Managing My Evolving To-Do List, Part 1: Using Boomerang to Achieve Inbox Zero

Over the years, I have explored several different ways of managing my to-do lists and I’ve found that, for me, the process evolves over time. I start with one methodology and tweak it so that it works best for me, and then I discover something new. I try to take the best of all of the systems I encounter. I’ve read David Allen’s Getting Things Done at least twice, and tried it, but that system is too rigorous for my habits. So I pick and choose what works for me.

One of the goals I have with managing my to-do list and tasks is to automate as much as possible. I don’t want to have to spend a lot of time prioritizing lists, writing and rewriting them, setting reminder, cleaning out my inbox. Most of my available time should be spent on actually getting things done as opposed to meta-management of lists and reminders. To that end, I have been using two tools for the last several months that have allowed me to take a big leap forward in the automation of my to-do lists and projects: Boomerang and Asana. Today, I’m going to discuss how Boomerang help me. I’ll leave Asana for another day.

Boomerang

Many of my non-project-specific t0-do items come in the form of email. I have always tried to keep my inbox pared down to the bare minimum, yet at the same time, I’ve used my inbox as a kind of to-do list. I’ll archive messages I no longer need to take action on, and leave messages in my inbox that still require action. Over time, I’ve discovered that this can be tough because the contents of my inbox steadily grows. This is where Boomerang has been revolutionary for me.

Boomerang is a Gmail plug-in application that allows you to “boomerang” messages. When you have a message in your inbox, you can using Boomerang to remove the message from your inbox until a specified time, at which point the message is returned to your inbox–and you are thus reminded of it. This allows me to quickly remove things from my inbox, while scheduling when I need to be reminded of them, all in a few quick mouse clicks. Here is what it looks like:

[pe2-image src=”http://lh6.ggpht.com/-Ig__EWL0J_E/URT8SAiF2NI/AAAAAAAAaV0/GuOHcJrQXPg/s144-c/boomerang%2525201.png” href=”https://picasaweb.google.com/103316545008269282896/JamietoddrubinCom2#5842572002917210322″ caption=”boomerang 1.png” type=”image” alt=”boomerang 1.png” pe2_single_image_size=”w550″ thumb_w=”550″ thumb_h=”” thumb_crop=”false” ]

Note that there are a number of options I can choose when I “boomerang” the message, many of them are presets to speed things up. So, for instance, if I want the message to return to my inbox in 2 days, I can simply click the “2 days” option. The message will disappear from my inbox and two days later, it will be back. I have the option of having the message returned to the “top” of my inbox as well.

Boomerang has a few additional features that have made my life much easier and saved me time. In the GTD world, there is this notion of follow-up lists. If I send someone a message and need a response from them, I need to add a note to a “tickler” list so that I remember to follow up with them if I haven’t heard back after a certain amount of time. Boomerang builds this functionality right into the email system.

[pe2-image src=”http://lh4.ggpht.com/-bJXY7Ahten8/URT-vddGnyI/AAAAAAAAaWU/q7zXx3p5V5s/s144-c/boomerang%2525202.png” href=”https://picasaweb.google.com/103316545008269282896/JamietoddrubinCom2#5842574707920379682″ caption=”boomerang 2.png” type=”image” alt=”boomerang 2.png” pe2_single_image_size=”w448″ thumb_w=”448″ thumb_h=”” thumb_crop=”false” ]

As you can see in the above image, I can check a box indicating that I want to be reminded of the message in a set number of days if I have not yet received a reply. No need to maintain a separate tickler list. Boomerang does it for me. (And those options are flexible. I can change the number of days, or the condition of the message, like if the message has been unopened, or regardless of whether a reply has been received or not.)

You can also see, from the image above, that I can choose to schedule the message to be sent at a later time, which comes in handy now and then.

One other really helpful feature that Boomerang has is the ability to auto-detect and set reminders. For instance, if I receive a message indicating that I need to take some kind of action by February 14, Boomerang will automatically preset my reminder:

[pe2-image src=”http://lh4.ggpht.com/-zUpCT6vDx1c/URUAq8EjCsI/AAAAAAAAaWg/ojwUnly_8Og/s144-c/boomerang%2525203.png” href=”https://picasaweb.google.com/103316545008269282896/JamietoddrubinCom2#5842576829262793410″ caption=”boomerang 3.png” type=”image” alt=”boomerang 3.png” pe2_single_image_size=”w550″ thumb_w=”550″ thumb_h=”” thumb_crop=”false” ]

Note how, when I look at the message above, Boomerang has already detected the date in the message and defaulted the boomerang reminder for “the day before” the date it detected. I could change this, of course. But all I really have to do is click the “confirm” button and my message is Boomeranged out of my inbox until the specified date.

Boomerang is a “freemium” application. There is a free version which allows you to “boomerang” up to 10 messages per month. However, the power and freedom (to say nothing of the uncluttered inbox) that Boomerang provided me with made it worthwhile to me to upgrade to the “personal” addition, which runs $4.99/month, but gives you unlimited messages and some additional features. I probably save the entire year’s subscription to Boomerang in one month just in terms of the time I would have had to spend managing my various lists, so for me it was definitely worthwhile.


I’ll write about how I use Asana to manage my project-oriented tasks and to-do items in the near future.