​For years Stephen Greenblatt and Adam Phillips have been two of the most interesting writers of our time about literature and ideas. Both are Jewish, astonishingly prolific and have a wonderful taste for fun titles. Phillips, a British psychoanalyst, wrote On Kissing, Tickling, and Being Bored and Greenblatt, an American literary critic who teaches at Harvard, is the author of Learning to Curse.

Second Chances is their first collaboration. It is about a rich subject: is it possible for us to have second chances in life? It is no accident that so many of our great stories, from Homer and the Hebrew Bible to Shakespeare, explore the possibilities of a second chance. Is there recovery after loss? Can we reinvent ourselves? Why, asks Greenblatt in his introduction, do so many of us dream of a second chance that is worth achieving at any cost? They attempt to answer these questions through the works of Shakespeare and Freud. “Shakespeare,” writes Greenblatt, “is the supreme virtuoso of the second chance. Freud is its supreme interpreter.”

Greenblatt, one of our greatest Shakespeare critics, explores these questions in the opening five chapters, all on Shakespeare’s plays. The comedies, he writes, offer the possibility of love and renewal, usually through marriage. But the tragedies are about “certain forms of damage [that] can never be repaired”. “For Shakespeare,” he writes, “life stories are stories of transformation.” Characters such as Pericles, Leontes and Prospero “recover something that seemed irrecoverable and find a way to begin again”. Shakespeare’s great tragic heroes, however, “are trapped in circumstances from which there is no escape” and their attempts are not just doomed to failure, they end in death. For them, there will be no second chance. “For Shakespeare,” Greenblatt writes, “the essence of tragedy is the absence of a second chance, or, rather, it is this absence conjoined with an unbearably intense, unrealisable desire for one.”

Greenblatt’s essays are based on close readings of a number of Shakespeare’s plays. Phillips, by contrast, looks at second chances in the work of Freud. Second chances, he writes, are “about what can and cannot be repaired, and about what that repair might be…” One of the problems with tragic heroes is that they are not very good at second chances. “Perhaps by definition,” Phillips writes, “a tragic hero is someone incapable of a change of heart.” Freud, however, and psychoanalysis in general, are all about second chances. “Freud,” he writes, “is our great modern champion … of the second chance.”

Phillips’s chapters offer fascinating insights. What decides whether “a new relationship can be a new start for me” or whether I am “likely to bring the tyrannies and dramas from my past into my remarriage”? Can we ever start anew and learn from our experiences or are we always going to end up stuck with the same kind of mistakes? One of the things that perplexed Freud was how often his patients “wanted to change by remaining the same”. In other words, they both wanted and didn’t want a second chance. This is what he called resistance.

Phillips is very good at asking questions such as: What would a life be like without second chances, a life in which we could not recover from past losses or resolve past conflicts? These are fascinating observations that help us think about how we can change our lives and live happier lives.

Shakespeare’s tragedies show us what lives look like when they are “hostile to and cannot conceive of a second chance”. His comedies show us how second chances can “help us get the lives we deserve”. But first, we have to recognise these chances and take the opportunities they offer.

‘Second Chances: Shakespeare & Freud’, by Stephen Greenblatt & Adam Phillips

Yale University Press, £20.00