I promised a few weeks ago that I’d make another post about “seemingly para­dox­i­cal matters”, and I’m finally making good on that promise.1 Be fore­warned, how­ever, that this post doesn’t really have any­thing to do with any­thing else. It’s just a cool para­dox (or “puzzle” or “problem” or what­ever other ‘p’-word you want to call it) I learned from my roommate.


The para­dox hinges on the notion of expected value, so first we’d better under­stand what that is. Let’s say I flip a coin, and if it lands heads I give you a dollar. But if it lands tails, you have to give me a dollar. Then your expected value from this game is $0 over­all—in any given round you’ll either gain or lose a dollar, but in the long run you’ll break even. Your aver­age expected gain from any single round is $0.

Let’s change the num­bers a bit. Now I give you $2 if the coin lands heads, and you give me $1 if it’s tails. Assum­ing I’m not using a weighted coin, this sounds like a pretty sweet deal for you, right? In any given round you have an equal chance of win­ning $2 or losing $1. Over many rounds you should aver­age a net gain of 50 cents per round (.5 * 2 + .5 * -1). So we say that the expected value of flip­ping the coin is $.50.

In gen­eral, you can cal­cu­late the expected value of any random vari­able by mul­ti­ply­ing the prob­a­bil­ity of some out­come by the value of that out­come, then sum­ming these over all pos­si­ble out­comes. For exam­ple, the expected value of rolling a die would be (1/6) * (1 + 2 + 3 + 4 + 5 + 6) = 3.5, since every value from 1 to 6 has an equal prob­a­bil­ity of coming up.

Now that we have this idea of expected value, we can also define what it means to play a game ratio­nally. Quite simply, a ratio­nal player is some­one who always makes the choice that max­i­mizes their expected value from the game.

Alright. With those pre­lim­i­nar­ies out of the way, let’s get to the good stuff. Here’s the game: I offer you two envelopes, both of which con­tain checks writ­ten out to you. One of them is worth twice as much as the other. With no other infor­ma­tion, you pick one of the envelopes and get to keep whatever’s inside. Not a bad game for you, eh?

So let’s say you’ve selected one of the envelopes. But before you can open it, I inter­rupt you:

“Hold up! If you’re having regrets, I’ll let you switch to the other enve­lope, no strings attached.”

“Well that’s kind of a dumb offer, Greg. If I had really wanted the other enve­lope, I would have chosen it in the first place. What do you take me for? Some kind of flippity-​floppity flip-​flopper?”

“Of course not! I’d never dream of insin­u­at­ing such a thing. But here’s the deal: I just so happen to know that the enve­lope in your hand con­tains a check for $10. (I know this because I put the check in there myself.) Which means that this other enve­lope—the one I’m hold­ing right here—has either $5 or $20 in it. It’s a 50-50 chance either way, right?”

“I… guess? Sure.”

“That means the expected value of my enve­lope is .5 * $5 + .5 * $20 = $12.50. As a ratio­nal indi­vid­ual, you should obvi­ously switch envelopes, since the expected value from switch­ing is higher than what you’ve got now.”

“But Greg, that is stupid. If I had chosen that other enve­lope in the first place, you could have gone through the exact same song and dance, con­vinc­ing me to switch to this one.”

“That’s true.”

“So why would I switch?”

“Because your expected value is higher, and you’re rational.”

“But I don’t want to switch.”

“But you should.”

“But I like this envelope.”

“So are you some kind of irra­tional crazy-​person, then? Is that what you are?”

“You know what? Screw this.”

And then you punch me in the face and snatch the other enve­lope from my hand. As you run away, you open the other enve­lope to find a $5 check inside.

“That sneaky snake! That snakey sneak! I knew he was full of baloney.”

But…. was I? Was there really any­thing wrong with my expected value argument?


1 You thought I forgot, didn’t you? I didn’t forget! I never forget.

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