Tools of the Trade: Radically Simplified OmniFocus Contexts

This is a post about my attempt to answer that deceptively simple little question: how do I organize my day?  And more specifically for those of us who have to do some heavy-duty writing every day, what writing do I need to tackle today and what supporting tasks (e.g. research, outlining, etc.) do I need to do to prepare for writing tomorrow and the next day?  

OmniFocus is a useful tool with which to tackle those questions.  If you aren't familiar with it, see my previous post here and explore the pages of some of the gurus I mention below.

The gurus rethink contexts 

Lately I've been experimenting with contexts, the category in OmniFocus (and the Getting Things Done system) that lets you restrict your choice of available tasks.  Traditionally contexts have been based on your locations or tools at hand - so "office," "home," "phone," and "email" are all classic contexts.  

For a while I never used contexts.  The classic contexts just seemed completely out of touch with way I worked.  Once I decided to start using contexts, I went completely overboard.  I had at least a dozen and I stressed about which to assign a particular task.  In many ways it was far more confusing than never using contexts at all.  I've been tinkering lately and I think I've at last found a system of radically simplified contexts that works for me.  

I've benefitted enormously from the work a lot of smart people have done in rethinking contexts for our new digital reality.  My biggest influences here have been Leo Babauta's Zen-to-Done variation on the Getting Things Done system, Sven Fechner's rethinking of contexts based on energy levels, and Kourosh Dini's meta- and nitty-gritty practical ideas about OmniFocus and flow.  What follows is an overview of the system I developed and have been using lately.  It is very much on a synthesis of these guru's great ideas, but like all acts of synthesis it is, I hope, also something a bit new. 

my radically simplified contexts

my radically simplified contexts

Big rock climbing

The idea of "big rocks," is at the heart of Zen-to-Done.  Essentially, you choose your 1-3 most important tasks of the day, make them your "big rocks," and prioritize them above all else.  Your big rocks are almost always connected to major projects or goals in your life.    

Let me give you some examples of recurring big rocks in my life.

  • Write 500 words in section X of dissertation
  • Revise section X of dissertation for 90 minutes
  • Write first half of lecture A for class B on topics C, D, and E.   
  • Grade 8 take-home essays for class B
  • Mindmap and/or outline upcoming conference paper
  • Write draft of new blog post
  • Make risotto/stir fry/fancy bastard sandwiches and watch movie with my significant other

These are connected to my larger goals to finish my dissertation, to be a good teacher, and to maintain my personal wellbeing and relationships.  They're the stuff I want to do, and that I want to do well.  

They're also things that require a good bit of time and energy.  That's why I put personal stuff under "big rocks" too: shopping for risotto ingredients, making it, and watching a movie essentially takes all evening.  I love doing it and it feels weird to make it an OmniFocus "task," but it helps to keep me honest about my plan for the day; like most of you, I bet, it's a struggle to keep from wildly overcommitting each and every day.

I often set my big rocks up as repeating tasks so that after checking them off they come back and are available after one, three, seven, or however many days.  Karoush Dini is the master of the philosophy and technicalities of setting up repeating tasks in OmniFocus, so check out his book, blog, and collection of OmniFocus resources

Personally, I try to tackle my first big rock first thing in the morning and to knock out any remaining big rocks by mid-afternoon.  If any survive beyond then, I've found that the chances of getting to them that day are slim.


Tasks that go in the "jogging" context are my meat-and-potatoes tasks.  They take a good bit of energy and time, so I only look at jogging tasks when I've some of both.  Examples of recent tasks in "jogging" include:

  • Read scholarly article X
  • Write essay questions for midterm exam in class Y
  • Scan pages 42-80 in book Z and upload to my course website
  • Edit blog post
  • Email person Z (if this is a long/substantive email)

Tasks that go in jogging usually (though not always) help to make possible my big rocks or otherwise relate to them in a supporting or subordinate capacity.  For instance, scanning and then reading scholarly articles is necessary for my dissertation writing, teaching, and conference paper writing; editing blog posts is a necessary next step after writing a draft of a post; substantive emails are often an important part of teaching.  And so on.


"Dashing" covers my quick tasks.  Sometimes these tasks require a decent energy level, but more often they can be done when I'm pretty tired.  Sven has a whole "brain dead" context, which is fun sounding, but not quite necessary for me.  It's easy enough to look at everything I've got flagged under "dashing" and see what I can do while brain dead and what I can't.  Recent examples from my dashing context include: 

  • Call person A (quick call)
  • Email person C (quick email)
  • Order book D on Inter Library Loan
  • Enter weekly attendance data into my spreadsheet
  • Cleanup downloads folder
  • Pay Bill E

I often find myself "dashing" in the lead-up to lunch, again in the late afternoon just before moving from the office to home for the day, and one last time before bed at night. 


My location contexts are mainly for geographically specific uses on my iPhone so that it will do things like chime at me when I arrive on campus so that I'll pick up a form from my campus mailbox.  I don't have a lot of location contexts and I use them quite sparingly.  

I also have a generic "errands" context under locations that I use to list errands I need to run.  I do *not* put lists of what I need to buy as I go about those errands in OmniFocus.  For me, a list like "milk, bread, salad, and broccoli" doesn't belong in OmniFocus.  Philosophically, it just feels wrong.  It demeans and diminishes the "task" as an idea, a unit for organizing my time and energy.  Instead I prefer to keep my lists in .txt files composed in nvALT and Notely, which sync brilliantly through Dropbox.  

Putting it all together

Flagging is key to putting this all together for me.  Every morning I flag somewhere between 5-15 tasks.  I check in as necessary throughout the day, flagging additonal tasks or (more often) de-flagging tasks I know I'm not going to make it to today.  

contexts and flags work together brilliantly

contexts and flags work together brilliantly

Basically I work from my flagged screen and choose a task that best fits the time and energy I have.  Flags combined with my radically simplified contexts has me covered almost all of the time.  You can do some amazing things with OmniFocus perspectives, but I have to be honest: they just don't fit into my current workflow, which I like and find useful.


Contexts have traditionally been about possibilities - what you can do in a given moment.  They're still about possibilities the way I use them, but now contexts are also about priorities.