I’ve been running my own business (sometimes businesses, plural) since 1993, and in that time I’ve tried nearly every prominent project and task manager that came down the pike. There’s no question that OmniFocus has been best in class since its initial release, and OmniFocus 3 is continuing that trend.

That said, there is a fast road to disliking and being discouraged by any tool or app you’re attempting to use, including OmniFocus: using it for things it’s not designed to do. The better approach is use OmniFocus for what it’s best at doing, and give yourself the necessary freedom to step outside when other tools are better for specific tasks.

For example, OmniFocus is the best tool I’ve ever found for coming up with a grand scheme that will take a decade to complete, and have it tell me what to do this Tuesday about it. It’s the first place I look in the morning and the last place I look when wrapping up my day. But it’s not the best place to store ideas I have in the shower.

A whiteboard is simply better than OmniFocus for that one particular case, and specifically the best tool for me. Your mileage may vary, perhaps if you share your shower with offspring who would take a marker as an invitation to use the entire wall as a sketchpad. So the trick is:

  1. Select a potentially better organizational tool or method for specific tasks, suited for your needs. (You can use a frustrating moment in OmniFocus as a cue to consider this.)
  2. Implement those tools for a trial run.
  3. Integrate these into your OmniFocus workflow, and stop trying to shoehorn that task into OmniFocus.
  4. If the tool and the integration work, keep it. If not, document what’s substandard about it and use that information to try again.

These integrations take place using a particular subset of your tasks. In my book Take Control of Your Productivity, I call these “pointers,” because they point you outside of OmniFocus to somewhere else you’ve stored information or project organization. The recurring task to take a photo of my whiteboard for my inbox is my pointer; the whiteboard itself is the external store of information that’s not in OmniFocus.

The key thing about pointers and external organization is that you can point to anything. In fact, you should point to anything you use as a store of information, and you certainly have such places: Do you have a table where you put your opened paper mail until you have time to deal with it? Does your spouse remember things for you that you only sporadically write down, or which they don’t always provide to you in a list of perfect bullet points while you enter them into OmniFocus? You need pointers to both places, such as, “Ask Sam during breakfast what I should keep in mind today.”

Just as your spouse is not the best place to store your project lists, OmniFocus is not the best tool for some categories of planning or storage—but it’s always the best place to keep your “meta-organization:” the pointers you use to keep it all on your radar.

When Not to Use OmniFocus

The key to using other tools is to plan to do so. When you have a recurring pointer to outside storage, you can put things there with a sense of how quickly OmniFocus will remind you to get back to them. When you create a new such place, you must create a pointer to make it a reliable location—otherwise, you’re leaving the next time you see it to the quality of your memory.

We’ve already seen the first category: you can’t use OmniFocus when you’re in a situation where technology isn’t a good idea. It’s generally frowned upon to take out your iPhone while you’re in some social situations; a notepad and pen, however, is generally more acceptable. This could also apply when you’re off the grid and conserving battery power. Have another method in place for such times.

Shared Documents

Your OmniFocus database should be intensely private. To make it reliable for your needs, you’re going to store information there that is detrimental or embarrassing for other people to see: gifts you’re planning for your spouse, or reminders to jog the memory of unreliable co-workers who may react poorly to learning that you think they’re unreliable.

(The multi-user feature on Macs is a great way to keep data private, which few people use; have an additional user account for when other people share your computer. On an iOS device, use a Parental Control profile to shut down your apps with private data, and turn it on whenever someone else uses it.)

That said, many projects need to be planned in shared documents. I use OmniOutliner for such things—it provides me with a fair amount of the toolset I have in OmniFocus, with better formatting options, and I have precise control over what data I store in those documents.

While a document is live and regularly being edited, it’s silly and time-consuming to replicate that in OmniFocus. So I use OmniFocus for two things for such projects:

  1. Recurring pointers that get me into that document as often as I need to reference or work from it.
  2. Reference data and tasks necessary to complete the project that I don’t want to share.

Once I’m done working with or needing to share a document, if the project isn’t finished I’ll move its remaining data into OmniFocus. If it is finished, I’ll simply attach the document to a reference task in OmniFocus to track that it’s done—especially when the work documented there is part of a larger continuing project.

