Calendar Integration - Part 3: More on Time Blocking & The Calendar

Today’s post is a follow up to two posts:

• Calendar Integration – Part 1: On Time Blocking
• Calendar Integration – Part 2: Convert Calendar Items to OmniFocus Tasks Using the Workflow App

After posting the Workflow app integration post, I received a message about the importance of going in the other direction, i.e. assigning a time in the calendar for any task in OmniFocus. While I address this to some degree in the Time Blocking post, I do not believe it goes far enough into detail. So let's get into it...

I continue to time block my individual tasks only sparingly. Usually, my work days are already blocked by way of meeting clients. My day to day tasks are already well curated enough that I have the time to do them between those meetings. However, on days where there is little structure, time blocking can be quite useful.

The image I’d used in the Time Blocking post was:

Here, I noted that you could drag and drop a task into OmniFocus and the Calendar app would automatically create an hour entry in the Calendar. It also creates a link back to the original task. While this is still true, there is something left to be desired. Let’s go through a planning session and see how this can be improved.

In the morning, I can go to may Today perspective (previously titled “Dashboard”) and see a set of tasks to work on:

I tend to use an overview project, called Land & Sea. It allows me to group the work of my day into sessions of work, rather than individual tasks. In effect, I create Channels of Work. In other words, each of these Today tasks link to another project, perspective, context, or otherwise. I do that work, and then return to the Today perspective, and mark the task complete.

To time block, I would instead transfer each task to the calendar. However, there are at least a few issues that arise:

1. There are now two tasks, one on the calendar and one in OmniFocus.
2. I could mark the task complete in OmniFocus as soon as it is transferred, but if I change my mind in the midst of planning, I have to recreate the task somewhere.
3. The calendar task, as transferred, links to the task itself. It does not link to the actual work, which is instead represented by the link I created in any task's note field.

We can solve these issues by the following.

As a preliminary step, we can use a default “Reserved” calendar in the Calendar application. That way, when we transfer a task, it is in a reserved status until we are ready to commit to it being on the calendar.

Then, in any planning session, likely in the morning:

1. Open and review the Today perspective.
2. Transfer tasks, one at a time, from the Today perspective to the Calendar.
3. Open a Today task's note field in OmniFocus (Command-') and copy and paste the link over to the one created by the Calendar.
4. Change the calendar from Reserved to one that signifies its committed state.
5. Mark the task as completed in OmniFocus.

For example, the initial state of the calendar item is:

I change the link and the calendar to:

In this way, we can transfer the working list from OmniFocus to the calendar.

There are two potential issues that I do not find to be that problematic, but are still worth mentioning:

1. Marking it as complete in OmniFocus no longer means that the work itself is complete, but instead that it has been scheduled for the today. It is a different habit/feel for working to adapt to.
2. I have to continue to transfer tasks to the calendar as they come up during the day. If I do not, then I end up with two locations for storing work, which can be problematic. Still, I can visit the Inbox with regularity.

I also don't want to give the impression, with the example above, that I only spend my family time staring at OmniFocus, dictating tasks. My upcoming family time will be spent with my daughter playing Cuphead, which is freaking awesome.