Quest for Organization: Not Really a Review of Things

Posted on Sun 16 August 2009 in Dispatches • 8 min read

I am not naturally a very organized person, which is something I’ve always struggled with. My tendency, from an early age, has always been to try and hold all my responsibilities, appointments and tasks within my head. I was fairly successful at it, which led to my developing an unjustified sense of superiority over those of my peers that were already dependent on their student planners to manage their homework and responsibilities. If I ever wrote anything down, it was just on a scrap a paper or in a margin, more to cement the information in my memory than as a reference to be referred to later. Even in the workplace, I only kept my calendars up to date in order to be able to share busy/free time more effectively. I didn’t actually reference them on a day-to-day basis.

This continued to be a successful strategy for me until about three years ago, when I began taking on more responsibilities and while also working on more personal projects at the same time. It quickly became apparent that I was going to need a better system for keeping track of all my tasks, but of course, at this point I was in my mid-twenties and I had no experience with organizational systems.

Early Experiments - Analog and Digital

With no practical experience, I began playing around with different approaches to structuring my tasks. I tried a variety of techniques, and each time I would begin with great enthusiasm and determination, only to have my discipline fizzle out several weeks into the experiment, where I would find myself once again managing my tasks by my memory alone, with limited to moderate success.

I tried carrying a small notebook to keep track of tasks, but I quickly began forgetting to carry it with me, and it produced too much redundant work to organize and structure tasks into a daily schedule. Imagine sorting through pages of notes and tasks, creating new ordered lists of tasks that could be tracked by bookmark or index card and you can begin to imagine my frustration with this process. The goal was to save time, increase productivity and reduce the likelihood of my forgetting to do something essential. This analog process was adding at least an hour or two of collective organizational time a week, and was prone to failure due to the number of moving parts (all those pieces of paper, bound or otherwise), as well as tying up my time trying to bring order to the chaos of those notes every day.

I then tried using a todo.txt file in an attempt to reduce the amount of paper to manage, since the file would be synced between any workstation I happened to use. This worked well when I was at a computer, but helped me not at all once I was out running errands. I attempted to supplement this with a notebook for capturing or reviewing relevant information while I was away from a computer, but I quickly discovered that the redundant step of re-entering the information into my text file once I returned to a workstation quickly sapped my interest in meshing these two approaches together, especially since I too often would forget my notebook. In addition, I still found myself spending a lot of time managing the list manually from day to day in order to track tasks logically, and it began to become necessary to track multiple files, which added additional administration time. I needed to have some business logic built into my system that would handle the majority of tasks automatically.

Why Not the Web?

It was clear that I needed to find a tool, or combination of tools, that would be ubiquitous, preferably accessible via my phone as I never leave the house without it. I naturally started looking at the web as an option, especially since at the time I was running Windows at work, Linux at home and Symbian on my phone. A web-app seemed like a natural choice, which led me to Remember the Milk. RTM is an online to-do list manager that is very flexible and powerful. It certainly helped that it was a very popular app, with a lot of positive buzz associated with it.

Remember the Milk

Remember the Milk - Task List View

Excited about RTM, I signed up and quickly created a several lists and excitedly began using the service to track all my various tasks. There were a lot of things to like about RTM, such as:

  • Accessible anywhere, which allowed for centralized data storage
  • Flexible list and tagging system
  • Lots of metadata available for describing tasks
  • Powerful search capabilities
  • Smart lists generated based off of search criteria
  • Integration with Twitter and other services

However, over time I discovered that there were some issues with using RTM as my task management tool:

  • Mobile web-app for phones was really bare-bones and difficult to use (this has improved over time). The iPhone mobile web-app was much better, but required a Pro subscription, and still felt slow from a data entry perspective since it involved so many screens.
  • Ordering of tasks in a list was only possible by means of sorting due dates, priority or name, meaning I spent a lot of time making up sequential dates for tasks that were not time-sensitive in order to get the list sequence I wanted.
  • An internet connection was required to work with tasks, as features such as Offline mode via Google Gears always seemed out of sync.

