Simplicity & OmniFocus

Simplicity is certainly a hallmark of maturity. But, it is not often a first step. It is a character of mastery gradually woven into our endeavors and lives.

Simple Dashboard

Test build of OmniFocus 2.3

After I’ve done my morning routines, I might open OmniFocus and see the above. It is a simple list. Should I care to delve into details, I can select a link resting in the note field of a desired task, and work from there. I could also just work from what I believe, in the moment, to be a good next action. The lists only support me in making my choices. At this point, the only costs in maintaining this simplicity are the weekly review and the occasional adjustment.

I often hear that OmniFocus is not simple. Compared to other programs, that can be the case. But, OmniFocus is complex to the degree that it can support a complex life. It can also be a means of assessing where life is more complex than need be and aim towards simplicity.

What you can do with a musical instrument is also not necessarily simple. But an artist can get there with time and effort. More importantly, it is not a simplicity of the instrument we aim for, but that of expression. The instrument is only a channel supporting that process. Its complexity is about supporting depth and nuance.

As we attempt any new craft or project, we build supports, not fully knowing their upkeep or maintenance. How could we know? We haven’t done it before. While we could take the word of those who claim experience before us, and it is certainly important to hear their thoughts, we must also experience it ourselves. Without grounding in the self, we are without play, and therefore without mastery.

As we continue to review and iterate our systems, we learn and re-learn, finding new ways of creating. The costs of supports become more readily known.

We can then ask, with greater assurance, of any support:

“Is this worth its cost for what I find meaningful?”

Each pass polishes our systems into a smoother simplicity.

Reading Lists & OmniFocus

I received a recent email that asks:

“Hi Kourosh,


… I’m having a hard time keeping up with all the reading material I’d like to read/watch and I keep adding links into a huge “Someday Maybe/Reading” project in a “Reading” context that grows and grows, because I’m adding way more than I am able to “pull out”.


So I guess my question would be how do you approach keeping up with all the reading material? Is there something I can do to help me make time for reading more? …”


– C

Dear C,

Great question. I’m still developing how to handle this one myself. Unfortunately, I will say upfront that I do not believe I can fully answer your question. My book list, too, grows faster than it shrinks. There are those who can read quickly, but I am not one of those individuals. Even if I were, there are more books than anyone can read in a lifetime.

Further, “making time” is a matter of renegotiating agreements, something Merlin Mann has called the ultimate ninja skill. Such a question taps into the much larger, “How can we spend our lives doing more of what we want?”

Beyond the careful examination and adjustment of our habits and commitments, I would argue that the growing list is a “fortunate problem” of our time. There was once an era when having more books than can be read was an amazing luxury.

As with much of our work, we must regularly acknowledge loss, including of those things we would have liked to read. Still, we can create methods for arranging our book lists to reflect and support our decisions of what to read, what to place on hold, and what to delete.

For this post, I will focus on book reading and not articles or videos. I tend to separate these from each other, though similar methods can be considered for either.

Method 1: External Book List

Some users recommend keeping a reading list outside of OmniFocus entirely. For example, Tim Stringer of Learn OmniFocus suggests using a Goodreads account. Aleh Cherp of Academic Worklows on a Mac suggests using a text file. Either are excellent ideas and maintain a solid simplicity.

In these cases, you could select one book from the external list and create a repeating task in OmniFocus to read it. This way, you still have your ongoing book reading task centralized in OmniFocus, while keeping the larger list removed from sight.

For example, if you use flags to signify your daily work, your task list might appear as:


Read Zen book today


Method 2: Internal Book List

I tend to keep my reading list in OmniFocus. The result is similar to above, though with some adjustments. My preferences include the following:

  • As above, I aim for a single book task that I am working on until I am done. The other book tasks might be useful in their own projects or folders, but I’d like to be focusing on one in my day-to-day if possible.
  • As you are doing, I would prefer to include my booklist in OmniFocus. While it does add to the database, I find that including books within their related projects outweighs any detriments. In terms of task presence, as long as I have a method of hiding the information when it is not relevant, yet keep it quickly accessible when it is, I have organized the information effectively.
  • Further, I wish to make the book I am reading on option, not a requirement.


