Telling stories

What? You want to freelance? Are you crazy?

Posted by southwrite on December 12, 2009

Image by Flickr user hall.chris25. Used under Creative Commons. Attribution-Noncommercial-Share Alike 2.0 Generic

There’re usually two points at which you question whether this freelancing thing is really a viable option.

The first one came before I took the plunge into full time self employment. I was working a 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 questioning whether I could really make a living. If I set out on my own would I be able to pay the bills? Would I lose my home and end up under a bridge with other poor souls?

You can probably imagine that moment of dread when the absolute worst that my fertile imagination could produce came forth in full form. I could literally feel the chill wind of a cold January night whipping through my tattered jacket as I huddled around a fire in an alley somewhere.

The second moment of doubt arrives much later – after you’ve made the plunge, set up your business and have probably amassed a long list of clients. A lot of us have wondered “did I make the right choice” lately as the long time clients disappeared into the sink hole of the recession.

Self employment is tough despite all those 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 freelancers 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.” That’s because we have our own ideas about how things should be and we innately know they are superior to yours.

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 progress 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 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?

Yet, given all that, I know of 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.

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?

6 Responses to “What? You want to freelance? Are you crazy?”

  1. Mickey said

    What makes me stick to freelancing? Bullheadedness, I guess, and a Pollyanna attitude that next year will be better. And then there’s the option to sleep in or burn the midnight oil — doesn’t matter as long as I meet my deadlines!

  2. So many things make me stick with it, but honestly, the main thing is the money and flexibility. I worked for years at daily newspapers and never made over $40k. I make much more than that now, and I love the thrill of going after new clients and representing someone I really believe in and enjoy working with. I also love the ability to cut loose a client who doesn’t see eye-to-eye with me. I have three small kids, and even though they’re in full-time child care/school, if they’re sick, I don’t really have to apologize to anyone if need to be with them. For me, it actually got a lot more interesting and enjoyable once I started doing more marketing and public relations work and got away from publication-based writing.

  3. Chere said

    I’m with you, Randy, like being on my own and I do do it better. 🙂 I also do it faster and when you work for a newspaper nowadays, that translates to “Make her do MORE!” But I love being home, on my own and accessible to my kids. Mo money would be nice…and it does get scary. Like really scary. But what a great life all in all.

    • southwrite said

      Chere, I agree. And, I couldn’t imagine working in an office again seeing the same people and doing the same work on the same topics over and over again. Still, I know what you mean about the fear. I’ve been reading a good bit about content mills that pay desperate writers 5 or 10 bucks story. To make a living you have to churn out an article every 10 or 15 minutes. I think: how can they do that? How could I do that? Then I look at what I am doing and realize, ‘hey, I don’t have to do that.’

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