Sounds awesome, Brad. Sometimes starting late gives you a chance to do things right.
What sort of freelance writing were you going to do? Environmental stuff? Magazine articles? What sorts of challenges did you face?
Before I started freelancing I had spent five or six years as an environmental journalist writing about climate change and ozone depletion for a commercial newsletter publisher. But I wanted to write more about field biology, ecology, natural history, and animal behavior, which were subjects closer to my heart. I had some credentials in that field, but I didn't realize there was so much competition in those areas when I started freelancing. I spent about 70 percent of my time researching and pitching story ideas, and only 30 percent of my time actually writing paying pieces for magazines and other publications. I wrote a few articles for Global Change magazine (now defunct) Earth magazine (also now defunct) and New Scientist (still around), and did get one nice assignment writing a chapter for a White House report, but the pay was low and it was a fixed-price contract...I think I would have made more per hour if I was flipping burgers at McDonald's! In the end, I discovered that specialized journalists tend to be like actors: you get typecast. Everyone knew me as someone who wrote about climate change and ozone depletion, and it was really hard for me to break out of that mold. Eventually I got some steady freelance work writing about climate change for a government agency (through a contractor), and that ultimately turned into the fulltime job that I have now.
The other big challenge I faced with freelancing was within myself. I'm a person who really requires external accountability: I need an assignment and a deadline if I'm going to get anything done. Even now I ask my clients to give me deadlines; it's the kiss of death to tell me "oh, there's no rush on this, just send it to me when you can." I inherited my mother's creativity and my father's lack of initiative; it's a dangerous combination. I have a few friends who are very successful freelancers (my former editor earned a six-figure income as a freelancer), and I think the key to their success is that they're very self-disciplined and aggressive about getting work. For me, it was just too easy to say, "oh it's a gorgeous day, I'll work for a couple of hours and then spend the afternoon in my canoe."
Finally, the big mistake I made was something I knew was a mistake right from the start but I did it anyway: I didn't have any cushion (aka emergency fund). Unless you already have clients lined up when you start freelancing, the first year is going to be lean and you should have enough saved up to live on for six months or more. I didn't have that, but I hadn't really planned on freelancing, the opportunity just fell in my lap when the publisher decided to fold the newsletter I was working on. They offered me another job writing about some topic I had no interest in, so I decided to jump ship and set out on my own. I made it, but the first year was scary...my total income was something like $6,000!