Deciding to Freelance

Freelance or employee? As a creative, it’s hard to know how to make this decision. For some, it’s an obvious choice and you’d do anything to avoid being an employee. Or the opposite . . . you love the security of having a corporate job and all the benefits and opportunities it provides.

For me, it was an easy decision. Early in my writing career I worked as a technical writer for a few different companies. Over the years, I honed my skills and moved up the ladder until eventually I became a manager of technical writers. This was rewarding, as I could act in more of a mentor role and share my skills with other writers. And I could wrangle the details of managing writing projects involving many writers and other contributors.

Fast forward a few mergers and acquisitions for my employer, and I was director of writing teams literally all over the world–Portland, OR, Orange County, CA, Boston, and Delhi, India. Working with these teams and leading them to work together effectively was exhilarating, but not without its challenges. Eventually the company I was working for became so large that the internal politics overshadowed the joy I previously experienced in my career. I began longing for a different work lifestyle. One where I could be more in control of how I spent my time and developed my core craft of writing.

Then along came the bust of the early 2000’s. As corporate profits plummeted, many companies, including my employer, began “reorganizing” to increase their profits. “Reorganize” is corporate code for “downsize.” My position was one of the ones on the chopping block, and I was faced with the decision to either leave, or to lay off one of my employees so I could take his or her position. First of all, saving myself at the expense of one of my employees left me with a sick feeling in the pit of my stomach. But more importantly, I wanted to do something different anyway. The company was offering a generous severance package, so I decided to take the money and run. Finally I had a way to move from employee to freelancer.

I know I’m making it sound like it was a no-brainer, easy decision. This couldn’t be farther from the truth. It was an agonizing, painful time of consternation. I worried about whether or not I’d be able to earn the same high income as my corporate salary. I wondered how I’d find clients. And I thought about giving up all the corporate benefits that meant so much–lots of paid vacation, holidays, stock options, and most important, health insurance. I eventually came to the conclusion that leaving behind the stress, overload, and lack of fulfillment I was experiencing was worth leaving behind all these things and taking the risk.

That was 15 years ago. Since then, my freelance business has had ups and downs. But thankfully, many more ups than downs. I’ve learned lessons from the downs, and had fantastic experiences thanks to the up.

What about you? Whether you’re an employee or a freelancer, what helped you make the decision to land where you landed? Or are you sitting on the fence, struggling with making a change?




Cindy Written by:

A communications expert with over 25 years experience.

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