I’ve been working with people and talking about their organization systems to help their systems help them. There are a few different systems that people use, and I wanted to figure out this question: what really are the essentials to have something that works?

If your system isn’t quite working, it’s easy to feel overloaded. There’s too much to do, it’s hard to prioritize, it feels really hard to get a handle on what you should be doing. First, if you haven’t read Getting Things Done, start there. But the goal is to gain some sense that you have things under control; that you are confident you are working on the right things, and aware of what things need to be done, and have a good feel for the order they should be done in, at least given current conditions. If you take nothing else away from the book, it’s that you need to capture everything and put it into a system you can trust.

After that, if you’ve read my posts on the agile organizer there’s a decent mix of “what I do” and what’s core to any good organization system. But what really are the essentials, separate from whatever it is I happen to do?

I dug into what the core bits of my system, at least as far as todos go. While the agile organizer system and other systems can cover a broad ground, todos are really the core. They are candidates of things to be done. I say candidates because not all things in your todo list should be done if you’re capturing everything. You will enter in things that shouldn’t be done, at least by you, but possibly at all.

The essence is you need a reorderable list of todos, a way to denote which ones are done or not, and a way to have todos hidden until a certain date. Reorderablity is a key element, as when you’re deciding what to do, you don’t want to look at all the things in your list – this introduces extra cognitive load, and can result easily in decision fatigue or being overwhelmed: two things which a good system should alleviate rather than create. You want to cluster the more important things towards one end; conventionally the top of the list. You want to cluster the less important things together, and you also want to cluster done things together. The goal being: when you’re looking for something to do next, you want to look at fewer, but higher priority things to make it easy. Or at least make it so that even if you choose the “wrong” thing to work on, you’ve still chosen something good to work on.

The reorderability is one of the fail-points of bullet journals. As much as I love the idea of a system like it, it falls into the problem I mention in the first Agile Organizer post

There are a number of mostly crossed off todo [items on my] lists that I can’t see what’s left, things are in the wrong place and it’s a ton of effort/pain in the neck to rewrite everything if I want to clean things up.

Depending on your work load, and when TODOs show up, and how many you can predictably plan to complete in a day, the copying can be less problematic. Likewise, if the number of TODOs isn’t large, being able to see what’s left can be less of a problem. But when you hit the limits there, it gets unusable in a hurry.

A good system makes reorderability simple. Suprisingly, a plain text file can actually work really well for this. You can just copy/paste lines around, or some editors have the ability to move lines up and down with a hot-key. One thing a text file doesn’t really do well is to “send TODOs to future you”, or recurring TODOs.

Google Calendar, or anything that can send you persistent notifications (e.g. email) can work for this. In my case, I have a series of calendar entries at 7:00 am whose sole purpose is to send mail. While my main electronic system is org-mode which has scheduled todos and deadline todos, but for me, some things work better entering my system as a calendar notification.

In Getting Things Done, David Allen refers to this idea of sending future you things as a tickler file. In the book, he mentions getting forty-three file folders to set this up, and there was a blog 43 Folders which riffed on many productivity things. I had a forty-three folder setup for a while, but it turned out I didn’t need to mail myself paper items all that much, and so during one of my retrospectives, I canned it in favor of using Google Calendar’s functions and/or the native features of my electronic org system. That said, the forty-three folder setup is an entirely valid option to send yourself things in the future.

No matter how you tickle, either deal with them as you get them from your tickler system – e.g. instead of entering the content of the notification email into your organization system, you can just “do the thing” and dispose of the email. The only caveat is that if it’s the kind of thing where you need to track timestamps of DONE, you might still want to enter it into your system for that. If you do need to track it that way, include the fact in the notification so future you doesn’t have to remember to do it. One of the points of organization systems is to help automate yourself. So try to leverage the system so you have to remember less.

And to be clear: you can use either or both of these. There’s nothing to say that you can have only one tickler mechanism. The main detail is it should fit the way you work, or you won’t use it. If you don’t use it, it doesn’t matter how perfect it is.

The other thing you can and should use ticklers for is the mundane things you need to do every day. Yes, after doing them day after day, you should be able to do it in your sleep, but why make yourself have to expend the mental energy to do this? Also, human brains sometimes do stupid things, tickling the every day things makes it so you can’t screw it up (or at least screwing it up by weirdly forgetting one day).

