1. Do Not Miss Deadlines.
Want to keep on doing what you're doing? Then do not give people a reason not to hire you again. If you feel that it's going to be a close-call, give the Art Director the head's up so s/he can make an adjustment. Doing this will accomplish two things: it will let the A.D. know that you are conscientious, and it will most likely give you more time/relief.
2. Keep Records.
It doesn't take that long to jot down your beginning mileage and your ending mileage if you keep a little notebook in your car. And keeping up with your receipts and logging them at regular intervals will make your Future-Self happy with your Present-Self. And your Tax-Time-Self will be the happiest of all! If you need cute little pens and cute little stickers to make bookkeeping attractive, do it. Whatever encourages you.
3. Say "Thank you!"
If you had a shop, and people came into your shop to buy something, you'd say 'Thank you, please come again!' Doing this in your metaphorical 'shop' never hurts either. These people are choosing YOU out of a LEGION of other artists, it's something to be grateful for. People remember who was pleasant to work with, and will choose to work with them again.
4. Remember That Telephone Manners/Attitude Are Important.
Building on the point before, keep in mind that as a freelancer, chances are most of your contacts with clients will be over the phone. Keep your tone friendly & professional, don't interrupt, and ask questions when you're confused over an art spec. Better to hash it out in the talking stage than after tons of time has been spent in drawing.
5. Get Health Insurance.
I know, I know: it's expensive. But it's important. You can go through a professional organization, but what I've found to be the most expedient is to go through your local Chamber of Commerce. They can hook you up with health insurance plans that cater to 1-person businesses. If you have a spouse who is employed and has health insurance, well, then, you've hit the jackpot! :-)
6. Get a Retirement Plan and Contribute Regularly.
Again, your Future-Self will thank you. Find a stockbroker that you trust and that can guide you through which stocks/ mutual funds, etc.will be best for you.
7. Time Management.
You know how much time the job you have will take, approximately. You know you have a deadline. You know you have to sleep, and eat, and probably mow the lawn. Designing is not just about putting little swirls on a piece of paper, it's about taking into account there only being so many hours in a given day. Giving yourself some padding, timewise, is never a bad idea. Gives you a chance to do any 'tweaking' on a piece, and you never know if someone's gonna get sick, or if the car will need to be taken in and you'll have to sit and wait for it.
I often hear the comment, "I could NEVER be self-employed! You must be so disciplined!" I don't think that I'm any more disciplined than the next person, and my answer is usually something along the lines of, "There's nothing more motivating than bills to pay." I think that there is a misconception that artists have to wait until there is a 'muse' who will inspire them towards creativity and industry. Nah. You work until 'it' comes, and THEN you ride the wave.
9. Work Schedule.
If you're going to be a freelancer, you're gonna have to know yourself pretty well. When do you work best? Are you a morning person or a night owl? Get sleepy at 2pm? Work during the times that you work best, if you can swing it. I know that there are other extenuating circumstances in a person's life that make working 9am- 5pm a more likely prospect, but: if you work at your best time, you work more efficiently, and get more done in a shorter amount of time. There will be days when NO time is your best time. Work anyway.
10. Managing Stress.
As a freelancer, I can pretty much guarantee that there will be stress in your life. Whether it's the stress of meeting a deadline, or the stress of finding work, or the stress of waiting for a check to come in: Count on it. But, deal with it, too. Exercise, eat right, get proper sleep: all those things that your mom told you to do when you were a kid but that you rolled your eyes at. Yeah, those things.
11. Dealing With People's Questions.
You will have interesting questions posed to you as a freelancer. Some people have ideas that all freelancers are of the of fuzzy slippers and jammy pant wearing, constant soap opera watching or constantly sleeping variety. There is really no solution to this line of questioning other than to answer their questions as honestly (not defensively) as possible. After awhile, they should see that you are a diligent worker who might have a slightly different schedule than most, but who still punches a "time-clock". Be patient, the comments will eventually stop.
12. During Times of No Work. Don't panic.
Panic causes productivity and creativity to come to screeching halt. You have other jobs to do during times when you do not have "paying" work. Market. Create a new promotional postcard. Work on some of your own projects that you 'never have time for'. Re-do your portfolio (online or real). Do some portfolio drop-offs. Got a backlog of laundry? dishes? yardwork? Do it! I have found from personal experience that more work always comes, and if I've spent the intervening time worrying, I have wasted the opportunity to get other stuff done, or have wasted the opportunity to rest/relax.
13. Support System.
Have one. :-) If you are working for yourself, by yourself, from your home, you will need human contact. Make sure you know some humans, and interface with them once in a while. If you are also fortunate enough to know other freelancers, form your own "support group".
