Success in Sweatpants

Why would anybody want to be a freelancer today?

Back in the old days—about ten years ago, give or take a few—the idea of “going freelance” was attractive to many of us. Working for oneself was (and still is) a big dream of people in the corporate world. There was (and still is) so much dysfunction in so many companies that make the work experience frustrating and downright painful for a lot of people. Ah, for the ability to ditch the suit, strike out alone, and still make the same money!

This was a pipe dream for most people; the only ones who made it work were well-seasoned upper management types who could “retire” to a cushy solo consultancy. The rest of the population of restless corporate employees either had to stay put or step way down in lifestyle and financial expectations to set up shop in the spare bedroom and start a freelancing career.

Just the word itself—freelancing—containing notions like autonomy, liberation, and self-determination, was enough to start the daydream projector.

“Wouldn’t it be nice if….?”
“Imagine what I could do if only…”
“There has to be a better way to…”

Freelancing was for people who wanted to make an income without the hassles of running a business. It was a vocation between art and commerce, where one could retain creativity and not “sell out.” Freelancers worked at home, were answerable to no one but themselves, and only needed to put on shoes if they were going to meet with a client.

Very romantic stuff.

But this leaves a few things out. The reality of freelancing has other aspects that aren’t quite so romantic, and that significantly limits one’s ability to grow revenues. I’ll go into the darker side of freelancing—and why it should be abandoned as a self-employment business model—in future posts.