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 file to 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, 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 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 file, or is (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 is good enough to capture vacations, restaurants, movies, and other social gatherings, and I want to keep it this way, I should have, and then make, 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 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.