Dating Other Task Managers

I've a confession… I've been seeing other todo lists.

I don't have great reasons. It started because I wanted to have the option of freedom from Apple despite having invested a ridiculous amount of time and automation capital into the ecosystem.

My approach has been:

1. Write a transformation/migration script to examine the file format and application features.
2. Try it out alongside my working Things 3 system, trying to do my daily tasks to compare experiences.
3. Find some downside (because nothing is perfect) and continue shopping endlessly.

Let's rant! 👏

Context for my search…

Things is beautiful and just works. It is still my recommendation for most people when it comes to digital task management. It taught me a few things in my journey…

Quick capture enables focus. I'd used a few systems with quick capture before, but none for as long a time or as useful as Things’ Quick Capture.

URLs are awesome. Things embraces the amazing power of a URL to summon a connection between context or applications. I can have a link on my phone to see all tasks tagged Errand that opens automatically when I leave the house. 👏

Commit to commitments, and nothing else. Things is an opinionated, bullet-journal-esque system that encourages you to only commit to what you can do Today and leaving the rest in Anytime.

Keep it simple. While I have griped that Things doesn't have advanced features like dependencies or reviews… the focus on simplicity is refreshing. I have less to tinker with and more energy to accomplish my goals.

The Brain and the List

I forgot where I first heard this metaphor¹, but it has transformed how I think about Task Management. Your task management system has two parts: The Brain is a smart storage unit where you can store all the useful things you could do, The List is the subset of things you commit to doing. It's a small distinction with huge ramifications.

Identifying the parts of my Task Management system that are Brain and List has been helpful. Things 3 has objects I identify as the Brain and the List: Today (and arguably Upcoming) helps you focus on The List while Anytime allows you to query the whole system as The Brain.

Still more intriguing: Brain and List could be separate systems. (For instance, Ugmonk's gorgeous Analog system looks preternaturally good at focusing on The List, but doesn't attempt to be The Brain.)

Disconnect to Create

Realizing the distinction between The Brain and The List has changed how I work on a daily basis. I plan with The Brain, but I work from The List.

Years ago I wrote a blog post about my feeling overwhelmed by my list… I now would characterize that struggle as working from The Brain rather than The List.²

I have always required that my task manager be equally accessible on my phone and computer… I have changed my mind. I don't need the full-featured Brain on my phone³. I can capture to some intermediate: Drafts, a Bullet Journal, a scrap of paper. It's not too troublesome to re-record it later next time I'm at a computer. Heck, I work from home. I'm at a computer for 8 hours a day… it's no problem.

Bullet Journaling has taught me to embrace the friction of that extra step. My resistance to re-recording helps me filter out trivial tasks that shouldn't make it into The Brain, much less The List.

Rituals vs Tasks

I have anchored my workday around several Rituals. Instead of trying to make habits out of 15-30 things I need to remember (clean out my inbox, check for unusual calendar events, look at time tracking for the day, etc.) I have one habit: go through the checklist.⁴

These Rituals are odd in the task management world:

• they recur regularly
• they have many sub tasks/checklist items
• I adjust them based on season of life
• I don’t care to store a history of completion
• sometimes they output notes/reviews that I do want to store

Here’s an example of the Workday Shutdown, arguably the most important of my Rituals:

🗃 Workday Shutdown

As a faithful steward, I put my work in order to be prepared for the next day, identifying the essential task for the next day.

obsidian://advanced-uri?vault=wiki&commandname=Periodic%20Notes%3A%20Open%20daily%20note

- [ ] 🕰: Review time logs. Log any missing time.
- [ ] 📓: Journal events/tasks. things:///show?id=logbook
- [ ] 📝: Process notes/tasks from notebook.
- [ ] 📨: Process Drafts inboxes.
- [ ] 📥: Dump your brain into the Inbox. Get it all out.
- [ ] 📤: Process Things inbox. things:///show?id=inbox (:estimate, $focus, !modality, priority)
- [ ] 🗓: Make time for critical projects in tomorrow’s calendar.
- [ ] 🎯: Write The Note. things:///show?id=tomorrow
- [ ] 😴: Shut down. (Close. Speak. Shut. Trash. Door. Go home.)
- [ ] 👨‍👩‍👧‍👦: Go live in Coram Deo this evening.

Tags: Rituals: Daily
When: Today

I have quite a few Rituals at the moment:

• Daily Plan
• Workday Shutdown
• Evening Review
• Weekly Review
• 12WY Review
• Family Weekly
• Family Monthly

I have been handling these in Things using their excellent repeating checklists… but there may be a better way.

Context is King… I think?

Work doesn’t exist in a vacuum. We do it using resources, for some purpose… I didn’t know I wanted my Lists (like a Project) to have attached markdown notes until I used it in Things. I put URLs, documentation, the names of team members, it’s excellent.

One of my favorite uses for this is to write the reason that this task exists as it’s context. It helps center me on the work, and if I can’t think of a reason maybe I should not be spending time on it.

Why move from Things?

Besides the desire to see what's new in the world… I have one⁵ complaint about Things 3: You can't search for the absence of a Tag. 🤦‍♂️

What this deficiency means is that I can't find tasks without a given tag. Since Tags are the only cross-list organizational structure in Things, this means you can't easily find To-dos that haven't been delegated, or haven't been estimated, etc. This means that there isn't any easy way to construct a Review of your tasks in Things. I've hacked a solution together using JXA… but the scripting is limited to desktop-only. More automation options through Shortcuts could fix this… but I'd be surprised.

For lack of a shoe… the nerd goes shopping for task managers. 🤷

The contenders…

Orgmode

All productivity roads lead to Orgmode: The king-daddy of all digital organization systems. If you make the investment, Orgmode will reward you. It has every feature you could imagine, and it’s endlessly customizable.

