I, like so many others, have gone through cycles of chasing after the latest productivity tool, the latest todo list, the latest organizational system. Wisdom is realizing you need some system to help you stay organized. Folly is chasing after every new tool. Wisdom is realizing the tool doesn’t matter so much as actually using it.
Text File Todo List
At first I just had a very long 20##-Todos.txt file that sat in a backed up location that I updated. I faked checkboxes and bullets as best I could. I created a custom Notepad++ language format to make things highlighted a little bit better. This wasn’t the best, but it worked. The best tool for the job is the tool you use, right?
Every day I’d roll over my todos, so I had a very, very long list of mixed todos and notes. The notes crept in over time until it was actually most of the day’s entries. At some point I realized I made a mistake by mixing them but I never really fixed it.
Instead I moved on to software to fix my issues for me!
EssentialPIM
I used this for a while and after a year of using a real tool I realized how little functionality I actually needed. It was simply too much, even tweaking things to be simpler, the urge to color code and prioritize and drag tasks around instead of doing them was painful. When the chips were really down I ended up using physical sticky notes on my desk. I was better than that. I had to drop the PIM software, I had to go…
Back to Text Files
This time I wasn’t going to mix notes and todos. I kept two text files, one for each. Naturally that was a disaster as I had to cross-reference two files, even in tabs in Notepad++ this was annoying. My place was always lost or I had to take longer than I wanted to make sure I was looking at the correct date… Too much.
I moved back to a single text file and just resolved to be less verbose about notes, or indent them far enough I could still skim down the list. This worked for me for several years, until I randomly discovered…
Obsidian.md
All roads lead to Obsidian. Don’t fight it. Accept it. Even this site is all published Markdown! Notion and others do similar, but I like Obsidian the most. And once again: wisdom is sticking with and using a tool. I’ve stuck with Obsidian for a year now for work and for home and I’m not leaving. It has its own issues, but nothing that any other system wouldn’t have somewhere.
Markdown files have the same benefits of plain text files in being software agnostic, while also providing desperately needed formatting. Real bullet, real checkboxes, real code blocks with syntax highlighting, and callouts have been a blessing for organization.
Loose Organization
- Meeting Notes by date and topic
- I like to keep at least loose notes on meetings, focusing mostly on things my team has to actually work on
- Dev Journal
- I keep a journal to document the random bugs I solved, CLI snippets I use, etc.
- This takes time to become useful but I’ve been able to search my notes several times for easy memory jogs
- This isn’t a daily update, I go weeks without logging anything useful
- Useful code snippets
- Especially around AWS I have a list of useful AWS CLI snippets I can run to find things more easily
- Rolling Todo List
- This is 80% of my notes
- I keep a todo list that I rollover daily and delete anything I finished
- Now I have a snapshot of what any give day looks like for later
- Makes it easier to see how long I was working on something in a way that I looked at daily, which means my memory is jogged more easily versus looking at Jira or another tool
The Future
When do I drop Obsidian? It’ll happen someday, but I hope it won’t. I actually have enough organization and critical mass that this sytem is working and nowadays I’m too busy to really fuss around with productivity tools.