Against Deadlines

I just counted: I have 205 tasks in my task manager – without my reading list, purchases list, or blog ideas list. And that’s only counting my personal tasks, not my work tasks! Now I keep stuff I only might do in there, and I probably have a wider variety of projects and interests with their own sets of tasks than an average person does. But the point is, participating in today’s society and remaining sane and organized requires keeping track of and doing an inordinate number of disparate tasks, from long and complicated to small but fiddly.

Many people turn to self-imposed deadlines or due dates to organize this avalanche of tasks. Having tried many methods of organizing these tasks myself, I’m going to try to convince you that self-imposed deadlines are a poor way to sort these tasks and suggest a better way based on understanding their priorities.

When we do need deadlines

Deadlines aren’t uniformly bad. Two situations all but require the imposition of a deadline:

• External circumstances require the task be completed before a certain time. For instance, if my task is to get Christmas presents, I have to complete the task before Christmas or there will be no point in doing it anymore. The date of Christmas, and presumably the time I’m celebrating it and need my presents by, is outside of my control (and anyone’s control, for that matter). Or if I’m organizing a conference, I probably need to give the presenters a deadline to submit abstracts so I can figure out the schedule before the conference starts.
• A large number of loosely organized people need to complete something together. Imagine a large company working on a major initiative. Later, I describe how a priority-based system, in my view, organizes work more effectively. But when dozens or hundreds of people have to cooperate, getting all of them to agree on their priorities becomes virtually impossible: each of them have their own team and individual concerns, and creating an artificial constraint (a deadline) may be the only way to coordinate everyone.

But it’s better to avoid deadlines if they’re not necessary. I’m particularly taking aim at self-imposed deadlines in this post, but what I say may also apply to small groups of people working together and sometimes even larger groups. Methodologies like Kanban can help organize teams without requiring deadlines.

The problem with deadlines

Follow me for a moment on a little thought experiment. Let’s say you own a small house and today (Monday) you notice your grass is getting long and you need to mow it. You decide that you’ll get that done by Thursday evening. There’s no particular reason to choose Thursday except that it seems to be a reasonable length of time to give yourself to do it in: nothing bad is going to happen if it goes longer, except that your grass gets slightly less presentable.

What happens next? Today you don’t do it, because after all you have three whole days left and you have other things to do as well. On Tuesday it rains in the morning, and you don’t want to mow with the ground wet, so you put it off until Wednesday. On Wednesday, you’re exhausted, so you figure you’ll do it tomorrow: still time before the deadline, right? On Thursday, a friend ends up in the hospital unexpectedly, so you go visit her instead. Now you missed your deadline and you feel disorganized and lazy, even if your choices made sense every day.

Here’s another scenario: as above, except on Thursday, you find out about a concert you’d love to go see, but since you decided you had to get the lawn mowed by Thursday, you skip it – even though a week from now you’ll surely wish you’d gone to the concert and just mowed the lawn on Friday.

I bet you can identify exactly with both of these scenarios! In the first experiment, the deadline discouraged you from getting work done early and made you feel bad even though you did nothing wrong; in the second, it encouraged you to make the wrong choice! This doesn’t sound like a great organizational system to me. To be specific, we can identify three common issues associated with deadlines from this thought experiment:

• Deadlines that are too far in the future can discourage us from getting started.
• Deadlines can make us feel bad and reduce our motivation when we miss them, even if missing the deadline has no consequences.
• Deadlines can discourage us from doing other, more important or time-sensitive, things.

Note: Of course, these are not really properties of deadlines per se but rather of people’s behavior when faced with them. But it’s hard to imagine us magically changing our behavior using some simple mind hack when we all know everyone experiences the same thing! For all intents and purposes, these issues are intrinsic, if not to deadlines themselves, to deadlines as used by people.

The truth is, outside of particular controlled conditions like a weekend set aside to complete some project, our priorities are constantly changing. Pinning deadlines on things reduces our ability – or at least our willingness, if we set them ourselves – to be flexible and change those priorities. While working on dozens of projects at the same time is inefficient, being comfortable rapidly switching over to something that appears suddenly and is more important or time-sensitive makes us look more efficient (even if we’re doing the same amount of work) and reduces the number of times we have to scramble to finish something we weren’t able to start early enough (because we were busy working on something less important).

Beyond reducing flexibility, deadlines can obscure our priorities. In the first thought experiment, maybe mowing the lawn was your highest-priority household task, but when on Monday you set a deadline of Thursday, suddenly it didn’t look so important and you wound up not doing it for three days.

A better way

Deadlines do a great job at inducing fear and encouraging work as they approach, but they’re terrible at helping us organize and at motivating when they’re far off. How do we fix that?

First, keep assigning and following deadlines for things that really do have to be done at a fixed time, and for coordination, when necessary. When you use them less often, they get more effective, especially if whatever tool you use to manage your work makes items with deadlines stand out.

But anytime you don’t have a fixed date assigned, don’t create one. Instead, keep track of all the work you need to do in one place (if you don’t have a good method already, prefab methodologies like David Allen’s popular Getting Things Done are available) and periodically prioritize it. You might do that every day, every week, or a combination. You can use fancy list-making software or apps or something as simple as sticky notes or index cards – you just need to be able to freely move the items around. Then you only work on the top couple of items, and adjust the ordering as needed.

With this method, you don’t need deadlines to motivate you to get work done; you just do the most important things at any given time. If you can’t work on the most important things for some reason or they’re hard and you need a break, you can always jump further down the list to find something appropriate – but in any event, when your priorities are up to date, you know exactly how important each task is to you and you’re not left guessing. When something more important or time-sensitive comes up, it jumps up to the top of the list, but you don’t have to feel bad about missing a deadline if you drop what you’re doing and work on that instead, because there wasn’t a deadline. Working on the most important tasks is the only goal you need, and the most important tasks self-evidently get done promptly, no matter what those are at any given time.

Essentially, deadlines are a way of forcing yourself to get things done when you haven’t taken the time to figure out what’s important. If you take that time, you can still get everything done, be more flexible, and increase your motivation at the same time, all at the low cost of a little bit of additional planning.