Self-Help for the Self-Employed

Thirteen years ago I left my full-time job as Editorial Manager for Old Navy Marketing to embark on a career as a freelance copywriter. I didn’t have any solid work lined up. I didn’t know where I would find my clients. I didn’t think my savings account would last as long as it needed to. In short, I had no idea what to expect, except that I wouldn’t have to be at Old Navy Marketing at 8:30 the following Monday morning, which at that point in life meant a whole lot to me.

This makes it sound like I didn’t do any solid thinking before I quit my job, which isn’t really true. I did think — about the freedom, about the opportunity I was going to have to really explore my potential, about the lucrative hourly rate. This kind of thinking can motivate almost anyone to go it alone, but before you let it inform your resignation letter, stop for a moment and consider your experience and personality. You should be able to handle all aspects of your work without someone higher up to bail you out of the tight spots. Ideally, you’ve developed solid relationships with talented coworkers who not only know and trust your ability but have a similar yen for greener pastures — pastures where they’ll drop your name and get you some plum assignments. And most importantly, you need a certain amount of guts (be honest here) and the stomach for risk and uncertainty.

The first few months will suck. Lots of people will say they’ll send you work; probably no one will. Don’t panic — this is the first step on your freelancer’s path, and though the road will never be bump-free, it will smooth out ahead. The key is to realize the pitfalls of the “job” before they arise and plan your coping strategies in advance. The rules below will help. You’ll probably have to finesse them to fit your specific situation, but I promise you’ll have plenty of opportunity to perfect your methods.

Rule №1: It’s a service job.

The sooner you abandon the myth of the “creative job” and replace it with the reality of the “service job”, the better.

Clients aren’t really looking for you to come up with something that’s going to make you famous, they want you to help them build their business. Oh sure, they’ll tell you to “think outside the box,” but when they say that, what they really mean is they want you to know what it’s like inside their box, and then give them suggestions about what they can do to make it seem a little less square. This is a tricky thing to do, and at times a disappointing one, especially when you’ve come up with something truly box-busting. But if your client doesn’t connect with your bright idea, you shouldn’t insist on it. Ultimately, the client’s the one paying for the work and who has to live with the consequences, so they really do have to love the final product.

It took me two years of freelancing to really get this, and then only because someone else pointed it out to me. I had been working on a big project with a graphic designer I really liked, and we were lamenting the fact that our client favored a more traditional creative execution over something we thought was more original. Or should I say I was lamenting it.

“I just don’t get it,” I whined.

“Don’t waste your time trying,” my friend replied.

“I explained why the other option was better, but they just kept telling me they disagreed,” I said. “It’s really discouraging.”

“Look, Christa, it’s a service job,” he said flatly. “You just have to accept that the client gets what they want and move on.”

I didn’t like hearing it, but he was right.

Sometimes it still gets me down — all this effort and real creative thinking pushed aside in favor of more conservative ideas. But then I remember the concept of the service job, and maybe the check for the work comes in the mail, and my mood improves. Rest assured that eventually there will be a handful of projects that you’re really, really proud of, and in the meantime no one’s forcing you to put the work you’re less excited about in your portfolio.

After all, you’re the boss now.

Rule №2: Be here now.

If you’re like me and grew up in the care of open-minded and semi-bohemian parents, you’re undoubtedly familiar with the phrase “be here now.”

The idea is that by focusing on the moment at hand, you let go of any thoughts about the future, and since it’s thoughts about the future that tend to make a person anxious, letting go of them will instead make you feel peaceful in the present. Or so they say, because if you’re like me you also grew up with the expectation that life would be filled with big accomplishments, and so you find it hard to let go of your thoughts about the future, since it’s those very thoughts and the careful plans that followed that have helped you attain whatever measure of success you can currently claim. If you’re like me, the very idea of letting go of your thoughts about the future is enough to make you anxious — and yet, I encourage you to try, for if there’s one consistent thing about freelance, it’s that it’s never, ever consistent.

As far as I can tell there is no rhyme or reason to the quantity or timing of work I get. Sometimes I’m swamped; other times I’m twiddling my thumbs; often it’s somewhere in between. I work frequently with big clients who send me lots of little projects — product identities, packaging copy — and they almost always call just when I’ve given up all hope and started toying with the idea of going back to grad school to finish my psychology degree. And then when they do call, they inevitably want it back tomorrow.

Last summer I got a rush project the morning I was supposed to fly to L.A. to visit my best friend — this after three weeks of little to no work. I was not happy. I was not “here now.” I freaked out.

“Why does this always happen?” I asked the cat, who took time out of his demanding nap schedule to look up at me with that bemused attitude of his before sighing and tucking his head under his arm, only to fall back asleep in the sun.

I took the job, finished packing in a whirlwind, and started typing furiously, stopping only to slide my laptop through the security screen at the Oakland airport and then during take-off and landing, and by the time I reached L.A. I had nearly finished.

The point is that you never know what’s going to happen. Plans will be ruined, work will ebb and flow without warning, you won’t be able to establish any sort of routine. Accepting this is your first order of business. You must also accept that your checkbook will fluctuate wildly. Toward that end, I try to apply the model of good government I picked up somewhere along my educational trajectory, whereby I save when my personal economy is strong and can support itself and then spend on research investments (shopping) and social programs (spa treatments) to keep the outlook positive during the slow times.

Once you’ve learned how to stop hyperventilating when three jobs hit your desk at once, to go ahead and meet your friends for dinner at that fancy restaurant even though you haven’t had a paying gig in weeks, to get on that plane to L.A., then, and only then, will you know you’ve arrived.

