Here's a fun little puzzle for introducing some issues in decision theory. You want to invest a sum of money that is very large for you (maybe it represents all your present savings, and you are unlikely to save that amount again), but not large enough to perceptibly affect the market. A reliable financial advisor suggests you diversifiedly invest in n different stocks, s1,...,sn, putting xi dollars in si. You think to yourself: "That's a lot of trouble. Here is a simpler solution that has the same expected monetary value, and is less work. I will choose a random number j between 1 and n, such that the probability of choosing j=i is proportional to xi (i.e., P(j=i)=xi/(x1+...+xn)). Then I will put all my money in sj." It's easy to check that this method does have the same expected value as the diversified strategy. But it's obvious that this is a stupid way to invest. The puzzle is: Why is this stupid?
Well, one standard answer is this. This is stupid because utility is not proportional to dollar amount. If the sum of money is large for you, then the disutility of losing everything is greater than the utility of doubling your investment. If that doesn't satisfy, then the second standard answer is that this is an argument for why we ought to be risk averse.
Maybe these answers are good. I don't have an argument that they're not. But there is another thought that from time to time I wonder about. We're talking of what is for you a very large sum of money. Now, the justification for expected-utility maximization is that in the long run it pays. But here we are dealing with what is most likely a one-time decision. So maybe the fact that in the long run it pays to use the simpler randomized investment strategy is irrelevant. If you expected to make such investments often, the simpler strategy would, indeed, be the better one—and would eventually result in a diversified portfolio. But for a one-time decision, things may be quite different. If so, this is interesting—it endangers Pascal's Wager, for instance.