This is a biggie. To be able to make a living without a job, not only do you have to be able to think outside the box, but know that what was outside of the box a week ago has just found a bigger box! You will need to be able to have the confidence that you can learn new skills relatively easily and well.
I strongly recommend practicing learning new things on a regular basis. Take classes as often as you can. If you have a ferret brain, this is your chance to let it go wild. You can pick anything you want to know how to do. Learn to knit, learn to make bouillabaisse, learn how to program in LOLcode, learn how to install plumbing or the history of kimono-making in Heian Japan. For the love of the Flying Spaghetti Monster, don’t waste your time trying to decide if this is a useful thing to learn. If you become fascinated with the effects of left nostril inhalers on modern culture, go for it and dive in! You may or may not ever use it professionally, but keeping your mind flexible is crucial.
I’m only 40, so I’m hardly a Wise Old Woman, but I’ve been around enough to have learned that time spent learning something almost always pays off at some point.
Remember when I said one of the things I’m good at is systems building. That’s true. It’s a strength, but when it comes to self-managing, it’s also a terrible weakness. I’d much rather plan out a system than deal with its execution. My favorite moment in writing a new piece is to open my word processor to outline view and write the outline for the it. Visualizing the flow of the work is all kinds of fun. As much fun as planning is, and as necessary as it is, it is also necessary not to get bogged down.
That said, there are administrative tasks that are absolutely necessary to running a business or organization. It’s why a competent administrative assistant never starves.
Now, if you’re going to be a one-man shop, you probably won’t want to be hiring an employee. That’s okay to a degree. But, since we’re talking sK1lZ, I have to ask, do you know how to:
- Choose a business form? If not, talk to an accountant or your local small business association.
- Set up a file system? It should be limited to one file drawer when you start out. If it’s more than that, you’ve got something too complex that you won’t use. I will answer one email from you about this if you need advice.
- Do taxes? Plenty of self-employed people just suck it up and hire an accountant. I cannot in good conscience advise you do to otherwise.
- Choose what business equipment is right for you? This is really going to vary depending on what you do. I’m a writer. I could work from a smartphone if I absolutely had to. In practice, it’s a laptop with a wireless connection. When you start working for yourself and deciding what goods and services you’ll offer, take into account.
Many people tend to develop their own Baker Street Irregulars gang of “go to” people when they want to make sure they know what they need in a particular category. Most of those same people are Irregulars for their friends, too. It evens out and is useful. Being a knowledge junkie, as well as being willing to pass on bits of what you know (barring giving away competitive secrets. And I assure you I’m actually not here) is a good thing to do in working for yourself.
 It often seems to me that weaknesses wind up being out of proportion strengths. Since I have no sense of proportion at all… Well, you get the point.
 I actually dislike the term “Administrative Assistant” because these days the admin does the job that was truly what a secretary did back when we started using names like “Secretary of State”. The name for the copy and file person was “clerk”.