Earlier quoted context omitted.
The forcing is weird, right? Why in the world does it take so much work to reach out to someone? The obvious explanation would be fear of rejection. Another story you could tell is fear of connection due to opportunity cost -- what if, among all the people you could connect with, this one isn't a great choice but will end up consuming a lot of your time? But I think it's probably the first.
It's simpler than that. I don't feel the need to maintain relationships for my day to day well being, but I force myself to, because I don't want to die alone someday. But I also recognize that I'm an extreme hermit/introvert who is happy calling my dog my "SO", and will probably end up dying alone in a cabin in the woods someday, so it may all just be futile anyway.
A simple system I’m using to stay in touch with hundreds of people
371–380 of 510 posts
Re: A simple system I’m using to stay in touch with hundreds of people
#372The biggest reason I don't maintain contact with people from my past is I was a much worse person in my past and I'm either embarrassed about my behavior or concerned that my shittiness is what led to our relationship in the first place. In any case, I find it's easier (and emotionally satisfying) to stay in touch with a couple people that I can have natural, unforced conversations with. Scheduling interactions on a…
Something I need to get back into. Interacting, at least casually, on a routine basis with a wide amount of people has lead to every job I have ever held - they came to me based on my reputation or past interactions. It's definitely the best way to get a new (and better) job rather than blindly fishing for them.
That's the real power of systems like this. Not to develop personal friendships, but to remain relevant in the eyes of a large number of people so that if they have a future opportunity you will be top of mind for how they can get it addressed.
I think it's why he stresses making the contacts personal and with meaning/value specific to that person. These aren't soulless automated computer generated emails, but a system to prompt him to write relevant and sincere contact messages.
Is it a lot of work? Sure. But building up a network of people who see you as contributing value is priceless.
Re: A simple system I’m using to stay in touch with hundreds of people
#373Earlier quoted context omitted.
I feel exactly the same, and honestly, it keeps me from approaching some people I‘d like to. If anyone has figured out a pretext or mental framework for warming up conversations that have effectively died long ago, I would be delighted to know about it.
I make sure to end each conversation properly. Something like "I have to go, I have something to do, that was nice talking to you". That way you can start a new conversation 6 months later and it doesn't feel awkward.
Re: A simple system I’m using to stay in touch with hundreds of people
#374My main issue with keeping in touch with people is that texting someone you only vaguely know is kinda weird. You don't see the other person, you don't hear them, you can't know what's in their mind. Those exchanges often just hang in a weird void after a few texts and it's unsure when/how to continue from there. On the other hand, calling someone you don't know well (even someone you do know!) feels even weirder and…
I agree with you. The author is trying to automate human connection - but it probably doesn't come off genuine.
Re: A simple system I’m using to stay in touch with hundreds of people
#375(I'm the guy he refers to in that post.) If anyone reading this builds software like this, and releases it publicly, whether free or for sale, please let me know. I'd be happy to send people your way. Because of https://sive.rs/dbt I get a few emails a week from strangers, asking if my software is public yet, or if not, what else I would recommend. (And I might never make my software public. It's too tied-in to my no…
Hi Derek! My implementation of your system is just a bunch of markdown files. The title of the file is a friend's name, the frontmatter at the top keeps info about them that doesn't change too often (ex: birthday, address, kids names), and each time I chat with them I add a section with an H1 title that's the date we chatted (ex: "# 2022-02-14\n"). My notes about the chat go under that heading. Based off of that stru…
In 25+ years of keeping people in my database, and writing plain text all day, I'd never once considered keeping my list of people in plain text files.
Thanks for the description and inspiration.
Re: A simple system I’m using to stay in touch with hundreds of people
#376(I'm the guy he refers to in that post.) If anyone reading this builds software like this, and releases it publicly, whether free or for sale, please let me know. I'd be happy to send people your way. Because of https://sive.rs/dbt I get a few emails a week from strangers, asking if my software is public yet, or if not, what else I would recommend. (And I might never make my software public. It's too tied-in to my no…
Glad to see you back -- at least for a couple comments, Derek!
Re: A simple system I’m using to stay in touch with hundreds of people
#377The biggest reason I don't maintain contact with people from my past is I was a much worse person in my past and I'm either embarrassed about my behavior or concerned that my shittiness is what led to our relationship in the first place. In any case, I find it's easier (and emotionally satisfying) to stay in touch with a couple people that I can have natural, unforced conversations with. Scheduling interactions on a…
Well I definitely heard that. I have a thing the voices in my head periodically inflict on me that I call Embarrassment Day, where I spend the day remembering past incidents that I'm embarrassed about. Lots of fun.
The silver lining of course is that if you're embarrassed about things in the past, it means you've grown enough since then to be embarrassed about them. If all you want to do is double down on everything you did, either you were already perfect or you haven't grown at all since then.
Re: A simple system I’m using to stay in touch with hundreds of people
#378Spreadsheets can work quite well for this. I made an iOS app as side project inspired by this post from Derek Sivers. https://amicu.app
https://amicu.app/ is a great example of this idea in action.
Re: A simple system I’m using to stay in touch with hundreds of people
#379The biggest reason I don't maintain contact with people from my past is I was a much worse person in my past and I'm either embarrassed about my behavior or concerned that my shittiness is what led to our relationship in the first place. In any case, I find it's easier (and emotionally satisfying) to stay in touch with a couple people that I can have natural, unforced conversations with. Scheduling interactions on a…
Re: A simple system I’m using to stay in touch with hundreds of people
#380Earlier quoted context omitted.
So we should become friends with people we don't value? Like random people on the street? It's a good idea, but would be exhausting.
At no point does he talk about making everyone into a deep friend. I guess english language is just incapable of explaining it due to not enough words to express the spectrum? Do note that he has different "frequency" categories (which don't have to map to "type of friendship" same way even in that one database!). Some are just people he is interested in meeting, maybe keeping in light contact over time. Some more of…
I think it's ok to just partition our lives into friends we value -- and largely ignore others. We'd be insane otherwise. So long as we remember to keep a general humanistic value for the man (or woman or trans or define-it-yourself) on the street...
As I get older I find it hard to even KEEP UP with normal friends flung far away and separated by the distance of time. Not everyone will agree with the OP, but I'm always impressed with old friends from 20 years ago that still keep contact.
Something to consider.