I can imagine a variety of reactions to this request. One might be “Why in the world do you need me to design a todo list when there are like a gazillion todo lists already out there?” Another might be a shrugging of the shoulders, thinking I’m giving you a chance to make some easy money to design yet another todo list. But if you’ve really been around the design block a few times, you’d know better than to assume that a seemingly simple request coming from a client really is that simple. (In my experience, that is rarely, if ever, the case.)

So, you dutifully inquire further as to what my specific needs are relating to a todo list, i.e. when and where I’d be using it, what type of todo items I’d be entering, how I’m currently managing my todo items and so forth. Here is one of my responses:

I’ve used all kinds of todo list software, from the new Gmail Tasks, to 37 Signal’s Tada Lists, to just typing stuff into notepad or Google docs. Many of these pieces of software are very simple and elegant and user-friendly, but, even so, what always happens is that I use it for a while, eagerly typing in everything I need to do, but then I stop using it after maybe a week or two, sometimes less, usually because it’s just too much of a hassle to have to type stuff into these lists. So I end up with todo items scattered all over the place.

Whoa, wait a second here. Maybe this todo list thing isn’t that simple after all. Taking an Alan Cooperish what-if-software-was-magical approach, you ask me what my ideal dream todo list might look like, setting aside any technical or logistical constraints.

For me, the issue is primarily with the hassle of having to enter items, of having to get in front of a keyboard and fire up some application when I think of something important, especially when I simply can’t or don’t have the time, maybe I’m riding my bike, in the shower, in the midst of a conversation with someone, don’t have internet access, whatever. So I end up not entering it, which of course negates the whole point of a todo list. So, in terms of my dream todo list, and this will sound a bit weird, I think it would have to be one which it basically reads my mind or something and when I think of something I need to do, it would add it to my todo list in the cloud, as in some kind of universally accessible list of stuff to do.

The other big issue is having to deal with categorizing and prioritizing todo items. While I’d like for them to be organized nicely, I don’t want to deal with having to come up with categories not to speak of having to do the categorizing. So it would need to be able to somehow figure out how to group my todo items in a sensible way, such as work-related and personal todo items. And as far as priorities go, I’d obviously want higher priority items to be more prominent, but the problem is that the priority of a todo list item changes for me depending on context and other factors. For example, if I am at the office, even though I absolutely have to remember to pick up a bottle of wine on my way to the dinner party this evening, I don’t want that todo item cluttering my list of office todo items. But if I maybe head out for lunch, then I’d want to see it, since my priorities and my context then has changed. Yeah, that would pretty much be the ideal dream todo list.

Ok, so on one hand this is a dream todo list app, but let’s look at what this imaginary software tells us about current todo lists and design in general.

The more contexts your design needs to support, the more complex it will be to design
A todo list is reflective of how the software we design is increasingly intertwined with people’s lives. As such, a todo list that a real person really can use in their day-to-day activity needs to work in all kinds of contexts. Compare this to a todo list that strictly is for work-related items: in that case, I can maybe assume that the user will always be in front of computer and as such as traditional todo list might work. But even that falls apart, since I may also be on the road, in a meeting with a client at a coffee shop, in front of a whiteboard.

Categorization is a Catch-22 Conundrum
On the one hand, users like for stuff to be organized in a way that makes sense to them. At the same time, they are unlikely to want to have to deal with coming up with categories or with the hassle of categorizing. While creating some generic todo list categories (e.g. work, personal, buy, etc.) is probably doable, user would still have to actually place stuff in those categories, which adds yet another obstacle, another micro-activity that will make the act of entering a todo list item less palatable.

Priorities are contextual
There are lots of things we think of as important, but only some of things are important in a given context. This means that we can either have multiple todo lists for different contexts, which means a lot of busy work, which means we are likely to stop using the todo list. Alternately, we could use category-specific indicators, such as high priority work, or high priority personal, but again, we are then back to the problem of too much hassle to deal with when enter a todo list item.

Sometimes there really is no great solution within the digital domain
With today’s mainstream technology, it is not possible to design a durable and truly useful todo list. Please prove me wrong on this.

Instead, this is the todo list solution that I always find myself returning to:

Yup, the back of an old envelope. Why is this tattered looking thing better than any of the todo list software out there?

It’s highly portable
For the very reason that it’s just an old used envelope, I can crumple it up and stick it in my pocket. If I spill coffee on it or it gets a little torn or whatever, who cares?

It’s always immediately accessible
No booting up an iphone app or, yikes, a laptop, just to enter a lousy todo item. No battery life or connectivity issues to think about.

It constrains me to a reasonable amount of todo items
One of the biggest problems with most current todo lists is that they, in a knee-jerk nod to the idea that infinite scalability is a good thing, don’t impose a limit on how many todo items I have on my plate at any one time. But a list of hundreds of todo items, I think, is pretty useless, as I am only going to be able to do a few of the items within the near term. So, the size of the envelope constrains me to a reasonable amount that usually matches what I can complete in a day.

It allows for ad-hoc prioritization and categorization
Since I can write anywhere on the envelope, I can add little stars or underlines or write in all caps or whatever to show that something is important.

But, of course, using the back of an envelope for a todo list has all kinds of drawbacks, which leads to another UX lesson:

Design is not about finding the ideal solution; it’s about finding the ideal compromise
Obviously, using the back of an envelope or a piece of paper has all kinds of drawbacks, from that you have to manually transfer todo items that weren’t completed to a new piece of paper, or that you could easily misplace it, or that all your scribblings could quickly turn into a big jumbled mess. But weighing all those drawbacks against the strengths of the solution, I still kep find myself returning to this method after temporarily trying some new software-based todo list.

Is it just me or are others having similar experiences, finding digital todo lists just not workable in the long term?