In search of the ideal task management solution - part I

The difficulty

I’ve spent the better part of my adult life struggling with various task management solutions: scattered notebooks, sticky notes, and legal pads; various free and paid programs (Remember the Milk, Todoist, Obsidian); eschewing task management entirely and relying on my brain to remember important events and deadlines. Most recently I carried a clipboard around everywhere containing a weekly list of events, weekly todo, monthly event calendar, and scratch graph paper for daily todos and other notes when necessary. This was a massive pain - I had to lug a letter-sized clipboard every-which-where, which was about an inch thick and stuffed with extra paper, to boot. If I forgot it, well, (redacted).

Todoist

I recently(ish) discarded the “analog” approach fully in favor of Todoist, something I’ve been utilizing for about a year and a half now. I am somewhat satisfied, but it leaves much to be desired. I haven’t replaced it yet mainly because I can’t find anything that replaces the convenience of having my phone act as a thought capturer that gives some modicum of organization and follow-up process to the thoughts immediately upon writing them down. Writing it down on a piece of paper pales in comparison to the mental relief I gain from this workflow. Despite glaring problems I have with Todoist, I’m still using it, which counts for something.

Pros:

• Syncs automatically between devices (primary devices are Windows desktop and Android devices)
• Smart date recognition and other such QoL shortcuts (e.g. @ for labels, # for project, p for priority, ! for reminders, all with autocompletion)
• Widgets on mobile for quick task viewing and adding
• Extensive filtering and sorting, to enable my views
• Reminders!

Cons:

• Proprietary (primarily, non-plaintext) - hence not compatible with other apps
• Data is stored primarily on a Todoist server, not on my devices. Export options are a joke.
• Treats everything as a task either to-do or completed - no notes, custom statuses, links between tasks (it does have something resembling full-text search, however)

My current workflow for Todoist looks something like the following (open phone, press “add task” button on homescreen, type the given text and Todoist does its magic to parse the shortcuts):

• Task that needs to be done today: “do some task tod” → goes to Inbox, due date today
• Non-priority task, idea, idle thought, link to view later: “do some task” → goes to Inbox
• Task that needs to be done at some point in the future (e.g. tomorrow): “do some task tom” → goes to Inbox, due date tomorrow
• One-off event that needs to happen on a given day at a given time: “Christmas Party 12/23 7p p1” → goes to Inbox, due date 12/23 7:00 pm, priority 1

The rest - recurring events, habits, grocery lists, etc - I set up accordingly and put in their own respective projects, when I have some down time and I’m not in the middle of day-to-day activities.

My filters (widgets) on my home screen look like the following:

1. All tasks due at a given time (“events”), due yesterday, today, or in the next two days
2. All tasks due yesterday, today, or tomorrow, but without a given time
3. All Inbox tasks with no due date, and/or tasks overdue more than one day.

About once a week I try to sit down and go through my various Todoist projects. For example, I maintain a “server thoughts” project where I write down any thoughts that occur to me related to my blog or self-hosting projects. This works to some extent, but inevitably I ignore certain tasks or projects. They probably weren’t priority enough for brainspace anyway, but still it irks me. I do maintain sort of a stopgap for this, to remove the noise but still maintain the task instead of deleting it for all time - I move tasks that I haven’t thought about for a while or are no longer relevant, but still technically “todo”, into a project called “archive”.

My goal, essentially, is to have a process to capture all my thoughts, quickly, and then not lose them in the aether. I used to add tasks directly to projects, but now I put them into my inbox and display them on my homescreen to give me a chance to mull them over until categorizing them or archiving them.

More than that, I also want to manage my important one-off tasks and day-to-day need-to-dos. Instead of having to arduously add a date, time, project, priority, to every single task, which is generally not necessary, I have set up this workflow through trial and error to dump tasks in there quickly and organize accordingly later.

Banging my head against the wall

Some other todo management solutions I have tried:

OneNote

• godawful

Notepad++

• It has its place. Not for me for todo-lists, though.

Todo.txt

• This one I am still giving some thought to. A couple of years ago, for a week or so, I used the Quake terminal in Windows running WSL to manage daily todos via Neovim. If I set this up on a remote server with Syncthing to my phone, there might be something here. It is also equally as likely that I am straying into ridiculously overthinking it territory.

Remember the Milk

• Similar to Todoist - I was already paying for Todoist at the time, so why pay for another app with similar functionality and the same unavoidable downsides?

Vikunja

• Basically Todoist lacking a bunch of features. I’m keeping an eye on this one, though. It’s still stored in Postgres (I think? Some sort of database definitely, NOT plaintext), but it is self-hosted and would alleviate that issue I have with Todoist. Bonus, instead of paying a yearly subscription you pay with the blood sweat and tears of a sysadmin (and the running costs of the server, but that’s multipurpose).

