OmniFocus's current Mac icon, shaped like a big purple checkbox.This year marks my tenth anniversary using OmniFocus, the small family of Mac and iOS productivity applications from the Omni Group. I do not exaggerate to say that the Mac edition of OmniFocus has served as the glue of my life as a doer-of-things over this whole span. Not consistently, mind you — more than once I’ve let weeks, even months pass without tending to its lists of lists. Exactly once I took the opportunity of a new major release to declare “OmniFocus bankruptcy”, punting countless stale projects to start fresh with an empty task-database. Either way, I always find reason to return and stick with it once again for a long time.

Today finds me stepping through a pleasantly extended dance with the big purple checkmark on my Mac’s dock. After so many years, I have found my best approach yet of working with OmniFocus, such that it feels far more like a companionable assistant than a burdensome nag. In this pattern, I consult the program’s Forecast pane throughout the day, both to whittle down my daily task-list and to build up the next day’s priorities. Between tasks I revisit the app’s Inbox pane, reviewing the jotted-down proto-tasks I’ve recently captured for later cogitation, deciding the next steps for each. These become the raw materials for actionable tasks that, eventually, wind up on the next day-long shortlist, with all its invitingly empty checkboxes.

In recognition of how much this software-assisted cycle has helped me over the years, and in the hope that it may help someone else as well, this article describes several strategies I use when working with this glorified to-do list program. I focus here more on overall approaches than on software-specific tips-n-tricks.

Goal: Mind like water. While I did read David Allen’s Getting Things Done back when I first started using OmniFocus, I ultimately found it more useful as a backgrounder for the program’s design philosophy than as a guide to using it. In a way, OmniFocus reifies GTD, giving you a single place to capture tasks, tie time-and-space contexts to each one, and then forget about them until it’s time to focus on them. When it all comes together, I really can approach the “mind like water” state that Allen espouses in this talk from 2008*.

I don’t expect anyone else who relies on the program to use it precisely as I do, so your mileage may very much vary regarding the following list of personal habits and philosophies — except, perhaps, for the first point, which I understand as a core tenet of OmniFocus’s objectively intended use.

Always Be Capturing. Reduce the friction between yourself and your OmniFocus inbox, minimizing the length of time a newly realized task must sit in your meat-memory. Ideally, as soon as you perceive the need to get something done — and it could be anything, in any scale or context, from “buy cat food” to “respond to this email” to “deliver this six-month client project” — you can have that noted in your inbox within moments, and then eject it from your active attention, letting you return your focus to your current task. (Less than ideally, you’re driving or showering or something when a possible task hits you — but you can hold one or two things in your mental cache until you have a chance to inbox them safely.)

An inboxed item can wait until you’re ready to focus on your next inbox-processing session, sometime in the next day or three.† At that point — and no sooner — you’ll promote it into a time-deferred project filled with sub-tasks, or recognize it as a ten-minute doddle you can knock off right away, or change your mind about its relevance and just delete it.

(This doesn’t include emergencies, of course! Sometimes things pop up for which we really do need to put everything else aside, because they honestly can’t wait a few hours. Crisis management lies outside the forte of OmniFocus. On the other hand, in assisting you with continuously storing and processing the “everything else” that you must put aside when crises do emerge, OmniFocus can help make the transition from tactical emergency-mode back into strategic normal-work mode much less painful.)

OmniFocus gives you lots of ways to add stuff to your inbox, both inside and outside the actual applications — some of which I must admit I’ve never really figured out, like “clippings” or direct Siri commands. I tend to use a mix of the apps’ buttons, the control-option-space global keystroke on Mac, and the email integration feature. The latter I use in two ways: I forward to it all non-emergency email that requires a response from me, and when an idea hits me while I’m out walking I’ll pinch my iPhone’s mic-button and say “Send a new email to My OmniFocus”, and proceed to dictate the item’s content as its subject line. (This latter trick works because I have an address book entry for someone named “OmniFocus”, first name “My”.)

Organize time via deferrals. When I want to mark a task or project as a candidate for my attention on a certain day, I mark it as deferred until (and not due on) that day. Because I set OmniFocus to include deferred items in my Forecast tab (via its checkbox at Perspectives → Show Perspectives → Forecast), I can see with a click everything that my recent-past self thought I could get done today.