When You Need a Side-by-Side Window

OmniFocus is great for showing you a lot of data in a neatly organized way, especially with OmniFocus 3. But there will be times you need data in a smaller side-by-side window than OmniFocus can provide. (I have one now that outlines what I’m writing here.) I could put that into OmniFocus and set up my iPad next to my MacBook—but at this Starbucks, the table’s not large enough for that.

Again, OmniOutliner to the rescue here, as it provides great outlining tools, and it’s simple to reformat to fit into whatever screen space you can make available. When a project is ongoing, I’ll typically leave all working windows, including the side-by-side ones, in its own Space in Mission Control. Meanwhile, OmniFocus lives in a separate fullscreen Space that I reference frequently. When I’m finished, or putting away the project for later, that’s when it all gets swept into OmniFocus with documented notes.

When You Can’t Have OmniFocus on Mac or iPad

Sometimes you’re using someone else’s equipment, and you can’t have OmniFocus there. (If those gizmos belong to a U.S. employer, you might not want your OmniFocus data there—any data you store on a work computer can be claimed as company intellectual property.) Almost always, I’ll be working from OmniFocus on my iPad next to whatever other tools I’m using. When I can’t do that, I temporarily store new organizational data in places that are universally available—I’m partial to Google apps under a personal account for such things, as that prevents data from being stored persistently anywhere else. (Of course, never store your password on other devices.)

Sometimes OmniFocus on your iPhone can also get you by in these situations. If not, and you need to reference OmniFocus data, go old school and print to paper or PDF.

When a Project is Obvious and Implicit

Finally, there’s a category of tasks that simply don’t need the overhead of OmniFocus organization. There’s always a time cost for outlining and setting up the right metadata for a project. Sometimes you don’t need it.

If there are three URLs you need to read later for three different reasons, you could inbox them all and properly move them to the right places in your project outlines later. But I just grab the URL out of the browser window and drag it to my Desktop. There’s a recurring pointer that tells me to go do stuff I’ve put there, which also includes various working documents (including the folder holding this one).

Use this technique when a task is obvious or a project is implicit: the title of a document tells you what it’s for, a folder of documents tells you they’re all for one outcome. But don’t do this if you have to think about your tasks every time you see these files; this technique only saves effort when immediately know what action a document requires. When you don’t, you should be writing better descriptions in OmniFocus.

When OmniFocus Is Where It Should Live

OmniFocus never becomes unnecessary when using the above tools; it’s crucial at all times to doing things outside itself. Before I started relying on OmniFocus as my first place to look for everything, all of these scattered tools created a hopelessly scattered project management system. You must have a first place to look, and it must get you everywhere else you need to be. OmniFocus is flexible enough to always be your first place.

OmniFocus is also the place where most of this external data will eventually live, for various good reasons. Following are the triggers for when to take the effort to move your data there and remove it from these external places.

When It’s Just Too Much

In practice, we all have a point where having multiple places to look just feels messy, just as we can let the basement accumulate storage for years until we finally say “enough!” and clean it out. This happens even when your OmniFocus pointers are perfectly reliable getting you to the work that’s stored elsewhere.

When you hit that point—which can be too much clutter in a particular place, too much clutter in all of your places combined, or just too many places—make time to OmniFocus some of it, until you feel what remains is under control. This is a psychological event, not an organizational one. This doesn’t have to be a regularly scheduled task—you can organize into OmniFocus only when you feel the need—but if you make it regular you’ll need less time each time you do it.

Anything You Want to Defer or Store for a Long Time

In theory, all your documents and email are stored forever. Most of us create documents at a slower rate than our storage expands when we upgrade our hardware. The problem is finding it again. Somehow, whenever I try to retrieve a document I created five years ago, between then and now something has happened to my storage methods that my search doesn’t reliably pull up what I’m looking for. The technical term for this is “bit rot”; our tools change but our stored data doesn’t keep pace.

If OmniFocus works well for you now, it’s likely to continue to work for you for the long term. That may not be true of your storage with 100,000 files from the last 20 years. So when I complete something that I may want to reference over the long term, that goes into OmniFocus, because I’m certain I’m going to keep that data up-to-date, searchable, and available.

(However, beware of bit rot for documents you attach in OmniFocus. You won’t be able to open a document in five years if that app no longer works. Exporting your long-term data as text to a second attached file is always a good idea.)

