The Pleasures and Perils of Freelancing


If you were to believe the Internet—and who doesn’t?—the word “freelance” harkens back to circa 1820 when Sir Walter Scott first used the phrase “free lances” in his novel Ivanhoe to describe mercenaries who hired out their skill with a lance. Picture Roland The Headless Thompson Gunner but with a sharp stick instead of an automatic weapon.

As a freelancer, and in tribute to Sir Wilfred of Ivanhoe, I still carry around a sharp stick—a pencil—which I deploy in the defense of fair maidens and the occasional mega-corporation.

And although we contemporary freelancers can trace our lineage back to those galloping guys in armor, the perils of contemporary freelancing in no way involves bodily harm. Nobody has rushed chased me around a conference room with a mace or a hatchet (yet) but if they do, I’ll take comfort in “the pencil is mightier than the sword.” That’s the expression, right?

There are still, however—along with the considerable pleasures of freelancing—considerable perils.

For example, the crickets.

I’m sitting in my office right now and, in the absence of projects with an immediate deadline, I hear them. Crickets. Not Disney, “When-You-Wish-Upon-A-Star” crickets. These ingrates are mocking me.

Cricket: “Hey, Bozo. The phone’s not ringing. What are you going to do about it?”
Me: “Don’t you have some little wooden boy you should be pestering?”
Cricket: “Have you considered a career at Burgerville?”

Yes, these squishable little darlings are quick to point out my insecurities. Insights, however, are not their domain. The fact of the matter is that freelancing is a balancing act: Long periods of holy-crap-how-am-I-going–to-handle-all-these-head-spinning-deadlines, followed by, well… crickets.

Then there’s this: over the years I’ve seen more than one freelancer accept a full-time position with a happy client only to be laid off at the employer’s whim. During that interim when he’s been collecting that regular paycheck, his former clients have migrated to other full-time freelancers. Re-entry into the world of freelancing can be next to impossible. So, in actuality, a successful freelance writer or artist has as much job security as one that’s on the payroll.

That’s my theory and I’m sticking to it.

There’s a flip-side, of course. If you’re laid off from a full-time position, there’s that moment, that heart-sinking episode, when you’re taken aside and given the bad news, whether it’s pack your stuff and security will escort you to the nearest gin mill or sorry, here’s six-months severance, best of luck to you.

But in the freelance world, when the client says adios, there actually is no adios. And of course, there’s no escort to the local tavern (although as a free spirit, you can make a pilgrimage to your favorite gin mill at 3pm, if you so desire) and certainly no severance.

Just the sound of those crickets urging you to sharpen your lance, hop on your horse, and head off into parts unknown.

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