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

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

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:

Transferring tasks from Omnifocus to Calendar app

Transferring tasks from Omnifocus to Calendar app

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:

The Today Perspective

The Today Perspective

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:

Review - Family Agenda - Reserved

Review – Family Agenda – Reserved

I change the link and the calendar to:

Review - Family Agenda - Committed

Review – Family Agenda – Committed

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.

A Daily Review Habit

“Falling off the GTD wagon” (or any task system for that matter) can be all too easy and all too disrupting.  Especially, when you’ve grown used to a system, the gradual loss of trust in that system can come with feelings of anxiety, the need for constant damage control, putting out fires, losing follow up tasks, losing communication trails, losing the state of projects, and more.

To keep a system useful, it needs to be reviewed regularly. I often say that I’m not sure a system even exists unless it is reviewed.

Getting Things Done author, David Allen, suggests weekly as an optimal frequency. I used to review my entire system weekly and had done so for several years. At times, the review process would take me about 1-2 hours. I’d often feel quite positive about doing a review as I know how on top of things I can feel.

But, that is a chunk of time.  I can easily see how a person would lose the interest in review especially at times, for example, when things are very heavy or very light. At those times, you may think either, “I have no time” or “Why bother?”, respectively. The problem is that work ebbs and flows, and you can get hit with a whole bunch at once.

Nowadays, I do both a daily and a weekly review, which interestingly saves me time. The Daily Review takes about as long as my coffee takes to brew in the mornings. The Weekly Review is more centered on system blindspots and now takes about 20-30 minutes.

The Daily Review

My Daily Review includes:

  • Clearing the Inbox,
  • Reviewing any projects that are in the Review indicator, and
  • Making sure my flagged projects are appropriate for the day.

Generally, I use the iPhone to do this:

Morning Mini-Review - Before & After

Detailing the process, I:

  • Examine my calendar to review my scheduled meetings and appointments.
  • Acknowledge any tasks that are due soon as noted from the Forecast view.
  • Process the Inbox to “0”
  • Review all projects requesting review, thereby bringing that number to “0”. Note that this is a different method of Review than what I was doing when writing in Creating Flow with OmniFocus. At that time, I was doing the Weekly Review session only. Now, I do this aspect of the review daily.
  • Review the Land & Sea project as needed. I set its review reminder to every other day, so it is examined very regularly as part of this Daily Review.
  • Examine the Dashboard and decide if it supports me for the day.
  • Process the Inbox to “0” again, as needed.

If I want to be more thorough, I may also:

  • Review my Communications perspective
  • Review my Filing perspective

When I can sit with my tasks and calendar with a sense that they will support me and nothing else comes to mind, about my day or otherwise, I can then pause and decide on what to do next.

This can seem like a lot, but when you’re practiced, all of this can take only a few minutes.  Even if you work from a simpler set of lists, maybe only a single todo list, the same applies.  Examining the list and waiting until nothing else about it comes to mind can be a powerful way to help you move through your day smoothly.


My Current OmniFocus Dashboard “Recipe”

My workflow has, in general, shifted towards a session-focused style, as is evident from my recent post.  Essentially, that just means that my dashboard of tasks number only a few (about 5-8, give or take) and each represents a session of work. They are not very specific tasks and are more orchestrating in nature.  This means that my choices of what to do next are simple.

In addition, I tend to work by habit. In other words, I often work on a project over multiple sessions.  Similarly, my routines for maintenance are also a matter of recurring sessions.

As a result, my Dashboard has largely become a series of repeating tasks, using the “Defer Another” function.  Tasks repeat at different frequencies – daily, weekly, monthly, or other.. My current Dashboard “recipe” includes the following:

  • 1-3 “Land & Sea” tasks daily (“Land & Sea” Project)
  • 1 Office Filing task on weekdays, (“Routine : Home & Office” Project)
  • 1 Home Filing task on Fridays, (“Routine : Home & Office” Project)
  • 1 Weekly Review task on Fridays, (“Routine : Home & Office” Project)
  • 1 Family Agenda review everyday, (“Routine : Home & Office” Project)
  • 1 Develop: Music task everyday, (“Music & Artistry : Music & Artistry” Project)
  • 1 Morning Communications on weekdays, (“Routine : Home & Office” Project)
  • 1 Afternoon Communications on weekdays, (“Routine : Home & Office” Project)
  • 1 Financial Maintenance task monthly, (“Routine : Home & Office” Project)
  • Rare odds & ends when they do not fit in the above.

Each task links to a custom perspective or project.

And, of course, there are types of habitual work that do not appear above. For example, I also have the clients I see throughout the day, so I often check on my @Office : Agendas context in the morning.  Clients are scheduled in the calendar.

Also, these tasks are not forced.  For example, a particularly busy day with clients means I may not make it to a Land & Sea project that I thought I could have. If that occurs too often, though, it is likely time for me to re-evaluate my workload. In that way, I use my understanding of how the system is stressed to consider where to make adjustments in my general workflows.

A Principle of Completable Lists

We can have any number of types of task lists, be they a perspective, a context, or a project. Some lists stick around: the daily list, phone calls to make, things to file, agenda items, and more. They fill up, we clear them, and they fill up again.

Two questions we can ask when approaching any list are:

  • Do I intend to complete this list?
  • If so, how often?

These questions are useful because completable lists affect us differently. When we can arrange a list to be completed regularly, we effectively create a reliable channel of work. Whatever we throw in there, so long as it isn’t large enough to clog the system, has a good chance of being done.  As soon as one task starts to stick around though, other tasks tend to stall, too, and soon we’re wading through cobwebs.

We can consider a Principle of Completable Lists:

Lists that are sensed as readily completable within an easily envisioned time frame are more enticing, readily done, and resistant to procrastination.

These lists tend to be short, easily envisioned, with tasks that are either made of habit or are themselves easily envisioned. For example, I use the Dashboard as a completable daily list. I hope to finish it by the end of the work day, though it is not always possible. When it is not, I consider what about it needs adjusting, be it that the tasks are not clear enough, or perhaps that I have taken on too much and need to delay or drop some things.

If we wish to make a list completable, then we need to pay extra attention to its tasks. Consider for each task:

  • Is it appropriate for this list?
  • Is it clear and specific enough? I.e. Is it broken down to the point of confidence?
  • Would it be useful to convert it to to repeating task? I.e. Is it better broken down in time, perhaps performed over several sessions of work?
  • Is there something that needs to happen before this task?
  • Is a next action actually scheduling a time for the task itself?
  • Is it well written?
  • Is it too large for this list? (E.g. would it benefit being converted to a Land & Sea project.)
  • Is it an actual action?

Notice that these questions are just as appropriate for use during review sessions. And of course for the entire list:

  • Are there too many tasks?
  • Can I imagine actually doing all of these tasks in the time frame I intend?