Logseq

• I tried this out today. Immediately turned off by the bullet-point everything. I also encountered issues with the Windows app where editing just quit working, which I didn’t take the time to investigate. It does fulfill some of the requirements - daily notes, FOSS, plaintext(?). Might be the most promising one if I can get over a few humps, unsure about scheduling and calendar events.

Obsidian

with roughly a million plugins (mainly Tasks and Dataview, but others like Leader hotkeys are a godsend) - this has been the most promising, but also the most confusing - perhaps too open-ended.

Pros:

• Ultimately stored in plaintext - markdown is close enough (compatibility with other editors, file-syncing, git versioning, full-text search)
• Extensible with community plugins
• Vimkeys (not perfect, but better than none at all)

Cons:

• Tasks are stored inside notes, and thus hard to reference directly or do fancy stuff like adding descriptions. All metadata needs to be stored on one line. I haven’t figured out a good workflow or setup to address this.
• Extensive customization needed to get my expected functionality
• Reminders???
• The Tasks plugin dialog sucks - to clarify, it’s come a long way, and looks good, but is just slow. I need to get this shit down quickly
• Mobile app is clunky, just due to the nature of the nature of Obsidian and how beefy my setup is with all the plugins (also, no widgets)
• Syncthing can’t handle constant edits between multiple devices. (I did try to set up self-hosted sync. It seemed fairly straightforward but it was not playing nice after I got everything set up seemingly correctly with a self-hosted couchdb instance. I also found several different versions of documentation which led to confusion. I decided it’s not worth the effort and I didn’t want to put it to use on my production vault for fear of data loss - my closest to successful attempt ended up overwriting all my theming and settings on my desktop instead of on my mobile, despite me setting it to the opposite, or so I thought.)

Note that the cons listed above are almost certainly achievable functionality with enough digging around in the community plugins. That doesn’t mean the solution will be intuitive, easy, or address all the problems I have with it. Simply my experience.

I did also try Obsidian about a year and a half ago, before I had a better understanding of what my requirements were, what sort of organization I wanted, and any sort of real motivation had hit. Right now, I use Obsidian for daily journal notes where I can create blog posts and documentation. Still working on that, I’m just not sure if it can be a full replacement to Todoist.

I think my biggest problem with Obsidian is it isn’t purpose-built for task management, it’s more a knowledge-management app, which can involve todo-lists. But you need to do extensive legwork to build in functionality that more purpose-built task management apps come with built-in. The question is, is it worth it?

A better question might be: do I value the core task management features of apps like Todoist, or do I value the open-endedness, extensibility, and plaintextedness of Obsidian at the expense of core functionality?

The Cycle

I’ve recently been reading Tom Limoncelli’s Time Management for System Administrators (I am not a vocational sysadmin, but I do fancy myself one, and I think a lot of my skillset, hobbies, and work duties reflect that). Disclaimer, not done with it, but I just finished Chapter 4 on the Cycle System. It struck me that the system I was using for so long (the clipboard method) shares so many similarities with this system.

Funnily, the book states that it is not intended to be a recommendation or tutorial for specific PDAs (Personal Digital Assistants) - thank god for that, as this book came out in 2005. I mean look at this! (I can sit here and bitch and moan about the solution not being plaintext or FOSS or what have you, but this used to be state-of-the-art! Counting my blessings!) I probably wouldn’t have received a recommendation for this book if it weren’t technology-agnostic - it’d be rotting among the shelves of various used bookstores in the Technology section alongside tips and tricks for Word 2000, mastering WordPerfect 5.1, etc.

So in this book he presents an approach, or a framework if you will, not a particular technology. It’s up to me to select one. Which is perfect, I am a master at overthinking solutions instead of actually working on the problem!

My thoughts here are still in the early stages but I got to thinking in the shower this evening and wanted to write down where I’m at. I’ve done a lot of thinking on this topic but rarely documenting - I know I did write down requirements for my ideal task management at one point, but it was almost certainly on a scratch piece of paper and lost to time (not to mention sorely outdated, but still useful as a time capsule if nothing else).

Tom outlines the following, I have added my personal notes next to each bullet point and added my specific additional requirements at the end.

Requirements for the system to be successful:

• Portable: so it needs to sync to my phone (PDA, if you will).
• Reliable: things I write down don’t need to be lost in the aether.
• Manageable chunks: so no “todo.txt” or single notebook of bullet points (what he calls the List of Doom)
• Calendar: my initial thoughts are this one seems like an impossible hurdle without using some proprietary solution, but we’ll see.
• Life-goals list: I’m not sure how to structure this one, but he phrases it as “a few blank pages”, and that seems a reasonable place to start. Not “tasks” in the Todoist sense, but tasks with custom statuses or note(s).
• A day-by-day section: this is how I currently manage in Obsidian. For all its limitations, it’s been great.
  • To-do list: can do.
  • Schedule: haven’t implemented.

