I consider the two fundamental resources in work planning to be:

  1. The calendar
  2. The to-do list

The calendar represents the hard landscape: events that are non-negotiable, time-based and require you to be doing a certain thing, at a certain time, at a certain place, possibly with another certain person. If it’s in the calendar, it’s a certainty. Calendar entries are commitments to yourself and possibly others.

The to-do list is used to track tasks needed to be done to move the ball forward. The list is potentially filled with a lot of items that may not necessarily be linked with one another. They are commitments to yourself, but they are not tied to being done at a particular time and don’t generally require the involvement of others. I use OmniFocus for managing my task list, but it really doesn’t matter what is used, as long as there is a trusted location to track everything to be done.

As a general rule, I’m not a fan of putting tasks onto calendars. I think they are two distinctly different things that should exist in their own dedicated spaces. However, like any good rule, there are times when this rule should be broken.

Leveraging multiple calendars

The beauty of using modern electronic calendar systems is they support multiple calendars. The classic and most obvious application of this is creating seperate work and home calendars. In addition to these staples, however, it can be helpful to create a weekly plan calendar.

Each calendar’s visibility can be toggled on and off, depending on the needs of the moment.

Using the weekly plan calendar can facilitate the addition of tasks onto a calendar view without gunking up your regular calendars that represent real physical events and commitments. This leads to the next step: time blocking and setting commitments for your future self.

Time blocking

The purpose of time blocking is to help establish a plan for a forthcoming period of time and build accountability for your time. The idea is to create work sessions that are linked directly to items on your task list. Transferring tasks to a calendar and applying estimated timeframes in the form of a timed calendar entry can help build a visual map of work to be done. Visualisation is a great tool to help identify whether your to-do list is realistically achievable in the time available. It can also help enforce urgency by indicating how potentially little time is available for meaningful work. Finally, it can be a reward system. If you get ahead of your schedule, you’ve earned yourself some relaxation time, safe in the knowledge that you aren’t falling behind!

My approach

I generally reserve the time blocking approach for when I have a lot going on, and I’m starting to feel overwhelmed by it all. Ideally, at the start of the work week I will set aside half an hour, and look at my calendar of commitments. These are the scheduled events with other people that are locked in (usually weeks in advance) and that I need to fit all my other work around.

The next step is identifying the tasks that represent the ‘big rocks’ that I need to progress. What projects need to move forward this week? What are the tasks that need large sessions of time to get into a flow?1

Once I understand what time slots I have available for task-based work, I start creating related events on my weekly plan calendar, filling my days more completely. I need to take some care here though. I’m not an automaton, so it is important not to schedule every last minute of time. Doing that is just setting myself up to fail. In any week, unexpected things are bound to arise and time will be needed for this stuff, in addition to the general administrative tasks of email, communications, management issues, and so on.

With the weekly plan calendar populated and tessellated with my other calendars, I end up with a clear picture of my work week. At any point of time I know what I can and should be working on. I know that if I stick to the plan I set for myself, I will be closer to my goals at the end of the week than I was at the beginning. It’s a practical approach to personal accountability.

The overhead of doing this planning is not always worth the effort, but when lots is happening and it feels like control is being lost, this is a great way to reassert your plans and ensure that the important is not being overwhelmed by the urgent.

  1. Writing is a great example of this - you can't really do it for 30 minutes here and there; you need a solid chunk of several hours. ↩