Every year my employer schedules two weeks for Open Enrollment in the benefits plan. This is the time period where you can freely change health plans, life insurance, etc. In the weeks before Open Enrollment we receive numerous emails reminding us that it is coming up. During the Open Enrollment period we receive numerous emails reminding us of the deadline. The day of the deadline we receive a final email saying that today is the deadline.

Then, every year after the deadline passes the deadline is extended an additional week, and the many people who procrastinated and missed the first deadline are given a reprieve. This happens so consistently that many people know it is coming and understand that the “real” deadline is the second one. So many that it is reasonable to assume that a sizeable number of these people procrastinate up to the second deadline and miss that one too. But there is never a third deadline.

You notice this kind of thing happening a lot. Artificial deadlines that you can be forgiven for missing but only once. It’s a puzzle because whatever causes the first deadline to be extended should eventually cause the second deadline to be extended once everyone figures out that the second deadline is the real one. For example if the reason for the first deadline extension is that year after year many people miss the first deadline and flood the Benefits office with requests, then you would expect that this will eventually happen with the second deadline.

The deadline-setters must feel on firmer ground denying a second request by saying “We warned you about the first deadline, then we were so nice and gave you an extension and you still missed that one.” But if a huge number of people missed the second deadline, no doubt they could still mount enough pressure for a second extension. Indeed the original speech of “We sent you emails every day warning you about the deadline and you still missed it” didn’t stem that tide.

Is it just that every nth deadline is a new coordination game among all the employees and the equilibrium number of deadline extensions is simply the first one in which the “no extension request” equilibrium is selected? I think there is more structure than that because you rarely see more than just one, and you almost never see zero.

I think there is scope for some original theory here and it could be very interesting. What’s your theory?