Recently, for a book I was writing, I needed to track down a statement that I believed came from John Henry Newman. And I knew just what to do: I googled it. I typed in the key words from the quotation and immediately got confirmation that the author of the statement was indeed Newman, though I had misremembered it slightly. But now, if I was going to quote the statement in my book, I needed to get a proper source for it—a particular volume, its publisher and publication date, the page number the quotation is on—and websites rarely provide that sort of information. But no problem: I could simply turn to Amazon.com's "Search Inside the Book" feature. Once I figured out which of Newman's books could be internally searched, it took me two or three minutes to find the one the quotation came from, to make note of the page number, and to copy the publication information and paste it into my book manuscript. Task accomplished.

But what the satisfaction of finding, immediately, "just what you're looking for" hides from you is the simple fact that you have not found anything you weren't looking for. That is, the technologies that enable such unerringly direct access to the object of your quest depend for their success on a simultaneous concealing of everything except that object. Google in particular is so good at this that it offers an "I'm Feeling Lucky" button, which takes you directly to the URL that—according to Google's algorithms—best matches your search terms. And it is truly extraordinary how often "I'm Feeling Lucky" indeed takes you right where you want to go.

But Google is just an exceptionally well–honed example of this kind of technology, which is becoming pervasive. For instance, in writing that last paragraph I needed a synonym: I had used "hides" in one sentence and didn't want to use "hiding" in the next, but couldn't immediately think of a similar word. Thanks to my Mac's built–in thesaurus, a couple of mouse clicks led me to "concealing," which seemed to work well enough, so there it is. And I moved on. Why not? I have work to do.

Perhaps there was no reason for me to do otherwise. But it occurred to me to see what my old hardcover thesaurus might offer. This required me to find my old hardcover thesaurus, which, because I had not used it in so long, had migrated to one of the least accessible shelves in my office. When I got it out and looked up "hiding," I was led again to "concealing"—but also to a couple of hundred related words that my computer's thesaurus didn't suggest. And I noticed this: that the major term preceding "concealment" in the thesaurus is "secrecy," and the major term succeeding it is "falseness." The thought that concealment stands somehow between secrecy and falseness is provocative and cautionary. But I would never have seen it if I had not taken the trouble to consult a book which did not return instant results, and which almost forced my eyes to scan information that I was not looking for.

I did not take that trouble when I was looking for the Newman quote, largely because that would have required me not to walk two feet but a hundred yards, to my college's library—where I would have had to undergo the staggering burden of looking up call numbers, trudging to the stacks, and lugging a pile of books to a table where I could spend who knows how long looking through them. But if I had taken up such a Herculean labor, I would certainly have—however inadvertently and even against my will—learned a lot more about Newman than I now know, and perhaps could even have found other passages in his work that would have illuminated the quotation that I had slightly misremembered, or even have served as a replacement for it. And perhaps I would have discovered that I was taking the quotation out of context and that, far from supporting my argument, it actually undermined it. And there's the rub, or one of the rubs anyway. Now that the possible shortcomings of my online Newman–searching have entered my mind, I'm just going to have to go to the library after all. Exposing oneself to the fortuitous has its dangers, and perhaps a subliminal awareness of those dangers is one of the factors—along with sheer laziness—that keeps us focused on what we already know, or already think we know, we want. (This is a familiar strategy in many of life's venues: it's the reason that national restaurant chains position themselves at freeway exits. Why should we drive past the familiar to take a risk on the wholly unknown?)

In effect, we adjust to the overwhelming variousness of our social world by closing off the possibility of surprise—by eliminating the fortuitous, which also means eliminating the serendipitous. The two terms need discrimination. "Fortuitous" derives, obviously, from fortune, in Latin fortuna, that is, chance. So aware were the ancients of the power of fortuna in human life that they elevated it to divine status: the Goddess Fortuna is the subject of innumerable discourses, pious and otherwise, and portraits of lucky or unlucky (fortunate or unfortunate) men strapped to her Wheel litter the surviving pages of old books. Dante even conceives of her as having been given—by God himself—the task of ruling the course of human affairs. I used to know a man, fierce of aspect but kind of heart, who at church helped take care of children, and would invariably distribute cookies or cupcakes without regard to personal preference: when one of the kids would complain that she preferred chocolate chip to peanut butter, or white icing to pink, he would snap, "Ya get whatcha get," and move on to the next kid. There spoke truly the voice of Fortuna. Indeed, that's the only thing that Fortuna ever tells us: Ya get whatcha get.

Serendipity is different. The word was coined by that curious man Sir Horace Walpole, known today (if at all) as one of the founders of the "Gothic" tale of suspense and terror, but more famous in his own time as an especially elegant and proficient writer of letters. In a 1754 letter to a friend he describes his discovery of some curious Venetian coat of arms, and pauses to say that "This discovery, indeed, is almost of that kind which I call Serendipity." And then he explains that "very expressive word" of his own invention: "I once read a silly fairy tale, called 'The Three Princes of Serendip'"—Serendip being an old name for Sri Lanka: "as their Highnesses travelled, they were always making discoveries, by accidents and sagacity, of things which they were not in quest of … (for you must observe that no discovery of a thing you are looking for comes under this description)." The finding of what one is not looking for will be the element of the letter most obviously relevant to what I've been saying so far; but equally important is the phrase "by accidents and sagacity," or, as Walpole puts it later in the same letter, "accidental sagacity."

Fortuity happens, but serendipity can be cultivated. You can grow in serendipity. You can even become a disciple of serendipity. The elevation of Fortuna to the status of goddess is a way of shrugging: an admission of helplessness, an acknowledgment of all that lies beyond our powers of control. But in the very idea of serendipity is a kind of hope, even an expectation, that we can turn the accidents of fortune to good account, and make of them some knowledge that would have been inaccessible to us if we had done no more than discover what we were looking for.

Indeed, it may be possible not only to cultivate the sagacity but also the accidents. It may be possible, and desirable, to actively put yourself in the way of events beyond your control. Thus, just as I was completing this essay, I—serendipitously?—came across these comments by the historian Timothy Burke: "there are many contexts where I have very constrained expectations about what I expect to find through search, where serendipity or unpredictability is not at all what I want. Then I expect to be King User, and woe betide the peasant interfaces and authority–category churls that try to get between me and my goal. But there are other times where I want search to be alchemy, to turn the lead of an inquiry into unexpected gold. I'm hoping that the rush to simplify, speed up, demystify and digitize search doesn't leave that alchemy behind."

The cultivation of serendipity, of this alchemy, is an option for anyone, but—so I wish to argue—for Christians living in conditions of prosperity and security and informational richness it is something vital, perhaps even necessary. To practice "accidental sagacity" is to recognize that I don't really know where I am going, even if I like to think I do; that if I know what I am looking for I probably don't know what I need; that I am not master of my destiny and captain of my fate; that it is a very good thing that I am not master of my destiny and captain of my fate; that the more often I succumb to the temptation to say "I am my own" the more completely I close off the possibility of a blessing that comes from beyond my own desires and self–love. The cultivation of serendipity is at once a self–abnegation, a disciplining of technological power, a form of trust in God, and an expression of solidarity with the vast multitudes of Christians from all generations whose poverty and powerlessness made it impossible for them to think even for a moment that they could control their own lives. An accidental sagacity is the form of wisdom I most need, but am least likely to find.

Alan Jacobs teaches English at Wheaton College in Illinois, and is writing a book about original sin. His Tumblelog is here.

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