Well I chose mine: living in Ancient Rome whether as a Roman senator under Julius Caesar, a woman under Nero, or merchant at the close of the Roman empire, there are many different choices you make to determine how you will end up. Most end in death seeing as how it's, I don't know, history! But there are a few ways to retire into obscurity.
Read Also:
There's a fun series "You Wouldn't Want to Be..." which tells it like it is, and from a contemporary viewpoint. Soon to be read: You Wouldn't Want to Be in a Medieval Dungeon
Jean Fritz's series about the founding of America includes titles such as And Then What Happened, Paul Revere? which puts a personal, first person spin on history. I've read her Shh! We're Writing the Constitution.