Being somewhat OCD, I keep the concept of a todo list close to my heart. I’ve gone through several dozen iterations of an excellent todo list and what I have arrived at works very well for me; I want to share some of the design decisions I’ve made in the past, since I’m sure that if you’re just as passionate about keeping track of things to do, you probably came across the same problems as I did.

I wrote my first todo list when I was in fourth grade (I was about 10 years old). I found the concept really useful in staying organized and keeping on top of tasks. I think the perfectionist in me hated forgetting things (most of us have a dislike of forgetting things–this is related to our irrational preference for the preservation of options) so I added a safety net for my memory early on in my life (also, as a youngster, I would tend to forget things really easily).

The todo list started as a collection of subjects for which the teach assigned homework. I would write three-letter abbreviations out on a small 2.5″ by 2.5″ of paper, squeezing Monday through Wednesday on one page and the rest of the week on another. The first lesson I learned was to write in a small, regular type so that things could fit on a small piece of paper that I could take with me anywhere.

Soon I realized that it’s better to attach the tasks to the day they are due (or the day before, to be precise) rather than the day they were assigned. This pushed Monday through Thursday on one page and the weekend on another (since I ended up doing most of the task on weekends).

At some point the list was enhanced to include items not related to homework: for example, I wanted to find a new wallpaper for my computer’s desktop, or finish a particular computer program or a game I was working on. Most of the things I had listed at this point were tasks–they were specific and achievable in the frame of one week. When I added longer-term items (for example, books that

I was supposed to read over a semester), I’d separate them visually from all other items with a different color. Finally, I started using icons to represent frequently-listed tasks, partly for increased efficiency, partly because I liked having a system that only I understood.

When I was 16, I went to high school in London. My tasks slowly amalgamated into goals, small and big; particularly as I started listing things I wanted to achieve for self-improvement. This was also the first time that I separated short-term things from long-term things: the latter was one large sheet of paper that I kept in my drawer; the former became post-it notes (yes! I discovered post-it notes!). This was mostly also due to efficiency — I didn’t want to keep copying the same items over and over again from one week’s post-it note to the other.

The move to post-it notes also forced me to keep everything on one page. This ended up being a good thing: I was realizing that I’m a hypervisual person–being able to grasp the entire week at once allowed me to get things done more efficiently (this is also why I prefer restaurants that display all the entrees on one page).

At some point in my senior year in college I finally moved to have an electronic form of my todo list. I held out for quite a long time, because the act of writing out my tasks seemed to make a longer lasting impression on me than typing them out. But through behavioral change I slowly got used to referring to my todo list on a computer. I worked out a few rules that made such a system possible: having the list open at all times (so that I would never lose sight of what I was doing–this also forced me to keep the list small), using simple formatting (I stuck with plain text notes formatted with tabs; simple formatting allowed me not to lose sight of the tasks, allowed me to edit the list very quickly, and made the list very compact). I worked out very efficient (“cryptic” to some) terms to denote tasks.

It was then that I started to think about the effectiveness of my strategy to get things done (mind you, that was back in the day, before someone decided to write a book about these commonsensical things and made a lot of money) as opposed to just the efficiency of the representation. It became more important to have a system that helped me achieve the things rather than a system that allowed me to write them down quickly. This is where a lot of the experimentation happened. I thought a lot about what makes me motivated and while most of the motivation is independent of the protocol for keeping track of goals and tasks, I found a fairly significant variability between which system I used and how effective I was at getting things done.

I toyed with an idea of a kind of game I’d play with myself, a kind of system where I’d reward myself for getting stuff done. I didn’t really need any exogenous incentive–earning virtual “points” was all that I needed (perhaps it’s because I’m a conceptual thinker, or perhaps because I’m a nerd). I’d assign myself points for every task, and the number of points was proportional to how “important” the task was. I would set goals for, say, a month. I went even more crazy than that, coming up with a number of point thresholds, exceeding each of which would give me a different “rank” (it’s incredible how much fun a kid can have with nothing but pen and paper). Recently I dropped any kind of scoring system because I noticed that I by and large knew how well I was doing and keeping track of my score became less of a factor in motivating me — in other words I realized that the desire to get things done had to come from something else than how many points I got for the day.

I also experimented with the timeframe for my short-term todo list. At that point I still had two lists: a short-term one and a long-term one, and every time I came up with a new instance of the former one I’d consult the latter. For about a year I changed the frequency of the short-term list to be biweekly but I found that a frequency of one week is optimal — the list needed to include at least one weekend (otherwise it wouldn’t be all that useful since I do get a lot of the stuff done over the weekend–the weekend is also a “buffer” for overflow work); but if it included more than one I would end up feel too complacent on the first weekend and postpone everything to the second one.

