Review of Build Your OmniFocus Workflow

I’ve been using OmniFocus for a long time. In fact, OmniFocus was the very first paid iOS app that I paid bought back in 2008 when the App Store debuted. At this point I’m definitely not a novice user, but I’m always looking for ways to use OmniFocus to manage my tasks more effectively. It plays a central role in my ability to get my work done so any improvement will pay dividends across a wide variety of areas.

In that vein, I recently read Build Your OmniFocus Workflow by Ryan Dotson and Rosemary Orchard. The book offers a comprehensive guide to using OmniFocus to manage your tasks, with an emphasis on how to fit OmniFocus into a larger system of task management.

Thanks to its customizability, OmniFocus has always been a bit of a “build your own task manager kit”. With the addition of tags, OmniFocus 3 leans even more in this direction thanks to the many new options for how to use the app. What started out as a fairly vanilla GTD app has become a very powerful and flexible piece of software that can be used to support many different takes on task management. As the book puts it: “There are two keys to getting started using OmniFocus: understanding the software and developing a workflow.”

Build Your OmniFocus Workflow does a great job of looking beyond the four corners of the app to talk about how to fit it into a broader context. It’s really a cross between a software manual and a higher level treatise on task management.

While the overall emphasis is at the system level, Build Your OmniFocus Workflow starts with the absolute basics (setting up the software, using the interface, and fundamental concepts) and builds up from there. As a guide to the apps, it’s quite comprehensive in exploring pretty much every feature, both on the Mac and iOS (there’s also a short section on OmniFocus for the Web, currently in beta).

Despite being a long-time user of OmniFocus on both platforms I still learned quite a few new things about the app. For instance I had no idea that on iOS you can drag the “add to inbox” button to add a task in a specific place. I also have to say that Rose and Ryan’s explanation really made me get how a single action list differs from a regular project, which is something that I’d never really understood despite a decade of using the app.

As one would expect from Rose, there’s quite a bit of material on automation. Everything from AppleScript, to IFTTT, to Shortcuts. There’s also an appendix listing and explaining all of the rules you can use to create custom perspectives. This is nice since not all of these rules are necessarily obvious.

Interwoven with the software guide are Ryan and Rose’s thoughts on how to build your larger system. Again, it starts with a very basic workflow (capture, process, review, and do) and builds on that. They talk about what does and doesn’t belong in OmniFocus, how to define effective projects, what to do when you get overwhelmed or fall of the wagon when it comes to keeping your system up to date.

I really appreciated their thorough take on the review process, not just using OmniFocus to review your projects and actions, but also reviewing your system as a whole. Another tip I really like is to tag actions that you’re procrastinating on so you can go back and think about why (Is the action unclear or not well defined? Is there some obstacle that prevents you from doing it? Is it really something you need to do?).

Finally, Ryan and Rose wrap things up by laying out their own workflows as examples, explaining how they use the app and the systems and practices they’ve built around it.

The book comes in PDF, ePub, and .mobi formats, so there are plenty of reading options. I read the ePub version on my iPad using the Books app.1

Build Your OmniFocus Workflow has definitely helped me get more out of OmniFocus, both in terms of running the app and thinking about my task management system more broadly. Not only is it a great guide to using OmniFocus effectively, I think it really encourages a thoughtful approach to setting up your task management system. I definitely recommend it.

Comparison with the OmniFocus Field Guide

One question I’ve seen asked on the Mac Power Users forum is how Build Your OmniFocus Workflow compares to David Sparks’ OmniFocus Field Guide. I think the two are quite complimentary. Some of this is just the differing format; it’s easier to get certain things across using video while other things are easier to explain textually. However, this is also a product of differing perspectives on OmniFocus and how best to use it; there are areas where Ryan and Rose have a different view than David.

In some areas one goes into more depth than the other. The book delves deeper into review, for instance, while the Field Guide has a considerably more thorough treatment of tagging systems.

