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Teshuva means return, and return in the ­Hebrew Bible and the Jewish legal tradition means return to God. It is the word for repentance. Some prominent modern Jewish thinkers have used the term teshuva to refer to the individual or the community’s return to itself. The list includes Hasidic rabbis and influential figures such as Rabbi Abraham Isaac Kook and my mentor Rabbi Joseph Soloveitchik. Few have spoken about the apparent conflict between defining repentance as turning to God and defining it as the discovery of some deep metaphysical or psychological resources within oneself. Theological liberals may not notice the problem. Many of them are not overly impressed by the otherness of God and the sizable gap between talking about God and celebrating the supposed powers of renewal within. As they see it, romantic effusion and contemporary therapies happily converge with mystical yearning, bringing together the object of religion, which is right relation to God, with whatever is admirable in us. The same cannot be said of authoritative orthodox texts and the interpreters mentioned above, all of whom reject liberal or modernist trends in Judaism. Perhaps they assume a solution to this conflict between return to God and return to self that is so obvious it need not be spelled out. The solution exists, but it is not so obvious, at least not in our times.

This particular puzzle regarding teshuva came to mind when students visited my home late this summer. They asked what I was doing with a copy of George Packer’s Our Man: Richard Holbrooke and the End of the American Century. Was it worth plowing through a six-hundred-page account of the successful and unsuccessful diplomacy in which the late State Department guru had a hand and an opinion? Was I trying to polish my foreign policy credentials?

As I explained, the biography is a chronicle of foreign affairs. That was Holbrooke’s métier. But Packer has greater ambitions. He attempts to explain the larger-than-life figure.

Packer often addresses the reader in the second person, trying to draw his listeners into Holbrooke’s fascinating personality. Again and again, he chides the reader’s presumed tendency to idealize great men and to ignore their characteristically ignoble motives and behavior. As often with a long novel, I “abridged” the book, skipping the accounts of adultery and skimming the repetitive passages on the politics of the moment. Yet the story has a cumulative power. Holbrooke and his flaws commanded my interest and, to a degree, my sympathy.

The Holbrooke that Packer presents was bright, hardworking, and exceedingly ambitious, from his first youthful posting to Vietnam in the 1960s through his last position as “our man” in the insoluble tangle of Afghanistan and Pakistan. In between, he served as U.S. ambassador to Germany and to the United Nations. At the U.N. he convened an unprecedented session of the Security Council to discuss the AIDS crisis in Africa, for which he earns Packer’s praise. He was the prominent broker of the Dayton Accords, which brought an end to the war that ravaged Bosnia in the 1990s, though Packer notes that peace meant conceding the results of Serbian aggression. After Dayton, his crowning achievement, Holbrooke campaigned for a Nobel Peace Prize. All along, his ambition was to become Secretary of State.

Yet the impressive resume is studded with failings. ­Holbrooke lied in order to get credit for the work and ideas of others. This is not unknown in bureaucracies, but his prevarications went beyond the accepted norm in his milieu. A compulsive social climber, he was notorious for ditching the person with whom he was talking at a cocktail party upon spying a target higher up on the food chain. He was not a faithful husband to any of his wives; he was a neglectful father. His efforts to conceal his Jewish background leave a sour taste.

These vices impeded his ambitions. As a political player, much of his behavior was self-destructive. To take a dramatic example: Having an affair with his best friend’s wife probably hurt his advancement when the ex–best friend became National Security Advisor and had Bill Clinton’s ear. The pattern becomes predictable. When Republicans rule, Holbrooke works in the private sector, waiting for his next chance. With every incoming Democratic president or almost president, he rates an audition. Each time, he is confident he has talked himself into a high-ranking job, maybe even the job of his dreams. As for Clinton, Gore, Obama—either they sense he doesn’t work well with others, feel patronized by his expertise, or are annoyed by his fixation on the ancient history of Vietnam. As the chances pass him by, one can’t help feeling for him.

Packer’s explanation: Holbrooke did not know himself, a failing compounded by the fact that he lacked a sense of humor about himself. Packer regularly refers to a Peanuts cartoon in which Charlie Brown, after another one-sided loss, cries out: “How can we lose when we’re so sincere?” The remark captures the tragic naivete of the American campaign in Vietnam that Holbrooke observed as a young man. But it comes to represent the frustration of his later career. The lesson here, in Packer’s telling, is that sincerity is no substitute for self-knowledge.

I’m not sure this is accurate, at least in the main claim that Holbrooke lacked self-knowledge. If knowing yourself means knowing your capacities and knowing what you want in life, Richard Holbrooke seems to have known himself much better than most people. If repentance means being faithful to oneself, then he had little of which to repent. Holbrooke’s problem was that when others came to know him, they had reservations about what they saw. Based on the biography, I’d say Holbrooke’s tragedy is not lack of self-knowledge, but an insufficient understanding of everybody else, which can become a great liability in life.

In a sense, Packer is right, however. I can have a very accurate inventory of my emotions, aspirations, and convictions—knowledge of myself. Sincerity works this way. It is loyalty to “who I am.” But we are social beings, and who I am is constituted in no small part through my relations to others. Insofar as I remain self-involved or in some other way blind to the reality of what others feel and think, then in a sense I lack self-knowledge, because I don’t see myself accurately in relation to others. Holbrooke indeed seemed to suffer from that kind of lack.

It is this distinction between Holbrooke’s quite accurate self-knowledge in a limited sense and his lack of self-knowledge in its broader, relational sense that illuminates teshuva. When our Orthodox thinkers teach that returning to God is also returning to the self, they don’t mean being sincere— renewing loyalty to my hopes and ambitions. The true self they urge us to return to is the self that is summoned by God. Repentance is striving to become not the visible, empirical self with a particular set of self-identified ambitions, sentiments, and beliefs, but the divinely confronted self. Traditional Jews try to conform themselves to God’s will through study and prayer and obedience. We return to ourselves by encountering the divine in his otherness. We know ourselves in the deepest sense insofar as we know ourselves in relation to God.

Is there anything here for the Holbrookes of this world? Divine otherness is absolute. The typical movers and shakers of our secular society rarely perceive the idea of confronting and submitting to God in his majesty as an option. Yet they may not be equally shut off from the palpable commands and demands of human otherness. In fact, given the challenges of managing people, commanding them, and winning their loyalty—so often necessary to ascend the greasy pole of power—in truth the movers and shakers may be quite sensible of human otherness.

This awareness should be encouraged as a path toward a secular analogy to teshuva. We discover who we ought to be not only in obedience to particular divine imperatives but also in our relations with the reality of other human beings. Sometimes the only thing that drives secular or nominally religious individuals from the prison of self-assertion and worldly ambition is the resistance of those with whom they interact. Earlier, I wondered whether lack of self-knowledge was the right description of what went wrong in Richard Holbrooke’s quest. Perhaps it would be more accurate to say that his tragedy, and that of so many of us, might best be put as lack of humility, for that is a virtue that breaks down our self-enclosed resistance to the reality of others.

Shalom Carmy teaches Jewish studies and philosophy at Yeshiva University and is editor emeritus of Tradition.