The $140 productivity app that’s managed my life for the past decade

A partially covered Ferrari car is pictured before the opening  of the Frankfurt Motor Show (IAA) in Frankfurt, Germany September 11, 2017. REUTERS/Kai Pfaffenbach – UP1ED9B0QPRMN
A partially covered Ferrari car is pictured before the opening of the Frankfurt Motor Show (IAA) in Frankfurt, Germany September 11, 2017. REUTERS/Kai Pfaffenbach – UP1ED9B0QPRMN
Image: Reuters/Kai Pfaffenbach
We may earn a commission from links on this page.

I have a strange obsession with optimizing my life for peak productivity. Part of it is the dopamine hit that comes with a task well completed. But what brings me even more joy is the creation of the perfect Rube Goldberg machine to deflect, swat, and conquer everything the information economy has to throw at me.

I put my money, and my time, where my mouth is. A few years ago, I invested $140 in a single app (along with its its 270-page manual) and dog-eared the crap out of a book with a very unsexy title, Getting Things Done: The art of stress free productivity. And I’m convinced that this one-two punch has served as both my second brain and a competitive advantage for the better part of a decade.


I see that side-eye that comes with recommending a book whose promise is that you can become “maximally efficient and relaxed,” let alone one that clocks in at 352 pages. But please bear with me.

Getting Things Done (a.k.a. the bible of the GTD method of productivity) was first published by productivity consultant David Allen in 2001 and lays out the first principles of productivity systems. Understanding those principles has been essential to my benefiting from every other productivity app, hack, or idea I have since layered into my process for filtering information and accomplishing tasks.

I’ve seen many of my peers skip this critical first step, only to find themselves frustrated (and with yet another unused to-do app purporting to help with things like to-do lists). Using a to-do list in isolation is analogous to building a house without a foundation: flimsy and unsustainable.

But once you have the basic GTD method in place, you can further customize many tools to fit your situation and needs.

GTD consists of five steps: capture, clarify, organize, reflect, and engage. To explain each, I’ll apply the method to the humdrum business of paying taxes, an item that springs up on every American’s annual or quarterly to-do list.

Capture: Think of capture as a gigantic brain dump, where relevant ideas both big and small are captured into some type of inbox—be it mental, physical, or electronic. In our tax example, we might capture two actions:

  • Pay taxes
  • Donate old clothes to Salvation Army

Clarify: Once captured, the ideas are clarified, or “unitized” into appropriately sized packets while ensuring that each task is indeed actionable. In our example, “Pay Taxes” is too broad a task and thus not actionable. We could break it down into its component parts:

  • Collect W-2 forms
  • Input information into tax software
  • Mail check to IRS

Organize: This is the act of triaging, ordering, and adding the relevant information. Gathering the W-2 forms, using TurboTax, and mailing the check have to be done sequentially, so they should be ordered as such. The check must be mailed by April 15, so we insert a due date. But the trip to donate old clothes to the Salvation Army throws a curve ball. It’s not a discrete event. It sorta has a due date, but not really. And if we’re really on top of it all, we’d be Marie Kondo’ing our closet every quarter to ensure we’re maximizing the tax deduction.

Reflect: A surprising number of to-dos in our life fall into this category, whether it’s pursuing a hobby, instilling healthy behaviors, or trying out new activities with the kids. There’s no “true” due date, they are important (but not earth-shattering if we forget), and are ongoing. Realizing when you’ve reached the reflect stage creates the appropriate trigger for just that, reflection on these “tweener” actions.

Engage: This last step ensures that we are tackling the right action at the right time. Monday morning is not the place for us to be reminded to empty our closets. And we should not be reminding ourselves to mail out the tax return if the first three steps have yet to be completed.

Putting it all in Omnifocus

So here’s the good news. Much of this can be done with pen and paper—and if you prefer a digital approach, most to-do list apps (such 2do, Things 3, and Todoist) cover a wide range of useful functions. I settled on a more expensive option, shelling out $140—that’s $59.99 for the iOS version and $79.99 for the desktop version—of Omnifocus. There are three main features that, to me, justify the expense.

Deferred start dates: This is deceptively simple, yet surprisingly few apps provide this feature. Recurring tasks can be weekly (“Check in with direct reports”), monthly (“Pay rent”), or annual (“Schedule physical”). But tasks like these can represent a significant portion of what’s on my to-do list—in my own workflow I have close to 50 tasks that repeat at least annually. I don’t need, or even want, to be reminded of them daily. But I also don’t want to risk forgetting about them completely.

Let’s take the annual physical example and assume the reminder pops up on Jan. 1. You see it and diligently schedule the appointment. Check. But because this is an annually recurring task, what happens next? The reminder for your next year’s appointment pops up on your list for the next 364 days. Ouch. Now multiply this prematurely resurfaced task by all your recurring tasks and you’ve got yourself a recipe for massive cognitive overload—exactly the antithesis of a good to-do list system.

Customized Views: One of my key workflow philosophies is inspired by productivity consultant Tony Schwartz and consists of optimizing your energy as opposed to your time. OmniFocus allows you to “tag” each task using what it calls a Context. Most to-do lists allow for tags, but what makes OmniFocus unique is its ability to customize views across numerous attributes. This plays a critical role in my quest to optimize for energy management.

As an example, I use three energy states in my own system: Deep Work, Sprints, and Tired. In case they’re not self-explanatory, Deep Work is a task that requires 30 to 60 minutes of uninterrupted time; Sprints require a 15-minute burst; and Tired is when I’ve hit the cognitive wall.

When I sit down at my desk at Quartz in the morning, with the touch of a button, I can quickly hone in on the tasks that deserve my best energy. This can span from writing an article to checking in with a project that’s gathering momentum. As the 4pm hour nears, I shift into the Tired context and start chipping away at clerical tasks like responding to email and queueing up my (work-related) social media posts.

Review Function: Our GTD example showed there’s a large number of tasks that don’t really have a due date but need to to be tended to with some regularity. Another useful productivity framework, the Eisenhower box, calls these tasks “Important, but not urgent.” A few examples from my own list: “Take my daughter to the zoo,” “Sign up for volunteer project,” “Rewrite my personal values.” Reviewing these is a pain point for both humans and to-do list apps—neither has a feature that forces the needed reflection on these kinds of chats.

The naive approach would be to slap on a due date arbitrarily for each task. This approach is inadequate for two reasons: first, because we know it’s arbitrary, it’s less likely to be adhered to, but more importantly it’s yet another source of unproductive cognitive overhead.

Here’s where the Review function comes in. Every group of tasks is assigned a review frequency, so daddy-daughter activities could be set at “each month” and your bucket list could be “each year.” The review feature acts exactly as its name would indicate—you get a reminder of these “important, but not urgent” tasks and literally have to sign off on them by pushing a button called Mark as Reviewed. Think of it as a self-audit, one that matches the broader time horizon of the tasks. This ensures that I chip away at these longer-dated tasks, without incessant reminders that quickly lose their efficacy.

All together now

There’s an argument to be made that investing this much money and set-up time in a productivity system is well, counterproductive. But cutting out the unnecessary worrying and never letting things fall through the cracks? Those are benefits that can compound over a career, and a lifetime.