It’s that time of the year again: Seated in the pews, bedecked in white, we slouch toward Yom Kippur as our rabbis urge us to give in to the season of contemplation and rejuvenation. But watching the faces of my fellow congregants at Rosh Hashanah services earlier this week, I could tell that something wasn’t right. The eyes and the hearts felt heavier than usual. The limbs tapped about nervously. As we listened to the sermons and the prayers, we all, it seemed, had other things on our minds.It’s not hard to guess just what those things might’ve been: Stateside, we’re wading through an impeachment process that is likely to make next year’s election even more jagged and contentious than its predecessor. There’s still no government in Jerusalem, and no sign of one forming anytime soon, and in Britain the clock is ticking on retreat from the European Union or some other cataclysmic occurrence. How are we expected to pray solemnly and with intention when all around us the world as we know it is crumbling into chaos? How should we mind the spiritual when the political is intruding into every corner of our being?Too many of us find ourselves staying up late to gawk at cable news shows. We scour Facebook for any sign of our friends expressing opinions we find unacceptable. We insist that our every conversation—about literature or film, about history or art, about our careers or our families or our future—be repurposed as a partisan polemic. We’re exhausted. Our rage yields no result. Increasingly, we feel as if we’re failing at life.How fortunate, then, that we’ve just the book to guide us along in this uncertain season. Entitled Sin•a•gogue: Sin and Failure in Jewish Thought, it’s a meditation on sin and failure in Jewish thought, and its insights couldn’t be any timelier or any more essential.The book’s author, David Bashevkin, is the director of education for NCSY, the youth movement of the Orthodox Union, and he brings the deft touch of one charged with corralling and inspiring teenagers to his work. The book splices up complex theological questions, personal anecdotes, and pop culture references that would make even the most yeshivishly challenged among us feel on sturdy ground. Bashevkin favors not conclusions but conundrums, attacking the idea of sin and failure from a number of perspectives, each instructive and inspiring, and inviting us to wrestle with those questions we find most troubling.What, for example, might we learn from failure and sin? Ask the mobs on Twitter, say, or the pundits on TV, and the answer would likely be harsh: To err these days is to eradicate all hope of resurrection; we’re all just one misstep away from having our careers, our relations, or both canceled. Bashevkin offers us better guides in the rabbis of the Izbica hasidut, who took issue with that old Talmudic saying that all was in the hands of heaven, except for the fear of heaven. To hear the masters of Izbica tell it, all was in the hands of heaven including the fear of heaven, which means that sin, too, is part of the divine plan.At first blush, this deterministic idea may sound too wild to ponder. If sin is out of our control, if we never truly transgress when we fail to live up to religious ideals, of what use is free will at all? Bashevkin offers a nuanced and deeply necessary answer. “Religious life,” he writes, “has both a floor and a ceiling. The ceiling is built upon the ideals and values we reach towards, which we may never attain. The floor, however, is the framework and perspective from which we deal with failure and those still mired in sin. Much of religious life is spent vacillating somewhere in the middle.” Viewed this way, the wisdom of the Izbica rabbis provides, in Bashevkin’s elegant phrase, “cushions and comfort on the floor of Judaism without altering the ceiling.” Every time we fall, these wise teachers know, we fall right back into the lap of God.It’s easy enough to dismiss such ideas for having the rarified air of abstraction, but Bashevkin refuses his readers such comforts. Instead, he devotes a significant part of his book to case studies that hurl these thunderous theologies at earth. We learn, for example, that the Bible, enumerating the various sin offerings, prefaces each one with the qualifier “if”—if a priest fails, say, or if the Jewish people stumble—but, addressing the shortcomings of leaders, states dryly “when a leader sins,” preparing us for our elected officials’ inevitable debasement. It’s a message worth keeping in mind when we seethe at our politicians for not living up to our highest ideals.Which, of course, isn’t an invitation to welcome each and any type of sin. Jews, Bashevkin playfully notes, have as many words for sin as Inuits do for snow, a testament, at the very least, to our complicated thinking about the subject. So if our leaders are sure to falter, is there a better way for them to fail?Once again, Bashevkin points out to the sages of the Izbica hasidut, and particularly to Rabbi Zadok Ha’Kohen, who died in Lublin, Poland, in 1900. “A Jew should never despair for any reason,” Rabbi Zadok wrote. “Even if … you have sinned in a matter of which it is said that repentance will not help, God forbid, or that repentance is exceedingly difficult, or you see that you have fallen and become absorbed in mundane matters, regardless, never despair on yourself and say that you will not be able to separate (from sin) any longer. Because there is no despair at all for a Jewish man and God can help him in any circumstance.”This, Bashevkin reminds us, is good advice not only for individuals but for corporations as well; quoting a Duke University professor of management, he shows that refusing to succumb to despair and instead seeing each setback as an opportunity to learn from past misdeeds and ascend to higher ground makes for very good business practice by serving as a “safety and survival-enhancing asset in organizations.”And if man must constantly reflect on his failures, shouldn’t God as well? In one of the book’s most brilliant passages, Bashevkin briefly retells “Somebody’s Son,” the famous story about a young man who had run away from home and, seeking to return, writes his mother and says that if he is forgiven, she should tie a white ribbon around the tree at the edge of the family’s field. A few days later, the young man travels by train, and is too nervous to look out the window and learn if he’s welcome back or not. He asks his fellow traveler to take a peek, and the man reports that there’s a white ribbon tied around every single branch and twig. You can, Bashevkin argues, read the story as a straightforward allegory of teshuva, or repentance, comforting us with the thought that we’re always welcome back in God’s house. But what, he asks, if we read it differently? What if the young man is a stand-in for the Almighty, asking us, His people, to forgive Him?“Once a year,” Bashevkin writes, “His presence seems more attainable. And once a year, we imagine God is asking us that we let Him back into His world. And as God symbolically passes by the shul on Yom Kippur, He petitions His people, ‘if you want me back in your life—give me a sign.’ And each year on Yom Kippur we all wear white so when God peers into our lives, wondering if the relationship can still be salvaged, we remind Him and ourselves that He is invited back. The whole shul is clothed in white.”Bashevkin has given us a manual for living with defeat, which, as our wise elders remind us again and again, is much more valuable than an invitation to a fleeting moment of joy.***You can help support Tablet’s unique brand of Jewish journalism. Click here to donate today.