The Psyche of Self-Employment

employer-formYesterday I filled out the annual paperwork update at my doctor’s office. Name, address, phone number… the information has been so mind-numbingly consistent the last fifteen years, it seems silly they still bother to ask.

And then I got to the next line, where it says “Employer.”

A few days from now, I will officially join the ranks of the employed. So I hesitated: should I write in “Self” one last time, or change my status before it was quite honest to do so?

After two decades of working for myself, going to work for someone else is a pretty big adjustment—at least psychologically. Since that someone else is my favorite client, Boats.com, my actual work life won’t be changing that much.

But that doesn’t make it a simple transition when it comes to the little stuff, like doctor’s forms or questions from strangers. “I work for myself” always results in an eyebrows-raised smile, and usually there’s a follow up question: “Oh, what do you do then?”

Even though I’ll be answering the same thing to the second question, I’m going to have to wean myself away from the confidence-boost of self-declared self-supportingness, as well as its underlying unsaid companion: “Don’t you wish you could do that too?”

Here are some other things that will be different as a result of becoming employed:
1. The postman may notice that I’m not always asking, “Any checks?” when he shows up each afternoon.
2. I won’t be trolling for potential clients at parties.
3. I will have to plan a vacation each year.

The list of things that will NOT be different is longer:
1. I’ll continue to work at home.
2. I’ll continue to do something different almost every day.
3. I’ll continue to work with a great group of editors and writers.
4. I’ll continue to go to regattas.
5. I’ll continue to take care of a handpicked array of existing clients, though now it will be “on the side.”
6. I’ll continue to have days that are very productive, and those other days too.
7. My desk will still be messy.

And hopefully I’ll continue to maintain this blog, because it clears my head to write out thoughts without considering SEO or publishing plans.

So the hardest part is psychological. For the past twenty years, self-employment has been a big part of my self-identity.

But the next time I’m filling out a form at the doctor’s office, I’m going to have to write a company name next to ”Employer.” Which doesn’t seem like it should be so hard.

Especially since I have another 364 days to get used to the idea.

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