My thinking here tends towards the short-term: at the start of my work-day, if that list looks short, I’ll often browse my projects to “defer” some tasks to today. I’ll also do this for new tasks important enough to deserve my more-immediate attention. If the end of the day approaches and I have some leftovers, I’ll defer them to tomorrow. (Items have a handy “+1 day” button under the Defer Until field in the detail-pane, and I hit that button a lot with no shame. Three times apiece, on Fridays.)

Of course, I also defer tasks that I know lie in my future, but, for one reason or another, I can’t focus on yet: for example, writing a wrap-up report for a project that doesn’t wrap up for another month. I’ll define as many of the project’s subtasks as I can, stamp the whole thing as deferred for four weeks, and then happily forget about it, secure in knowing that OmniFocus will float it back into my sight-line just in time.

I also made myself a custom “Deferrals” perspective-tab which lists only deferred items, ordered by their defer-dates relative to today; OmniFocus intelligently and pleasantly groups these into today, tomorrow, next week, next month, and finally a fuzzy three-months-out blob. This view omits due-dates and calendar appointments and other stuff I can’t actually do anything about, giving me a nice summary of my likely future actions into time-chunks that grow appropriately coarser with greater distance from the present’s certainties.

This perspective will also show tasks whose deferral-dates have slipped into the past — something that happens to me frequently. This doesn’t mean failure, or even anything overdue; it just means that I expected to work on something during a certain day, and it happens that I didn’t. In this case, I feel no regret in just kicking ahead its deferral-date as needed.

Make and use a “Waiting” context. I have a context called “Waiting”, whose status I marked as On Hold, and which has no particular location or other information associated with it. When the next step in a project literally involves me waiting for something to happen — an email response, a package arrival, and so on — then I represent it with a task — “Wait for Jim-Bob’s reply”, say — and assign that task the Waiting context.

The task will then inherit the context’s On Hold status, causing OmniFocus to represent it as a blocker, preventing access to all subsequent tasks even though I cannot act on it myself. The program draws the task as grayed-out, with its “Waiting” context acting as a nicely self-documenting label.

But as we usually don’t feel content to wait for something indefinitely, I will most times set the Due field for that task to the date at which I shall be done waiting. (By default, I’ll just kick the “+1 week” button here.) Should the task become overdue, then it’s time for me to take action. If it’s an email reply I’m waiting on, for example, perhaps I’ll send another status-request email, and kick the due-date into the future for another week. (And also note this on the task’s notes-field, so that if it happens for two weeks running I’ll know to escalate appropriately.)

For most of the time I’ve used OmniFocus, “Waiting” has been my only defined context. I just haven’t used contexts very often, though I’ve very recently started experimenting with them once again, as I describe further below.

Use due-dates only for literal due-dates. I set the Due date-field only on tasks that actually have real-world deadlines attached to them. The due-date of my “Pay taxes” project is April 15; the due-date for obtaining a present for a friend is the day before their birthday. This sets an upper-bound in time for focusing on its constituent sub-tasks, and so long as I’m on the right side of that boundary I will use the Defer Until field to lightly pin times I intend to actually focus on the tasks, as I describe above.

(My exception to this restricted use of the Due field involves the way I pair it with the “Waiting” context, described earlier.)

I used to set the Due field to the date I thought I ought to work on a task, rather the way I use the Defer Until field now. This had the effect of items falling into cherry-red “overdue” status all the time, and my phone reminding me every day of all the ways I continuously fell behind schedule, in tasks both crucial and trivial. This made me not want to use OmniFocus. The Omni Group paired the release of version 2.0 in 2014 with a set of advice-articles from other long-time users; from one of these did I glean the strategy of using Due only for real, hard deadlines, and Defer Until as a more flexible date-pin. After declaring task-bankruptcy and starting with an empty database, I adopted this strategy myself, and I haven’t looked back since.

Use contexts only for physical-location prerequisites. Much like I use the Due field only for tasks that have real-world deadlines, I create and assign contexts (besides my beloved “Waiting”) sparingly, limiting them to physical locations representing the only places that certain tasks can get accomplished.