Both encourage using OmniFocus to build your own unique task management system. Build Your OmniFocus Workflow takes a somewhat broader view of OmniFocus as one element embedded in a larger system while the Field Guide concentrates a bit more on building a system within OmniFocus. They also take a somewhat different approach to presenting these systems. The book mostly lays out a series of options throughout the text that the reader can assemble into something that suits them, then details Ryan and Rose’s workflows as examples at the end. David presents six different systems (in varying levels of detail) giving the viewer a look at several widely varying approaches. He also spends a bit more time talking about the pros and cons of various ways to use tools or features within OmniFocus, and why one approach might fit a particular set of needs better than another.

Both Build Your OmniFocus Workflow and the OmniFocus Field Guide are quite good, and I think that if you get a lot out of one of them, you’d get a lot out of the other as well.

  1. One nice thing about the Books app is it makes it much easier to copy text than the Kindle iOS app. I did this quite a bit to take notes while I was reading. ↩︎

Getting Things Done

The first in a series on how I deal with task management.

The level of complexity in a task management system needs to be commensurate with the number and complexity of the tasks that you’re managing. David Sparks relates that when he was a student, his task management system was to write down the day’s tasks on the napkin he got with his morning coffee. I never used a napkin, but as the complexity of my life has varied the complexity of my task management setup has waxed and waned from simple checklists (both paper and computerized) to powerful task management software.

Right now I’m at a fairly high level of complexity: my task management system involves two different pieces of software, a notebook, and a whiteboard. I’ll talk about these tools in future posts, but to start with I wanted to talk a bit about the conceptual framework that underlies it all.

That framework is the Getting Things Done system by David Allen. GTD is one of the most popular task methodologies, there are a lot of people out there using it. However, everyone seems to have their own particular take on the system. I sometimes think there are as many was of implementing GTD as there are people using the system. So what I describe certainly should not be taken as canonical. It’s more like, “This is my GTD system. There are many like it but this one is mine.”

Clean Sweep

Of all of the aspects of GTD, the one that was the biggest benefit to me when I first started was getting all of my tasks out of my head and into some sort of system. This is important for a couple of reasons: First, since I am terribly absent minded, any task I just try to rely on remembering is very unlikely to actually get done. I have to get it written down in a place where I’ll come back to it later. Second, (and this is the reason that David Allen emphasizes) having these unfinished tasks bouncing around in the mind is a distraction. It’ll be there, gnawing away until it gets done. Perhaps because I’m so forgetful this has been less of a problem for me.

The cure for both these ills is to get tasks out of my head an into some sort of system. For me, that system is OmniFocus. I’ve got it set up so that it’s extremely easy to get tasks into the software and as soon as I think of something I need to do I’ll pause whatever I’m doing and get it in there. I know from experience that there’s not a moment to waste if I don’t want to forget it.

Next Actions

The next step in GTD is to group tasks into projects and organize them as a series of “next actions”. One of the things I had to learn how to do when I started with GTD was distinguish between projects and actions. When I’m capturing a task, it might go into my system as “learn programming language X”, but that’s not something I can just sit down and do. It’s too big and involves too many different steps to bite off in one go. The next actions might be “Search Amazon for books on programming language X” or “Download programming language X software”.

The critical idea here is that taking a larger project and figuring out the next step requires mental energy. If I have to put in that energy right at the moment when I’m trying to start the work it creates an additional barrier, and the harder it is to get started the more likely I am to do something else. By putting in that thought about what the next step is up front, it lowers the amount of effort it takes to get started with the task when the time comes to actually do it. So when I’m looking at my task list all I have to do is pick one and do it.

While the “action” part of next actions is important, the “next” part is critical as well. One of the things I’ve struggled with is when my task list gets too long, it becomes harder and harder to go through the list and pick something off of it to work on. This makes it important to limit the task list to stuff I can actually do right now. There’s no need to clutter it up with something I can’t start on until next week or tasks I can’t start until I hear back from a colleague. This is where software can make a really big difference. One of the things I really like about OmniFocus is it’s ability to defer tasks (hiding them until a future date) or to make tasks sequential (you don’t even see Task B until you’ve checked off Task A). It really helps keep my list of available tasks manageable.


