In a deep black pit lies a prone figure menaced by an enraged and partially disemboweled bison. Head back, eyes wide, arms and fingers outspread, the man in the cave at Lascaux, France, confronts the knowledge of death. This drawing, the world’s oldest narrative depiction of a human being, may convey one man’s mortal surprise and sorrow, but it also seems to say something momentous about humanity. French philosopher Georges Bataille proposed that it reveals the instant, some 17,000 years ago, when we separated from the animal world. He links the birth of art with the birth of human history. But if this picture recounts the beginning of history, it also tells of the beginning of regret. “If only I had thrown my spear a little straighter…,” the hunter might have been lamenting. Beyond this momentary thought, in the imminence of death, he seems to gaze into his unspooling past—wishing, perhaps, that life had been different.

The etymology of “regret” connects it to an old French term for bewailing the dead. Regret belongs with grief, but signifies more than mourning. To use the words of Confucian scholar Michael Ing, “Regret means a kind of sorrowful longing for things to be otherwise.” Confucius considered regret, however painful, to be a proper feeling, because it arises from moral reflection on personal actions or from thoughts about how unavoidable conditions in the world can harm things we value. It can certainly lead to improvement: Thinking “I wish I had done things differently,” or, “I wish things were not the way they are,” might be the catalyst for positive action.

At about the same time, give or take 100 years, Plato was also reflecting on regret and how to avoid it. His account of Socrates preparing for death by execution is that of a man unwilling to pass out of this world with personal regrets—although he certainly wished his circumstances could have been different. His friends, Plato among them, pleaded with Socrates to find some means of escape, but Socrates rebuffed them, saying he would neither dissimulate nor grovel to survive. “The difficulty, my friends,” he said, “is not to avoid death, but to avoid unrighteousness.” His admonition in Plato’s Apology that “The unexamined life is not worth living,” has served as an almost eternal guide for avoiding personal regret.

This statement could be understood as the theme for one of the best-known tales of regret in English: that of Ebenezer Scrooge, the “squeezing, wrenching, grasping, scraping, clutching, covetous, old sinner” in Charles Dickens’ early Victorian story, A Christmas Carol. It depicts a smugly unexamined life jolted into righteousness. Scrooge’s long-dead business partner appears as a ghost and bemoans his own unalterable lifetime of greed. He offers Scrooge a way out of the sad fate he suffers—the most painful aspect of which is the fact that in death “no space of regret can make amends for one life’s opportunity misused.” Aided by three spiritual guides, Scrooge reemerges after a long night of moral reflection determined to seek life’s opportunities for virtue and generosity: “He knew what path lay straight before him, and he took it.”

Regret, in our own time, can act as a powerful frame for action—as long as we avoid it. The rallying cry of “No regrets!” for sports teams and graduating classes is persuasive. It’s also more uplifting than Friedrich Nietzsche’s 19th-century “formula for human greatness”: the concept of amor fati, meaning an enthusiastic acceptance of one’s fate.

Sadly, for many people, this defiance comes too late to be helpful. Specialists on dying and end-of-life care note how frequently regret clings to death. Accordingly, they provide helpful, instructive lists of reflective measures to follow in life: Be kind; take things less seriously; work less; take risks. The advice to take risks underlies the 21st century’s newest tool for regret avoidance, the “bucket list”—an ambitious personal catalog of things to do before dying. One thing that should perhaps be on everyone’s list: a visit to the Shaft of the Dead Man at Lascaux.