I didn't notice those things at the time, though. At sixteen I was about as observant as a lump of rock. I can see more now in the fragments of memory I preserve of that age than I could see at the time from having it all happening live, right in front of me.
So the ability to ferret out the unexpected must not merely be an inborn one. It must be something you can learn. How do you learn it?
To some extent it's like learning history. When you first read history, it's just a whirl of names and dates. Nothing seems to stick. But the more you learn, the more hooks you have for new facts to stick onto-- which means you accumulate knowledge at what's colloquially called an exponential rate. Once you remember that Normans conquered England in 1066, it will catch your attention when you hear that other Normans conquered southern Italy at about the same time. Which will make you wonder about Normandy, and take note when a third book mentions that Normans were not, like most of what is now called France, tribes that flowed in as the Roman empire collapsed, but Vikings (norman = north man) who arrived four centuries later in 911. Which makes it easier to remember that Dublin was also established by Vikings in the 840s. Etc, etc squared.
Collecting surprises is a similar process. The more anomalies you've seen, the more easily you'll notice new ones. Which means, oddly enough, that as you grow older, life should become more and more surprising. When I was a kid, I used to think adults had it all figured out. I had it backwards. Kids are the ones who have it all figured out. They're just mistaken.
When it comes to surprises, the rich get richer. But (as with wealth) there may be habits of mind that will help the process along. It's good to have a habit of asking questions, especially questions beginning with Why. But not in the random way that three year olds ask why. There are an infinite number of questions. How do you find the fruitful ones?
I find it especially useful to ask why about things that seem wrong. For example, why should there be a connection between humor and misfortune? Why do we find it funny when a character, even one we like, slips on a banana peel? There's a whole essay's worth of surprises there for sure.
If you want to notice things that seem wrong, you'll find a degree of skepticism helpful. I take it as an axiom that we're only achieving 1% of what we could. This helps counteract the rule that gets beaten into our heads as children: that things are the way they are because that is how things have to be. For example, everyone I've talked to while writing this essay felt the same about English classes-- that the whole process seemed pointless. But none of us had the balls at the time to hypothesize that it was, in fact, all a mistake. We all thought there was just something we weren't getting.
I have a hunch you want to pay attention not just to things that seem wrong, but things that seem wrong in a humorous way. I'm always pleased when I see someone laugh as they read a draft of an essay. But why should I be? I'm aiming for good ideas. Why should good ideas be funny? The connection may be surprise. Surprises make us laugh, and surprises are what one wants to deliver.
I write down things that surprise me in notebooks. I never actually get around to reading them and using what I've written, but I do tend to reproduce the same thoughts later. So the main value of notebooks may be what writing things down leaves in your head.
People trying to be cool will find themselves at a disadvantage when collecting surprises. To be surprised is to be mistaken. And the essence of cool, as any fourteen year old could tell you, is nil admirari. When you're mistaken, don't dwell on it; just act like nothing's wrong and maybe no one will notice.
One of the keys to coolness is to avoid situations where inexperience may make you look foolish. If you want to find surprises you should do the opposite. Study lots of different things, because some of the most interesting surprises are unexpected connections between different fields. For example, jam, bacon, pickles, and cheese, which are among the most pleasing of foods, were all originally intended as methods of preservation. And so were books and paintings.
Whatever you study, include history-- but social and economic history, not political history. History seems to me so important that it's misleading to treat it as a mere field of study. Another way to describe it is all the data we have so far.
Among other things, studying history gives one confidence that there are good ideas waiting to be discovered right under our noses. Swords evolved during the Bronze Age out of daggers, which (like their flint predecessors) had a hilt separate from the blade. Because swords are longer the hilts kept breaking off. But it took five hundred years before someone thought of casting hilt and blade as one piece.
Above all, make a habit of paying attention to things you're not supposed to, either because they're "inappropriate," or not important, or not what you're supposed to be working on. If you're curious about something, trust your instincts. Follow the threads that attract your attention. If there's something you're really interested in, you'll find they have an uncanny way of leading back to it anyway, just as the conversation of people who are especially proud of something always tends to lead back to it.
For example, I've always been fascinated by comb-overs, especially the extreme sort that make a man look as if he's wearing a beret made of his own hair. Surely this is a lowly sort of thing to be interested in-- the sort of superficial quizzing best left to teenage girls. And yet there is something underneath. The key question, I realized, is how does the comber-over not see how odd he looks? And the answer is that he got to look that way incrementally. What began as combing his hair a little carefully over a thin patch has gradually, over 20 years, grown into a monstrosity. Gradualness is very powerful. And that power can be used for constructive purposes too: just as you can trick yourself into looking like a freak, you can trick yourself into creating something so grand that you would never have dared to plan such a thing. Indeed, this is just how most good software gets created. You start by writing a stripped-down kernel (how hard can it be?) and gradually it grows into a complete operating system. Hence the next leap: could you do the same thing in painting, or in a novel?
See what you can extract from a frivolous question? If there's one piece of advice I would give about writing essays, it would be: don't do as you're told. Don't believe what you're supposed to. Don't write the essay readers expect; one learns nothing from what one expects. And don't write the way they taught you to in school.
The most important sort of disobedience is to write essays at all. Fortunately, this sort of disobedience shows signs of becoming rampant. It used to be that only a tiny number of officially approved writers were allowed to write essays. Magazines published few of them, and judged them less by what they said than who wrote them; a magazine might publish a story by an unknown writer if it was good enough, but if they published an essay on x it had to be by someone who was at least forty and whose job title had x in it. Which is a problem, because there are a lot of things insiders can't say precisely because they're insiders.
The Internet is changing that. Anyone can publish an essay on the Web, and it gets judged, as any writing should, by what it says, not who wrote it. Who are you to write about x? You are whatever you wrote.
Popular magazines made the period between the spread of literacy and the arrival of TV the golden age of the short story. The Web may well make this the golden age of the essay. And that's certainly not something I realized when I started writing this.