This is likewise true for reminders I want to defer for a long time. I’ve created tasks with several years of lead time, and some of them have triggered. That only works when you’re using the same system over that entire time—and it’s my observation that people who rely on OmniFocus rarely switch to other apps.

That’s one more reason why you want a tool with the power of OmniFocus. People who work with simpler tools often find those apps don’t keep pace with their increasing needs over time, and when you’re forced to migrate you might lose data. If you’re new to OmniFocus 3 and find it complex, switch off the display of any features you’re not using yet—they’ll be there when you need them, and you probably will.

Anything You Do Regularly, but Infrequently

Checklists are crucial to getting recurring tasks done right, especially things you do infrequently enough that you’ll never remember every step. You’ll save yourself a ton of work next time if you document what you’re doing now.

The problem with creating these checklists is you need to remember where to look for them when you next need them. By putting all your checklists into an OmniFocus project folder, you never need to scour your hard drive for those instructions you wrote down three years ago. When you need to do it again as a project, copy-and-paste the checklist as a template into your current project list.

When It Needs More Thought Than You’re Giving It

A key concept of technology design is affordances. An affordance is anything that encourages the user of that tool to do something better than they otherwise would, because the affordance makes it the simplest path of doing so. For example, password managers afford using complex and unmemorizable passwords, which increase your security over anything you can store in your head.

OmniFocus is the best affordance you’ll ever have for developing better, and more humane, work habits. Any time you route around your OmniFocus database with these outside tools, you’re risking losing those affordances. The proper balance is to use different tools granularly for those tasks they’re suited for, but only those tasks, and no more often than necessary.

The key affordance of OmniFocus, in my opinion, isn’t the tags or the cross-platform capability or any software feature now or in the future. It’s that OmniFocus puts you into a mindset of thinking about what you’re doing before you do it, or even before you decide to do it.

Before OmniFocus, any number of Internet GTD discussions indicated that the part of the system people were most likely to skip was the regular review—it didn’t relate to accomplishing things (as those people saw it), so why put that time in? But review is a crucial moment to consider whether a particular project is well-documented and still worth doing, therefore OmniFocus—by making reviews easy and a prominent feature—increases the likelihood of managing your system well.

The same can be said of the OmniFocus inbox. The ideas I capture are ten lifetimes of work; most of what I inbox, I’m never going to do. Processing my inbox is my triage stage, when I can cull what is no longer as great an idea as when I had it, and defer many things onto my Someday and Maybe lists not because I don’t want to get to them quickly, but because my time is already filled to the brim.

By putting everything in one place, and by making it a reliable place for the long term, OmniFocus is the best tool I’ve ever seen for considering your tasks and commitments each and every time. When I don’t have time to complete my flagged tasks reliably, I flag fewer of them. When I’m working from my Forecast too much and neglecting my flagged tasks without due dates, I see which recurring due tasks can be relaxed a bit to free up time. When I add a new project, I change around other projects—dropping some if necessary—because otherwise, I’m committing to working more hours when I’m likely already at my sustainable maximum.

This give-and-take works best when most of your organization is in one place, which is why you eventually process your external data into OmniFocus. Pointers can hide the projects they point to from your awareness, leading you to commit to too much. You don’t have to completely empty those other spaces, as they’ll collect new things all the time. But once you’re working with what’s already there, that data should gravitate to OmniFocus naturally.

You can’t “work smarter” out of this problem, and you can’t continue to work longer hours—eventually you’ll hit your ceiling. What you can do is make better decisions about how much you commit to, and control those commitments such that your life still includes all of the fulfilling things that don’t become OmniFocus projects. Otherwise, you’re going to eat into that fulfilling time—and when you do, no wonder you feel less fulfilled.

OmniFocus functions as your to-do list, but perhaps more importantly, it also functions as your not-doing-yet lists. Measure your outcomes against your available time, and note when you’ve bitten off more than you can chew. Then adjust your OmniFocus structure such that you’re making humane demands on yourself. For this process, you’re your own teacher, but only if you pay attention to your lessons. OmniFocus (and your overall sense of satisfaction) is your curriculum.

Jeff Porten is an IT and business development consultant — and Mac guru — who writes for TidBITS. His most recent book is Take Control of Your Productivity, which is about using OmniFocus and other apps to help you be more productive.

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