OmniFocus and iCal for Realistic Tasks-for-Today Planning

Time is an equal opportunity employer. Each human being has exactly the same number of hours and minutes every day. Rich people can’t buy more hours. Scientists can’t invent new minutes. And you can’t save time to spend it on another day. Even so, time is amazingly fair and forgiving. No matter how much time you’ve wasted in the past, you still have an entire tomorrow.
Denis Waitely

Update: Strange, I’m having sync problems lately. Might it be the case that dragging tasks to iCal causes them? Might be a fluke but it is very strange. If this is the case, then creating the entries manually would be a better option. Meh.

I find OmniFocus extremely useful to keep track of my tasks. Especially at work. It’s available on my MacBook, on my iPhone and on my iPad. Because I paid for all three apps. Yup, the disadvantage is its price, especially when taken together. But it just works. The syncing is fast and robust, and it’s got lots of useful features (talking about version 3.8 here).

However, while it is easy to have all the tasks available, I found it very difficult to realistically plan the tasks for the day. The usual problem — too many tasks for the day. I would carry over 5 to 10 tasks each day because I just did not manage to get them done — sometimes due to lack of time or simply due to a lack of energy.

At at least the time problem is solvable.

Unfortunately, OmniFocus does not make this easy for you. There is a Forecast tab, and you can set it up in the Perspectives menu (Perspectives > Show Perspectives > Forecast). For example, which iCal calendars should be shown (Note: I refer to the Apple calendar as iCal here, even though it is — now — simply called “calendar” on macOS and iOS). In the Forecast tab, you can select a single day or deselect the chosen day to see all future tasks, incl. the ones that were due in the past but not done. Very useful, and one of the main reasons for me to use the “Due:” entry of tasks in OmniFocus.

However, while the tasks are shown by date and in the order of the time, and even interspersed with the iCal calendar entries, that’s about it. Some things are missing:

  • The “Estimated Duration” information is not used. Unless you do them in parallel, it would be easy to give an indicator of just how much time all (planned) tasks for the day would take.
  • You cannot drag and drop the tasks to change their order, given that you do not have a vertical timeline (as in iCal). It makes planing the day very cumbersome. You have to manually change a lot of information.

In short, OmniFocus gives you a Forecast view, but — and perhaps for good reason — does not try to compete with a calendar.  Apparently, there was a way to sync OmniFocus with iCal in a prior version, but I haven’t found out how to do it. Looks like it was discontinued. Shame, because even a synced calendar with iCal — handled by OmniFocus and then subscribed to via iCal — might be really useful. And it’s not really made for planning.

But there’s a — manual — workaround. Or rather, you can and might want to do it manually … and use these conscious decisions to plan the day.

On the Mac, you can simply drag and drop OmniFocus tasks on the calendar:

OmniFocus tasks (right) can be dragged and dropped into iCal (the Apple calendar app, left). The day view is helpful here. BTW, the blue and orange calendars contain the same information. They are (manual) copies and are handled by two different servers. I love digital calendars, but I deeply distrust auto-synced solutions. If one fails (never happened), the other likely works. If not … well, then these appointments are irrelevant any way.

You can use any calendar, but I have created a new calendar for it (“Tasks”, which I have deselected from the OmniFocus Forecast perspective, otherwise I’d have the same information twice). I also have my default alarms (15 min prior) deactivated for this calendar (in iCal, right-click the calendar, then “Get Info” and check “ignore alerts”). Planned tasks are important, but the alerts should not compete with scheduled appointments with actual people. Also, if the day really runs completely different than planned, I do not want to be reminded of each and every scheduled task I have missed.

And yeah, again, the duration information is not used, all tasks start out as 1 hour calendar entries. So, still no reason to enter any duration information in OmniFocus, but with iCal, you can simply use the mouse to drag the calendar entry according to how much time they take. And move them quickly between the already scheduled appointments. Also, the dragged tasks automatically contain a link back to OmniFocus. You click on it in iCal and you get to the task in OmniFocus with all information contained in that entry (attachments, further links, etc.). Seems to work on any device — Mac, iPhone, iPad — if both iCal and OmniFocus are installed.

So far, it looks like this could work. I plan which tasks to do each morning anyway. But by dragging the tasks into iCal, I can now get an overview of how many tasks I could realistically fit. And how much time they likely take. Also, given that I can leave the calendar-tasks-entries in the calendar (that they are independent of OmniFocus is a strength, not a weakness), I can afterwards change the duration (quickly via the mouse, or in more detail with the keyboard) according to how much time they actually did take. So this might even allow me to reflect on my time planning with accurate data, plan better in the future … if I learn from it. Plus, there is at least some information what I did during the past. What I actually did work on. This is also something that OmniFocus does not make that easy. You can show past tasks, but usually it makes more sense to have them disappear once you have done them. Not that good for reflection/reflective learning.

Main problems so far are:

  1. Still wanting to put more tasks into the day than I can do. But now I get immediate feedback whether my planning becomes unrealistic during the planning phase. It becomes immediately obvious visually.
  2. I have to remember to leave at least part of the time free for the usual interruptions (more often than not actually welcome), emergencies (not that welcome, esp. if it involves a fuck-up with an unpaid bill in accounting), and the usual breaks (making tea) and way times (walking to/from work and listening to podcasts). So I can only plan part of the day. I can simply block that time, though. Copy-paste entries for walks to/from work and the like. Might be something to try.
  3. I have to be a bit careful with the planning, as I usually resent strictly planned days. I find them constricting and a natural tendency to do it differently immediately becomes … an almost overwhelming force. Reactance — I have to plan around it, without letting myself know I plan around it. So, planning the day this way only during the morning of that day and only as the first thing at work might help here. Then it’s an active decision in the moment, compared to something my past self left me days ago (I still have a love-hate relationship with that guy, but so does he. And if we could work together better, that guy in the future might look more happy and less desperate.).

And yeah, it would be a really bad idea to do this with all tasks. The two-minute rule still applies. Anything that takes two minutes or less you should do immediately if you can. It would just take more time to make an entry, whether it’s in OmniFocus or iCal, and deal with the entry itself later. These quick tasks can be done during the planning phase if they could not be done when you got the task. But for anything that takes more time, yeah, might work. I’d go for tasks that take at least 15 minutes.

So far, it looks like this might actually work. Or at the very least, could be eye-opening in the future (among others, because you can export whole calendars as ics file, which you can in turn import into R and run some analysis … hmm, something for the future 🙂 ).

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