Jake runs Phoenix-based Boomvang Creative Group, writes an advice column for freelancers as Dr. Freelance, and is a regular contributor here at Freelance-Zone.com—most recently posting on “The 7 Scariest Words in the Freelance World.”
1. How did you wind up a writer?
I got my first encouragement from a high school English teacher, which led to writing for the school paper and later for my hometown paper in Massachusetts. After graduating college, I worked for about two years each at several different magazines. I realized at that point that my freelance stable had a lot of successful, independent-minded people in it…and I thought, “Why not me?” That was in 1999, and I’m happier with each passing year.
2. Was the road to being a writer what you expected? Why or why not?
Approximately. I consider myself fortunate to have worked for and with some outstanding businesses, which taught me more than an MBA ever could. I honestly don’t *love* writing the way some freelancers do, but the entrepreneurial aspect is what motivates me—which I credit to my dad.
3. What has been your best moment or biggest accomplishment as a writer?
Ha, I’d like to say it hasn’t happened yet. But I still get a thrill from each new client, had a blast ghostwriting my first book a few years ago, and I’ve really enjoyed the opportunity to interview some of the world’s top professional speakers for Speaker magazine. And I’m looking forward to publishing my own first book in a few months.
4. What has been your most difficult moment?
I think the shock of my first non-paying client. I’d done a big web project for a local business, which went belly-up before I got paid. It was a cold, hard reminder that, particularly if you’re doing a sizable amount of work for an unproven entity, you need to ask for a deposit. If they say “no”…there’s your sign.
5. Can you share your top piece of writing advice with Freelance-Zone readers?
Be the writer who you’d want to hire if you were an editor or client. Some folks want lots of communication and updates, some just want the finished product. Figure out what the person wants, and deliver it.