I’m Not Good At This Self-Employment Thing

The last time I held a full-time office job was right about this time in 2009. I think my last day was September 30th. I worked on-site on a project out of town until 10:30 that night helping my team finish up a report, went back to my hotel, and flew home the next day.

I then took off the next three months, something I had never done before since I worked through college, both during the school year and summers and all breaks. I’d take a two-week vacation most years after college, but the rest of the time it was work, work, work. Often sixty hour weeks.

I spent part of that time off traveling around New Zealand. I cannot tell you how amazing those six weeks were. Such a beautiful country, such amazing people, such fun things to do. I wanted more of that and less of the stress and deadlines of full-time work.

So January 1st, 2010 I got back to work as a self-employed consultant who worked from home (which in those early years turned out to be New Zealand a lot of the time). I’ve stayed working as either a self-employed consultant or writer ever since.

Now, you might look at that and think, “Well, you seem to be doing something right since you’ve been self-employed for seven years now. Don’t most businesses fail after five years?”

But I’m not really. It turns out I was so good at being full-time employed that it allowed me to coast into self-employment.

In two ways.

First, almost all of my consulting business has come from people I knew when I was full-time calling me up and offering me work. That’s what happened in December 2009 and it’s continued to happen since. Only one project I’ve worked on in the last seven years came from someone I didn’t know before I started consulting.

Worse, I like to work from home and I know that if I go out to companies and say, “Hey, you have any work for me?” and they say, “Yes. And it’s on-site in this random city” that I’m kind of stuck taking work that involves travel I don’t want. So I have sat back and waited for people to reach out to me and say, “Any chance you’re free?” so I can then say, “As long as I can work from home (and as long as the rate’s good).”

That’s not a way to run a sustainable business. A successful entrepreneur should be out there hustling for new clients or for more business from their existing clients. Instead I do things like decide that the work a client was giving me wasn’t challenging enough and wasn’t using my expertise (even though it was highly lucrative) and move on at the end of the project instead of hanging around for more opportunities.

That’s a horrible way to run a business.

And the only reason I can do that is because of the other thing that being good at full-time employment gave me: savings. I can walk away from a good-paying project because I know I can cover my rent this month one way or the other out of savings.

But you can only do that kind of thing for so long. And the longer you do it for the worse it all gets. The savings go down, the people who remember you become fewer and more far between. Your skills atrophy or your knowledge becomes stale.

It’s amazing how long you can coast without realizing that you’re failing.

I envision it sometimes as my early career was one of those ramps you see at the X games and I’m some motorcycle that has gone flying off the end. The initially trajectory was even higher, but at some point now that I’m off the ramp, I’m going to start coming down.

I think the year that happens is 2018.

Unless I finally get my head out of my ass and get disciplined about being self-employed and start to treat it like a real bona fide business that requires deadlines and focus (for the writing) or actually pursuing work (for the consulting).

(Before you get out the violins, I am in the five-figure range with the writing this year, so it’s not like I’m selling three copies. It’s just that it’s not enough for how I want to live.)

Anyway. As part of that effort to break myself out of this funk, today I read one of the books in the NaNo bundle: Time Management by Kristine Kathryn Rusch. Reading it brought home yet again that I don’t treat my writing as a real business. I’m still treating it as a hobby, which I can’t keep doing unless I want to go get one of those day jobs I’m so good at but hate.

So there you have it. Even though I’ve managed to do this for seven years now, I’m not actually good at this self-employment thing. But I’m going to get better at it, damn it.

I swear. (And I’ll get right on that after I waste the rest of this morning on the internet…)

Author: M.L. Humphrey

I'm a consultant with a focus on financial regulation and a writer with too many pen names.

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