Keeping a journal has become a transformative experience for me. I tried to start writing out my thoughts multiple times last 5 years or so. But it didn’t click until my last attempt.
What helped me in the end was to concentrate on analyzing problems that really bother me and be curious and frank about it. I won’t tell you there was any particular tool or magical method that helped me to jumpstart it. In my case it was long-term counseling and not giving up on the idea. I guess the most important thing here was getting comfortable with listening to my own thoughts.
As for tools, I figured out that for me the most important thing is just plain old text. That’s why I don’t use any special software, only a text editor. It doesn’t get in the way of spitting out words and allows to concentrate on writing and not formatting or other bells-and-whistles. I just have a text editor window maximized to the entire desktop and (as usual) have all notifications silenced both on my computer and on the cell phone.
All my journal entries are kept in one directory, ~/org/journal. I have one file per day, and name them as YYYYMMDD.org. This allows me to easily list them in a natural order with
ls and apply any unix tools like grep and sync the files with Dropbox. Keeping files in plaintext also makes it future-proof and I’m always certain that it will outlive me.
To this date, I have 527 journal files, that take 2.7 megabytes in total. Some of you may think that this is a lot, but modern operating systems and computers work with such amounts without any problems. Even if I write every day for 30 years, it will only take about 10000 files, which even a 20 year old computer won’t even notice.
The only thing that I figured out I need in addition to that is to reduce friction in opening a journal file. I want it to take as little effort as possible, because the process of writing is already mentally taxing. So I have a script for my editor that is bound to a hotkey that checks if there is a file for current day, creates it if necessary, and then opens it in a new window.