Creating Kinder To Do Lists

…Where lists are regularly reviewed and any item could instantly become a task or a project with defers, dues, reminders, repeats, etc.

As a perennial newbie to OmniFocus, I thought this was how the program already worked.

Maybe I’m just thinking of my too-neglected Inbox with its dozens of items that could become an immediate task by my doing it. Or it could become a project with just a click or two and thus have access to defer dates, repeats, etc.

OK, here goes.

Software I use depends whether it’s for work or personal.

Work: for. context, I’m a freelance project manager.

I use:

Mindnode or iThoughts mind mapping. to produce the high level shape of the project

Omniplan for the formal plan

DEVONThink as the information repository (documents, mail and notes)

Tinderbox to collect notes and organise decision-making

Curio as the “control centre” - pages (“idea spaces”) for major areas in the project. Example - I’ll have a` template page for the Project Board - new copy for each report and meeting with templates in it for the report, minutes, notes or whatever I need each reporting period. Relevant documents or links are embedded in the relevant bit of Curio.

I get tasks from Curio into Omnifocus manually and they’re usually not very granular. So, for the monthly project report, I’ll just have a task “Do Monthly Report”, with a link back to the Curio page with the report guidance on it. I create the task manually. If. OF linked to Mac Reminders fully, I could automate this via Curio sync to Reminders.

Only if there’s a specific, non-standard task associated with the monthly report will I create another task in OF.

Similarly, for the other major work areas (planning, people, testing and so on), I try. to keep the higher level view in Curio, fed from the other applications.

At home I work a little differently. For day-to-day activities, I have some OF projects and tags (Household is a project, Car, Decorating, Shopping etc are tags) and I’ll record “tasks that need to. be in OF”. I don’t put everything there (no weekly garbage collection, no weekly shopping lists) - only things I’m likely to need to be reminded of, either because missing them would be bad (due dates for bill payments) or because I might lose sight of them (doer some more water softener salt).

I have some creative stuff (I’m learning to draw and I’m an amateur musician). All OF will have is “Practice time” or “Rehearsal time”. DEVONThink has lists of material, actions, songs etc and I just refer to those to decide what to do with that time.

I’m not sure how much that helps. In a sentence, Omnifocus is for specific things I need to do - not for goals or aspirations or plans. It’s too granular for that other stuff.

If some. fo that needs explanation, ask away - it’s helpful for me to have to think about what I do and how


Great post, as always, Beck! I had to laugh at something as I read it. I have very frequently had the same reaction about the computer–OmniFocus in this context–being my taskmaster, relentlessly telling me what to do, when to do it, and how far behind I am on various things. Then, I remember that I was the one who told the computer to do that to me! I’m my own slavedriver.

It also made me think of something else related to task managers. Let’s say I have a goal to reconcile my bank account on a certain day of the month. Putting aside OmniFocus, or Reminders, or a yellowpad, I might be reminded of that task on the appropriate day, realize I’m too busy to do and and just do it another time. I’m not “late” in any real or meaningful sense. I just did not achieve an aspirational goal. If I get to it the following week, or the beginning of the next month, it does not matter. Still, I don’t want to forget it.

The problem with digital tools is that there is no such thing as creating a “fuzzy” deadline. And it’s kind of draining to look at a task manager and see 39 past due tasks. Sure, you could just push the date off. Sometimes I do that. The problem is that we (at least some of us) use dates in task managers to (1) remind us of tasks that are actually due on that date, (2) remind us of tasks we want to do on that date, (3) try to plan our days and weeks in a comprehensive way, and (4) remind us of tasks we are afraid we are going to forget.

Which, leads me to this point about GTD.

As you know from some of our prior dialogue on this point, I decided to re-engineer my GTD system a while back because I had fallen into this trap of having too much on my plate and no reasonable way of recognizing the value of completing one task over another the way my system was set up.

When I re-read some key sections about GTD, I realized that the system is supposed to do what you described–help you remember everything you want to do–but it is not a system that is designed to present you everything you need to do at all times.

The amazing thing about our digital tools that wrecks havoc on practicing GTD is that the tools combine next action lists with project plans. In paper GTD, you may have a project plan that lists all the things you might want to do on a project. On your next action list, would go only the thing you need to do next to move that project forward. Once that’s done, you add the next next-action.

OmniFocus is wonderful because it allows us to create project plans and source the next actions from them. It’s been a life saver for me to have one home base where everything I need to do and the projects to which those things are related exist.

Finding the way to manage it such that we do not forget things, we “get things done,” and yet we are kind to ourselves is the challenge. Your proposal is a lovely method of bridging that gap.

My new system has helped resolve some of these issue for me, and I hope to carve out the time to share it and see what others think. We certainly share the same goal: achieve and accomplish those things we want in a way that does not make us go mad. :)

This is why it’s so important to regularly use the Review perspective. Simply looking over projects for a few seconds acts as a spaced repetition interval—causing indefinite retention of your captured to do’s.

Yes, for me, a better review process gave me the confidence not to have to over schedule—although, it still takes a lot of discipline to avoid falling into the trap. That review process consists of the GTD weekly review (a practice that I had been using since before GTD popularized it, thanks to Seven Habits) coupled with the use of a few specific OmniFocus perspectives designed to surface certain project types that enable me to have a couple of quick targeted reviews. My weekly review process takes about 45 minutes most Saturdays. The mini-reviews take 3-12 minutes. The longer duration is only if I have project updates; e.g., I have actions I am ready to do or new actions to add to the applicable projects.

