It really does depend on how much you win and how you intend to live. 1 million bucks doesn't mean a whole hell of a lot anymore, you can pay off your bills, max out your RRSP and maybe have enough left for a house (or condo out here in Vancouver). 5 million, now you start to get close, depending on what you spend and how large you live. If invested, you should be able to get $250K or so a year from 5 Mill, more than enough to live on, if you do it right. 10 mill plus, you are only working if you want to. Me, I would cash out and maybe volunteer occasionally to keep busy, but working for anyone else would end immediately at 10 mill and up. 5 for me means retirement much earlier, like 45 to 47 tops. 1 or 2 makes my life much more comfortable, but doesn't change that much.