Up until recently, I did the freelance route for my lone source of income.
A few tips:
- Broaden your work: Do sports, music, news, photo (a huge money maker), magazine, PR, book editing, etc. I worked my way into all of them and was close to breaking into photos. If you can do everything, you'll get to a point where you don't have to take **** assignments. Nothing is beneath you, but also remember that it's like any other job. If you hate what you're doing, you're not going to last long. (At the same time, the fact that you'll rarely do the same thing twice is a benefit; you shouldn't get bored.)
- Become very good at bookkeeping: This doesn't only apply to writing down what you have done, what you're owed (and paid for) and what you're going to do. But also, you need to start thinking about your taxes. Investigate whether you need to pay quarterly and find a really good accountant who can suggest write-offs and expenses, etc. Essentially, use some of your best reporting skills on the business side of it.
- Work your connections: One of the best gigs I got came from someone on this board. It turned into a regular weekly assignment reprinted in some major publications (not to mention paid all of my bills every month in one check). It's often better to be lucky than good, but you can work for your luck.
- As messed up as it sounds, don't assume that papers who are laying people off aren't going to pay for freelancers. As guilty as you might feel about it, that paper who just cut 10 people has pages to fill and paying someone a few bucks for a story a couple times a week is a hell of a lot cheaper than paying a full-timer with benefits.
- Continue to work your way into a community. It will open up work on the PR, Photo and Advertising side away from news, and it can be profitable.
- Lastly, when you aren't working, make looking for more gigs your full-time job. Even if you can't land anything for a week or two, it isn't the end of the world. When it rains, it pours, and the more your name is out there, the more you open yourself up for consideration.