Robert F.P. Ludwick

DevOps Software Engineering Family Man(ager) based out of Portland, Oregon metropolitan area. Doting father, video game enthusiast, general nerd, & technologist. Eater of 🍕 & 🍣. This is my "blog."

Keeping in Touch

Post - September 20, 2022 - social, family, friendships

It’s Been Awhile

For the past few weeks I’ve been thinking about how some folks do a great job at keeping in touch with others, while most everybody else just simply don’t. I’m in the latter camp. I’ve known for pretty much my entire adult life that I’m piss-poor at keeping in touch with others. I’m not sure how many friendships I’ve had wither on the vine where all they needed was a little bit more of my TLC. It’s not that I don’t want to keep in touch with folks… It’s that I’m busy! I have a lot going on. Heck, it’s not that I don’t care about your anniversary or birthday, I’m just shitty at remembering when it is!


Some years ago I decided to try to use the power of iCloud Calendar to track annual milestones. Year after year of my adult life I’d find myself scrambling to give someone a call or text them when their birthday arrived, and too many times I’d end up messaging them the day after, when some family member would ask “Did you wish Joe Schmoe a happy birthday yesterday?” Unfortunately, I found using iCloud Calendar to be insufficient for my needs. By default, birthdays will show up if you have the individual as a Contact with their birthday listed. Then at 9am on the day of their birthday, you’ll possibly get a notification that it’s their birthday. But that’s really it. What if I miss the notification? What if I need to buy them a gift in advance? This wasn’t meeting my needs. I needed something with more reminders and some semblance of permanence until I achieved my goal and marked it as done - buying their gift in advance, wishing them a happy birthday or anniversary, etc.

I decided to try out using Home Assistant to store my expanded reminders system. For milestones where I needed to buy a gift in advance, I had the following sequence setup:

  1. A reminder at 4 weeks before the milestone, imploring me to plan the gift I will buy
  2. A reminder at 2 weeks before the milestone, telling me to buy the gift I planned
  3. A reminder the day of the milestone, to send them well wishes

This system started to work a little better for me - I was now better able to remember important dates for others! Unfortunately… using Home Assistant in this manner was unwieldy and cumbersome to manage. I had to have three configurations per milestone, and there were a number of milestones I had in play. So while this system was working well for me, the technology I’d chosen to implement it was insufficient and didn’t scale well if I wanted to add more milestones. Enter Todoist.

I’ve been using Todoist for quite some time now, and it’s done wonders to help me keep my life organized. I figured since it’s been the key organization system to keeping my life organized, I’d give it a go for milestone reminders. All I did was to copy over my three-sequence process (and single reminders for milestones where a gift was not necessary) with one main task listing their birthday and year (so I could remember how old their milestone was), with three subtasks for my sequence above. It looks similar like this today:

Todoist task & subtasks

The result? A vastly improved and manageable milestone reminder system. I haven’t missed a gift since I started doing this in Home Assistant, and now it takes me almost no time at all to check off a Todoist item when I’ve bought a gift. Additionally, switching to Todoist has indeed made management of milestone reminders much easier - I have a friend getting married this upcoming January, and at that time I’ll add an annual reminder to wish them a happy anniversary, and it will take me all of 30 seconds to add that reminder.

As an aside, I highly recommend Todoist to help organize your life. It’s helped me tremendously.

Keeping in Touch, Regularly

About 6 months ago it occurred to me that I could possibly use Todoist to help me keep in touch with folks on a more regular basis. Outside of these milestone dates, I had a spotty track record in keeping in touch with virtually everybody from close family to professional acquaintances. So, roughly six months ago, I setup a weekly reminder on Sundays titled “Reach Out To Someone And Say Hi.”

At first my approach was pretty ad-hoc and scattershot. I started by going back about a year or so in my SMS history and picking out folks I knew I wanted and needed to stay in touch with more regularly. Even this approach alone led me to reconnect and strengthen connections with many folks where we’d let the threads of our connection fray. From there I would circle back to my SMS history on a weekly basis and try to refresh most of those conversations at least every month or so, depending on whomever I was talking with. Close family were more frequent; professional acquaintances I’d let linger for maybe 3 months or so.

I would occasionally try to make sure I kept in touch using other platforms as well (I don’t use Facebook or any other Meta product, which is a severe hindrance in terms of keeping in touch with folks). SMS represented the bulk of my efforts to keep in touch with others, but there are a few who use Signal, some who use Discord, and even two folks I keep in touch with using LinkedIn. Trying to remember to keep in touch across all platforms, and who used what platform, turned out to be something I could not just keep in my head and remember.

A few weeks back I decided to setup a note in Joplin (the application I use to take notes, much like Evernote) to pair with my Sunday efforts. Over the course of a couple of weeks I fully fleshed it out in tabular format to track the following:

Person Methods Last Contact Target Fequency
Father Ludwick SMS/Signal 2022-01-02 Every 2 months
Sister Ludwick Discord 2022-03-05 Every month

For the record, this is not how often I contact my father and sister. I have a few tables, all marked with some overarching category like Family or Professional. This helped me really make sure that I was keeping in touch with those most important to me in various arenas of my life. So far, a few weeks in, this pairing of Todoist and Joplin is working out quite well for me.

As a second aside, I highly recommend Joplin as your primary note-taking app. I hooked mine up to a WebDAV server I’m hosting in my home and it’s been excellent for me.

Most People Are Bad at This

Now that I’ve been regularly trying to keep in touch with folks the past 6 months or so, I have reached a conclusion: most people are bad at keeping in touch. Years ago, my best friend once lamented that he had to be the one to keep most of his friendships alive - that most people, even close friends, just let him be the one to initiate conversations way more than 50% of the time. At the time I said “Surely you must have had a run of bad luck!” I have since changed my tune. Most people are pretty bad at keeping in touch with others (this is not a rigorous study, but I can easily track data from my own efforts). It certainly seems to be the case that as we age, our meaningful social connection skills continually degrade. I do wonder what social media’s role is in all of this, however.

On average, I’d say that I’m initiating conversations with a substantial majority folks in my Joplin note. If my Last Contact date plus my Target Frequency is in the past, then I’ll send a message just to check what’s up and see what’s new in their life. Roughly 80% of the time, when I go refresh a connection with a new message, the last conversation we had will have been from the last time I went through refreshing connections.

It’s a bit dispiriting to come to this conclusion, but I think I knew it all along. Most humans are bad at keeping threads of connection alive over lengthy periods of time - they aren’t naturally the ones to proactively strike up conversations when those threads start to stretch thin. One might argue that I myself don’t really care about others if I’ve resorted to technological means to ensure I stay in touch, and there’s some merit to that argument. However, at least I’m trying to do something about it: I’ve realized that I simply cannot do so “organically” so I’ve supplemented my processes to ensure I stay in touch.

Maybe I’ve helped inspire you to be more proactive in keeping in touch with those you care about? If you develop a solid method to keep in touch with others that isn’t just blasting life updates all over social media, I’d love to hear it.