After reading through the whole Orgmode manual, I wrote ThingsToOrgmode as an exporter from Things to .org files. All the exporters use a combo of Applescript and screen scraping to grab as much data as possible.

For a couple weeks I’d open Emacs next to Things and try to do my daily workflows in Orgmode alongside things, and I ran the exporter to keep Things synced to Orgmode.

Orgmode wants to be my everyting. I do indeed like thinking in outlines. org-refile is like a plaintext version of moving branches on a mindmap and I like it a lot. Orgmode has every feature (or a plugin) you could possibly want (calendars, time tracking, auto imports). There are iOS or Android apps if you want.

However… I don't want Orgmode to be my everything. In addition, I don't think I want to add emacs to my toolchain… I'm a fidgeter. Another config file in which I waste time would be anti-productive. If I used eMacs as my code editor things would be different.

I did spend some time with nvim-orgmode. It’s impressive… but not quite to feature parity.

Taskwarrior

TaskWarrior’s most interesting system is a prioritization algorithm that analyzes task attributes like age, priority, and dependencies to attempt to determine a weighted priority list… or just the next task. It is solid out of the box, but you can customize the weighting of attributes or add your own aspects to it using its custom fields.

TaskWarrior feels more "unix-like" than anything else on this list: single purpose, pipeable, simple. Aimed at people comfortable with terminals and scripting. TaskWarrior as a data system with customizable tools and views is an excellent Brain. If you want you can configure customized views to generate The List.

Because it’s essentially a CLI app, it’s harder to interact with away from a linux device. There are some attempts at mobile apps… but they feel immature.

While playing with it, I haven't found an easy solution for my Rituals.

As with Orgmode, I wrote an export for Things. The JSON format that TaskWarrior uses for interop makes import/export far easier.

ThingsToTaskwarrior

Todoist

Todoist has a great reputation in the field. Unlike the other examples, it’s not 0data, so its harder to get your data out. However, its prodigious web API makes it easy to get tasks in or automate creation of tasks based on Zapier events or however you like to automate.

Todoist has a Kanban view that is a compelling way to manage some projects. I do wish you could manage Projects that way… but you can always create a meta-project with links to the Projects since Everything is URLs.

Todoist has an incredibly cool integration with Fantastical that lets you put a task at a time… you can't set the time to longer than 45m, but it's a great start for time blocking.

I like project comments as a form of context. It seems to be aimed more at collaborative updates than a source of truth. You can’t nest tags like in Things, which is a shame. I have people tags sorted by team, so I can get my questions for you or anything related to your team. Very handy!

There are a couple Obsidian plugins available to view or sync tasks between Obsidian and Todoist or you could try…

Obsidian

Just using Obsidian! Obisidan is 0data plaintext… and it's basically a code-editor web-browser… so you can create pretty much create any system you want.

Besides the built in - [ ] task functionality, there's a number of excellent plugins for Obsidian to expand it's capabilities:

• time blocking
• task reports in dataview
• scheduling tasks

Obsidian has a lot going for it. I used the Tasks through Dataview on a side project for a month or two. It works pretty well. I could create tasks anywhere in the notes for the project, and they'd all be surfaced on the main Tasks note.

However… Obsidian is currently where I write and create, and I don't want my Productivity System mixed up with my Creativity System. Even without that, I found the tags I'd want for a task system to pollute the structure that I want for my knowledge system… it got confusing.

Bullet Journal

Bullet Journaling has been a part of my life for a few years. A Bullet Journal works as The List very well. Serving the function of The Brain is hard and requires a lot of upkeep. I've been using my Journal as an analog The List, and using my digital Task Manager as the Brain.

Since I first started this whole journey my work has shifted, or maybe my mindset has. Where I used to plan individual tasks into the day as time blocks I have started to block off a section for a Project List. The List (sometimes on The Note, sometimes a calendar block, sometimes Today) just contains the meta-task prompt "work on Project." This especially works with systems where the tasks aren't in "my one system." (JIRA, Trello, etc.)

As an experiment I have removed most of the quick capture tools off my phone. I capture most of my todos either through Siri or by jotting down in my journal. I'm enjoying the filter that comes with a little friction.

My deadlines live in external systems, my personal list is relatively simple and my Bullet Journaling has leveled up a good bit. I'm seriously considering returning to this 100%. The downside is that I'm at a computer 8 hours a day… so much of my work and capture needs to be a URL… and analog isn't super good at that.

Omnifocus

It's always lurking in the shadows. I haven’t touched it properly other than a trial. But it’s there, calling out my name…

Where to from here?

I don't know. 🤷 Here's what I am doing:

Moving Things 3 into "brain-only" mode

I'm trying not to work out of Thing's Today list… copying it into my journal each morning. (I decide the most important task the previous night and that ends up time-blocked and put on a sticky note on my keyboard.)

I'm also trying to avoid using Quick Capture. By relying on analog and Drafts as input I'm hoping I can break my addiction.

Splitting Rituals

I'm experimenting with splitting my Rituals into a "trigger" and "list."

The "trigger" is a task with a link to the "list." Because I'm still experimenting… the "trigger" is in both Things and Todoist at the moment while I learn how Todoist works. One dealbreaker seems to be that moving a single instance of a repeating task in Todoist breaks the repeat.

The "list" is a "Sloppy Operating Procedure" document in Obsidian. Because many of my Rituals involve reviewing, and the results of my review is logged in Obsidian this feels natural. I wish Obsidian had more automation for setting up splits with commands and files… and I don't have a way to reset the checklist… but it works great for now.

…

If Things were to go away, I'd predict that I'd end up in TaskWarrior as a Brain, Obsidian/ZK as context and Kanban, and Bullet Journal as my timeblocking/The List. But who knows.