About three years ago I came up with a framework for a high-level structure of the todo lists that I had by and large accepted and tried to follow: I listed things which I wanted to do every day (for example, get up to speed on the blogs that I was following; or go jogging) in a kind of “checklist”. Generic todo items would follow, at first scattered arbitrarily throughout the week. Specific events had dates attached to them. I had a separate file that listed events happening on a particular date if they were more than a week away, to not litter my todo list too much.

I went back and forth on whether I should explicitly include the daily tasks on my list or not. At first I thought that by including them I would be more incentivized to do them every day. At the end updating them ended up just wasting my time so instead, my short-term list now has a list of these things to remind me what I have to do every day, but I don’t keep track of whether I actually do.

Finally came the iPhone and for the first time since I switched to a computer-based todo list I could carry the lists with me at all times. It was great as I no longer had to email myself notes (or keep them in some separate
container and then get them out of my iPhone). I’m still pretty adamant on keeping the notes as simple and unformatted as possible and accessible from anywhere so I wanted to stick to text files. Fortunately I found an app called SyncBook which did exactly what I wanted it to do — it allowed me to sync a folder of text files between my computer and the iPhone and–most importantly–it allowed me to edit the text files on the iPhone (there are several good apps that work in a similar fashion — take a look at Evernote if you don’t need the notes to be text files and don’t mind slightly bigger overhead, or just sync native Notes if you don’t mind Marker Felt. There are also apps that allow you to edit richer documents if you do care about the formatting).

About three months ago I settled on a final design for my todo lists. I like it because

It’s simple–there is minimal overhead; I only need to update pretty much one word when I complete a task (or want to add a new one)
The important information, and only the important information is with me at all times–I have the todo list open on my computer, and when I’m away from my computer I have it on my iPhone. Syncing is as easy as pressing one button in SyncBook, and I can sync over the local network, which is great (I can do it anywhere around the house)
My todo list is organized in a three-tier structure: day, week, month, which is a natural structure to think about tasks
- week (a short term list) enumerates all days of the week with things which I have to do that day. It also has a general “grab bag” of items which I simply have to do at some point in the week. Finally it has a list of items which are my daily tasks (I don’t repeat them for every day) and a list of items which are my weekly tasks. All the daily and weekly tasks derive from my goals. Finally, it contains a list of problems in my life that I want to solve in order of how anxious they make me.
- thisMonth enumerates all items which I’m supposed to do at some point in the month. I also include longer term periodic things such as what books to read and what miniprojects to do. Every week I take some items from this list and put them in the week list.
- nextMonth enumerates all items which I’m supposed to do next month. Every month I move them to the thisMonth list.
- calendar which contains all events with dates attached to them. I tried to use something like iCal but I like the flexibility of specifying indeterminate times (e.g. some time in the latter half of January) and I found the existing interfaces of iCal insufficient
All the items are available offline — I hate not being to access something because it’s online, or having to deal with slow web-based interfaces. Changing a status of an item takes me a couple of seconds at most
It’s short–the short term list consists is a text file measuring 20 rows and at most 50 characters in a row (so it can fit on one page on my iPhone). All thanks to efficient representation of todo items — there’s no need to be verbose since I remember most things that I’m supposed to do given a short prompt. For example, I know that “nprAlarm” is a task to set my computer up so that it wakes me up every morning by playing the live podcast of WNYC.
It’s fast–syncing is fast, editing is fast, viewing is fast. Moving items from one list to another is fast.
All my goals are represented in one form or another on the short term list. That way I’m constantly reminded of what I’m supposed to be doing and how it connects to my goals.

Of course, this framework is just one of many and which framework works for you depends very much on your personality and what makes you tick. I do, however, encourage you to follow a few principles:

Have a list. Some people say that having a list is bad because you stop relying on your memory. I solve this problem by training my memory in other ways (e.g. with Brain Challenge). Don’t conflate training with work
Experiment. Switch things around. A kind of “evolutionary” process–an informed random walk–allows you to find the most effective system
Keep it simple. Complicated lists end up wasting time and detract from actually getting stuff done
Keep it available. You never know when you have some time to knock something off the list, and you never know when you want to add something to the list
Keep it flexible. After all, we think in free-form way, not in a highly structured way, especially when we go about our daily activities and let our mind wander