“For on this day He will forgive you, to purify you, that you be cleansed from all your sins before Gd.” — Leviticus 16:30

It may feel longer, but from start to finish, it’s actually under 26 hours. And there is much to accomplish in that short time.

Because from the moment the sun sets on Yom Kippur eve, as we stand together (this year, still mostly masked and socially distant) to cancel our vows during Kol Nidrei until the final moments of Ne’ila, when the gates of repentance clang shut, Jews throughout the millennia have been given the gift of cleansing the grime that’s clung to us and a fresh start at being whom we were meant to be. 

Starting at sundown—this year, the 10th of Tishrei begins on Wednesday, Sept. 15—Yom Kippur is the grand finale of the 10 days of repentance. Though it’s by no means the end of the season’s holidays; in fact, in many neighborhoods, you’ll hear hammers hitting wood for sukkah-building right after the break-fast—first things first—since Sukkot arrives just five days later.

But it’s Yom Kippur that’s the day set aside for Jews to “make teshuvah,” to repent for our missteps and seek G-d’s pardon (it’s also customary in the days prior to ask forgiveness of anyone we may have harmed, inadvertently or intentionally). By not eating or drinking, bathing, using oils or cosmetics, wearing leather shoes or engaging in sexual relations—and often, wearing white to symbolize purity—Jews the world over mark this as the most sacred day of the year. 

But focusing on the holiness of the Yom Kippur can be challenging, especially when your stomach is signaling wildly to feed it … pretty much anything. (Just imagine how the high priest felt on this day, walking into the inner sanctum of the Temple in Jerusalem, which holds the Ten Commandments—the only time of the year anyone was permitted to enter—with nothing less than the sins of the entire Jewish people to expiate. All on an empty stomach.) 

The truth is to maximize the day’s power, it’s best to plan ahead. Here are 10 expert strategies for making this the most transformative Yom Kippur yet:

  1. Preparing Your Body

Like athletes embarking on a long marathon, the Jew needs to prepare for Yom Kippur. Entering the fast fully hydrated is certainly a sound strategy, but not all fluids are created equal. Dr. Rabbi Mordechai Halperin remembers well when he was an Israeli soldier fighting in Israel’s War of Attrition 52 years ago. “Just beforehand, I drank a full liter of natural grape juice, and it was the easiest fast of my life,” recalls Halperin, who served as chief officer of medical ethics for the Ministry of Health and continues to head up the Schlesinger Institute for Medical-Halachic Research. “That’s because natural grape juice and grapes themselves contain the best form of sugar, glucose, to get into your blood and keep you hydrated for hours.” But many are not able to fast due to medical conditions, and Judaism also allows for such individuals to drink a cheek-full of water every 10 minutes, and in some instances, a bite of food as well. In such cases, check with a health-care provider and rabbi. But for healthy specimens, there’s nothing like a mid-afternoon nap to quell the hungries, adds Halperin. “And if it’s hot out, stay in the air-conditioning to minimize fluid loss.”

  1. Preparing Your Soul

What better way to begin to immerse in Yom Kippur than with a meditation? Here is one, inspired by the writings of Rabbi Tzvi Freeman to be used following the Kol Nidre service before falling asleep or upon awakening: “Yom Kippur is not so much a day of regret for who I’ve become, but a day when I can feel my pure, Divine soul and experience the bond my Divine soul has with G‑d. On this day, I am strong enough to rid myself of some unbecoming things I’ve picked up on the road and return home, picking up some beautiful mitzvahs along the way. On this day, I will experience not so much atonement as at-one-ment, returning to the One who sees and embraces me for who I am.” So “instead of promising to let our sins go because we’re afraid of being punished, why not focus our mind on this beautiful opportunity to come close to our Creator, knowing we can make that connection last forever if we chuck some bad habits, do teshuva and raise ourselves up?” says Freeman, creator of the online “Daily Dose of Wisdom,” a senior editor at Chabad.org and author of Wisdom to Heal the Earth, as well as creator of KabbalaToons for children of all ages. “Yom Kippur is a real opportunity to leave our negativity behind before it swallows us alive,” he adds. “And channel it into simcha, into true joy. 

