There are several things that I always find when playing this game with others. The first is that many people have the impression that a large fraction of lottery winners go bankrupt, and that's not really accurate. It does happen, but it's almost never a case of people not knowing where the money went, it's a matter of making bad investments like starting a business that doesn't work or buying into some scheme. Virtually everyone who hits it big and then goes bankrupt loses the money in one or a few big losses.
The second is a misunderstanding of debt pattern. Virtually everyone I know who talks about winning more than $1M says they'd pay off their mortgage, but most people I know pay lower than average portfolio rate for their mortgage so they'd be better off setting up a fund to pay down the mortgage as normal and investing their winnings. Because of the first paragraph and stuff like this, I tell everyone that the first step to winning a big pile of money is to figure out which financial professional you'd talk to right after you hang up with the lottery commission.
The third is that once you get over a million dollars, most people lose perspective. There are many I've seen who think that a million dollars isn't life-changing, and that $5M is on the edge of life-changing, until I point out that investing $1M at a rate of return around four percent (which is way below an average portfolio), you earn a yearly income of $40,000 with absolutely no penetration of capital (meaning your $1M stake never gets smaller if you take out 40K or less). With this, $5M would net you $200,000 a year. Since most of us don't earn anywhere near that kind of money, it would be very easy to make changes like a maid or a new house or quitting your job or whatever at that income level. Getting paid $40,000 a year just for the effort of getting out of bed in the morning would certainly change my life. The best example I figured out for this is to show that you could live exactly the same life you live right now, but take a first class trip around the world for two weeks every single year without eating up half of the money you'd earn without shrinking your stake, if you had a million dollars.
So, how does that perspective change things?