I actually decided I wanted "freedom" tattoo'ed on the side of my neck on a weekend home leave from a low security prison. I was drunk (if they would have tested me when I went back to the prison they would have sent me back to high security. The first time I had a weekend leave I got drunk after being in high security for 8 months. I got the tattoo and it still exists on my neck today. Another time I was drunk I was going to get a teardrop tattoo'ed under my eye and was thinking about getting some names printed on my eyelids. Alcohol was the reason I made the decisions to end up in prison in the first place.
Probably not the smartest ideas but life is a constant learning experience and I wouldn't change it for the world.