Of course the most critical problem that I had with using a web-app is also the most obvious. I had to remember to log in to the site if I ever wanted to add/view/manage my tasks. There was nothing to prompt me to do this, and in the time that I used it I never found a good desktop solution for this in the form of an application or a widget. Desktop widgets always seemed to be out of sync with what was on the server, and application support didn’t seem to be an option. Now, to be fair, RTM has a ton of reminder options, including Email, IM, Twitter and SMS notifications, so if the task had a due date associated with it, you were guaranteed a reminder, which made sure you remembered a previously set up task, but did not help with ensuring that I continued to manage and stay on top of my tasks within RTM itself.

RTM took some big steps forward on this issue when they released their iPhone app with push notifications, but in some ways the iPhone app’s data entry still felt a bit strange to me. More of an issue, however, was that use of the app required an existing pro subscription with RTM, for which I was paying $25 a year, and I did so happily. Let me be clear here, with a few small shortcomings, RTM is a great service, and for many of you it will fit the bill perfectly, but over the years that I intermittently used RTM, I found it very difficult to fit into my workflow, which is completely a personal preference.

What Now?

Several months ago I realized that I needed to do something different. My approach to using RTM was not working for me, and there would be spans of time, sometimes months long, where I would neglect my task lists there entirely, instead using a mish-mash of paper, memory and my preferred research tool, Evernote. I began hunting around for other options and discovered Things, which is a desktop application for the Mac. Things is also available in an iPhone version capable of wirelessly syncing with the desktop edition while functioning as a standalone application.

There were several issues with Things that prevented me from using it initially. First of all, since my work computer is a Windows machine, I would need a way of updating and managing tasks effectively when I was not at home. My experience working with the iPhone app that RTM provides made me leery of the thought of managing my tasks through my phone when away from my MBP. Secondly, Things is expensive: the desktop application is $49.95, and the iPhone app is $9.99. However, a few weeks passed, and having not found anything else that particularly thrilled me, I downloaded the one month free trial of Things for Mac in order to try it out. I knew that to fully test it out I would need to experiment with the phone application as well, so I decided to just eat the $10 fee and purchase it for my phone. I have not regretted it.

Things for Mac works wonderfully for me, providing a number of tools for me to organize my tasks such as Projects, Areas (basically ad hoc lists) and Tags. Along with these “metadata-powered” organizational solutions, any list can reordered by simple drag-and-drop, independent of any other task properties, which is a huge plus for me and one of my few gripes about RTM. Things is clearly inspired by GTD and so there are also a number of familiar conventions that will be immediately recognized by the productivity crowd such as the Inbox (for collecting unprocessed tasks), Today’s Tasks, Next Actions, Scheduled Tasks (which do not appear on any list or reminder until a given date) and of course the Someday folder for storing ideas that I may or may not choose to follow up on. However, it does not require me to use any of those features unless I want to, and this is the most essential feature for me. Things does an exceptional job of getting out of my way and allowing me to manage my tasks how I want, while providing support for more advanced organizational approaches if I need them. This kind of flexibility is crucial to me, because I do not want to spend unnecessary time tweaking my productivity system when I should be doing something productive.

Things for Mac Screenshot

Things for Mac: note that this post is overdue. 😉

The iPhone app functions great as a standalone application, and I could easily have gotten by with just using it to manage everything. It has not slowed me down when at work or on the road and data entry, as well as task management is effective and pleasant to do when working with the phone application. The only thing that the iPhone app does not support that the desktop app does is the creation of recurring tasks, which if you have the desktop app is really a moot point since the two applications will sync with each other any time your phone and computer are on the same wireless network. However, be aware that if recurring tasks are important to you, you will need the desktop app for now, although I have read that the developers are working on incorporating that feature into the iPhone app.

Things for iPhone - Home Screen Badge

Things for iPhone displays the number of tasks assigned to the current day on the application’s home screen badge.

Things for iPhone - List Selection

Things for iPhone - List Selection Screen

Things for iPhone - Today View

Things for iPhone - Today View

When my month long trial for the desktop edition ended, I happily paid the $50 to purchase a license, and I have continued to use both apps for about two and a half months now. When I am seated at my MBP, I prefer to work with the desktop app, as the mouse/keyboard interface allows for quick and sophisticated entry, but the iPhone app continues to be a very effective management tool while I am at work or on the road. I have finally found the tools that enable me to build an organizational system that works for me.

Simply put: Things makes task management easy. If you have been struggling to find an effective task management solution, and you either have an iPhone or a Mac, than you owe it to yourself to give Things a shot.

Get Things here.