Bogging down in the flexibility

In theory, I’m a big OmniFocus fan, and I’ve read enough GTD (including the book) and blogs and tips related to both to feel like I have a decent handle on the fundamentals. In practice, though, every time I’ve attempted to put all this into action by using OF myself, I got too bogged down in the minutiae to make it work. One of my biggest stumbling blocks was contexts, which always made sense when I read what other people did, but I couldn’t master. One never felt like enough. With the introduction of tags in OF3 I’m prepared to give it another shot, but let me give an example of the kind of thing I get stuck on, in hopes that the gurus here might help un-stick me.

Without any reliance on OF or any other productivity app, I’ve been making a recent push to de-clutter and organize my home. I’ve kept my momentum so far by picking and working on small achievable zones or projects each day, since “De-clutter house” is too big to ever start. One day might be purging old t-shirts I never wear anymore. Another might be choosing an out-of-control drawer to go through and trash what I can, and then use the new space to better arrange stuff so most-frequently used is most accessible. Bit by bit, my home is shaping up, even though nothing much changes in any single day. While I have some sense of things like, “I gotta get to that shelf in the garage…”, I basically just look around and pick something. Every room presents multiple areas in need of attention.

I would like to manage this in OF so I don’t have to keep the remaining to-dos only in my head, and for the satisfaction of ticking off “complete” actions, but I get stuck on how to organize this in OF itself. Let’s say I want to capture the action, “Purge unused t-shirts”. That’s pretty much a single action, and the location it occurs at will be Home. I could just process it that way and be done. On the other hand, I’m also trying to improve my habits, so if that task occurs in my bedroom, and I’d like some sort of tickle reminder every month or two to “Assess bedroom for things that need de-cluttered, purged, organized, fixed”, then entering small tasks in isolation as they occur to me won’t really keep that habit going. I have trouble deciding what should be a tag, a folder, a project, or a single action. With tags, I’m tempted to have a whole tag hierarchy like, “Household:Bedroom, Household:Kitchen, Household:Garage, etc.” so I can sort by room if I want to focus on one, but I don’t want every task I enter to require 5 tags (since that’s not my only hierarchy). I’m having trouble striking the balance between too much detail (my natural tendency) and not enough.

So, as a test example, how would you handle the objective of capturing list of projects throughout the home, and if that ever gets “caught up”, periodic reminders to check each area for new stuff since that kind of complete doesn’t stay complete forever? If you want to be able to quickly see any and all “Bedroom” projects/actions, would you group those under an “Organize Bedroom” SAL project, tag those actions with “Bedroom”, or maybe just make sure any such action is entered with the room name in the title? Or something else?

Think in terms of what information you want to see at any particular time. I’m assuming you have someplace you go to work – an office or some other workspace that takes you at least 15 minutes to get to. You have to get in a car and go, or maybe walk a few blocks if you live in the city.

So that means you want to have a tag for “home,” for things you only see when you’re at home. You can’t clean out your T-shirt drawer when you’re not in the house.

Now you set up a project for “Declutter house” (and OMG do I need to do THAT). Make a list of actions under the project:

  • Purge unused T-shirts.
  • Assess bedroom (recurring)
  • Organize area around desk
  • Clear kitchen counter around sink
  • etc.

It probably doesn’t make sense to have a tag for each individual room. I mean, you can walk from one room to the other in a trivial amount of time unless you’re a billionaire and live in a compound. And you’ve been doing pretty well just identifying a little area at random and jumping on that. So why add unnecessary complexity?

On the other hand, maybe it does make sense to have a tag for each room. Here’s a possibly useful analogy: I travel frequently for business and have a re-usable list called “packing.” Each item on the list is tagged “suitcase,” “briefcase” or “wear.” Those are for items that I need to remember to bring in my suitcase, items that I’ll carry in my briefcase, or items that I’ll wear or carry in my pockets. Some might say, “Why bother? Everything’s just going to be worn or carried by you?” But it makes sense to me because of my packing process – I do briefcase and suitcase separately, packing the night before I go, and then get dressed and load up my pockets with the rest.

Also, while I open and close my briefcase frequently to access items in transit, the suitcase ideally stays closed between the home and hotel.

