Fasting aside, most non-Jews I know envy Yom Kippur, holiday of atonement. While not intended as the only day for Jews to expiate their sin against God and man (the daily prayer of tachanun, or supplication, is supposed to give you annual coverage), Yom Kippur exists in the popular imagination as a kind of concentrated power-cleanse for the soul—the spiritual equivalent of the detox diet. Twenty-four hours of repentance and fasting, and that's basically it: You're good for a whole year. Not for the chosen the weekly whispers of forbidden acts and thoughts behind some Gothic latticework. As Jon Stewart once put it, even in sin, goys pay retail.
Yet Yom Kippur in the age of telecommunications runs the risk of becoming a compulsive ritual without any genuine feelings of contrition. Undersold teshuva, or repentance, is worse than a mere lapsed New Year's resolution—it substitutes atonement for pro forma guarantees on righteousness. Plenty of High Holy Day Jews cut corners on the sacred practice by resorting to what Rabbi Yehuda Sarna at NYU's Bronfman Center calls the "spray-fire" method of atonement. Instead of humbly approaching those you know you've wronged over the past year, you dial up everyone in your Rolodex or e-mail everyone in your address book, and seek a pardon for any offenses you might have given—a hollow gesture if ever there was one. Operating on the Don Corleone-ish principle that a request can't be refused during a blessed event, these Jews literally phone in their apologies and expect forgiveness for all sorts of trespasses, be it a missed birthday, an unpaid loan, or nasty gossip.
The trouble is, hedging your bets this way is bad legal practice. A major no-no in teshuva is insincerity, and one can't sincerely repent for hypothetical sins. According to Jewish law, there's a five-step program for sin eradication during the Days of Awe, the weeklong period beginning with Rosh Hashanah and ending with Yom Kippur, when God's judgments of each man's righteousness (or lack thereof) over the past year gets indelibly inked in the Book of Life. The first is mere recognition of the sin, followed by remorse for having committed it. Next comes the physical cessation of the sin, the act of restitution toward the sinned against, and, finally, confession before the Almighty, which includes vowing never to do it again. In the Mishne Torah, Maimonides stressed the importance of genuine remorse as the gateway to mechila, the forgiveness that comes with the removal of a moral debt owed to another person. But since remorse can't be compelled, the offended is under no obligation to accept a factitious apology. If the offender is genuine, he's got three good-faith tries to get it right. (It probably doesn't help that recidivism gets an easy pass in the Kol Nidre, the prayer recited on Yom Kippur, which Rabbi Meir ben Samuel controversially altered in the 11th century to ask God to pardon any vows that might go unfulfilled in the coming year.)
Spray-fire atonement does for the immortal soul what crash dieting does for the body—the weight almost always piles back on. Worse, it's psychologically debilitating because the more a person grows habituated to cyclical behavior, the more desensitized he becomes to original purpose. It helps to think of teshuva as sin OCD.
In one of his earlier essays, "Obsessive Actions and Religious Practices," Freud likened habits such as interminable hand-washing or extreme linen-folding to religious ceremonies. Both are performed out of fear of punishment (what will happen if I stop?) instead of a rational or transcendent motive. Not checking the pilot light on your stove every five minutes might lead to an explosion; not checking in once a year with everyone you've wronged might lead to limbo. Freud called the ceremonial an action of "defense or insurance, a protective measure." The spray-fire atoner, like the obsessive-compulsive, is seeking short-term reassurance with the frustrating foreknowledge that it can never lead to any long-term material benefit. He'll be right back there next year, sending out his template of penitence to the same mass recipients list, thus defeating the whole purpose of teshuva, which is to avoid repeating the same mistakes.
One way cognitive behavioral therapists treat obsessive-compulsives is through behavior-modifying "exposure" exercises. If you're germophobic, you're told to touch doorknobs, passed-around dollar bills, or the sole of your shoe as often as possible, always envisioning the worst case-scenario of what might ensue (i.e., you'll get Ebola and die). The key is to increase the emotional stakes of a routine performance. In so doing, you begin to alter your brain chemistry enough that it becomes that much easier to exit an anxiety-laden vicious cycle. In his instructive primer on OCD therapy, Dr. Steven Phillipson, the clinical director of New York's Center for Cognitive Behavioral Psychotherapy, writes: "It is essential that one's method of generating cognitive responses not be pre-programmed, rote, reflexive reactions. The more one infuses a genuine emotional emphasis into the responses, the more they will enhance the potency and efficacy of the therapy."
How might this translate for spray-fire atoners? Pretty much the same way the Talmud specified. Stick to apologizing for the sins you know you've committed and have truly bummed you out. Stop trying to make amends in a perfunctory manner—follow up on the formal restitution with a bonus invitation to dinner or a bottle of wine. All the while you should be telling yourself that by ignoring the innumerable sins you may have committed against others, you're running the risk of getting a check-minus next to your name in the Book of Life. (If you're Jewish enough to be this observant, you're Jewish enough to be pessimistic.) By focusing the annual ritual of teshuva on a manageable handful of people, not only will your actions conform to the authentic spirit of Yom Kippur, you'll also train yourself to break a cynical yearly habit that everyone sees through anyway. Their inboxes and answering machines will thank you for it.