Bonus Features

For any electronic system, while the above covers the essentials, there are a whole lot of goodies they can provide which can multiply the value of the system.

Dated TODOs

If your system natively supports dating of TODOs, this can save you many interactions with Google calendar. For me, I only really use Google Calendar notification emails for things that recur. It’s not that org-mode (what I use) can’t do them, it’s just that the ones that come from the calendar are more “disposable”; many of them are the same every day, and quick to do, so it’s easier to process the emails for them.

A more systematic filing away of DONE things

While you can keep a done section and move your completed TODOs to that section via cut/paste, which I did for a few years, having a hot key to just take care of it makes it less work to take care of this, and so the high priority area of your TODO list will tend to not grow a bunch of DONE items that haven’t been moved. This goes to TODO-list hygiene, if you make keeping it clean and only containing TODOs easy, you’re more likely to keep your TODO list free of DONEs, and thus reduce the cognitive load when you go to it to find the next thing to do.

Flexible variants of TODO and DONE

For TODO items in your list, it can be worthwhile to use alternate tags like WAITING for started, but blocked on something outside of me, IN PROGRESS for started but just not finished yet, or done states like NOPE, where you decided to just not do it. There are other possibilites here, but these are the ones I’ve felt useful.

Timestamping of when something became DONE, and generally easy ways to insert a “now” timestamp

Especially as a manager or other leader, being able to establish timelines after the fact can be extremely valuable. Making it easy (or even automatic) to timestamp things as you do your normal work makes it that much easier when you need to go back to figure out what happened when.

Text Format

Organization systems can be a trap if their file formats are opaque. Part of choosing one includes the near certainty that the first one you pick won’t be the last one, and if your data is tied up in some non-text format, or in some online service, migrating out can be extremely painful.

Text also has the nice side effect that you can version control the files. For example, I version control my org-mode files in git, and have a script to make a commit and push it to Google Drive. This way if my machine ever decides to barf, I would lose at most a day’s amount of stuff, and probably less. Also, if you accidentally delete something and don’t notice for a few days, you have a history to go back to. This isn’t theoretical, I’ve used it more than a few times even in the last year.

Also, text gives you the ability to process it with whatever text tooling you might choose. If you’re in tech, tools like grep, sed, awk, etc. can be used, whereby a non-text format cuts you off from the mass of tooling available for text.

Some Kind of Scriptability

There will be common things you’ll want to do consistently that are specific to the workflow you’ll grow. If it remains manual, you may not do it consistently, which can lead to problems later, or you may just stop marking things a particular way because it’s too much work. With scriptability, you can encode your recurring usage patterns.

Some Form of Query Language

As the current set of active and historic TODOs grows, you’ll want to create custom views of things. It may be things like: what do I do today, or find me documents I read (for which I made document reading TODOs in a particular way) with some word in the name, or things I did related to some subject (again, which I made some tag for), or show me completed TODOs for the last two weeks.

Some Common Tools, and Opinions

If you’ve read my blog, you’d not be surprise that I use org-mode currently. It has all the “Bonus” features, and more, but the amount you need to know to get started is not much. However, many people seem to be somewhat allergic to Emacs, despite that I think even if org-mode is the only thing you use it for, Emacs is worth learning. Also, if you’re not conducive to programming, this might not be your best choice.

I’ve also used Dropbox Paper which also can work well. Paper isn’t text based, but it it’s lightweight, no-installation, and can be a decent place to start to figure out what things you really want/need. In a pinch, you can export a doc as markdown for searching.

I’ve looked at Obsidian, and out of the box it doesn’t provide much past TODO checkboxes, but plugins may provide the extra bits you need. It seems more oriented towards the zettelkasten-like knowlege base than a TODO productivity system, but I know a few people taking it out for a test drive.

LogSeq looks promising too, but I’ve not used it.

Summary

In any case, the symptom your system isn’t working is feeling overloaded and out of control. The symptom of a system that is working is a feeling of control, and mental peace: a mind like water as David Allen puts it. Consider the nature of what you’re making yourself evaluate when you want to pick something next to do. Is your tool helping, or getting in the way? Is there a better way to tag your information? Is there a plugin that can help you get what you want? Can you write your own? Or did you pick the wrong tool?

Do the retrospectives, try things out where your system isn’t functioning as well as it could. Give them a period of time to see if it does make it better, but don’t hold onto something that’s not working.