So having those tags makes sense. And I’m even thinking of setting up sub-tags for “toiletries” and “cords & chargers.” This is all so I can do the actual packing in about 20 minutes and not forget to bring pants, which is a thing I have totally done.

1 Like

Thanks, Mitch. You uncovered one of the aspects that I’ve struggled with trying to use OF. While it’s a reasonable guess that I have a separate workplace and home (like most people), it’s not the case with me. While I have some work goals (mainly writing-related), I’m essentially a full-time dad. “Home” has never been a useful context to help me narrow down the list of projects/actions to choose from, because I’m home most of the time. Contexts tease out some not-home stuff like errands and appointments, but whether I’m writing (work), parenting, maintaining household, or lots of other personal stuff, I’m mostly at home. The home bucket is always overflowing.

I think your project suggestion for the big decluttering objective makes sense, with a combination of recurring tasks (“assess”) for each room that repeat every month or whatever from completion. Tags won’t tickle, but recurring projects will. At time of assessment, I would just add any particular tasks (e.g. “Purge t-shirts”). The top-level project would never be fully complete, but it would serve as my repository of tasks to choose from and I’d still get to tick those off for the endorphin rush that checkmarks bring.

As you point out, it can make sense with tags and sub-tags, too, so it’ll probably just take some trial and error to see what works best. I’ll continue to keep my eyes open for how anyone else has handled similar sprawling projects once more people are using tags.

1 Like

Your problem is similar to one I used to have, which is to try to find some kind of platonic ideal for organizing tasks. Now I just try to organize the APP, which is different.

When I am looking at this task, what other tasks do I want to see? What tasks do I want hidden?

I work from a home office. And even so, I think it might be useful to have separate tags for “home” and “office,” because those are different modes. And also because, as I said, I travel often for work. I can do “office” tasks anywhere I have my MacBook Pro and an internet connection. But I can’t take out the trash unless I’m home.


Thinking about this further: maybe you don’t need a to do list at all for these kinds of tasks. You want the satisfaction of writing them down and checking them off. Which is very reasonable! Maybe just keep a journal? Nothing fancy or highly ritualized, just a fast list of tasks completed. A “have done” list, if you will.

1 Like

While the satisfaction of checking off items on a list is a piece, it’s not the only or main thing I want from OF. The household example is a good example of ways I get stuck figuring out which of many ways to proceed, but there’s other areas of focus, too. I agree with your “Platonic ideal” observation that I’m probably letting perfect get in the way of good, but an old-fashioned checklist wouldn’t work, either. (I’ve tried.)

I’m always impressed by how much thought respondents put into helping each other out in these forums, even if most of the time I’m just lurking. Thanks for helping me think through this.


My pleasure! Although there is a payback to this helpfulness. I face a similar problem with organizing my tasks. Writing out my thoughts helps me think the problem through.

I really think the key is to think about organizing the tasks in a way to maximize the utility of the application, rather than for some other more lofty goal. For example, right now I am on a business trip to another city. I have some home tasks deferred to Friday, the first day I am back home. I could also tag those tasks with “home.” Either one of those would work. Neither approach is better.

Actually that’s not true. Tagging the tasks with “home” and “anywhere” would be a little better. On the other hand it may not be worth the trouble. The goal here is not to optimize the application. Is to get these things done.

1 Like

Just a suggestion:

Simplify your “trusted system”.

Simplify your contexts (and perspectives). You need one for “Home” if you want to declutter it: you can’t do it when you’re not at home.

Simplify your projects. In my opinion, the idea that we have to create long lists of to-do actions is seriously problematic. We end up with maybe thirty instructions to ourselves; not too different from being harassed by thirty different people. We go back to the stress that we were trying to avoid. Those things aren’t off our minds at all, they’re swamping our minds. Who needs an app badge reminding us that we have 15 things to do before lunchtime? “Recategorise the shelves in the garage” sounds like a good idea when I write it, but when it turns up on my screen on Saturday morning, it’s a burden, not a help. I’d rather have a cup of tea and put my feet up, thanks.

I try to make sure that I don’t use my system to harangue myself.