The other way GTD is set up to limit the number of available tasks is by dividing tasks into different contexts. If the task is to fix a leaky faucet at home that’s not something I need to see when I’m at work.

This is one aspect of GTD that I’ve always struggled with, and I know I’m not the only one. When David Allen wrote Getting Things Done back in 2001 the canonical contexts where things like Phone, Computer, Internet, and Office. The idea was on an airplane you could ignore tasks that require phone calls or internet access. If you didn’t have your computer with you didn’t need to see tasks that require a computer or internet access. The problem is the proliferation of mobile devices and cellular data connections have blurred these lines tremendously. Unless a task requires me to be in a particular location, it’s usually something that I could be working on wherever I am.

So, I have three contexts: Work, Home, and Computer. The real divide here is between personal stuff and job related stuff. Work is for everything job related. Personal stuff is divided between Home and Computer. The tasks that require me to physically be at home go in the Home category and things that I can do anywhere I have access to a computing device and an internet connection in the Computer category.

In turn, this means that contexts don’t do a very good job of limiting my available task list. If I’m at home I could be working on everything on my Home and Computer tasks lists and almost everything on my Work task list (with the exception of a few tasks I need to physically at the office to do). This means I’ve always got a ton of different things I could be working on, which makes choosing one of them to actually work on more difficult.


The final piece of the puzzle is to review outstanding projects and next actions every week. It’s really a series of questions about each project: Is this something I still need or want to do? Are there any tasks associated with this project that haven’t made it onto the list of next actions? If I haven’t made progress in the last week, why not?

This is another area that I’ve struggled with and it’s really a critical one. When I fail to do my review for a couple of weeks cruft builds up on my task list and things fall through the cracks. I’ve gotten better about this in part by scheduling time for the weekly review. I review for my personal projects on Sunday evening and my work projects on Monday afternoon. I’m also using an app called Due that’s another part of my task management system to remind myself to do the review on a regular basis. My track record on weekly reviews still isn’t perfect, but it’s getting better.

Getting Things Done has really been a godsend for me. Without it I would be blowing deadlines and missing tasks left and right. It’s really essential for me to be able to function as a responsible adult.

Next up in the task management series: OmniFocus, my task management software of choice.

Doing Deep Work

Sometimes the right book comes along at the right time. It’s not so much that the idea is life-changing but that it reinforces a change that is already going on in your life. Deep Work by Cal Newport was like that for me. 1

Newport’s thesis is that work requiring sustained concentration that pushes your brain to the limit, is both valuable and rare. Such “deep work” is rare because we live in a culture of constant, distracting, stimulation that rewards busyness rather than productivity. It’s valuable because it is more productive, particularly for certain kinds of creative or technical work.

The book is divided into two parts. Part I is dedicated to convincing the reader that deep work is important, valuable, and rare. Honestly, it didn’t really grab me that much because I was already on this train. Part II, which is about about 2/3 of the book, is full of techniques and recommendations to help you do more and better deep work. This was really what was worth the price of admission for me.

One of the things that Newport emphasizes is that the ability to concentrate on deep work is not something that you either have or you don’t. It’s also not just a habit you can pick up through willpower. It’s a skill that you can train yourself to do.

He lays out four potential philosophies for doing deep work: The monastic philosophy is to isolate yourself from the distractions of the world and dedicate yourself to deep work over a long period of time. Bimodal philosophy alternates days or weeks of deep work with similar time periods dedicated to shallow work. The rhythmic approach is to dedicate a certain time period each day to doing deep work. The journalistic philosophy is to stick short bouts of deep work in whenever you have the time.

