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Waaaay back before I was a freelancer, I worked at a real job. In an office. Then I couldn’t handle it anymore and I realized I wanted to be my own boss so I quit. It was a Friday. I was adamant about my decision when they asked me to stay.

I convinced them that they couldn’t change my mind, and since I was in management and had keys and security clearance, they told me just not to come in on Monday and they’d pay me out for my two weeks.

I had a nice weekend with my spouse. Then, on Monday morning, I walked into my spare bedroom/new-home-office, turned on the computer, and I was a freelancer.

Uh-oh. Looking back on it now, it was funny. I was totally unprepared but I had enthusiasm and I was motivated (I didn’t have a job to go back to!) so I started working. I had my first client by the end of the day and my second client by the end of the week and enough work to last me the month.

But if I had to do it all over again, here is what I would do different:

I quit on a Friday but I knew in advance that I wanted to freelance. Truth be told, I knew about two years in advance that it wasn’t going to be a lifelong career choice and that I’d much rather be freelancing.

I put up with the periodic lack of interest in my job because freelancing was never the right thing at the moment. But about two months before I quit, I had become fed up and knew it was time to leave.

In retrospect, I should have started positioning myself as an expert much earlier than after quitting. I should have started two months before when I knew. In fact, I should have started two years before when I knew it wasn’t the career for me! I should have been writing articles. (Blogs weren’t really around much at the time or else I’d say that I also should have been blogging).

So, if I were in my situation today, and I could somehow send a message to myself about what I should be doing, this is it:

  1. Identify what I’d much rather being doing. (In my case, freelance writing).
  2. Narrow down the subject matter to a set of niches. (In my case, there are three very specific niches).
  3. Start writing a regular blog. A daily blog if possible but a weekly blog at the barest minimum.
  4. Start writing and publishing articles on the web, in magazines, in trade journals.

I wouldn’t position myself as a freelancer (because I definitely would lose my job before it was on my terms) but I would position myself as an expert in the field… just someone who likes writing and thinking about the subject matter.

If I did this two years in advance – or, at least two months in advance – could you imagine the body of work I’d have built up and the authority I’d have achieved in the field long before I hung out my shingle?

A few other things I’d do if I had the time and could do it over again:

  • Start a newsletter.
  • Read everything I could get my hands on about the topic.
  • Interview people who would later become my competitors.

They say hindsight is 20/20. Well, if you are thinking about freelancing, look in my rear view mirror and do what I wish I’d done.