To freelance or not to freelance, that is the question

by Dwight Hobbes
published Feb. 2, ' 09

I reflect, when folk give admiring smiles and extend compliments upon learning I write freelance as a profession. Reflect and say little while they speak on how excitingly adventurous and profoundly rewarding working such a job just has to be. Not that it’s not adventurously rewarding. It also ain’t nothin’ nice. Jackson Browne put it well with “Ain’t bad work if you can get it, but you gotta make it stick.”

That’s key. And even if you make it stick, there’s no guarantee you’re getting rich. Hell, you’re lucky to keep your neck above water. Which is why I rarely admit, much less brag out being a writer when I’m anywhere. I sure don’t broadcast it to women. There’s no surer anti-aphrodisiac than a man dancing one step ahead of the devil to keep a roof overhead.

Works for me. Been in more relationships than I care to recall, ain’t real sociable to begin with and manage to keep the rent paid.

It is a tightrope. Especially these days. A magazine I steadily wrote for, for about a decade, is turning more and more to staffers. That, of course, is where the fat money is, signing off on a contract with one of the glossies. So, it means a whole lot of scrambling after as many small paychecks as you can get your hands on. On the bright side, I scramble better than eggs: no brag, just a fact—like Yogi Berra said, “You could look it up.” Cobbling a check here with one there and another from somewhere else, the job gets done. The bills, it goes without saying, are always late (it’s when they don’t get met at all that you need to worry). Might sound funny, but frankly, I feel like I’m way ahead of the game. Live in a decent neighborhood, don’t punch a clock and do exactly what I want for a living. How many people you know can say that?

Wasn’t always this bed of roses, though. Starting out, I starved like a dog. Had got fired from yet another office job and it finally dawned on me. Anyone with a good ten years secretarial experience under his belt (didn’t really have the legs for it, but typed well enough and could charm your drawers off on the phone) who loses, what was it, four jobs in roughly a year and half, is meant to do something else. So, instead of brushing up my resumé and hitting the bricks, filling out applications, I took stock of things. While working days, I’d sporadically placed articles regularly at a weekly paper. The apartment cost give or take what I made each month from the paper. My daughter, then 18 months, lived with her mother. And I wasn’t getting a day younger. Hell, it was time to go for it. I’d like to be able to say I sat down, figured out a budget: x amount of money for this, for that and so forth. But I didn’t. Yet, I stayed no more than a month or so behind on the rent, made at least three child-support payments out of four every month, and counted myself lucky. Each and every day I showed up at the neighborhood soup kitchen and food shelves.

A grumbling stomach didn’t bother me much and, for that matter, kept me from getting a gut. The landlord’s complaints, though, did keep my teeth on edge. So did the telephone and electric company disconnect notices. Fortun-ately, the faster you play the music the harder I dance. Six months into subsisting basically on peanut butter, jelly and hotdogs, the worm turned. The time I’d spent moonlighting had resulted in a good enough rep to get semi-regular work. Which I gobbled up with both hands. The rest, as they say, is history.

I don’t recommend this line of work. It’s hell on the blood pressure and, truth be told, I wonder whether my daughter sees me as a failure because I can’t provide for her some of the things her friends take for granted. But, like birds gotta fly and fish gotta swim, I have to write. Sue me.