Right now, I have only “Home” and “Office”, and then “Hardware store”, “Supermarket”, and a few other shops. And even though I accomplish most of my work in my home or office, I assign these contexts only when I must be at that location to fulfill the task. For example, only my home has a printer in it, so I’ll assign a “Print this out” task to “Home”. Only the hardware store will sell me a new screwdriver, so its context gets affixed to the “Buy new screwdriver” task.

The vast majority of my tasks, though, involve doing something on my computer. And since my main computer, a laptop, travels with me throughout the day, I don’t bother setting the context field for most of my OmniFocus items. That works out just fine!

Only quite recently have I begun geotagging contexts, letting OmniFocus send me a little reminder-ping through my phone whenever I approach a location tied to an available task which I can accomplish only there. I haven’t used this feature long enough to call it a definitive part of my long-term OmniFocus strategy, but I will admit to finding it pretty cool.

Trust the judgment of your past self. Often, a task will come up in my list of tasks for the day, and I’ll think: Is this really that important? Often it seems too “fun”, a next step in a personal project mixed into a daily task-list otherwise full of bread-winning client work, perhaps.

But here, I have learned to put faith into the judgment of the past self who found this task valuable enough to put into OmniFocus, and then to furthermore assign a deferral-date to. I can try to put myself into the mind I had then, and feel free to ask whether the value I saw in the task then remains true today. But unless I today find the task completely outdated or otherwise disagreeable, I’ll make an effort to focus on it exactly as my past self wanted.

I seldom regret this.

Drop stale projects ruthlessly. As I wrote above, I think very little of clicking the “+1” buttons below the Defer Until field on tasks for which I just don’t have the attention to spare today. There comes a point, though, when it seems like so much can-kicking, especially if I find myself marking the project as reviewed without any changes for week after week, stretching into months.

Very often, these fall into the category of “nice-to-have” goals — either personal projects, or work that would benefit clients or myself professionally but which nobody’s explicitly asked for. In any case, potential progress on these projects keeps getting shouldered out of the way by more important or interesting work.

In time, and for each of these, I have to face the fact that I clearly don’t want to work on this project. With no other force in the world (such as money) encouraging me to do it anyway, I’ll just keep kicking that can. And that’s when I mark the project as Dropped.

To lessen the sting, I reserve the right the copy the project’s checklist and paste it into an project-ideas archive file, outside of OmniFocus. This leaves the door open to picking it back up again, someday, when I feel actually ready to give some time and attention to it. But OmniFocus is about what deserves my attention today, and so it doesn’t belong there.

Take joy in completion, but do not dread commencement. Checking tasks’ checkboxes brings a feeling of forward momentum throughout the day. Completing (and dropping!) entire projects delivers an extra boost, causing whole rows of work to vanish in glory from your OmniFocus sidebar. When I don’t check myself, this pleasure in making things go away drifts inexorably into an adversarial relationship with my OmniFocus database, something not so much to complete as to defeat.

Seeing my inbox as a column of enemies to mow down may feel fun in the short term, but I try not to lean hard on this visualization — because it makes inboxing new items, or adding new tasks to an existing, evolving project, feel terrible. It makes the very act of planning feel like a step backwards, like fighting a boss-creature in a video game who keeps healing itself away from an end-point of ultimate victory.

Thinking of work as a foe to vanquish forever represents a category error, one whose impossibility to achieve can lead only to frustration. So long as I remain alive and healthy, I will have work to do — much of it, happily, of my own choosing, with a pace I set for myself. OmniFocus helps make this possible. To keep my use of it meaningful, I must see the act of capturing a task less as another burden to struggle against and throw off than as an investment, one which after some tending will sprout a profit of accomplishment, or wealth, or — yes, even just relief.

And that’s how I use OmniFocus today! I hope it proves at least as useful to me for another ten years.

* If that video looks a bit dated, note that it coincides with my adoption of OmniFocus. Watching it way back then did help me set my initial attitude towards the software and its use, and I expect that the talk still holds up today.

† I’m sure some OmniFocus fans get all meta about this, making a repeating project just for inbox-clearing! I personally don’t find that necessary. That little pale-blue stripe signifying unprocessed items in the Inbox tab feels like a pebble in my shoe, and I look forward to shaking it out.

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