I thought I'd share my list of 11 things I've discovered from being self-employed. Your experience may differ, of course, and I'd love to get your tips if you've been down this road. This long, hard, scary, lonely road.
1) Your pay may vary, but the mortgage company or the landlord, the utilities, the health insurance, and things like that are pretty constant and none of them are known to have a sense of humor. It is very helpful to have a spouse with a normal job. At least there will be one steady paycheck in the family, one source of income on which you can rely, even if it doesn't cover all the expenses. You know what they call a guitarist without a girlfriend? Homeless.
2) You're not just going to go straight from college to running your own business, unless perhaps you've invented something. If you haven't written killer code or invented the Topsy Tail, however, you will need to develop a reputation in the field before you go out on your own. That means a few years in the salt mines. You'll need it to learn how the business works, not to mention all the jargon.
3) When you're ready to take the plunge, write a nice letter to everyone you think might help you. An individualized, friendly, upbeat, proofread letter, explaining what you're doing and asking for work or for contacts that might help you find work. Do not send a general e-mail to everyone, much less a social media blast---it's not just unprofessional, it's junk mail.
4) Never go out in a blaze of glory. Last year I got furious at a client who had assigned me a proofreading job after it became quite obvious that the editor had never had the thing copy-edited. (Copyediting is more time consuming and complicated and gets a higher rate of pay.) Either it was a major miscalculation on the editor's part, thinking the idiot authors had provided clean text (wrongo!) or I was being chiseled, getting proofreading pay for copyediting work. I was about to quit in a massive burst of anger, complete with badmouthing the company and maybe reporting them to any agency that would listen, but I did not. Somehow, probably God's help, I kept my head. I did the job for the rate I'd agreed to, but they were made quite aware of my feelings about it even though I was not rancorous. While I've still had some issues with that company, it's become my main source of income in the year since.
5) Stay motivated -- work as if you're still at the office and your boss's boss is waiting for what you have. And is looking at you funny because you're in pajama pants and a ratty old tee. It's easy to get distracted at home, especially if you have a long deadline for a project. Don't do it! A long deadline is an opportunity to be lazy, but get the project done early and fit in more work. Avoid time sucks like online gaming, Facebook, or committing to daily blog writing. (😀)
6) Screw days off -- take as much work as you can handle. Don't make yourself insane, but don't treat self-employment as a hobby, something to do to pass the time until your next vacation. If you don't need the money then you're taking work from someone who does. If you do need the money, work like you mean it.
7) People who tell you to set your price and stick to it are unrealistic, or are already successful in more lucrative fields that you probably work in. Maybe Annie Leibovitz can demand the moon and the stars from Condé Nast for a photo shoot, but the guy with a studio in the converted garage isn't so lucky. It's tough when they ask you to name your fee, because you don't want to go cheap but you don't want to price yourself out of the market, either. One employment counselor I met told me that whoever names a dollar amount first is the loser, but you may have no choice. Regardless of whether they make an offer or they demand you tell them what you want, it's certain that they have an idea of what they will pay and will not likely budge much because they've already budgeted for it. Use your most pleasant wiles to try to find out what that number is without naming one yourself.
8) Never blow off a client or job. You may not be able to take every job. You may find some jobs personally repulsive and have to refuse them for the sake of sanity. But always be nice, and do what you said you would do, or at least try to work it out if you can't. Even if one client is hideous, you don't know where your next and better contact will come from -- maybe even from the hideous client. (See also Blaze of Glory: Never Go Out In, above.)
9) Send presents. If someone gets you a contact, that leads to work, send a gift. When yuletide rolls around, send your clients gifts (something in keeping with your budget and how much work they gave you). So what if the person you're sending a gift to makes more than you do? Gratitude matters; acts of appreciation matter. Why do you think we even have the Popcorn Factory and Edible Arrangements?
10) Be HONEST. If you're billing by the hour, don't pad the hours. If you have an expense budget, keep strict accounting. It's a slippery slope when you start giving yourself gratuities, and eventually it gets noticed.
11) Do the best you can every single stinking day. Even if you fail, you won't wind up in a cardboard box under a bridge. Trust me. (Those primo bridge spots are all taken anyway.)