Here are two variations on a tactic that I find useful: Create repeating routines that are specific enough to be good reminders of what to do next, but still allow freedom to interpret and move. So, using decluttering the house as an example, I might create one routine in the “Declutter” project to “Chuck out 20 things” with a context “Home” and set it to “defer another 3 days” as a repeating task. And another task “Do something useful to declutter the house” and set it to “defer another 14 days” as a repeating task. Then I might set up a sub-folder of potentially useful things to do, within my Declutter project, but I’ll set the sub-folder on pause, so that they don’t appear until I look at them.

I find it helpful to combine that approach with a minimum number of active projects, so that I am less swamped with to-dos – which I find just as off-putting as having no system at all.

Minimum Contexts; Minimum Projects; Tasks that repeat, and are specific enough to be able to confidently check them off as done, but flexible enough to allow me choice at the moment they appear.

Just a suggestion based on my own personal trials. ;)


I like the sound of that. Whether I can do it remains to be seen, but what you’re suggesting makes a lot of sense to me. The appeal of GTD (and OF) to me has always been it’s potential for simplifying things, but the road to that simplicity seems paved with complication. In GTD (as I understand it, which included reading the book), pretty much the first thing you have to do is a brain dump to get out all the things you need or might want to remember to do. I’m predisposed towards…let’s call it thoroughness…so for me it’s like taking my first step into that field and stepping on a landmine. My dump on any given day if I’m trying to abide by GTD’s encouragement to dump it all results in a pile so big I never get it fully processed out of the inbox (project, context, status, etc.) and if I try to start just using it, I’m simultaneously worried about all the unprocessed items in there. I never even get to where I can usefully do the “Review” step, because I’ll defer 200 items a week just to try to start doing some things, and a week later there’s all 200 items as though I just started. In about 4 attempts spread over years (and versions), I never manage to clear the initial capture hurdle to get to the part where it’s supposed to make things easier. Or to borrow your lingo, to get past the point of just feeling harangued.

Thanks for your examples, mrlikeable. I like the idea of fewer generalized projects to keep the ambient noise down, with paused folders buried beneath that I can draw from when wanted, but that won’t feel in such constant need of processing. I know all this potential has already been there, but I get derailed by my own attention to detail that in non-OF ways is one of my strengths.

I’m back to the forums briefly and, while it has been a couple weeks, I do have a few thoughts on this, as someone who has a huge OF database and eleven years of experience with the app (I started with Kinkless GTD, a set of scripts for OmniOutliner, and alpha-tested the original OF).

First, if you end up deferring 200 items a week, you may be using the wrong view. I currently have 680 actions remaining in 169 projects. But usually I’m not working in a perspective that shows all of them. I start off my day in the Forecast perspective to get an overview of what really needs to be done first (and I like the ability in OF 3 to add a tag to Forecast). If I knock everything off that list, or at least the ones that are necessary, I’ll switch to another perspective and work from there.

Sometimes that’s a tag perspective (I still want to call it context!), if I really do need to be somewhere to do an action. I’m an academic; some of what I do I can do anywhere with a laptop and an Internet connection, but some things are constrained by location. Often, though, I will start with the Projects perspective, choose one or more areas of responsibility (defined by folders), and then Focus on them before switching to another perspective. I block out time each day for working on my research and writing projects, and by selecting those folders and then hitting Focus, I ensure that extraneous tasks are excluded. They may be important, but for the 2 hours (or whatever) I’m working on my writing, they don’t appear in OF. Once I reach the end of that time—or a critical email comes in and circumstances force me to recalibrate—I unfocus and have access to everything else.

I also occasionally find it useful to restrict my view in tags or elsewhere to the next available action. Some of my projects I plan out in reasonable detail, which can result in a large number of available actions. By limiting a perspective to next action, I can clear out that clutter and better decide which of those 169 projects really needs to be advanced right now. I’m also getting better at using sequential projects and action groups if things really must be done in a particular order.

A final thing that helps me stay in control is to have a couple of someday/maybe projects where I dump things that I might eventually get around to, and a related “On Hold” tag that has a status of On Hold. That keeps those tasks out of my active to-do list. Things that are truly not likely to happen any time soon go into a separate OmniOutliner Someday-Maybe file that I review every 3-6 months.

1 Like