A simple system I’m using to stay in touch with hundreds of people

Yeah, it's seems like poor empathy or a lack of imagination or life experience to not be able to conceive how people can forget things they care about. We'd all do well to remember that any given thing that's easy for us might be difficult for someone else, and not necessarily through some personal failing on their part.

Also, I see what you did there. :)

It never ceases to amaze me how computer programmers can take the simplest things and make them mind-numbingly complex. Oy ve (and yes, I'm a programmer)! But if it makes him happy, more power to him.

Because valuing close friends through the lens of what personal gain they may yield is more than a little sociopathic?

I have read the article top to bottom... and yes, it's relatable, comparable, it leaves me with envy that I despite numerous attempts I haven't managed to build a reliable system like that and turn it into a habit.

In no way do I feel it makes any of the connection cheap.

Some comments here claim that he is treating people not as friends. IMO these comments are not charitable a interpretation. While it is a plausible interpretation, I have strongly learned from HN to be charitable and optimistic when reading someone else's point of view. I know with topics like this that perspectives vary more wildly among people, so let me show you why I can be more optimistic in my interpretation.

I think it's perfectly fine to separate emotions and reason like this. The reason: I am on the other side when it comes to managing my friends: I am not separating reason and emotion. Because of that, I am failing hard at staying in touch with people that I would like to stay in touch with (I am noticing it with certain friends of my as well). I am succeeding to stay in touch with a few people, but if I'd have a system like this I might be able to stay in touch with many more people that I'd like to stay in touch with anyway but for some unknown reason have some sort of blockade or friction.

Other than that I think the interpretation is not charitable enough, I also have personal experience that it might be wrong. For example, I view the dating markets strictly from a market perspective that is heavily inspired by micro-economics and "common sense". Initially, such a perspective is detached from emotion, but there are certain points where it is attached (e.g. with supply/demand questions like: "what do I want/need from a partner" or "What can I offer? What do I want to offer? What do I need to offer?"). Moreover, upon meeting people there is empathy, sympathy and human intuition involved. Sometimes the emotions will be so strong that I have a compulsion towards meeting a person again (e.g. falling in love). Those emotions are not helping! Sometimes I feel the right amount that is also in line with my other needs and in other cases I don't feel enough about a certain person when I don't see them (but when I do see them, I am delighted to catch up).

Management of personal life != how people are on a moment by moment basis in personal life

I think by having a system like this, you can put Dunbar's number to shame.