I do have a @Book Reading context:


Book Reading Context 2


Within this context are numerous tasks, each representing a book I wish to read:


Book List 2


The @Book Reading context itself is rarely visited. I could create a task to read from it regularly, but then I would be confronted with a large list every time, making it difficult to use as an action-oriented list. Still, a task to regularly review the task could be useful when considering what to keep or remove. For example, a monthly repeating maintenance task could work:


Book reading maintenance task 2


The list is one that is not regularly fully cleared. A context such as this does take on more of the storage tank role. There are definitely contexts and perspectives that I try to clear daily or nearly so. My flagged list is an example of tasks I fully intend to complete daily.

The important thing is that I acknowledge how I use any particular list. We build our systems upon trust. But trust is not a boolean concept. It is not on or off. We can ask of any component of our environments “How do I trust this?” to reveal a more nuanced picture.

To better enable focused action, I select one book from these @Book Reading tasks to read regularly until done. I then convert it into a “Considered task”, by:

  • Setting it to repeat daily,
  • Changing its context to @Considerations, and
  • Altering its wording to include the word “Consider …”

In Practice

To see how this works in action, let us begin with the daily view. Notice the daily repeating task to visit considered tasks:


Dashboard 3


Selecting the link presents the considered tasks:


Considered Task Perspective 2


The number of considered tasks is kept low (preferably below five to seven). Therefore, it is generally not overwhelming when seen.

When ready to move on to the next book, I delete the task and change another @Book Reading task to a Considered task. The cycle continues.

In this way, one book remains in progress. It does not need to be read daily as it is a “considered” task. Other books remain hidden from view. However, those other books remain accessible to their related projects or perspectives.

A Retired Habit Context

Much of my use of OmniFocus is about guiding habit. It is useful to create repeating tasks that I check off regularly. The process develops a habit.


For example,


However, after some time, these sorts of tasks can easily bog down the system.  Many repeating routine tasks obscure those that we would prefer to otherwise call our attention.  For instance, an important task to contact your employer could be lost in an array of deferred tasks, as seen here in the Forecast perspective:



(Note, the deferred tasks option is turned on):



One means of solving this issue is to have a Retired Habit context:



Whenever you feel that you have internalized some habit:


  • Assign it to @Retired Habit.




  • Create a repeating task to visit @Retired Habit.


I have the task as part of my weekly review template. In this way, I can decide if it is truly a task that I can delete or something I would like to return to my active system.  In this way, repeating tasks can act as training wheels that I can take on and off as needed.

Show Folders in Outline – Review Mode

There are lots of little additions that I’m liking about OmniFocus 2. As an example, from the change log:

View menu, including option to show a project’s enclosing folder in the outline, to provide a hint of hierarchy.

Here’s an example of how this can be helpful: I have a number of projects titled “Overview” which are essentially administration type projects that oversee the rest of the projects sitting in a folder.  Something like:

  • Big Project
    • Overview
    • Folder A
      • Project 1
      • Project 2

One of the issues has been that in Review mode, I would have to guess which “Overview” folder I was reviewing. It wasn’t a big deal, but it was something. In any case, this feature totally helps out. To turn it on,

  • Go to review mode (Command-6) by default.
  • Select the view icon (or type Shift-Command-v)
  • Select the option “Show Folders in the Outline”:

Show Folders Now we can have a better view of the hierarchy:

Folder in Hierarchy - OmniFocus 2

The “Considered” Task

An issue of task management appears when we do not wish to do a repeating task on a particular day. Without modification, we can either:


  • Check off the task, without actually completing it
  • Change its start date
  • Delete the task


In fact, several months ago, Chris at pxldot.com1 wrote a post called “What’s Eating OmniFocus?” in which he raised this very point, noting that without a “muffle” option, we would introduce a dishonesty into the system by any of these above solutions.

I believe he is correct in that, with the exception of deleting the task, these solutions would introduce a dishonesty to the system. As trust is the central pillar upon which we build our systems, this would be not only unacceptable, but likely damaging.

However, there is a solution that has little to do with OmniFocus, so much as our own agency:

Agency is the degree to which we may create and decide upon intentions non-reactively.


The Considered Task

We can introduce agency with a simultaneously very simple and advanced technique. It is simple in that it is easy to implement. It is advanced in that there is caution to its use.


To create a considered task:

  • Place the word “Consider” before a qualified task
  • Change the starting verb to end with an “…ing”


An Example in Filing

As an example, we could have a daily repeating task such as:

  • “File”

The task would be used to visit a context which holds a series of filing tasks.

In my own use, the task links to a perspective that consolidates several filing contexts as an adaptation of Sven Fechner’s “Brain Dead” context. It’s great for gathering those short organizational tasks that would otherwise derail me in the middle of a session of work.

