Once upon a time, I graduated from a liberal arts college and thought, vaguely, "I wanna be an artist." I sent out what may be one of the worst sets of samples ever recorded, and a month or so later, sensing that it was gonna be a long, hard road, I went and got a real job. Reading insurance malpractice claims. No, it wasn't fun. I'll spare you the gruesome details of all the jobs I worked between then and now, but for our purposes, know that it took four years from graduation to going full-time freelancing, and without having a husband who makes money a bit more regularly than I do (although still not as regularly as a normal job!) I wouldn't have made it. The first few years I made probably less than a thousand dollars on art. Total. Only in the last year did things really start to pick up for me.
What I have learned...
1. Freelancing is sporadic. Some months I make more than I did at the highest paying job I ever had. Some months I make less than I would flipping burgers two days a week. Often these months will be back-to-back. In order to survive, it is best to have A) a Significant Other with a reasonably solid job, or B) a savings account to live on when your client is waiting on the check from their publisher before they pay you. This also keeps you from having to do "Pity Auctions" and so forth, which is a huge turn off for a lot of buyers. It's not just paychecks, either--right now I've got a commission waiting list out to May. Last year this time, I couldn't have sold paintings for five bucks with a free candybar. Work is sporadic. It will not trickle in gracefully in measured doses. (My husband and I had a system for about six years whereby one of us would work a Real Job while the other one freelanced/went to college/worked on a Big Project/whatever. Finally we're at the point where he's reasonably steadily employed as a contract environmental artist, and I can freelance, and we both work at home.)
2. Deadlines are a sacred writ. If they say "I need it by Tuesday," then be sure you can have it done by Friday, because the odds are good they'll want changes. Always leave a few days padding for changes. Miss a deadline so that they miss their publishing date, and you can probably kiss future work from that client goodbye. If you don't think you can get something done by a deadline, don't take it in the first place. Most clients will respect you saying "I'd like the work, but I know that I can't get it done by then, I'm sorry, keep me in mind in the future." They will not respect "Sorry, it's not done." Occasionally a desperate client will ask you to do something heroic, like paint an entire cover in five days. If you can do it, you will make a friend. If you know you can't do it, tell them so. This can occasionally work to your advantage--I recently finished a cover where the author wanted a major revision three days before the deadline. I confronted the editor and told him in no uncertain terms that while I could've done it a week prior, I had severe doubts that I could get that much repainting done that fast--I was willing to try, but I couldn't promise anything. We reached a compromise that was a lot more feasible. The Deadline is Sacred.
3. No excuse is good enough. If it's not done, it's not done. If it's not right, it's not right. Unless you're in a coma or dead, there is no excuse that will change the fact that it is Not Done. Not right can be fixed. Just be sure you allow yourself plenty of time for the fixing. If it's not done, then unless you own a time machine, you're screwed. Don't tell them WHY it isn't done. They don't care. Just get it done as quickly as humanly possible, and hope that they don't tell their friends about you. I realize it goes against the grain, but crappy art done to spec, on time, is often better than brilliant art a week late.
4. Learn to work a schedule. This is a hard one. I get up every morning, eat breakfast, run any errands I need to run, and then I start working on the projects of the day. After about five or six hours, I take a nap. Then I work on personal artwork, or any projects that I'm really jazzed about or that I think might need extra time put in. Generally I'm doing at least ten hours of art a day, usually more. I keep a schedule, planned out a week in advance, based on what projects are coming due when, and alotting at least a day more than I think they'll actually take. This can be a really easy one to slack on, since nobody's forcing you to punch a clock. I don't clockwatch now. I don't have time. Nobody pays you overtime as a freelancer--if you get it done in a morning, you get the same amount of money as if it took you a week of sixteen-hour-days.
5. Take out tax money in advance. This is a BIG one. Don't spend everything you make. It will come back and bite you in the ass next year if you do. Dump more into savings than you think you'll need--at least a quarter of your income, if not more. You'll be glad you did.
6. Most jobs come from exposure. I've done a fair amount of mailings--not as many as I SHOULD, I'm sure, but some. I've garnered a fair amount of rejection slips. A large amount of my work has nevertheless come from people seeing my stuff on Elfwood or VCL or DeviantART or whatever. These are small presses--they don't pay huge amounts, but it's work, and it's what's keeping me afloat at the moment. I still keep contacting people, and I should send out more mailings than I do, but I also try to maintain a pretty big web presence, including my own website and galleries on all the major archives. Mailings DO pay off, but you have to do it in quantity.
7. Take time for personal art. This one is what keeps you from burning out. On the weekends, I try to work on stuff for me. A lot of it may be marketable later, but I have to enjoy it. This isn't set in stone--if I've got a big deadline, or if I'm inspired on something, I'll work on commissions, but I have to have SOMETHING that I enjoy painting, be it my comic or random furry stuff, or whatever. These usually turn into money later, so it's a good thing.
8. Learn to juggle. Projects, that is. You can't just work on one thing, and then one thing, and then one thing, or it'll be a long time between paychecks. You gotta keep a half dozen going at once--when you send something off to someone to approve halfway through, switch over to the next project, don't sit and wait for their response.
9. Keep in constant contact with the client. Send them intermediary stages. It's much easier to make changes to the pencil sketch than the oil painting. When you have to do a proposal, send them a couple of things that are exactly what they asked for, and at least one thing that isn't, but that would look cool. They'll be impressed that you've taken the time to think about the project in different ways, and a surprising amount of the time, they'll go for the design that looks really good, even if it isn't exactly what they thought they wanted. You just gotta give 'em the choice. Even if they go with one of the standard designs, they usually will appreciate having had the option.
10. They will change their mind. Always plan for this, and give yourself at least a week extra to deal with it when scheduling. Don't take it personally. It probably doesn't mean that your work isn't working, it probably means that somebody said "Hey, we gotta get a chicken in that painting!" or something. Much art is designed by committee. This is the breaks. Bad art that looks like what they wanted is better than good art that isn't right for what they need.
11. Relax. You'll be poor for quite awhile. Your art won't be amazing for years. You'll get a lot of crappy jobs designing incredibly stupid stuff, or painting over brilliant bits of art when the cover design changes. You won't get to paint just what you love. Learn to live with it. Don't plan on having kids for awhile. If you're in art for the money, you need a seriously reality check. But on the other hand, this isn't brain surgery or rocket science, no one's life depends on you rendering a squid exactly so, and my god, art as a career sure...as...hell...beats flippin' burgers.
Life is too short to do something you don't love. Whew, that was long, wasn't it? However, speaking of flipping burgers...a new Gothbat.