Navigating the Digital To-Do List

The last post talked about the digital calendar, the extent to which I am seeing them used among the people attending this summer's workshops, and recommendations for how to move to better productivity with them. This post looks at a second pivotal part of the organizational system—the digital to-do list.

While audiences are approaching a 50/50 split between those who keep paper calendars versus those who keep digital ones, far fewer are keeping to-do lists digitally. In an average group, less than 20 percent raise their hands when asked who keeps the to-do list digitally. I believe several factors contribute to this relatively low number.

We have always been better with calendars
Our ability to use a calendar effectively has always been superior to our ability to construct a to-do list, regardless of the form in which it is kept. The average person can pull out of a pocket or purse a calendar, navigate quickly to a date, and read to you any appointments on that date. When adding a new date, the average person can flip to the correct date and quickly jot the new commitment.

When it comes to the to-do list, ask someone what tasks are scheduled for next Thursday, and you likely receive a blank stare. To-dos are jotted on scraps of paper. Many claim they can simply remember their to-dos. Is it any wonder when our ability to organize a to-do is weak using paper, it will also be weak with its digital counterpart?

The literature on time management reveals conflicting strategies on how to construct the to-do list. Some authors recommend ABC priority codes. Others recommend scheduling tasks for specific times on the calendar. Still others recommend listing to-dos according to the contexts or locations where they will be performed. We have none of this conflict with the calendar.

Digital to-do lists can be confusing
The methodology for using a digital to-do list has been lacking. The flexibility offered by the software adds complexity. When entering a new task, we can select a start date, a due date, and even set a time. We can set a reminder, a context, and a repeating pattern. We can add tags, indicate the task's status, specify a location, and add an expected length. We can add contacts to that task, as well as related notes. Sometimes, we feel it would take less time to do the task than to enter it in the first place.

Which fields do we really need to complete? How can we get in and out of the list as quickly as possible? Until we can answer these questions for ourselves, we are likely to resist the digital list.

Syncronization is more complex
The ability to synchronize our phones with our computers presents a second challenge. Synchronizing calendars and contacts has been something the makers of smartphones have made easy. The task list has been a different story. Those who use the Outlook task list have always been able to sync with a Palm, and later, the BlackBerry. Syncing with the Outlook tasks list with the iPhone was a challenge until iCloud, and syncing with Android devices requires third-party software as a go-between.

Many people have been on their own to figure out a solution. The Catch-22 situation is to make a good choice on software, one needs to have some experience with digital to-do lists. But how do you get experience without using the software? Rather than wade through a research project on available options and the nuts & bolts of making synchronization happen, it's simply easier for most people to stick with paper.

Finding direction
I made the transition from paper calendar and paper to-do list to digital calendar and digital to-do list almost 11 years ago. The software then was good and had all of the components I would look for today: start and due dates, the ability to handle repeating tasks, a note section to record details about the task, and the ability to search the list for a particular word or phrase.

The thing that made the digital system work was the ability to synchronize data from the computer to the mobile device. I could type on the computer with all of my fingers and make small additions with two thumbs on the mobile device. When I got up from my computer, I was taking all of my organizational information with me on my mobile device. As smartphones have become more the norm, more people have the ability to do what I was doing way back then.

In the next post, I will share suggestions for those getting started with a digital list. In the mean time, I would welcome your comments. How to my observations stack up with your own? What parts of your system are digital and what parts are paper?