I lasted two weeks. Of course, if I had known the economy would tank I might have stuck with it.

A friend of mine asked me what the disconnect was, since it was work I did, I had the apparently (key word there) flexibility, and the pay was good. The people weren’t bad at all (no, they were great, actually) and the company was particularly good to work for. I hemmed and hawed and he–who runs his own company as well–said, “You were no longer self-employed.” I said, “Exactly.”

One of the key issues to being a freelance anything is ownership. I’m running my own business and I have clients. I’m not working for someone else. And in your head that can be a big deal. As I more articulately explained it, I worked very hard to get to where I was and I seemed willing to chuck it when someone threw money at me, but it didn’t take long for me to sort out my priorities. Your mileage may vary.

Really great post. Good to see the costs and benefits of two different lifestyles laid out so plainly, without much of an agenda (AND IF YOU FREELANCE, YOU’LL BE HOMELESS SOON!!!). Thanks.

Firstly, I’m a type A personality. I do things my own way, on my own time, at my own pace. I don’t respond well to over-bearing authority types. In fact, I lack the tact to deal with them. I have a confrontational nature, and having a bad boss just brings out the worst in me. I cannot stand having someone standing over my shoulder, telling me whether or not I’m performing up to their standards, complaining if I’m 5 minutes late, or took 5 minutes over on lunch, or that if I take a sick day off of work I’m going to lose my chance at promotion, yada yada yada.

The closest I came to being employed was a few years back when I was working as a sub-contractor for a guy up in Steamboat Springs, Colorado, on a series of resort condos and custom spec homes before I moved to Europe and transitioned into freelance writing. However, it was the one time that I truly enjoyed being underneath someone else. He never once nit-picked about anything. He allowed me creative freedom and trusted me enough to let me run the show. If he had suggestions or ways that he thought I could improve, he would do so in a positive-reinforcement manner, which is far more productive than someone point-blank telling you “I’m the boss, I write your checks, do it my way or you are fired”. If someone can build your ego up while they are suggesting alternate ways to do things…sure, I’ll try your way. After all, you just buttered me up! And he and his family were just great people, with plenty of outside-of-work-related functions like dinner parties, just hanging out at their house, and otherwise. It was an absolute pleasure to “work” for him.

But I enjoy my freedom. It is why I’ve been self-employed since I was 19. I’ve spent the last 10 years of my life doing exactly what I wanted to be doing with my life, in my own way, on my own time, blazing my own trail. I wouldn’t trade that for anything in the world. My freedom is far more important than a paycheck (although obviously if someone offered me a million dollars or some ridiculous amount for a “job”, I’d more than likely take it!), and I really can’t see myself doing anything but what I want to be doing for the rest of my life.

My wife is the same way, which she inherited from her mother, who runs a chain of grocery stores here worth over 16 million Euro. Her mom took the company left behind by her father and transformed it in the last 20 years from a tiny, two-store corner shop company into a 15+ mega-store business. My wife is currently working a part-time job while she finishes up her degrees, but her goal after she is done is to start her own business, separate from the family business. She is going to take her degrees, and her ideas, her passion and joy for the subject matter, and she’s going to run with it. Right now she’s working part-time and while she has an AMAZING boss who, for example, just let her take 3 weeks off for finals week, and lets her take time off whenever she wants and never pressures her about her hours, she just doesn’t care for the whole “be in the office by X” and having to deal with four to five or more people above you bossing you around.

Both of our families were entrepreneurs. We both seemed to have inherited those traits, and I’m content. I much prefer doing things on my own time than someone else’s.

As for the infrastructure piece, however — tax simplicity, benefits, insurance, all that — there is an option for freelancers to get those, and win the best of both worlds between telecommuting and real freelancing / consulting. A Portable Employer of Record (MBO Partners, my company) lets independent consultants operate on their own, set their own rates, have multiple clients, and KEEP all the cool business expense tax deductions of being in their own business, but while gaining the simplicity of W2 tax status, cushy group benefits, and having a professional team handle your invoicing and collections. The modest fee is generally more than offset by tax and insurance savings, although every situation will vary. [Free E&O means IT folks get a big bottom line bonus.] I love the company, and I hope your readers investigate this “middle path” as an option for running their business.

Oh, I’m @liz_greene on Twitter! http://www.twitter.com/liz_greene

Lisa

I’m so glad that you’ve been developing/growing the site here all along – I’m sure this has to help give you some sense of security as other opportunity rise and fall, right?