[Apologies for the clickbait title!] I taught philosophy for at least 20 years. Long enough to become reasonably confident in what I was doing and then realise that at least some of that confidence was misplaced.
We tend to think we are teaching philosophy when we explain arguments, optimistically set readings, and guide students through texts. And of course, those things matter. But after a while, it becomes clear that they are not the thing itself. Students can reproduce arguments, summarise positions, even write quite sophisticated essays, without ever quite encountering what philosophy is. What matters is something harder to quite grasp. It is whether students can ponder questions without rushing to resolve them. Whether they can tolerate not knowing, and still keep at it. Whether they notice how their own assumptions shape what they take to be obvious: and are up for that shifting. Philosophy as an experience for the student is not the production of answers, but a change in the conditions under which answers are formed. That is not easy to teach.
Partly because it sits awkwardly with many of the structures we build around learning – although this is not always in the way people think. Large lectures, for instance, are often assumed to be poor environments for this kind of work. I’m not sure that’s quite right. Some of the most intellectually alive moments I’ve seen have happened in large rooms, when something unexpected cuts through and attention gathers (I wrote about this a while ago: https://davewebster.org/2017/02/12/no-sleep-till-bloomsbury-learning-small-lessons-from-big-lectures/). But those moments are not guaranteed. They depend on something less tangible than format. They depend on how we inhabit the role of teacher.
Over time, I’ve become increasingly convinced that we teach philosophy less through what we say than through how we relate to the subject in front of students. They notice what we attend to, what we dwell on, what we get slightly (or very) excited about. They notice whether we are still thinking, or simply repeating. They notice whether any of it actually matters to us. In that sense, teaching philosophy is as much about modelling a disposition as it is about conveying content.
Curiosity, in particular, matters. Not a polite, instrumental variety, but something closer to appetite. A hunger to follow an idea a little further than necessary. To read something not because it will be assessed, but because it might be interesting—and, in a sense, to find almost everything interesting. To find things unexpectedly funny, or strange, or unsettling (and sometimes they are funny, even if that doesn’t always work out as intended: https://davewebster.org/2019/07/05/is-that-meant-to-be-funny/).
This is difficult to systematise. It sits uneasily with attempts to standardise teaching or optimise delivery. It is also difficult to fake. Students are, in my experience, very, very good at detecting the difference between someone who is genuinely engaged in the work of thinking and someone who is merely performing it (though performance and rhetoric skills matter!) I don’t think this means we abandon structure, or technology, or any of the tools we have developed (though some of our enthusiasm for them has, at times, been a little breathless: https://davewebster.org/2017/03/19/chatting-about-cheap-tech-breaking-things-and-teaching/). But it does mean recognising their limits. They can support learning. They cannot replace the presence of someone who wants to know—and who is committed to the class understanding why they should want to know too.
Which brings me to something I used to say a lot at Open Days, and now believe even more strongly. It is not foolish, or naïve, to study philosophy. If anything, it is slightly perverse to think that we should make decisions about what to do with our lives—how to live, what to value, what to pursue—without engaging, in some way, with the kinds of questions philosophy raises. We all end up doing philosophy anyway, whether we recognise it or not. The only question is whether we do it well or badly, attentively or carelessly. What else would you study, before you decide where to direct the finite efforts of your short life?
In that sense, philosophy is not a niche subject. It is a way of taking seriously the fact that we are, each of us, trying to work out how to live within our span of time.
After 20 years, I am less convinced that we teach philosophy through content alone, and more convinced that we teach it through attention, through example, and through a kind of visible commitment to the work of understanding, or at least to an enthusiastic and cheerful struggling to understand.

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