Unlike Joaquin Phoenix when he said he was going to retire I think Justin Bieber actually thinks he is going to retire. Maybe he fully intends to stop his endless touring and just sit back and live off his millions for the rest of his life. It is exactly that reason why he won't. Can you imagine Justin Bieber with nothing to do all day or night forever? Yeah, if you think he gets into trouble now wait until a 19 year old has nothing to do all the time except think about what pot he is going to smoke that day or which women to invite over to pass out. All Justin has to do is look at Michael Jackson who had way more money than Justin Bieber and was nearly bankrupt before he died. The only reason Michael Jackson was going to tour and play all those shows in London was because he was broke. You get used to spending a certain amount of money based on all the money coming in and when it stops coming in you don't cut back and live within a budget. Does Justin have enough money to retire? Yep. Will he cut back? Nope.
He probably also thinks he can come back at any time when he needs a few bucks and he will be fine. This is a lot like the actor who jumps to movies and bombs at it and thinks they can go back to television. It is really hard to go back. Justin will always be able to make a living touring but it is not going to be in 20,000 seat arenas. It is going to be in the 5,000 seat (insert name of Indian casino here) arena for a fraction of the pay.
Being a recording artist means never taking your foot off the gas. Ever. If you are successful you have to keep pressing the gas forever or never be able to get it back.
Source:
http://www.crazydaysandnights.net/2013/12/justin-bieber-says-hes-retiring-but-he.html