Calendar Versus To-Do List: The Battle Marches On

Jun 12, 2015

I wrote awhile back about how to decide what to put on your Calendar versus what to add to your To-Do List. Now it seems about time for a pop quiz to test the systems.

As a finalist judge for Teach for America’s Annual Social Innovation award, I recently received a very helpful email that WARNED me about three hours of pre-work I’d need to complete ahead of time. Event organizers: this is awesome. Huge! And an even bigger thanks for the HARD COPIES of the materials delivered to my door!

The Pop Quiz Question: Do I add these preparation tasks to my To-Do List? Or do I reserve the time to attack them in my Calendar instead?

Hmmmm . . . What would you do?

There are two schools of thought here:

Option 1: Because these To-Do’s surpass my 30-minute threshold of what I can easily “squeeze” into a given week, I could enter them directly into my Calendar at a time I’m likely to complete them.

Option 2: If I’m not sure when I will actually tackle these To-Do’s, I should enter them on my Later List. As the time gets closer, as I’m reviewing this list during my Weekly Round-Up, I can decide where the tasks will hit my Calendar.

In general, you all know I’m biased SLIGHTLY toward the Calendar because, as I often say, “Lists are limitless, but Calendars have constraints.” And constraints are the only way we can reconcile our millions of To-Do’s against our most limiting resource – time.

So, in sum, here is how I would make the distinction on where your To-Do’s go:

  1. Personal preference. Let’s not sell this short. It matters. More “task-driven” people feel literally overscheduled when they are forced to put something in a time slot. I won’t force you to put something in a calendar appointment, but be aware that as your list grows longer, it may need to be labeled by amount of time something will take. Know thyself.
  2. Threshold of time. My personal rule is that is something will take me more than 30 minutes, it has to go on to my calendar. For some people, this threshold may be 15 minutes; for others, it may be 3 hours. Some super busy leaders I know don’t even keep a NOW list, but painstakingly enter every To-Do from their Later List into their calendars each week.
  3. An actual deadline. If your task has a REAL HARD BONAFIDE deadline, I suggest plopping that deadline directly into your Calendar as an all-day appointment. Don’t even let the task touch the Now or Later List. Instead, work backwards to block off the necessary time in your Calendar to prepare.
  4. Likelihood of completing the To-Do at a particular time or place. This is new thinking for me. I knew I wasn’t likely to complete my judge’s pre-work until my flight from DC to San Francisco. The organizers likely anticipated this as well, hence the bound hard copies delivered to my door! If there is a natural reason that the To-Do should fall into a particular calendar slot, enter it there directly. Another example of this is coupling my recent trip to the UPS store to return a million online-ordered things on my calendar with another errand, like taking my kids to swim lessons.

So, I’m still talking myself into my original hypothesis. Slightly biased toward the calendar, but still in favor of lists! And regardless, both need to be fed and cared for daily. How do YOU decide?