To say that a person can fail successfully sounds really weird. To succeed at something is to achieve some goal that you’re aiming at, and to fail at something is to not achieve a goal that you were trying to achieve. I might succeed or fail at bench-pressing my body weight. I succeed if I try to bench-press my body weight and manage to do it, and I fail if I try to do it but don’t succeed. So, success and failure seem to be incompatible.

But this isn’t the end of the story. In fact, it’s just a short-sighted and pedantic beginning. If we loosen up and shift perspective a little bit, the idea that it’s possible to fail successfully not only makes sense, but turns out to have a whole lot going for it.

The principle of successful failing is significant for me as a teacher, and it’s something that I introduce right at the beginning of my introductory undergraduate philosophy classes. Here’s why. Despite its head-in-the-clouds reputation, philosophy is very much a hands-on discipline. You can’t learn it without doing it. So—to borrow an image from my scientist colleagues—each of my philosophy courses has a “laboratory” component where students roll up their intellectual sleeves and get down to doing philosophy.

This is where the trouble usually starts. Students become terrified of getting things “wrong,” and their fear of failing paralyzes them. But when you do philosophy, you always get things wrong—or rather, there’s always some way of calling a line of reasoning into question (just add or subtract a premise or two). So, we find ourselves at the end of a dead-end street unless I can help the students in my class make friends with failure.

One way I do this is to introduce them to the philosopher Daniel Dennett. Dennett is a big fan of failure—or, as he prefers to call it, “making mistakes.” In fact, the first chapter of his book Intuition Pumps and Other Tools for Thinking is a paean to the unique value of errors. Around four hundred years ago, Francis Bacon, the granddaddy of the philosophy of science, observed that “Truth emerges more readily from error than from confusion,” but Dennett takes this insight to a whole new level. If the fast lane to truth is paved with error, then anyone who’s interested in getting to the truth had better get on with making some good, productive errors rather than waffling around, terrified of putting a foot wrong. When I get my students to read Dennett’s chapter, I cross my fingers that they’ll take to heart his sage advice, “you should become a connoisseur of your own mistakes, turning them over in your mind as though they were works of art, which in a way they are.” And I hope that I can stay mindful of it too, so as to avoid getting tangled up in the fruitless getting-it-right game beloved of some philosophers.

This is great and inspiring stuff, but it doesn’t come anywhere near to exhausting the importance of successful failure. Sigmund Freud was another aficionado of errors. In fact, he wrote a whole book about a special kind of error that he called Fehlleistungen, a term that’s entered everyday English as “Freudian slips.” To appreciate what Fehlleistungen have to do with failing successfully, have a look at what Bruno Bettelheim has to say about them in his book on Freud and Man’s Soul.

The term combines two common, strangely opposite nouns, with which everybody has immediate and significant association. Leistung has the basic meaning of accomplishment, achievement, performance, which is qualified by the Fehl to indicate an achievement that somehow failed—was off the mark, in error. What happens in Fehlleistung is simultaneously… a real achievement and a howling mistake.

The idea of a successful failure is only strange if we make the false assumption that the human mind is unified, transparent to itself, and a relatively conflict-free zone, rather than, as Freud so forcefully argued, a chaotic hotbed of incompatible desires. Suppose that you have two desires that just don’t get along with one another, so satisfying one makes it impossible to satisfy the other. Under those circumstances, the failure of one desire may be a requirement for the success of the other. Here’s one of Freud’s examples. On one occasion the President of the Austrian Lower House opened a session of parliament by declaring, “I declare this sitting closed.” Of course, he intended to say “I declare this meeting opened,” so his botched utterance was a failure. But his contrary desire not to open the session got the better of his tongue, and from this perspective his failure was an unqualified success. For Freud, our lives are littered with successful failures—bungled actions, misspeakings, misrememberings, and the like—which, if we resist the temptation to think of them merely as failures, offer great opportunities for gaining insight into our complex and contradictory inner lives.

My third and final witness for the defense of successful failure is the Irish writer and Nobel laureate Samuel Beckett. Unlike Dennett, whose take on successful failure has to do with the forward march of knowledge, and Freud, whose twist on it concerns the humbling task of getting to know yourself, Beckett’s approach is a deeply ethical one.

Nowadays, a lot of people have encountered the phrase “Fail better,” because it’s been adopted as an upbeat mantra by the entrepreneurial set. But its source is Samuel Beckett’s darkly enigmatic 1983 prose piece entitled “Worstward Ho!” The passage in which it appears reads: “All of old. Nothing else ever. Ever tried. Ever failed. No matter. Try again. Fail again. Fail better.”

If you want to understand what Beckett’s on about here, you’ve got to trash the motivational speaker-ish connotations that “fail better” has become encrusted with and think of it—as Beckett intended—against the backdrop of our journey towards oblivion. It’s a basic condition of life that death and decay await us all, so ultimate failure is always looming on the horizon. And along the way, there’s no avoiding the fact there are many smaller failures that each of us must contend with.

So, what’s the best that we can do in the ever-shrinking time that we have? Struggle to your feet and try another time—like poor old Sisyphus pushing that boulder up a hill, only to have it topple back down again—and so to fail once more, but perhaps gaining a shred of wisdom so as to fail a little better next time, and live a life which, although inevitably ending in failure, fails successfully.