Productivity and Procrastination

I wrote this essay as a way of not completing another, more pressing task.

By Ryan McGreal

Posted September 09, 2009 in Blog (Last Updated October 29, 2009)


2Eliminating Distractions Doesn't Work
3Trick Yourself With Seemingly Important Tasks
4Procrastinating Well
5Procrastinating Badly
6Procrastination as Perfectionism
7Perfectionism as Procrastination
8Good Enough
9Smart Collaborating

1 Introduction

From outside, it sometimes appears that I manage to produce a lot of output. At least, people sometimes ask me, "How do you have time to do so much?" This confounds me, because from inside, I'm painfully and continuously aware of my essential laziness, weakness for easy distraction, and inability to set priorities.

As the joke goes, I was going to start a procrastinators' club but never got around to it. In the meantime, I seem to be getting stuff done, but not necessarily the stuff I ought to be getting done.

So it came as a tremendous relief when I stumbled across this essay by John Perry, a Stanford philosophy professor, in which he identified, labeled and described my situation exactly:

All procrastinators put off things they have to do. Structured procrastination is the art of making this bad trait work for you. The key idea is that procrastinating does not mean doing absolutely nothing. Procrastinators seldom do absolutely nothing; they do marginally useful things, like gardening or sharpening pencils or making a diagram of how they will reorganize their files when they get around to it.

Why does the procrastinator do these things? Because they are a way of not doing something more important. If all the procrastinator had left to do was to sharpen some pencils, no force on earth could get him do it. However, the procrastinator can be motivated to do difficult, timely and important tasks, as long as these tasks are a way of not doing something more important.

I read this and thought, Yes, yes, a thousand times, yes!

Structured procrastination means shaping the structure of the tasks one has to do in a way that exploits this fact. The list of tasks one has in mind will be ordered by importance.

Tasks that seem most urgent and important are on top. But there are also worthwhile tasks to perform lower down on the list. Doing these tasks becomes a way of not doing the things higher up on the list.

He concludes:

With this sort of appropriate task structure, the procrastinator becomes a useful citizen. Indeed, the procrastinator can even acquire, as I have, a reputation for getting a lot done.

In a clear stroke of words, Perry easily reconciles the seeming disconnect between the fact that I seem to get a lot done and yet am perpetually engaged in trying to avoid fulfilling my responsibilities.

2 Eliminating Distractions Doesn't Work

He points out that many procrastinators try to address their procrastination by eliminating every task or responsibility except for the few most important commitments.

Of course this fails miserably, because in the absence of distracting activities, the only way to avoid doing what's left is to do nothing.

Again, this is exactly my experience: I can only seem to accomplish anything when I have far too much to do, for the simple reason that I have no shortage of projects to work on as a way of not working on the most important ones.

3 Trick Yourself With Seemingly Important Tasks

Perry cautions that the best way to maximize the utility of this strategy is to arrange your affairs so that the ostensibly most important jobs - the ones you avoid by doing other things - should "seem awfully important (but really aren't).

"Luckily," he adds, "life abounds with such tasks." Of course, this "requires a certain amount of self-deception," but my opinion has always been that a little bit of denial helps us get through the day, so I can live with that.

4 Procrastinating Well

In a 2005 essay, hacker evangelist Paul Graham makes a similar argument:

Most people who write about procrastination write about how to cure it. But this is, strictly speaking, impossible. There are an infinite number of things you could be doing. No matter what you work on, you're not working on everything else. So the question is not how to avoid procrastination, but how to procrastinate well.

He posits three types of procrastinators: those who avoid working on a project by working on a) nothing, b) something less important, or c) something more important. In effect, Graham argues that people who manage to accomplish "real work" do so by avoiding "errands".

The reason it pays to put off even those errands [that get worse if you put them off] is that real work needs two things errands don't: big chunks of time, and the right mood. If you get inspired by some project, it can be a net win to blow off everything you were supposed to do for the next few days to work on it. Yes, those errands may cost you more time when you finally get around to them. But if you get a lot done during those few days, you will be net more productive. [emphasis added]

He notes in passing that avoiding errands may be annoying for those people who expect you to get them done, but argues that it's probably not possible to do "big stuff" without annoying people who depend on you doing small stuff. That's rather more self-serving that I feel entirely comfortable endorsing, but I'd be lying if I tried to claim that I've never disappointed someone who was counting on me to do an errand. :/

5 Procrastinating Badly

Graham also tackles the other side of the coin: people who avoid doing important work by doing errands.

