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That’s how many jobs I racked up in my journey to full-time freelancing. At least, that’s how many I can remember at the moment. From the age of 16 to 28, I was nearly constantly in a cycle of becoming dissatisfied with a job, looking for a new one, interviewing, getting hired, loving the new job, doing the best I could there, realizing it wasn’t quite right, becoming dissatisfied with it, etc., etc.

It’s an important cycle for people with high expectations for themselves, isn’t it? Trying on lots of different lives, getting way into them and then raising the bar a little higher? I could do better than this. I can reach higher. I could be more. This is how we get to where we want to be, by climbing, very sincerely, all the way there.

I just wrote up a list of all the jobs I could remember having since I was 16. Longevity has never really been my thing. Until (gulp) now.

I just wrote up a list of all the jobs I could remember having since I was 16. Longevity has never really been my thing. Until (gulp) now.

Apparently, it’s also an addicting cycle. Now that I’m successfully doing what I’ve always wanted to, I still get an inexplicable thrill from job postings. A communications director job within walking distance of my house? That could be amazing! A downtown development position in a community with lots of potential? I love doing that stuff! They’re hiring cashiers at Aldi? That’s almost next door! Maybe a few hours a week of interacting with discounted Fage would be fun!

Obviously, there is really no rhyme or reason to these reactions. Taking any new job, from corporate communications to retail would be totally disruptive to my career. To boot, I make more money now than I ever have before, and taking any of those positions would actually lower my income. Oh, and I totally love what I do.

So what is this urge? Why do I feel seriously tempted to put in an application at T.J. Maxx? All I can figure is that I harbor a weird infatuation with new jobs, and now that I’ve stumbled on the one I want to keep forever, the idea of “forever” is sort of freaking me out. I have career commitment issues. And I don’t think I am alone in this, am I, fellow freelancers?

I think, for us freelancers, part of the appeal of this life is that it’s ever changing. After a lifetime of trading one “not quite it” job for the adrenaline rush of diving into the next, we decide to build our own perfect(-ish) job. It’s perfect(-ish) not only because we get to define what we do, but because there are always new clients, new projects. Getting new work is part of the deal. And apparently, we sort of love the thrill of doing exactly that.

So I’m trying to interpret my irrational urges in the context of my “real” job. Maybe I’m just hankering for a new client, or a new project. Maybe, instead of staring dreamily at the hand-written sign taped to the window of Aldi, I should be browsing publications, sending off queries, or buckling down on my creative writing — or diving into something that hasn’t even occurred to me yet.

That is the real thrill of freelancing: the great depth of opportunity for newness and change. The great challenge is figuring out what that next new thing will be. Whatever it is, it’s imperative to focus on the ideas that propel us forward, not drag us in reverse. And alas, being an Aldi checkout girl is probably the latter.


* After being reminded by a very friend of mine that I neglected to include that one job that I wrote an entire book about, I updated this number to 17. I guess writing about it really helped me exorcise the entire experience!