Greetings, data-tamers!
I found myself distracted by some rather major (but positive) life events unfolding during the last week or two, and digital organization tasks have ended up on the back burner.
This kind of availability hiccup is bound to happen from time to time, and when it does, we just have to roll with it. However, there are other factors that make procrastination more likely even when we don't have a solid excuse. One of the worst of these factors is a lack of clarity about what to do next.
Think about this. If you have a goal in mind, and you know what the next step towards that goal, and you have the knowledge and ability to carry out the next step, it's usually almost easy to find time to take that next step. Sure, sometimes things get in the way, but that's how it feels--other things are getting in the way of the productive thing you want to do.
In contrast, if you have no clear goal, or you have a goal but are unsure of the best "next step" to take you towards that goal, nearly anything can push that project to the side: an unexpected phone call, the temptation of checking your email, a new episode of something on Netflix, reorganizing your bathroom cabinets...you get the idea. Even with a goal in mind, the lack of a path from "here" to "there" means the goal might as well not exist.
So, while I did have some good reasons for my recent focus shift, I can also say that if I'd had a very clear idea of exactly what to do and in what order, I'm pretty sure I could have found some time to fit in progress. It's not like I was going full-bore working 100% non-stop on other things for 10 days straight.
In light of that I thought I would use this week as an opportunity to talk through (or type through?) some real brainstorming to help get back on the right track. It will help me avoid inaction due to missing clarity later, and it might be instructive for you to see what goes through my mind with a project like this.
First, let's step back and regroup a bit.
My fourth-quarter 2025 Consistency Challenge project is to help my mom migrate her documents into a system that works for her. And I'm not going to do it for her; I'm going to do it with her, seeing together what works and what doesn't, until she's comfortable enough to do the rest herself. This is admittedly less specific than some of my previous goals this year, partly because it depends on how well things work for somebody besides me--which is hard to predict.
The vast majority of documents that my mom has are some form of notes: daily notes, task lists, meeting notes, research notes, etc. Therefore, a nice note-taking system with backlinks (to support the Map-of-Content note-linking organization trick I described a few weeks ago) seems like the best option. After quite a bit of research and one false start with Craft as a note-taking tool, I decided to go with a pre-configured installation of Obsidian, with just a few well-chosen plugins to give the simplest experience that still provides the features set I believe she'll need.
Then, while my mom had some downtime of her own, I spent a little while creating the basis of an experimental tool to analyze and convert thousands of Word documents (and related files) using local and private AI, so we can more easily bring in the most important stuff--and only that stuff, at first--from her old document collection into her new note platform.
And here we are.
So...what now?
Well, I have a lot of material to work with, and a few ways I could go about it. There are many things that I could do on my own; I could importing documents into Obsidian so they're ready for her to peruse and explore. I could focus more on the local AI analysis tool. I could look for documents that clearly have no further use today and exclude them from the collection. I could try to rearrange and clean up some of the folder hierarchy currently in use, so that it's easier to go through together when we're both available to do so.
But in the interest of doing this with her instead of for her, I don't want to get ahead of myself--and I don't want to work on a strategy that makes sense to me if she's not along for every step, to see both how and why I would make certain decisions along the way. If she's not there to participate in the process, the end result won't feel natural and intuitive to her, even if it does to me.
I think the best option at this point is to give Obsidian a shot in a simple, non-committal way. Specifically, that could (and probably will) mean finding one of the most recent documents she's made it Word and then repeating the process in Obsidian instead, just to see how it feels. We can identify similarities and differences, aspects that are either easier or harder, and investigate any points of confusion or friction.
If that goes smoothly--which I expect it will--then we'll import a few more recent documents from Word into Obsidian and explore the concept of linking related notes or documents together.
Both of those things require us to be available at the same time for a while, which has recently been a bit challenging. But hey...at least now I have a more concrete plan! I know what to do next, and I know what I'm not going to try yet, and why I'm not going to try it (the tempting solo stuff I could do by myself). For now, that's enough to break out of the paralysis of being unsure what to do.
Thanks for listening. That was helpful. I appreciate it. 😛
That's all for now. Until next week, happy data-taming!