However, I do not wish to file everyday. Therefore, I convert it to a “considered” task:

  • “Consider filing”

Here it is in action:


Repeating file task


That’s it. That’s all there is.

But as simple as it is, it can be more powerful than first appears. That it bears caution, may even indicate its potential as a powerful tool.

Before addressing its advantages, let’s consider important cautions.



The caution required should be apparent. To highlight the concern, take the example:

  • “Exercise” (repeating daily)


  • “Consider exercising” (repeating daily)

Writing “Consider” before a task is very easy to do. It almost seems to be a gimmick or “cheat” potentially fraught with thorns of procrastination. The word can be abused, allowing a rapid and easy path into doing nothing. We could simply add the word “Consider” to every task and eventually find ourselves in some form of Youtube-silly-cat-video-watching-induced] stupor.


Example – Caution in Filing

For example, returning to the filing example, a fear may be that I will continually check off the task and not visit it. The tasks within would then pile up with many Filing tasks, effectively clogging it. My trust in that part of the system would then be lost.

However, this has not happened. I know when I have and have not visited the list. I can look at it and decide in the moment as to whether I should do the tasks resting within it now or not. If I sense that the list of undone tasks is growing large, I also sense that I will lose my trust in that list unless I do the work.

Therefore, the test of its use is continual. If ever the context becomes stagnant or fills faster than it empties, then I know it will no longer work. I would know that I could not trust it and therefore would need to do something to change it, whether it is doing the work itself or changing the system. The same is true for any aspect of the systems we design.

The guide is our trust:

Trust is a belief, developed over time, that something will continue behaving as it has in the past, such that it may be relied upon.


Example – A Non-Considered Task

Just to show a contrast, if something is important to do daily—for example,

  • Play piano

I leave it as “Play piano”. Such a task would not receive the “Consider” term. I mean to play the piano daily, honoring the habit to the greatest degree that I reasonably can.

Work tasks, agenda items, etc., also would not receive the “Consider” phrase. In other words, we can and need to use the phrase quite deliberately.



There are at least several advantages that a “considered” task has to offer. It can:


  • Function as placeholder and reminder of decision
  • Help assess a task’s necessity
  • Apply a buffer to a task system
  • Reduce the necessity of completing a task, while maintaining our awareness of it and its accessibility
  • Reduce an overall “compulsive” sense to a task system
  • Help us maintain honesty with, and therefore trust of, our systems.
  • Improve general integrity of system via our enhanced trust


A Placeholder and Reminder of Decision

In the case of the filing task, I do not need to file daily. But, the task functions as a placeholder and a reminder of the decision I can make to file. It is easy to get to the filing perspective by selecting the link should I wish to do so. In addition, I can think about whether I want to file today or not, rather than be forced to compromise myself in order to maintain the system.


A Means to Assess Necessity

We can use “consider” to assess how necessary a task is. For example, if we have a task of checking a certain site daily, but that information is rarely if ever useful, adding a “Consider …” phrase allows the task’s review. After a period of simply checking off the task without actually doing the work, we can realize that the task is redundant or would otherwise drain better spent resources of time and attention. The task can then be deleted.

Meanwhile, the task is not cluttering the system. It appears, is considered, is checked off and ultimately deleted without compromising the system’s integrity.


A Buffer for the System

We may have time to complete some tasks and not others. The “consider” clause adds a mild prioritization component. In this way, we can do tasks that do not have the “consider” clause first, and return to the ones we do wish to consider later.

By moving the task’s action from its content to our decision of doing it, the compulsion to do the action in order to maintain the system’s integrity is removed.


Agency, Trust, & Habits

In this way, the “Consider” technique is both very simple and advanced not because of some technology or our finesse in its direct use, but from our ability to be attuned to our own sense of experience and our habits.

It is important to note that our habits themselves are a part of our systems of trust. The more we trust ourselves, the greater is our confidence to impose the demand of agency at a point that it would be useful to do so:

Confidence is a trust in our ability. It is a developed sense of our own capacity to meaningfully decide and act, such that it may be relied upon.

We may desire our programs and environments to do the thinking for us, but this is not their role. They only hold onto, more or less, our stored intentions. We, then, process them at their points of relevance.

The attempt to front-load a system with as much decision as possible is certainly helpful, but it can only be relied upon to the degree that we trust it. As we do not know the future, the process of developing the system is continual.