  1. Inspiration Between the (Book) Covers

A few Jewish Book Council staffers got together to recommend some books to spend time with before or on Yom Kippur. Among them:

  • The Forgiveness Tour: How to Find the Perfect Apology by Susan Shapiro and Recipes for a New Beginning: Transylvanian Jewish Stories of Life, Hunger and Hope by Kinga Júlia Király.

Others you may find inspiring on this special day include these classics:

  • To Heal a Fractured World by Rabbi Lord Jonathan Sacks
  • Words That Hurt, Words That Heal by Joseph Telushkin
  • This Is My God by Herman Wouk
  • Positivity Bias: Practical Wisdom for Positive Living Inspired by the Life and Teachings of the Lubavitcher Rebbe by Rabbi Mendel Kalmenson
  1. Funny, the Whale Wasn’t Fasting

Isn’t the story of Jonah being swallowed by a whale a bit of an odd choice for the holiest day of the year? Not according to Rebbitzin Tziporah Heller Gottlieb, author of The Balancing Act: How to Bring the Power and Passion of Torah Into Our Homes, Our Children—and Ourselves. “Like Jonah, we try to escape from the things we know G-d wants us to do,” says Gottlieb, who teaches at Neve Yerushalayim College for Women in Jerusalem. “But by seeing how futile his efforts of escape are, we can truly examine our own.” Even deeper, she adds, is that “though he did the wrong thing, G-d cares enough about Jonah to make him suffer just enough to turn to G-d in prayer. And then, to answer those prayers.” She continues, saying, “the storm at sea, being thrown overboard and swallowed by the fish, he didn’t understand why it was all happening to him, but realized that whatever the reason, it was G-d’s doing.” When trying to understand today’s struggle with the coronavirus, for example, she adds, “we don’t know why G-d puts forth harsh decrees; all we know is He has His reasons, and it’s all part of His plan.” 

  1. Honor an Old Tradition

One Yom Kippur tradition dates back to the beginning of the State of Israel when businesses, buses, TV and radio—basically everything besides emergency and security services—shuts down for the day. And, in an unwritten law of the land, cars also stay put, transforming the streets into playgrounds for kids on roller skates and bicycles or being pulled in wagons by their parents. (Teens like to lay right in the street and stare at the sky.) An even older tradition is donating to charity in the hours before Yom Kippur—something Jonathan Sarna witnessed growing up in Brookline, Mass. “People would come to Mincha [afternoon services] with pockets full of bills knowing they’d find pushkas [charity boxes] set out for a variety of causes,” recalls Sarna, the Joseph H. and Belle R. Braun Professor of American Jewish History at Brandeis University and author of the 2004 classic American Judaism; A History, among other books. “On some level, they knew they were being judged as to whether they would live or die and that Judaism teaches that ‘charity saves you from the evil decree, from death.’ ” Deeper still, this was a potent reminder that “we are related to, and responsible for, every other Jew—something we feel even more keenly in these times of COVID—and there can’t really be full atonement as long as there are needy people in our community.” One modern expression of this: going online to donate to your favorite charities in the final hours before Yom Kippur.

  1. Create a New Tradition

This could be anything that raises you higher: starting to read the daily psalms, tehillim (covering all 150 in a month) or a chapter of Tanach (at 929 chapters, reading one a day will take you roughly two-and-a-half years). Or resolve to take your elderly uncle out every month, volunteer in a local soup kitchen or make challah with your kids or grandchildren each week. One tradition that Alissa Zuchman began years ago is reading the six chapters of Pirkei Avot (“Ethics of the Fathers”) every Yom Kippur. “It’s a day all about looking within and then looking at the big picture, to be able to see what we personally can do to change our world,” says Zuchman, who directs Chicago’s Board of Jewish Education and JTeach.org, a national training and curriculum program for teachers. “Pirkei Avot, with its powerful ethical teachings speaks to each of us, reminding us that change doesn’t happen if we don’t change—the perfect message for Yom Kippur.” 

