Omnifocus & Time Boxing

Some time ago I used Fantastical for planning my tasks in Omnifocus. Using Omnifocus together with iCal (dragging the tasks into the calendar) did not work properly. Now I realized that dragging tasks with Sonoma works properly. I would now like to switch to “Time Boxing” for better planning (both privately and at work). Does anyone have experience and can provide explanations and tips for this planning process?

One advantage that fantastical has is the ability to recognize the OmniFocus estimated duration. If you drag an OmniFocus task into fantastical, the appointment will adjust the appointment length to the OmniFocus estimated duration.

Apple Calendar won’t have the capability to honor the estimated duration.

I’m a fan of scheduling just one big rock appointment in the morning and one in the afternoon. That’s the “must get done” task that I want to complete and feel victorious. If I can get those two rocks done then everything else is gravy.

I’ve found that Life can and will change my plans if I try to schedule too many task. Overscheduling just made me feel like a failure because my plans never got done.

If I get those 2 rocks done, I can dip into OmniFocus and choose an optional task that I want to get done.


Timeboxing generally means you assign as certain amount of time to something you do and stick to it. This makes you think about what can actually be finished about a topic within that time. (My interpretation.) Used this in agile project teams regularly. Therefore, I have less and less 1h meetings in the office.

What I did a few months ago at that time still with OF3:

I created an Apple Shortcut that allowed me to take selected actions with their duration to an app called Sorted. I got that app a some time ago (even for free if I remember correctly). If a duration was not set, the shortcut asked my to enter a duration. Each Sorted task had a URL that allowed me to jump to the corresponding actin on OF. What Sorted is good in is this: Sorted knows your calendar and can calculate a sequence of actions with their duration around the events of your calendar.

So I took some actions from Forecast or one of my next action lists. Not more than 5 at a time. The idea was to have a time-based plan for the next 1-2h.
The issue with timeboxing for me was that there are a lot ad-hoc topics that can immediately kill your plan. Sorted helped me (just recalculate) to regenerate the plan in case of interruptions from a colleague. Often it‘s just right to support them in that moment.

Sorted was never an alternative to OF. In my opinion it does not scale well for more complex projects. Also, it was always OK for me to throw away the actions I put in there.

Why don‘t I use it anymore these days? Depending on the context of what actions you select where in OF, the URLs shared to an Apple Shortcut look quite different. Could not yet figure out a rule why that‘s the case and did not have the nerve to go after that.

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For Deep work, I block out a time and assign it to a named Task.

For Shallow work, I block out a period of time (say 1 hour) and when that time comes, I open my Shallow Work perspective in OF and start working down the list.