Errands are so effective at killing great projects that a lot of people use them for that purpose. Someone who has decided to write a novel, for example, will suddenly find that the house needs cleaning. People who fail to write novels don't do it by sitting in front of a blank page for days without writing anything. They do it by feeding the cat, going out to buy something they need for their apartment, meeting a friend for coffee, checking email. "I don't have time to work," they say. And they don't; they've made sure of that.

As someone who has tried and failed to write a novel on more than one occasion, I can again attest that this is exactly right. Graham cites the three questions Richard Hamming poses for anyone working on something:

  1. What are the most important problems in your field?
  2. Are you working on one of them?
  3. Why not?

Of course, the answer to 3. is that I'm a procrastinator, and procrastinators avoid working on important problems by working on less important problems - as Perry argues so eloquently.

Graham posits that the reason people avoid important problems is that they're intimidating, even "terrifying". He suggests:

You can't look a big problem too directly in the eye. You have to approach it somewhat obliquely. But you have to adjust the angle just right: you have to be facing the big problem directly enough that you catch some of the excitement radiating from it, but not so much that it paralyzes you.

He offers some techniques - what we might call hacks - that might help in tricking you into working on important problems: work on small things that turn into big things, or bootstrap to bigger problems from smaller solutions, or collaborate with others to make your individual share of the problem more manageable.

That's all well and good, but it has the feeling of recommendations tacked on out of a sense of obligation rather than real solutions - which brings me back to Perry and the reliable method of self-deception.

6 Procrastination as Perfectionism

While Graham characterizes procrastination as a fear mechanism, Perry argues in a more recent essay that it's a form of perfectionism, in the sense of the perfect being an enemy of the good.

Perry describes what starts out as an assignment to referee a manuscript and spirals into an odyssey of setting up proxy servers ... and I find myself thinking back to the night a week ago when I set up a backup server in my basement as a way of avoiding another, much more pressing and time-sensitive task.

Of course, just as it was important for Perry to set up his proxy-server (to access the J-store from home), it was also important to set up the backup server (assuming I actually use it and follow through on scheduling backups). Computers are unreliable, and catastrophic data loss is always one hard-drive crash away.

Yet there's a reason I had to set it up that particular night, and it's not because my data had suddenly entered into an intolerably immediate peril of crashing.

As it happens, I had already been putting off setting up the backup server for several weeks, and I only got around to doing it once something even more important landed on my desk, i.e. the time-sensitive project that I avoided doing by setting up the server, ostensibly so I could back up the project once I finally worked on it.

7 Perfectionism as Procrastination

Perry argues that procrastination is a response to his desire for perfection, "a way of giving myself permission to do a less than perfect job on a task that didn't require a perfect job." After all, he did manage to write a perfectly serviceable referee report at the last minute.

But it seems to me that at least in my experience, the dependency flows the other way: rather than procrastination allowing me to be imperfect, I find that perfectionism allows me to procrastinate. It's just one more tool in the service of not doing what's most important.

8 Good Enough

Still, Perry raises a very important question:

You need to ask the questions: how useful would a perfect job be here? How much more useful than a merely adequate job? Or even a half-assed job? And you need to ask the questions: what is the probability that I will really do anything like a remotely perfect job on this? And you need to ask: what difference will it make to me, whether I do or not?

This immediately reminded me of the Cult of Done, a manifesto for getting things done - small things, quick things, disposable things - for the sole purpose of being able to move onto still other ephemera.

Essentially, the Cult of Done sacrifices everything else for expedience. Don't wait until you know what you're doing - just pretend you know and get on with it. Don't waste time editing - just publish. If something takes too long to do, abandon it and move on to the next thing.

Yet the Cult of Done, in a manner somewhat analogous to structured procrastination, allows the transformation of a careless, throwaway approach to work into the creation of enduring accomplishments, in what we might call the Wikipedia Effect.

While waiting for experts to grind out fully formed and exhaustively researched online encyclopedia articles, a loose group of collaborators with no special knowledge collectively built up a peer-edited encyclopedia that quickly matched and then surpassed professional encyclopedias in its breadth and depth of embodied knowledge.

9 Smart Collaborating

This seems to hearken back to Graham's recommendation that the best way to make a big project more manageable is to collaborate with others so each individual contribution is small enough to finish while the overarching goal of solving a big problem is still being served.

(As a startup funder, Graham strongly encourages his startup developers to develop in partnerships, partly for this reason.)

It's the thinking behind the Release Early, Release Often philosophy, an approach to development that sees any project worth doing as a work in progress.

Speaking of good enough, I'm going to wind up this essay now, even though it would almost certainly benefit from some editing to cut out the fat. Maybe one day I'll come back to it and give it the edit it needs - when I have something more important to work on.