I realized that I was already pursuing the rhythmic approach, by doing things like turning off my email client until after lunch. My morning hours are the most productive when I’m trying to do technical or creative work (I’m writing this post on a Saturday morning, for instance). After reading about this I’m going to be more aggressive about defending that time from meetings and other distractions and dedicating it to the kind of deep work that I can do best during those hours.2

For a “productivity” book Deep Work really emphasizes the importance of downtime to recharge your batteries and renew your reserves of concentration. Newport is not at all a fan of putting in a huge amount of hours. His position is that there’s a limit to how much deep work you can get done per day (maxing out at about four hours). The rest of the day can be filled with shallow work, but beyond a certain point adding more shallow work will actually decrease the amount of deep work you can do, making you less productive overall.

I’ve always tried to avoid working late or bringing work home (though not necessarily as a productivity booster). It’s nice to have additional justification for this approach.

An area where Deep Work has lead me to try really changing my approach is scheduling. Newports advocates scheduling your entire day; writing down what you’ll be working on and when. This is advice I’ve heard from other sources but I’ve never put it in to practice because it felt too rigid. However, Newport presents a much more flexible approach to scheduling. He emphasizes that you don’t “win” if you stick to the schedule you laid out or “loose” if you have to change it. The goal is to avoid putting yourself in a position where you have to choose what you’re going to work on in that moment, because that makes it too easy to choose some sort of distraction.

To implement this more flexible approach he advises rescheduling as necessary throughout the day as things change and ignoring the schedule to follow up on interesting ideas or finish something if you’re on a roll. One tool he talks about to help with this is “conditional overflow” time blocks. If you are uncertain about how long something will take, schedule a block right after it that you can either use to complete the first task if it runs long or to work on a second, optional task if you finish up the first one.

Newport has in interesting benchmark to quantify the depth of a particular activity: How many months it would take to train a smart college graduate with no specialized training in the field to do this task? If the answer is relatively short, then the task is not that deep (and probably not all that valuable, since it implies almost anyone can be trained to do it). If the answer is quite long then it’s much more likely to be deep work. He recommends thinking about your various tasks using this benchmark and setting a shallow work budget to limit how much time you spend on these sorts of tasks.

One of the big shallow work time sinks that’s not pure distraction is email, and Deep Work lays out some techniques to reduce the email burden. On one side of the equation, he advocates making the people who email you do more work. If possible, don’t have your email address out there in public. Set expectations that email from people you don’t know may not receive a response. Then you don’t need to feel guilty when you don’t respond. As Newport puts it, “it’s the sender’s responsibility to convince the receiver that a reply is worthwhile.“ Unfortunately, these aren’t really an option for me in the day job. My work email is on our website and part of our job is being responsive to the public.3

Perhaps somewhat counterintuitively, Newport advocates doing more work when you do respond to an email. Specifically, he recommends putting more effort into an individual email (preferably your first one in the conversation) with the goal of minimizing the number of emails needed. So instead of asking someone if they want to meet for coffee, propose a specific place and time up front and avoid the tedious back and forth. I’ve heard this sort of advice specifically around scheduling meetings before, but he advocates this sort of “project” focused email technique more broadly. Think about the end state that you want to get to and use that first email to accomplish (or prompt the person you’re emailing to accomplish) as many of the steps to get there as possible.

As I said in the intro, this book came along at just the right time for me. It provided reinforcement for some of the changes I was already making in my life. It’s also helped me better articulate what I’m doing and why. In addition to the larger conceptual stuff it also gave me quite a few techniques and insights about how to do deep work that are already proving their worth. I’d definitely recommend the book to anyone who does work that requires sustained concentration that pushes your brain to the limit. If you’re still on the fence, Shawn Blanc has a nice podcast interview with Deep Work author Cal Newport.

  1. I first heard about Deep Work from Shawn Blanc
  2. It would be nice to dedicate days or weeks (or years) to deep work, but my job and schedule wouldn’t really allow it. 
  3. Thankfully, what we do is boring enough to most people that we’re hardly deluged.