  1. Second Chances: The World Series and Sharing Health

Hall of Fame pitcher Sandy Koufax made the news when he refused to play in the first game of the 1965 World Series, which fell on Yom Kippur. Although a Koufax-less Dodgers team lost that game to the Yankees, he was back on the mound the next day to lead his team to victory. Indeed, Judaism’s value of second chances is forever symbolized by that second set of Ten Commandments Moses brought down, 2334 years ago on Yom Kippur—an irrefutable sign that G-d forgave the Jewish people for the sin of the Golden Calf. Rabbi Ephraim Simon of Teaneck, N.J., also knows about second chances. The father of nine (and grandfather of four) has given two of them: one a kidney he donated 12 years ago and the other a section of his liver he shared with someone nine years later. “I see it as them giving me so much more than I gave them,” says the 54-year-old religious leader of the Chabad of Bergen County, N.J. “To bring life and health back to another human being,” says Simon, “is an honor and, since I was given good health myself, it’s something I could share with others.” On Yom Kippur, adds the rabbi, “we’re asking G-d to give us the blessings of life: health, love, sustenance, family. But what are we doing to create a vessel for those blessings? We can’t all donate organs. But we can all push beyond our comfort zone to bring blessing to someone else.”

  1. Yizkor

Yom Kippur is the first opportunity of the Jewish year to say this traditional prayer service for departed loved ones, and something we prepare for by lighting the memorial candle alongside our holiday ones. During Yizkor, we honor family members by praying for them to be “bound up in the bond of life” and pledge to give tzedakah in their names. “Memory is important psychologically as well as spiritually; it allows the touching of souls between generations,” says Rabbi Karen Fox, a psychotherapist and rabbi emerita at Wilshire Boulevard Temple who teaches pastoral counseling at Hebrew Union College in Los Angeles. The Reform movement tends to schedule Yizkor in the afternoon, she says, “so people come back for it with intentionality.” And, adds Fox, “it’s an opportunity to think about what aspects of my loved one I want to incorporate to strengthen me in the new year.”

  1. Ne’ila: The Eighth-Inning Stretch

Hear that creaking sound? It’s the gates of repentance swinging shut as the sun begins to set on Yom Kippur. And, at your lowest point of hunger and exhaustion, here comes the final Ne’ila service when standing before the open ark, we no longer ask to be written in the proverbial “Book of Life” for a good year but to be sealed in it. “Yes, the gate is swinging closed, but the Chassidic way of seeing that is G-d is locking us in with G-d and not out because Yom Kippur is a taste of the world to come,” says Rabbi David Aaron, founder of Isralight in Jerusalem’s Old City and author of The Secret Life of God, among others titles. “Every year at this time, G-d offers each of us a new and higher level of connection with Him, so by the time we get to the end of Yom Kippur, if we’ve taken advantage of His invitation, we are face-to-face with G-d, seeing Him more clearly in our lives, and determined to love Him and live the connection more deeply this year.”

  1. Breaking the Fast the Smart Way

After all this transformative work, is there anything more tantalizing than a simple hard-boiled egg when your body has been deprived of food and drink for 26 hours? But be careful with what—and how—you break the fast, cautions one expert. “Think light foods with some simple protein,” says Paula Shoyer, Washington, D.C.-area author of The Healthy Jewish Kitchen and, most recently, The Instant Pot Kosher Cookbook: 100 Recipes to Nourish Body and Soul. “Though a piece of the noodle kugel your mother and grandmother made is like getting a hug from your past, you need to balance it with good clean foods like baked salmon.” (And, yes, even that delectable-looking hard-boiled egg.) But just as important for a healthy break-fast is what not to indulge in, according to Shoyer. Chief among them are too many sugary treats and the urge to go back for seconds—or thirds. “If we do overeat that night, we’re pretty much guaranteed to wake up the next morning feeling bloated, which is not the best way to end the Yom Kippur experience.”


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