I'm not the best artist or art director since sliced bread (who, by the way, was so successful he was practically rolling in dough), but I have been lucky enough to have worked on both ends of the art director/illustrator spectrum. For four years, I was an art director to illustrators, sculptors, retouchers, and graphic designers for a large corporation. For the past three months or so, I've been a dedicated freelancer.
I learned more about how to be a good freelance illustrator from being an art director than from any other source. With this in mind, I thought it would be a good idea to share some tips from an art director's point of view on what to do and what not to do as a freelancer. And now that I'm a freelancer, these are all things that I myself intend to live by.
1. Ask questions. If there's any ambiguity in a job, check with your art director. This is much better than guessing and sending in something incorrect. And don't feel stupid for asking questions either. Often, art directors have been at their jobs for long enough that they take certain bits of information for granted. If it's your first time working for them, they may forget that their company's jargon is unfamiliar to outsiders. And unless they're particularly surly characters, they'll appreciate that you're making an effort to get it right and do a good job.
2. Be as resourceful as possible in finding your own references and coming up with your approach. Art directors love freelancers who are problem solvers and don't need their hand held at every turn.
3. Don't let yourself get lonely. I could always tell which freelancers didn't get out of the house enough, because they'd keep me on the phone forever. A bit of fun conversation with an art director is great, but don't become someone that people have to make up fake meetings to get away from.
4. Send your invoice in a timely manner. Different companies work in different ways, but to me, the best time to send your invoice is within three days of completion of the job. Some of my freelancers would send their invoices along with their finished work, but I preferred those who gave me a chance to confirm that I didn't need any revisions. Waiting too long is disconcerting to an art director; it's another loose end that they can't tie up.
5. Don't be a pest about your invoice. Respect the terms of your payment schedule. If you're supposed to be paid within 30 days of the job's completion, don't start calling after a week to check the status. There were plenty of art directors at my previous job who wouldn't even work with certain illustrators because, even though they were talented, they nagged too much about their invoices. On the other hand, if a repeat client is taking an uncharacteristically long time paying an invoice, don't be afraid to give them a nudge. Sometimes paperwork slips through the cracks, and they may have forgotten or lost your invoice.
6. Have a good attitude. I was one of the many art directors who would not work with illustrators who were jerks. There were always plenty of talented and pleasant alternatives to choose from. I remember one illustrator in particular who laughed at me and talked down to me when I told him my project's tight deadline. I never contacted him again. I chose someone less skilled but more pleasant. When other art directors asked me about him, I told them that he was rude. A lot of other people had their own unpleasant experiences with him and avoided him as well.
7. Do remind your clients that you exist. If you haven't heard from an art director in awhile, feel free to give them a nudge and let them know that you're available, and perhaps send some new samples. But don't send out mass emails, and don't nudge your art director too frequently, or it becomes an annoyance. Once every few months is generally enough.
8. Don't procrastinate. Work on your assignment as soon as your schedule permits. You don't want to have to turn down any new incoming jobs because you procrastinated on an old one and no longer have spare time.
9. Whenever possible, send in your job a few days before the deadline, in case any changes are needed or if there are any technical difficulties with the file.
10. Do a good job every time. Imagine you do a crappy job on an illustration and send it off, and the art director says "Thanks, it looks great!" Are you thinking, "Yay, this art director is a pushover!"? News flash: sometimes art directors lie! They might just not have time to go over all the revisions with you; they might be planning to send it out to someone else or fix it themselves because they don't have faith in your skills anymore. And if you do a bad job the first time working with a new client, you may never hear from them again. You may be screwing yourself out of a repeat client. I sent far more work to the illustrators who did a good job every time than the ones I felt were "hit or miss." Give yourself the best chance possible by never sending in work you know is subpar.
(But don't worry; a lot of times "It looks great!" actually DOES mean "It looks great!" If you put in a solid effort, have faith in your skills and take the art director at their word.)
FYI: art directors absolutely do talk to each other! I worked in a building with maybe about 30 art directors, and there were no secrets. We'd often go to each other for recommendations on who would be good for a job, and we'd complain about the freelancers who were being a pain. One freelancer sent me a drawing for an angel figurine that was supposed to be feminine and elegant. When the angel turned out more buff than anyone on Dragonball Z, I showed everyone on my team, and we all had a good laugh. Some of us even had a "wall of shame" for bad illustrations. I know it sounds cruel, but it was a way to make the best out of a bad situation. Again, this is why it's so important to do a good job every time.
11. Don't miss a deadline. Seriously. Just don't. I was more forgiving about this than some other art directors; many of my colleagues would never work with someone again if they missed a deadline.
12. Take very good notes. (This applies more to direction given over the phone than through email.)
13. The last thing you should do before sending your completed work back to an art director: REREAD ALL THE JOB SPECS and all of the instructions the art director gave you, and make sure you covered all of your bases. This is probably the most important thing on the whole list, because it's the thing the most people seem to forget. It is SO important to be able to follow directions; an art director should not have to ask for the same thing more than once.
14. If you can't fit something in, be honest and decline the job. Don't miss your deadline or do a poor rush job (unless the art director has explicitly told you that they're desperate and will take anything you can possibly give them).
Just FYI, if you turn down jobs too frequently, art directors will give up and stop contacting you. (Hopefully you're turning down the jobs because a higher-paying client is keeping you too busy! If that's the case, good for you!)
15. Don't dump your personal baggage on your art director. It's not their problem that you're struggling to pay your bills, that you have a mortgage, health problems, etc. They can only give you as much work as their job allows, and they can only pay you as fast as their job permits. Sob stories only make things awkward and uncomfortable.
16. Clean up your work before you send it out. This applies mostly to stuff like pencil sketches. Adjust the curves, remove scanner burn, crop out the edges of the paper, etc.
17. Don't throw anything away. Keep all your old projects. You never know when a client might have a hard drive crash and need you to resend it. Also, components from old projects (like textures and references) can often be used as resources for future projects.
18. Don't lie or exaggerate about how much time you spent on a job or how difficult it was. (I've had illustrators do this in hopes of getting more money, and it was annoying.) And don't underestimate an art director's intelligence. True, some art directors may not be familiar with oils or Photoshop or whatever you use to create your work, but a lot of times they are. Often, they're not outsourcing a job because they don't have the skill to do it themselves, but rather because the parameters of their job don't allow them time to do it themselves. Don't claim to have spent all night lightening up your Photoshop illustration if the truth is you just played with the curves tool for thirty seconds. (And if you actually did spend all night lightening up your Photoshop illustration? Next time consider spending thirty seconds with the curves tool! Time is money, dude.)
19. If an art director asks for something that seems ridiculous, don't assume that they're wrong or stupid. They know what's acceptable to the higher-ups in their company, and they know what sells best to their customer. I've had to ask illustrators for things that went against my own artistic tastes all the time. Sometimes these were things my boss or general manager requested. Sometimes they were licensor requirements or technical requirements. If something really doesn't make sense, respectfully ask the art director why they want it that way. They may or may not have a good reason. If you think you have a better solution, consider presenting a rough sketch of your solution alongside what they asked for, but accept whatever choice they ultimately make, and don't take it personally.
20. Price your work competitively. If you're too expensive, art directors just won't send you work. If you under-price your work, you're screwing yourself. The ones who get the most work are those who do a good, consistent job at a reasonable price. I always preferred the reliable illustrator at an average price than the hit-or-miss illustrator who was dirt cheap. Ask upfront what the art director's budget is and go from there.