The other day, I mentioned how my projects file in org-mode is basically a huge mess that makes it difficult to be on top of things, and then an idea occurred to me during a shower, as all good ideas do: organizing is important when I save and store things, not when I’m working on them.

When I work on something, I deal with a dynamic environment with tasks, reminders, attachments, comments, and a bunch of other things. This is the information-gathering phase. The main point is to collect everything quickly so I have it available later. It’s when I’m done with a project that I need to clean it up and store it in its place so I can find it later.

I was considering (still in the shower) the “now page” phenomenon. What if I change my project.org file to now.org? Technically it will look the same but conceptually it will be different. A place for things I’m actively working on in the present moment.

The real change should take place in the org files I save my projects into. Work projects will go into dedicated files, depending on the kind of task. Personal things will fit into their own files. As a matter of fact, the work-personal separation is not as important as it used to be, as each activity (work or personal) gets a separate file anyway.

For example, if I’m working on a vacation in now.org, I have a project with the location, the hotel, a map of the area, a couple of places to see, and a packing list. When the vacation is over, it will go into an events.org file under a “vacations” header. When I place it there, I will also include a link to the photos I took, tag it with “journal” if I wrote about it in my journal, and add a couple of annotations to the map, depending on where I’ve been.

In the future, when I want to reflect on the vacation, I will know exactly where to look. Keeping these files small is important so they don’t become overwhelming. An indicator for that could be casual reading: Can I just open the file, read through it, and enjoy it? Maybe even make it into a PDF and print it? The answer to these questions should be yes.

The trick is to know when a certain “thing” happens often enough to have its own file. For example, would I need a vacations.org file, or is events.org (which also includes going out to restaurants and movies) good enough?

For this, I think the size of the file itself could be a good indicator. In org-mode, the files contain only text. So if a file contains more than, say, 50KB, it means it has 50,000 characters. This roughly translates to 7,000 - 10,000 words. Since the characters in org-mode are also symbols for syntax for meta information, I think this is a roughly good number for now; I can always adjust it later.

This concept also works when I’m happy with the category the file captures, but as it grows, I can split it by months or years. For example, if events.org is good enough to capture vacations, restaurants, movies, and other social gatherings, and I want to keep it this way, I should have event_2024.org, and then make events_2025.org, etc. It’s possible some things, like certain work activities, will need to be broken down every couple of months while other personal tasks only every year or even only a couple of years.

I started storing some of my completed tasks yesterday, and I slowly chipping away at my big projects.org mess. As I go through it, I will get a better idea of how it’s working and if I feel like I am back in control again. Since I need to wipe my Mac and start fresh (this is a story for a different time), I will have a nice clean start this weekend. That’s the goal, anyway.