I’m reading a book at the moment called Stumbling on Happiness, by Daniel Gilbert (thanks to Derek Sivers for giving me his copy), which takes a look at how our brains remember the past, make sense of the present, and imagine the future. Our brains get this sort of thing wrong quite a bit, which means we end up being rather bad at predicting what will make us happy (or unhappy), and how strong our feelings of happiness (or unhappiness) will be. I’m not finished with it yet, so I may be missing out a key point, but I think that’s the gist.

One thing really leapt out at me, on page 18/19:

Forestalling pleasure is an inventive technique for getting double the juice from half the fruit. Indeed, some events are more pleasurable to imagine than to experience (most of us can recall an instance in which we made love with a desirable partner or ate a wickedly rich dessert, only to find that the act was better contemplated than consummated), and in these cases people may decide to delay the event forever. For instance, volunteers in one study were asked to imagine themselves requesting a date with a person on whom they had a major crush, and those who had had the most elaborate and delicious fantasies about approaching their heartthrob were least likely to do so over the next few months.

Is this perhaps a part of what procrastination is about? Some of the tasks that I put off longest are the ones that I have thought about in detail and which I have built up in my mind to being some sort of behemoth. It’s not necessarily that I think they are difficult or complex, but I have thought – or even fantasised, if you like – about them a lot. The fantasy might not necessarily have been ‘delicious’, but it would have definitely been elaborate even if the task itself wasn’t.

Of course, standard advice is to break tasks down into small, bite-sized portions – next actions that you can complete quickly and easily. Indeed, this is what many productivity and ‘to do list’ tools do – they allow you to break your tasks into small bits, and keep track of each one so that when you’ve done one bit you can move on to the next.

But perhaps that might end up being counterproductive, at least, if you put too much thought into it. If imagining doing something provides more pleasure than actually doing it, then it will seem preferable to delay doing it forever. At times like that, tasks that feels easier will be more attractive, such as reading RSS feeds, Twitter, IM or email (but not necessarily replying to the email – that itself can be something in which we’ve invested way too much imagination and which therefore takes on gargantuan proportions).

I think it’s important to know what you have to do, and to be careful to prioritise well so that you know both intellectually and emotionally that you’re doing what you need to be doing, or that you’ve done what you needed to have done. But I suspect that thinking about it too much, e.g. having your To Do List open in front of you all the time, might just turn out to be the straw that breaks the camels back.

One way to think less about what there is to do is to use Marc Andreessen’s approach:

On another topic, the tactic of each night, write down the 3 to 5 things you need to do the next day has struck some people as too simplistic.

That may be the case for some people, but I can’t tell you how many times I’ve arrived home at night and am at a loss as to what I actually got done that day, despite the fact that I worked all day.

And I also can’t tell you how often I’ve had a huge, highly-structured todo list in front of me with 100 things on it and I stare at it and am paralyzed into inaction (or, more likely, structured procrastination).

So a day when I get 3 to 5 concrete, actionable things done in addition to all the other stuff one has to do to get through the day — well, that’s a good day.

Writing down tonight what you have to do tomorrow gives you a good night’s sleep (hopefully!) during which you can forget about the longer To Do list, and clear your mind. I personally find that I get a lot more done when I can forget about everything else and just focus on what’s important.

But given the background noise of all the stuff that needs to be done but which isn’t important enough (yet) to claim my full attention, it’s very easy to feel like I’m drowning in a flood of equal priority tasks, until something genuinely important pops up and I can focus on that. If there isn’t something genuinely important, I search for it by repeatedly checking email and, if that doesn’t reveal anything pressing, I focus instead on easy but pointless things like Twitter or IM.

Instead of searching for that big thing, I shall pick five lower-priority things and just ruthlessly ignore everything else until those five things are done. If something urgent comes along, I shall deal with it, but I won’t search for it. I shan’t think too hard about all the other things that I have to do, and will attempt to stop myself fantasising about doing them or having them done, lest I end up ‘complixificating’ them to a point of self-paralysis.

Note to clients: Obviously, I’m very efficient when working on client projects. Money is a great motivator.