for several reasons. First, writing is a definite skill that not everyone has, so good writers are always in demand. Second, it pays well enough to be a nice little side job, in addition to the books and my real job. Third, I’m a firm believer that, if you’re good at something and you enjoy it and you can get paid for it, then it’s not a bad idea to pursue that kind of work. So I do. Maybe some day I’ll do it full-time. Maybe it’ll always be a side gig. Who knows? For now, I’m satisfied.

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Thanks for the question, Sean. Tomorrow I’ll answer Sean’s second question about how to find freelance writing jobs.

What about you? Do you have any questions about writing or freelancing? If so, leave a comment.