I often find I’m pretty bad at keeping in touch with folks. I don’t really have any good system.
So what I try to do more these days is “micro check ins”:
“Hey – I was reading this article/book and was thinking about you”
“Just a random ping – how’s everything?”
“Thought you and s/he should meet, hence this random casual intro”
“Go (sports team that I know the other person is a diehard fan of)!”
So far it’s been working out pretty well for me. These micro check ins are occasions-driven, so they’re kind of random and I’m not keeping in touch with everyone on my Rolodex. But I get to think of some people, and they appreciate the fact that I thought of them.
I guess “perfect is the enemy of done” can be applied to relationships as well.