I’ve always found it an interesting philosophical conundrum — in a truly (truly) free society, can you sell yourself into slavery? Is it permissable to want to be a slave? Or should people be forced to live a certain way, despite their own desires? How far can freedom go?
You can sell yourself into slavery, and agree to be treated like a slave and act like a slave, but you can't, in a legally binding sense, sign away your right to change your mind later. In a legal sense, involuntary servitude is prohibited under the 13th amendment; in a philosophical one, inalienable rights are just that. You cannot give them away.