Four parts in the organizer:

• 365 to-do lists per year: daily notes in Obsidian.
• Today’s schedule: Todoist.
• An appointment calendar: Todoist can handle.
• Notes: Obsidian-only

10 minute planning at start of day:

• Create today’s schedule: I somewhat do this. No reminders or time blocking as of yet.
• Create today’s to-do list: I do this.
• Prioritize and reschedule: I don’t do this.
• Work the plan: I do this, albeit with the limitations my current system has.
• Finish the day: I have a system to track overdue tasks, I don’t really dedicate time to this.
• Leave the office
• Repeat

My specific requirements:

• Plaintext (markdown is close enough)
  • Needs to support third-party syncing or access from a server on multiple devices from potentially different apps
  • Needs to support full-text search
  • Need to be able to backup and restore easily
  • Git versioning
• Reminders
• Mobile widgets (if at all possible - this might be wishing too hard)

A big hump for me, something not stated in the above, is that he recommends using the same system for both work and personal. I agree on this point, it’s been something that makes sense to me but I haven’t found a good solution for. At work, we use Microsoft everything. Luckily, since we are a small company, I can install whatever I want on my computer, and I already use my PC for both work and personal everything. It is my daily driver for all of my personal projects. So this leaves my options open, I just need to figure out the approach and use some time off to integrate everything.

My issue is that my todo management is fragmented between Todoist, Obsidian, and my Outlook inbox and calendar, primarily. Obsidian is a recent addition (last couple months) and has worked very well for managing my work tasks (NOT my work events). I don’t use it to manage any personal tasks, but I do use it for my personal blog and notes. My Todoist is for personal thoughts and on-the-go. (I actually tried, about a year and a half ago, to integrate my work and personal Todoist - it was simply too much overhead to add a separate @work or @personal tag to every single task created. I then tried creating a separate account for Todoist. Even more of a nightmare.)

Wrap-up

My final thoughts for now, as this is intended to be part I - my initial mullings finally put to paper and out of my damn head.

• Am I overthinking this? Probably.
• Will this be an overnight process? No.
• Will there be a perfect app for my needs? No - probably not even if I write it myself. My needs will change, anyway. I need to remind myself to be realistic. At least it’s not 2005 anymore.

Potential solutions to look into - e.g., next actionable steps:

• Give Logseq a fair shake
  • Does it support plaintext?
  • Those damn bulletpoints…
  • Tasks, scheduling, calendar?
  • Windows app bugs
• Investigate certain things in Obsidian
  • Widgets / quick add / open to daily note on mobile
  • Reminders (mobile AND desktop)
  • If the above work out…figure out sync again
• Try to integrate work tasks with personal Todoist again
  • Even though Todoist doesn’t handle the notes aspect, I could live with this for a time.
• There is also Obsidian integration with Todoist, and Todoist integration with Outlook (coming soon). Could be something worth looking into. I am just hesitant to patchwork everything together with more plugins maintained by someone else, whether that be a company or a hobbyist developer. Nothing against the hobbyist developers, I credit much of my workflow to hobbyists who are nice enough to post their experience on their blogs and/or their code on github. Just for a core task management workflow, I don’t want to rely on someone to stop maintaining a plugin and it terrorize my entire workflow. I probably do enough of that already.
• Get a damn moleskine pocket organizer and try it out. Maybe that will help translate my actual instead of idealistic needs more clearly into a digital solution, or maybe that will Just Work.

This is fairly early along in my blog (I didn’t actually intend to start a blog when I started this vault, but here we are), and I wrote it post-haste. The requirements will evolve and we’ll see where I go in terms of a solution. I tend to be a perfectionist with my documentation which generally means that I don’t write shit down. That’s something I’m trying to change. It’s not perfect, it never will be, but it’s recorded. I know approaches like this, taking a “snapshot” of where I am at a particular point in time, will be more helpful to me down the road than not writing anything down, even though it hurts my ego. (I am also making a pact to myself not to come back and edit this post. The list of requirements is particularly irking - I know that’s not everything I thought of, but it’s all I can think of in this stream-of-consciousness context, and writing things down in the shower isn’t part of my requirements. Perhaps it should be. I will write down more requirements in a separate note as I inevitably remember them.)

As much as I try to, I simply can’t get every thought I have committed to paper (or rather, bits). It’s something to strive for, though.

EOF