After my last permanent position, I took a few months off from work, and then tried to start a career as an independent consultant/contractor. After many years of hearing about the freedom enjoyed by consultants, and the exhorbitant fees they charged, I wanted to get my piece of the action. People encouraged me to give it a try, because I had many of the traits associated with independents: desire for variety, lots of knowledge, no trouble voicing my opinions, and no dependents who would go hungry if I couldn't find work.
My primary motivation was the desire to be independent. I wanted that whole be-you-own-boss thing. I wanted to be able to work less than 40 hours a week when I felt like it. I wanted to be able to choose which assignments to take. I wanted to be able to decide what new computer to buy and which development tools to use.
Unfortunately, this was mid 2002, and as all you people more clued into reality than me know, that was a bad time to try to start a contracting career. Established contractors were having trouble finding work. Those who were finding work had to charge fractions of what they used to charge.
The biggest reason I failed as a contractor was that I didn't have the business sense for it. I didn't know anything about marketing. I didn't know what my market niche would be. I didn't have a lot of contacts in the industry. I hoped I could just post my resumé on my web site, and jobs would start rolling in.
I did get a few calls, but most of them were for things that I wasn't really prepared to do. For example, my resume lists Oracle and OpenVMS. I was contacted by someone who needed me to provide training for employees who would be administering Oracle on an OpenVMS system. Ten years ago, when Oracle on OpenVMS was what I was doing, I may have been able to do it, but it had been so long that I didn't think I could do a reasonable job, so I had to pass. There were several other similar opportunities that I passed on as well.
In hindsight, I wonder if I should have taken a few of those jobs. I wouldn't have known what I was doing, but it would have been work and it could have led to something I knew better. I have never been comfortable claiming to be able to do things that I don't really know I can do. Other consultants don't have that problem.
I did manage to land a contract with a former employer. They did pay me well, but unfortunately only had a few hours of work per month for me to do.
Eventually, I gave up on the idea of being completely independent, and signed up with one of those organizations that hires people out as contractors. I got a good gig with them, but for no more money than I would have received as a permanent employee, and without security or benefits.
So, I gave up on contracting, and got a permanent job.
Will I ever go independent or start my own business again? Maybe. I think I do have a strong entrepreneurial streak, and a disdain for working at the direction of others. But I'm not going to try it again until I have a better idea about what products or services I will provide, and who will pay for them.