When should a supervillain retire?
You should retire at the same time as any other job: when it's not fun for you any more. We get into villainy because it's exciting, it's profitable, and it fills a need for us. We get out because it's not those things any more, plain and simple. You may not always recognize when you've reached that point. If you find yourself taking risky chances, or blowing off your usual precautions, consider those warning signs that villainy is wearing thin for you.
The more powerful a villain gets, the more they become alienated from humanity at large. This can be good or bad. It means not getting so fucking irritated with people, but it means you can't get as much joy from the awesome things people do any more. I can't stress enough how important it is to have something to hold onto. For a lot of us, it's villainy. But you must have something.
Other than that, there's no point past which you really must retire. You can never have enough stuff, as long as you're able to keep track of it all (or don't mind losing the rest).
What should I do to retire without getting caught by heroes, the cops, or whatever?
If you have a lot of stuff you want to hold onto, you'll need to exert some effort. Here's a few suggestions on how to proceed.
- Move your stuff out of the country. Get as many material assets together as you can, and go settle in some lawless location for awhile. Establish yourself there for awhile. You'll want to slowly move these things through the local economy to launder them.
- If you've maintained a secret identity, keep maintaining it. Your goal is to seemingly come into money (your illicit earnings). You'll need to find a suitable cover story, then get your assets from wherever you stashed them.
- If you haven't maintained a civilian identity, things get trickier. Whatever identity you were born with has left a big person-shaped gap in the system. You can try to go back to that, but I don't advise it.
- Think about whether you want to naturalize somewhere else, or try and regain U.S. citizenship. For the latter, you'll need a passport and plenty of supporting evidence.
A lot of American expats make good money selling their services as fake parents for this purpose, if you can't find an official who will play ball, and can't afford forged papers. This should be the means of last resort, but I felt compelled to mention it.
Frankly, I think the effort required to come back to America and live isn't worth it for a lot of people. For them, go retire in some sunny tax haven. Those guys just want to see money and have some confidence that you won't stir up trouble.
No matter what happens, you need to stop using your recognizable powers. You can masquerade as a Stage 2 - just being super isn't itself illegal - if something happens to you.
Can I retire from villainy to try being a hero?
Absolutely! Just remember that knowing how villains think, that having that level of sympathy with us, may compromise your ability to take action. I'm going to talk more about this in a series on villain morality, but instead of heroics, consider life as a rescue worker or something - a job that won't bring you into conflict with your former associates, and that could still be personally rewarding for an altruist.