14. Don't Be Under the Misguided Notion that an Agent Will Work Magic For You.
Maybe they will, I don't know. But don't think that once you have found an agent that is willing to take you on, that this will instantaneously bring you in truckloads of work. I would also suggest that you still 'keep on top of' your business. Do not abdicate your role as CEO of your company to your agent, or to your accountant, or to whomever else has a piece of your business. Know where the numbers are coming from. As my dad says, "Trust but Verify."
15. Don't Be Too Proud to Call.
Haven't heard from a client for awhile? Do not assume that they no longer like you, or your work, or that they think that your mother was a hamster that smells of elderberries. Contact them, remind them that you're still around, that you'd LOVE to work with them again, that working on the blahblahblah project was a blast, etc. Gentle reminders have gotten me work. Put your pride in your back pocket.
16. Keep Yourself Creative.
You know that old chestnut, "All work and no play makes Jack a dull boy." Well, how can you keep putting out creatively if you're never taking in? Go to a museum... Go look in the children's section of a book store... Take your camera with you on a walk... Take a class...Take up a new hobby... Get a pile of magazines on a subject you know nothing about.... You'll be surprised what following these other creative pursuits will do for your "paying" artwork.
17. Book your holiday in advance.
Book your holiday (if you're going to go away somewhere), 6 months in advance, and buy tickets, etc., at least 3 months in advance (of course get insurance just in case), so that you're obligated to go. Everything else will take care of itself (including timing and money). I have a "vacation" fund, and I save up for several small trips through out the year, and thankfully also have friends all over the country. I'll take long weekends to go visit them. I also have a special fund which is my "fun" vacation. I put a little in it every week and once a year I go some where - alone or with a friend - a bit more extravagant. My advice on that would be to block out some time in your diary way ahead of when you want to take your holiday, then when work comes in for that period, say 'I'm sorry, I have commitments during June'. Clients will think that they can persuade you out of a holiday, but they won't question 'other commitments'. And remember that it *is* an important commitment - to yourself.
When times are good, (or evening not so good), make sure you put money away in the bank. Not only will it help you through the sparse times when work is thin on the ground, it will also mean that you have money available should some sort of disaster befall you. If you spend from your savings, make sure you top them back up again as soon as you are able. This, of all things, takes a lot the stress out of freelancing, which is usually about money.
19. Don't wait until you are short of work to start doing marketing.
Freelancers are susceptible to the 'feast or famine' cycle, i.e. you either have too much work or not enough. It's far better for the nerves to level this rollercoaster out a bit, so try to always have some kind of background marketing going on all the time. Blogs are really good for this, so for those who don't yet have one, get one! Try not to fall in to the trap of 'I am so busy with this client I don't have time to market myself' because that will inevitably lead to 'Oops, no work.' Make time every week to do admin and marketing.
20. If you get really busy, put your prices up.
Instead of trying to cram more work in, try to earn more for doing less. Yes, I know, it's difficult for those of us with an over-developed work ethic, but seriously, if you're too busy it means you're not charging enough.
21. Always get a jump on a job.
If you procrastinate because you have a generous deadline, you may end up having to turn down other work that comes in when you're up against it.
22. Sensitize your antennae to what the art director says.
It may be something like, "The sketch looks great. . . at first I was a little concerned about the guy's hairstyle, but then I thought, no, I'm just over-thinking, so don't worry about it, everything's fine." That means--change the hairstyle!
23. Communicate early and often.
If time permits, fax or email the art director rough sketches before going to tight sketches. This has saved me a lot of wasted effort.
24. When you get last-minute or seemingly arbitrary changes, or stinging criticisms, accept them cheerfully.
Never express the irritation you may feel. The extent to which you can do this will go a long way toward creating successful long-term relationships. Some art directors have poor people skills. If you're one of the illustrators they feel comfortable dealing with, you'll be amply rewarded.
25. Have a slightly different take on vacations.
First, I tend to take many more short breaks than full-on trips. Second, I often combine them with work-related travel trip, tagging on a few extra days at the end of a conference, etc. Third, on the advice of my first shrink, I retrained myself to think of "vacation" as "different from everyday." So even if my "vacation" is moving my work to a remote location for a week, it still feels like a break.
26. Attend conferences and seminars.
They are a great way to stay visible, keep your skills up to date, and meet prospective customers, partners and suppliers.
27. Don't be afraid to (graciously) turn down work.
A project or a client that is not a good fit for your skills or your temperment will make you unhappy or worse, and interfere with your ability to do profitable work that you enjoy. You are defined not only by the work you have done, but also by the work you have refused to do.