I spent 20 years as a career criminal.
To do this and not be a career convict, your entire lifestyle has to fit your career choice. A few examples:
Overall, the life of a career criminal is very restrictive. I couldn't have a tattoo, couldn't casually mingle with people, couldn't dress in a way that stands out. You can't ever really relax.
Don't get me wrong, it was tons of fun, the money was decent, and I don't regret doing it all those years. But it is truly a lifestyle, at least if you don't want to spend the rest of your life in prison getting raped.