“Let nothing surprise you,” says the wise person, who seeks and in many cases succeeds to align his beliefs with reality and thus learns not to expect too much from people. Outstanding individuals are quite rare*, as are those at the opposite end of the spectrum. The principle of Gaussian distribution indicates that outliers are highly improbable and that the vast majority of the members in a set stand in relative proximity to the mean of the set. This point is represented in statistics by a bell curve. In general, almost all members reside inside the head, shoulders, and waist of the bell. Few settle at the curves. Almost none sit at the lips or tails.
It is hence the case in matters of intelligence and morality that most folks are average or close to it. If one recognizes this fact, as the understanding person likely does, one has no reason, in general, to anticipate either much more or much less than the ordinary from people, and therefore one is unlikely to be inordinately disappointed or vexed or surprised by them. One might even come to appreciate most folks for what they are, namely, the hearty and pragmatically-oriented middle class that provides something of predictable stability in the economy of human intellectual and moral character. The experienced university-level teacher understands this point: term after term and year after year, most students say the same sorts of things in class, write the same kinds of papers, produce the same kinds of results, have similar background information and experiences, have learned and failed to learn the same content at lower levels of schooling, have comparable levels of comprehension, suffer similar confusions, and so forth. Such students maintain the life of the university — such as it now is, at any rate. But extraordinary students are, well, you probably get the gist.
To meet an outlier is an unusual event; yet the wise might not be surprised even by this unlikely occurrence, though he might find it noteworthy and be impressed. Nevertheless, our wise person experiences wonder in the world. This is the kind of wonder that is the beginning of philosophy, according to Socrates and Plato. What is the difference between such wonder, with which the wise is acquainted, and the surprise noted above, which the wise usually do not experience?
A rough and working answer is that, on one hand, wonder concerns the aspects of the world — such as that it is what it is rather than some other possible world, or that it is to some degree intelligible to and includes rational beings like ourselves — which are unknown and perhaps strictly unknowable for us humans, at least during this life. The wise person, after due reflection, can come to obtain reasonable but epistemically uncertain beliefs about such philosophical matters, while recognizing that others might have similarly reasonable but uncertain beliefs that oppose his own. He thus realizes that, concerning philosophical propositions, most of them are open to debate and doubt. To borrow one of Kierkegaard’s titles: De omnibus dubitandum est. Or perhaps this is better: Omnia dubitari possunt. It’s not that everything must be doubted, but rather that nearly everything can profitably be doubted. And even this fact is a source of wonder for the wise.
On the other hand, surprise, as I use the term above, concerns the features of the world about which the sagacious have already acquired reasonable beliefs and thus have come to understand what is and is not likely with respect to human affairs and other matters that fall under the category of things about which we humans can obtain epistemically probable judgments.
*Which, by the way, is why they are called “outstanding.” But these days, the word is overused. Think about it: if everyone is outstanding, then no one is.
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This doesn't sound quite right: "who seeks and in many cases succeeds to." Latin is always appreciated, however, it's an odd title to borrow from Kierkegaard, given what Kiekegaard thought of Descartes.