OK, so I picked a pretty good profession. I generally get to be creative and get paid at the same time. Since college, I have always worked for someone else. Later, I wanted to create something I could benefit from financially.
Having a day job and branching out from there has been OK. It has been some money on the side and a way to keep my skills sharp. Most of the time, work is good, but at times, it can feel like incarceration. That's especially true when you work in a cubicle that's about the size of a prison cell.
I would say that people who have a skill might start off on their own by looking at what they already know and going from there. It's a good idea. I must be like a lot of people who start out with something they have a passion for, and it turns more into art than a business.
I've gotten better about this, but when working on software, it's very easy to assume I know what someone might like to see, and what their needs are. Also, as the guy writing the software, there is an endless number of features that would help, and they all "should" certainly be included, or else no one would want to use it, right?
For a tech startup, it's pretty cool to be able to save all the money on software development, since I can do all that stuff. On the other hand, if I'm too busy enjoying what I do, it won't just turn into an actual business on it's own.
Hence, the double edge.