So, here’s the thing: I’m not always good at remembering details. I find myself repeating parts of conversations with people: “how old is your son again?” and “I forget, what’s your husband’s name?”

I’ve tried to be more mindful of this, because I know it’s just a matter of remembering these details when people tell me them. I’m better about it than I was, to be sure. At different times, I considered keeping text notes—just plain text files, one per person—to keep notes about conversations I have with people. Things like, “spoke on April 14 about upcoming shoulder surgery.” Nothing invasive for deeply personal, but the kind of details that I want to remember when I’m catching up with someone, but can’t keep straight for everyone that I talk to now and then.

So, having tried this a little bit, I found two roadblocks so far.

  1. It can be difficult to remember to keep these files up to date. I open a new text file for every meeting or event or idea, but I don't always remember to go back and update this information, and I will need to actively maintain this information to keep it useful.
  2. It's kind of creepy, right? This one worries me a lot more. It seems weird to keep a dossier on people that I know. I mean, I know that I don't mean anything weird by it, and I'm sure the people that know me well know that this is just an aspect of my OCD information tracking (for which I am often mocked), but how do I explain that to people I don't know well?

The second point is what keeps me from putting more time into this. I could easily spin up a Drupal site or even just create a folder on Dropbox to contain a text file for each person that I interact with. That way, it would be readily available when I get on the phone with someone, or have a conversation online with them, so that I can review information and not seem quite as—well, as inconsiderate as I really am, I guess.

So, what’s your opinion: creepy?