This is wonderful, Nick. Thanks for going into such detail. We have similar flows except I do not use Curio (though you have me curious!). Would you mind sharing a screengrab of one of your curio spaces so I can get a better sense of how you’re using it? And also, what level of the software do you have?

What I’m gathering from your setup is:

  1. You do thinking-style visualization/mapping/outlining in TBX
  2. You collect and find things in Curio and Devonthink
  3. You use OF to trigger visiting those collections (do you use links in your OF notes or just know where to look?)


Ain’t that the truth.

Hi Tom! Nice to hear from you. I would very much like to know more about your perspectives. Right now I feel pretty stuck in the default ones, with the exception of two that really help me focus and see what needs to be done (these are my reading list and my email). I know a more clever use of perspectives would help with other tasks. I’m sure any light you can shed on making this work would brighten many of our OF repositories.

Perhaps… I feel like the main demotivators for me are that the task is unpleasant to do, or that I feel anxiety about it. It’s possible my own imperatives to myself are eroding motivation, but I’m not sure how much a factor that is. I think it’s worse when it’s someone else bossing you around, subsuming your will into their own. When it’s you, it’s the same will. And if you don’t like the orders your past self is giving, you can just delete or amend them.

I was just wrestling with this issue yesterday when needing to find appropriate language for a task I didn’t want to do, didn’t have to, but felt I should do. I’ve long been a proponent of not shoulding on others or myself, so what to do?

The act of having difficulty with the item was a moment of insight in itself. (Not that I didn’t know it already, but) I realized that I was in an unbalanced relationship with what was being expected of me from this person and my own personal sense of agency. At the same time, this person is important and I really shouldn’t (there’s that word again) leave them hanging.

I came up with the language, “You’ll feel better if you ____.” and that’s what I did checked off today, when I completed the task. It was a sort of compromise with that person’s expectations of me and with my own shoulding of myself. It’s not a panacea, but it helped in that case.

This is interesting. My immediate reaction is that the more verbose statements, while friendlier to one’s future self, will be harder to write, scan and read. I generally dislike having to look into the middle of a sentence for the meat when we’re talking about a big list of things. Still it’s worth thinking about. I do spend a fair bit of effort fiddling with my OF instance to keep the lists from being overwhelming…

Tone can be quite briefly retuned – a question mark ?

Perhaps degree of concision is really an orthogonal issue – the OP’s helpful and well made point is that imperative tone (however lengthily or briefly expressed – some bosses are brief, but others are very wordy) can have unnoticed, almost somatic, costs.

Fair enough, although the examples in the blog post are all longer than the imperative ones. I certainly don’t mean to prevent others from using the idea, and if it helps people feel less stress, that’s great.

Personally, I find “pickup library books” clearer and more direct than “your library books are ready to be picked up”, and I don’t find the former more intimidating. It’s just a note from myself to myself at a later time, not a command from a micromanaging evil boss.

One thing I 100% agree with the author on is that there’s an art to writing to do lists – how much detail to include, where to include it, how much to break down tasks in OF, vs other places vs. just in my mind. The emotional voice of the tasks is a relevant dimension for sure. I just personally find most of the examples to be a bit on the flowery side in a way that gets in the way of the communication.

This reaction reveals a potential difference in how we view efficiency and speed in processes and software. I see a lot of value in things that slow us down.

Yes, this is exactly what I was intending to get across. Well put.

I’m actually more excited about the practice of future-self kindness this “kinder” orientation invites, but I have also personally experienced that a hundreds-long list of commands affects my relationship with OF. As I posted originally, I don’t expect this to resonate for the majority of users.

Agreed. It’s a work in progress.

I do too, actually. But in this particular case, I guess I lean more towards scanability, not because it’s more efficient per se, but more because it reduces the cognitive load in absorbing and evaluating a group of items.

In the same vein, I put a fair amount of effort into making the lists that I’m actually dealing with at a given time, relatively small. For example, during a weekly review every Sunday, I pare down my list of items for the week to around 30 at the most across all areas of life. Then when I’m actually working, I often pare it down further by clicking on an “area of life” tag.

Anyway, interesting idea. Thanks for the discussion.

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I’d love to hear more about your process for keeping lists limited. It’s something I haven’t figured out how to do. Have you written about it elsewhere?

This reminds me, re brevity, that the hallowed tradition of framing lists around ‘actions’ (whether commanded or kindly alluded to) is itself a source of redundancy.

Simply naming a fine-grained outcome (pruning out the apparatus of ‘actions’ and ‘actors’, compelled or willing), is often shorter, more appealing, and more helpful later on.

(Not unlike refactoring code from imperative to functional – C is more verbose than Haskell).

I’ve never published it, but I do have a write up:

The main idea is to heavily use defer to push things out into the future. I have a “this week” perspective, which is essentially everything that’s available. That’s the view that I pare down to 30 items or fewer. (Note: if there are a lot of sequential projects in that 30 items, there will be a whole bunch of hidden items. If I’m feeling like that will be a problem, I sometimes use a “this week” tag to make those visible in a similar perspective.

Simply naming a fine-grained outcome

Another interesting idea. “Begin with the end in mind.” I think that would work well for writing projects. Unless it’s obvious, that doesn’t feel like it would tell you “this is the next thing you need to do to move toward that outcome”. Also, there’s definitely a dopamine hit related to checking off items on the list. At least for me.

Side note, I really wish that Evernote was better on iOS. I loved (past tense) the app and would love to use it again, but right now it’s unusable on iOS. It just hangs and restarts constantly.

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