Waxing philosophical about task management in OmniFocus

In the lead-up to my Learn OmniFocus workflow session, I wanted to share some of the nitty-gritty details of how I manage my tasks with OmniFocus. That session will focus on the magic of Omni Automation (✨!). So, over this week, I’m concentrating on the more foundational, structural side of things, like projects, tags, and perspectives.

At this point, we’ve covered:

• my main ‘dashboard view’
• more custom perspectives
• some automation magic that helps with window management and navigation
• using the ‘focus’ feature and tags to switch between contexts
• my prolific tag usage, and
• my project list.

For the last post in this series, I’d like to zoom out and consider some of the overarching principles I try to keep in mind as I iterate on my OmniFocus set-up.

Iterative and incremental

This system might appear overly complex or overly engineered to some. That’s fine! And the reality is, if you tried to implement a system identical to mine overnight, it almost certainly would not work for you.

My workflow is specific to me and has been gradually honed and refined over the eight or so years that I’ve been using OmniFocus.

Although I’ve certainly had a few overhauls of the whole database during that time, I try to resist the temptation to do this unless it’s really necessary. Sometimes, a significant shift in life circumstances precipitates a big shift in the structure of OmniFocus, and that’s okay. But, in general: small, incremental changes are the way to go.

One in, all in

I keep everything in OmniFocus.

Some prefer to keep the minutiae of their lives outside of OmniFocus, and that’s fine too! I understand this perspective; it certainly adds simplicity. David Allen writes in ‘Making It All Work’:

…the more mundane the level you’re trying to organize, the more complex your system must be to manage it well.

This is 100% true, in my experience.

But for me, the benefits of keeping everything from ‘drink a glass of water’ to ‘complete XYZ really big project’ in OmniFocus are:

• I always know where to look, and I always know what I need to do next.
• On days when life is difficult—maybe I’m sick, maybe my son is sick, or maybe I just had a baby and am now living the madness that is life with a newborn (none of these are hypothetical examples…)—the ‘obvious’ things can be less obvious. I’ve found it beneficial both to have a reminder to do these obvious things that I know keep my body, brain, house and life ticking along happily; and also to be able to look back at the end of the day and know that if I have done all of these things, even if I achieved nothing else. Sometimes remembering to wash your hair is an accomplishment, and that’s okay!
• Over on the OmniFocus forums, Jeff Hester wrote “A single keystone habit – in this case open up OmniFocus first thing in the morning – could be used to bootstrap a great deal more. That includes setting in motion a day of checking OmniFocus on a regular basis.” I don’t think I can do a better job than that of describing exactly how powerful I think OmniFocus can be in building a habit stack. If I put something in OmniFocus in the right place in the right way, I will almost certainly make myself do it.
• In that same post, Jeff refers to the dopamine hit of checking off an activity. I’m not going to pretend that I don’t get some satisfaction from the simple act of checking items off that list.

Focusing on the next steps

I have a natural tendency to want to map out projects in their entirety.

However, I’ve found it’s often more powerful to get back to GTD basics and focus on the next step, or the next few steps. In recent times, I’ve switched my default setting for projects and action groups to not autocomplete and instead:

• added a prompt to my ‘Custom Complete’ plug-in that asks me what to do about any action groups or projects with no remaining actions, and
• added a ‘Stalled’ perspective that I check as part of my daily and weekly reviews.

Both of these things help me to make the mental shift to not try and plan out projects, particularly big projects, too far in advance.

A related tip I picked up from Kourosh Dini’s Creating Flow with OmniFocus 3 is the idea of a repeating ‘Work on:’ task. I find this helpful in cases where:

• The next action is relatively obvious. For example, I recently ripped my family’s old home movies from DVD because that was the only place they had been stored. For that project, it was just a matter of sitting down and doing the next thing. The project was, more or less self-emergent and didn’t need to be defined further than that. I wouldn’t have gained anything from doing so.
• The project is more ‘creative’. And by creative, I don’t necessarily mean art or music; instead, I mean that the project is open-ended – it might be writing a report or pulling together my son’s baby book. The main thing I need to do is show up and sit with the project for a while.

I use my ‘Work On…’ plug-in to help manage these tasks.

Do-ability

I like my lists to be short and feel ‘do-able’. This is, I think, a large part of why my dashboard view works so well for me: it breaks everything down into multiple lists and helps avoid overwhelm. It’s why I like to defer tags that aren’t relevant, and why I like to switch between my ‘focus’ and ‘no focus’ modes.

This is also an important thing that I try to keep in mind when I’m creating individual tasks: is this something I can sit down and do in one sitting? Is it clear exactly what I need to do? If not, I may be deterred from starting it.

Automation as a hobby

I am not deluding myself here: I know that the amount of time I have spent developing Omni Automation plug-ins and related automations leaves me on the wrong side of this xkcd comic.

But I’m okay with that, because I love to learn and I love to code, and I enjoy sharing the results with other people and seeing them get use out of things I’ve produced. Actually getting to use the plug-ins in my OmniFocus workflow is kind of a bonus!

And to that end, I hope you’ll join me over on Learn OmniFocus tomorrow, where I’m planning to share a bit about my set-up and several of the aforementioned automations.

For now, that’s a wrap on this OmniFocus series. I hope you’ve enjoyed our whirlwind tour of my database, and perhaps picked up a trick or two to test out in your own workflow.