Telling stories

The Utter Madness of The Freelance Writer

Posted by southwrite on June 13, 2014

Homeless Jobless

There’re two points at which you question whether this freelancing thing is really a viable option. You ask yourself “am I crazy to be doing this?”

The first one comes just before you take the plunge into full time self-employment. I was working 9-to-5 office gig when I began writing articles for trade magazines and a local newspaper. The number of assignments I was getting grew at a rapid pace. Soon the “spare time” didn’t exist and I had what was literally a second full time job. Still, I hesitated about making the jump —  could I really make a living doing it? If I set out on my own would I be able to pay the bills? Would I lose my home and end up sleeping under a bridge?

You know that moment of cold dread when the absolute worst that your imagination could produce came forth vivid and full blown. I could literally feel the chill wind whipping through my tattered jacket on one of those cold January nights in Atlanta. I huddled around a fire in an alley taking long drags on a cheap cigarette even though I don’t smoke.

The second moment of doubt arrives much later – after you’ve left your seemingly secure job, set up your business and gotten really busy. You wonder “did I make the right choice” as a long time clients vanishes and another doesn’t respond to your emails.

Self-employment is hard despite all the stories about how owning your own business is the only way to get rich. That’s true for some people, but for most freelance working stiffs the goal is just a comfortable life doing what you love.

At least that’s what we tell ourselves. For many the reality is that we don’t want to work for someone else doing what they tell us every single day of the week. We were those kids who came home from school with report cards that said “does not play well with others.” Freelancers are the little girls who were told they were “bossy.” They’re the stoners and the artists that the jocks and cheerleaders couldn’t stand.

We have our own ideas about how things should be and we want to live a life of our making – not someone else’s..

Moments of doubt also come when you realize what a disadvantage you (and all small businesses) are at in the modern economy. It begins with paying both sides of the social security tax and progresses through indignities such as little or no health insurance and bankers who snicker when you ask for a loan.

No matter how often Obama or some Republican congressman solemnly declares that small business is the heart and soul of the economy, we know that we have little influence on national policy. We don’t make big donations to candidates – in fact most probably never make political contributions at all – so why should they pay attention? While we might join an association like The Freelancers Union, (which bills itself as a “federation of the unaffiliated”), we know it’s not really a union and we’re still really on our own.

Given all that, I know few people who would give up the freelance life. Whether it’s the ability to meet the school bus every afternoon or wear fuzzy slippers to a home office, there’s an odd almost masochistic appeal to self-employment. We struggle, but find joy in a corner table at Starbuck’s with a steaming latté next to a laptop. We even allow our pride to rise as we think of ourselves as valiant and independent entrepreneurs. In guiet moments we think of ourselves as the direct descendants of the cobblers and shopkeepers who built America.

And, if anyone asks me if they should try freelancing what do I tell them? Why of course you should! Get out of that soulless office and become a real business person. There’s nothing better to do with your life.

So we’re back to the question: are we crazy to freelance? What do you think? Have you thought of giving it up? What makes you stick with it?

One Response to “The Utter Madness of The Freelance Writer”

  1. tammyyoga said

    I’ve not taken the plunge like you have. Too scary to not be sure when the next paycheck will hit the bank. But you make it sound very tempting to learn more about.

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