The to-do list’s original sin

Plus, why calendars rule.

To-do lists are like Jesus.

We look for them when we feel overwhelmed, lost. In the midst of dealing with despair, we brand them as saviours and visionary guides to our ideal selves. For surely they will repent us from our sins of procrastination. And then they’re betrayed by some Judas called “human behaviour.” I know plenty of people to whom this has happened. It has happened to me. I’m pretty sure it’s also happened to you at some point.

So this got me wondering.

Is a to-do list the best solution for tasks?

To-do lists exist to help us remember things. I don’t take it as a surprise: my memory sucks big time and it always has. To say it’s selective is an understatement: random useless facts are hugely favoured, but never mind remembering that very important thing I need to do next Tuesday.

So I started using to-do lists. And soon realized they share a problem.

First, here’s why to-do lists are great: they help us list (obviously) the stuff we need to do, set priorities, even organize them by groups of things or projects. So what’s wrong with them? Well, while they’re great at listing stuff, they suck at setting limits to how much stuff we can get done.

Meetings, in that sense, get some things right. Ask any manager and he’ll say meetings suck unless you have a clear agenda and schedule. Agendas help us understand the rough amount of time a meeting requires. This in turn helps us decide if we’ll need a full hour, two hours or if we can just drop by a colleague’s desk and chat for five minutes.

The foundation of a meeting, then, is time. We need a certain amount of time to do something, and we know that time is limited. Especially because there are other scheduled meetings before and after.

In short, meetings are context-sensitive.

Meetings exist within the context of other meetings

We use calendars to organize meetings, so what if we could use calendars for organizing tasks as well? Lists do one thing right: adding and organizing things we need to do. But only a calendar can provide the broader context of a day, a week or a month in which those things exist. If we have a meeting at 2pm, we don’t schedule another meeting for that time slot because we’re already busy. Context matters in how we organize meetings… and tasks too.

Calendars help make tasks time-bound, thus assisting us in not only organizing stuff but also organizing the time we have to get stuff done in relationship to everything else we need to do.

Now, we suck at predicting the time we need to get something done. A calendar doesn’t solve that entirely. But it does help us organize the time for task A in relation to task B and meeting C. It also helps us make the best of Parkinson’s Law, which states that “work expands so as to fill the time available for its completion”. In short, the amount of time we have for a task typically is the time we take to complete it (exceptions apply).

If tasks are best tackled when they are time-bound, the calendar might just be the best to-do list there is.

Hacking behaviour to get shit done

Tools alone don’t solve productivity. We still need to figure out the human part, i.e. we can’t understand productivity without understanding behaviour. So what sparks behaviour? According to Max Ogles at The Next Web, it’s the result of three things: motivation, ability and triggers.

For example, if you’re trying to get yourself to go to the gym, that might mean having the desire to exercise (motivation), having the time and resources to get to the gym (ability), and setting a calendar event to remind yourself to go (trigger). The best health and fitness apps incorporate some or all of these components in the user experiences that they offer.

Often we have motivation (“I want to do this”) and ability (“I believe I can do this”). What fails are triggers. That’s why we see a lot of people who want to write more often but don’t, or who want to get chores done on time but don’t. Lists help line up what we want or need to do, but they don’t help trigger the action that actually gets it done.

This matters because it turns out the key to productivity might not be goals, but systems. Triggers are the result of systems that foster repetition and context. That’s how we create routines, which are nothing but automatic behaviours that helps us save mental energy. If we aim to change behaviour (including our own) without tackling triggers, we will fail.

Behaviour is connected to habit, and habits are produced by triggers until they become automatic.

Technology can help with that. Calendars are just an example. This is not about Fantastical being better than Clear (I am a huge fan of both and use them daily for separate things). It’s about figuring out the cogs of the technical and human systems and hacking them to generate triggers that help us master our own behaviour.

While this may sound freakish and overly anal, I’m pretty sure it’s better than failing on our responsibilities. The to-do list’s Second Coming is not only its original sin, it’s also its biggest lie.