Over the last month I have been experimenting with extending the usefulness of Omnifocus 2 (OF2) on my Mac. Of all the things I’ve tried, applying the Pomodoro Technique is by far the most effective.

The Pomodoro (Italian for tomato) Technique uses a timer to break down work into intervals. These intervals are traditionally 25 minutes in length, separated by short breaks. Four Pomodoros are followed by a longer break. To get a sense for the technique, watch this short video.

The original description of the Pomodoro Technique used a kitchen timer, but over the last several years Pomodoro Apps have become available. When I dabbled with Pomodoro in the past, my favorite app was Eggsellent. Eggsellent had a clean interface and, more importantly, would auto-populate flagged items from Omnifocus. Unfortunately, since the release of OF2, Eggsellent has been broken, forcing me to look for alternatives. The two applications I’ve spent the most time with are: Vitamin-R2 and Tomatoes.

Neither Vitamin-R2 or Tomatoes are completely right for me. Although both apps have quite a bit of flexibility in timer length and both have visual records of how I’ve spent my time, neither is automated enough for my taste. Neither app can pull information directly from OmniFocus like Eggsellent could. Vitamin-R2 has limited capabilites to check off completed activities in OF2, but that is the extent of its integration.

Since neither app is just right, the deciding factor for me was aesthetics. In this realm there is no comparison: Vitamin-R2 is clearly inferior to Tomatoes.

Here’s how the workflow in Tomatoes takes place: I slide an OF2 task into Tomatoes and tell Tomatoes how many Pomodoros the task will take. I click the timer to start and then follow the countdown either in my menu bar or in the app itself. The app records how many Pomodoros have been completed. I’ve been amazed at how competing against a clock solidifies my focus (and helps me to get more stuff done).

That being said, I’d really like an app that is functional, visually pleasing, AND can autopopulate items from OmniFocus 2. The best situation would be for the app to pull a particular perspective out of OF2. If it’s too complicated to pull a whole perspective out of OF2, I would settle for flagged items. Other aspects of the perfect app would be sharing tasks and statistics across computers (and iOS devices) and logging the Pomodoros in my calendar.

Give the Pomodoro Technique a try and let me know how it goes. If you’re a coder and are interested in developing the perfect Pomodoro application, please give me a shout.