Send me a postcard when you get there and let me know what it’s like.

Rule №3: Perfect the art of polite disengagement.

Most clients are nice. They respect what you do even if they sometimes ignore your advice and they genuinely want your working relationship to be a pleasant one. They inquire as to your well-being and the state of the weather in your neck of the woods, and those small questions go a long way toward making you feel welcome in their working world.

But there are the bad seeds. These clients will push your buttons, take advantage of your willingness to meet their impossible deadlines, send you down paths you know are dead ends before you even begin. Nine times out of ten you won’t know you’re dealing with such a person until you’ve already accepted the job, and by then it is far too late to back out. There are three things to keep in mind when this happens: First, be grateful you’re a freelancer and not this person’s full-time employee. Second, limit your communication with them; engage only so much as required to get the job done. And third, don’t give in to your impulse to tell them off.

I’ve only had one truly bad seed. For weeks, she was sweet as a bunny, and then one day she went all hyena on me, tearing at the work with bared teeth, barking out a series of inconsistent and self-contradictory orders, clawing and scratching to emphasize her power. This made me furious, and I found it difficult to make it through her project, much less make it any good.

During this time, I spoke to a P.R. executive I often collaborate with. After we finished discussing business, talk turned to more general topics, and I found myself telling him the whole story of The Bad Seed. At the end, I said, “I just want to call her up and tell her that I don’t appreciate her attitude, that I’ll never work with her again, and that I’ll tell every other freelance copywriter I know to avoid her.”

There was laughter on the other end of the line, and then, “Don’t.”

“Oh, I know,” I said. “But it’s just so tempting!”

“I understand, but I can tell you from personal experience that reprimanding a client never works,” he said. “It feels good for about ten minutes and then you realize how unprofessional you’ve been and guilt rushes in and you feel stupid about it for the next ten months.”

“So you just have to suck it up?” I asked.

“Enough to get through the project. But then you go into what we like to call ‘polite disengagement’ mode, where you are just too busy to take on other work from this client. That way you avoid working with them, and you also avoid making any enemies.”

Is it any surprise this guy’s in public relations?

So I finished The Bad Seed’s project, and the next time she called I was “too busy” to help. She said she understood — and I secretly think she understood I wasn’t really all that busy, which is fine by me. When I told a dear friend (and fellow freelancer) about my situation, she gave me the advice that an old mentor of hers had given her when she was in a similar situation: All current clients eventually become former clients.

I love a phrase that blends truth and cynicism by equal measure, and so I adopted its line of thinking then and there, assuming I’d seen the last of this particular bad seed. But then in a completely shocking twist, she sprouted again six months later with another job, and this time I took it and everything went fine. Sure, I don’t trust her any further than I can throw her, which given my lack of upper-body strength isn’t very far, but it seems backing off sent the right message.

So next time your hackles are up, pause for a moment and consider polite disengagement. Tell off your car, your computer, your couch— just don’t tell off your client. You’ll feel stupid if you do, and you might lose more than just this one client. It’s a small world out there, and unless you’ve really perfected the financial aspects of Rule №2, that’s something you definitely can’t afford.

Rule №4: Always brush your teeth.

I’m not going to spend a lot of time on this, but freelancers, you know what I’m talking about here, and the rest of you can stop your snickering.

It’s only natural for those of us who spend the vast majority of our time at home alone to occasionally forget to comb our hair or take all day to put in our contact lenses. Since turning freelance, my wardrobe has gone from dress pants and designer shoes to consisting almost exclusively of yoga clothes, the slightly more stylish version of sweats, which I wear whether I’m doing yoga or not. The point is comfort, and unless I’m going out, or until video conferencing becomes an all-day, everyday reality, I just don’t see any reason to put on fixed-waist pants or hard-soled shoes when I could just wear yoga clothes instead.

My husband calls them my “day pajamas,” meant to differentiate them from my night pajamas, which tend to have more print in the pants. He pretends not to notice when I sometimes fall asleep at night still clothed in the day version, and luckily he’s not around to see me on those days when I finally take a break at noon only to realize I’m still wearing the night version. In adhering to Rule №2’s “be here now” principle, I’ve abandoned all hope of ever having a routine, and it seems this applies not only to what I do but to what I wear as well.

But there is one thing I’m a stickler about. One thing I know it’s not okay to stop doing, no matter how few people I see in a week or how often I actually leave the house. I can wear the same clothes four days in a row, wash my hair only once in a week, but I will always always brush my teeth. The day I forget to brush my teeth is the day I start looking for a full-time job, and I encourage you to think about it the same way. You want other people to take your work seriously, right? So you need to take yourself seriously. Me, I can do this even if I’m in yoga clothes and my hair is falling out of the ponytail I put it in at 7 a.m., but I can’t do it if I haven’t brushed my teeth. You’ll feel better about yourself, I promise, and it will mean fewer trips to the dentist, which is a good thing since you’re probably paying for that out of pocket now.

Once you’re established, freelancing really is a joy. You may work some weekends, but you’ll have lots of random afternoons off. You may worry about money from time to time, but you’ll have lots of months where you’ll feel excessively flush. You may long for clients in the beginning, but eventually you’ll have the privilege of choosing for whom and how much you work. You can manage your money and your time any way you see fit. You can take work from the clients you like and leave the rest. And you can do it all in your day pajamas or your night ones, and only you and the cat will know.

Just please, brush your teeth.