• Strategic thinking gone awry

    I can’t help it. I’m a strategic thinker, though I’m not claiming I’m a good one. I just think about things from all conceivable angles and as many moves ahead as I can. It’s just what my brain does. It keeps me up at night.

    Moments ago I approached the envelope on our office kitchen refrigerator door. The purpose of the envelope is to collect contributions for a gift for our janitorial staff. I don’t have to contribute, but I always do because I think it’s a nice thing to do. I enjoy participating in showing appreciation for those who help keep our space clean.

    This year, I had a new thought as I faced the envelope. What if my contribution is a lot less than everyone else’s? Now, nobody would know it, so I need not worry about appearances. But still, to take an extreme example, I’d hate it if everyone kicked in $100 bills and I put in a penny. The collector would know that someone is a cheapskate!

    I recognized this as a completely hypothetical concern, just another example of over-analysis. Welcome to my world.

    Still, now I had a puzzle. What if I wanted to kick in, say, a five dollar bill but I thought everyone else had paid with twenty dollar bills. Moreover, what if I didn’t want the collector to think someone was not being sufficiently generous. (I have to presume an assumption that the collector would think everyone only contributed a single bill of some denomination. Since this is my own hypothetical game, I have no problem with such silly assumptions.)

    In a flash, I had the answer. What I ought to do is contribute a five and a few single dollars. Now, next to the twenties my five dollar bill would look small, but next to the ones it would look big. I’d look relatively more generous without paying a lot more than I wanted to.

    This all occurred to me in seconds. The next second after that I contributed what I wished–the same as every prior year–and headed back to my office. As I did, I laughed at myself for thinking such thoughts. That’s when I knew I had to post it.

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    • i would have just asked.


    • This might be breaking the rules of the exercise, but I would assume that people contribute according to what is in their wallets, which is likely to vary by denomination. Most people (depending on the workplace) won’t hesitate to contribute two $10s rather than one $20. If you think you can guess the typical denominations your coworkers tend to carry, you could get away with contributing less.