The Highs and Lows of Elul

Edited and Co-authored by Rabbi Neil Fleischmann

Over the last few years two feelings have dominated my experience of Elul: hope and regret. The Selichot prayers inspire me to abandon various unhealthy habits; the shofar sounds motivate me to wake up from my religious slump and desire a closer relationship with Hashem. However, the arrival of Elul also prompts me to reflect on last year’s shortcomings and experience regret. Another year went by, I still can’t stop binging Netflix shows, still can’t get to minyan on time, still can’t stop biting my nails, still can’t find a partner. The experience of both regret and hope can bring members of our community sincere religious growth over Elul and beyond.

The connection between Elul and regret became apparent to me upon starting adulthood. Most kids and teenagers view Elul as the beginning of school or the start of the NFL season, while adults see it as a time to review personal feats and setbacks from the last 12 months. For me, self-reflection on last’s year imperfections evokes self-critical thoughts about underperformance and underachievement last year. Everyone tells me I have potential for great things, and at each year’s end I feel like I didn’t actualize that potential. Self-reflection on last year’s missteps generates acute feelings of regret and disappointment for any growth-oriented person.

On Erev Yom Kippur my rebbe sets aside time to write himself a reflection letter about what to improve on for next year. I have adopted this yearly practice and can testify that it generates disappointment and regrets. However, it can be constructive to undergo feelings or moments of failure or disappointment. Moments of disappointment can help you become vulnerable to acknowledge your weak spots and plan accordingly. Moments of regret can help you figure out what goals to set.

My co-author and friend, Rabbi Neil Fleischmann, likes to reference the quote attributed to both Rebbe Nachman of Breslov and the Kotzker Rebbe about the connection between regret and religious growth: There’s nothing more whole than a broken heart. Rav Joey Rosenfeld suggests that the inverse of this is also true: There is nothing more broken than a whole heart. A person is broken if they feel that they don’t need to grow or change because they are complete as they are. Sometimes it can be good to fall so that you can then rise higher

The connection between Elul and hope goes back to Moshe Rabbeinu’s first year as our leader. On the 17th of Tammuz Moshe came down from Har Sinai and observed thousands of Jews worshiping a golden calf. Outraged by this behavior Moshe smashed the tablets God had personally inscribed for us. The sin of the golden calf prompted God to contemplate destroying Am Yisrael forever and provide Moshe with a different nation, made up of his offspring, to lead in our place.

On Rosh Chodesh Elul, God commanded Moshe to climb back up Har Sinai. Moshe prayed there for 40 days and 40 nights, drinking no water and eating no food. On the 40th day God told Moshe to descend the mountain and provide the Jewish people with a new set of tablets.

Once the Jewish people witnessed Moshe holding a new set of tablets, they knew that God had forgiven them. This day of forgiveness occurred on the 10th of Tishrei, also known as Yom Kippur, the day on which we as a people earned a clean slate with God. Our tradition deems these 40 days between Rosh Chodesh Elul and Yom Kippur as days of favor and mercy, a time anyone can change for the better, a time of infinite hope.

One legendary story of hope has inspired me to dream big every time Elul rolls around. I heard it from a prominent out-of-towner at Camp HASC named Carl*, who shared the story about his niece’s wedding. Carl’s brother Steve* had two daughters, one named Rachel* and the other named Rebecca*.

The older niece, Rachel, had recently gotten engaged, and her family jumped for joy to make wedding plans for her. Delighted by the news Carl offered to pay the wedding’s catering bill. However, Steve refused the offer. “No need.” But Carl persisted. “I love Rachel, and besides, this is going to be the only wedding you make for a child of yours, please let me pay for it.” Steve became enraged by Carl’s comment, “You don’t think Rebecca is going to get married?” Rebecca had a disability and her uncle slipped and shared his prediction that she would never be a kallah.

After this encounter, Rebecca’s father visited a great rav in his area for a consultation. The rav learned of Steve and Carl’s dispute and predicted, “Next year you will be dancing at Rebecca’s wedding.” The next year a new Jewish mailman moved nearby and began delivering mail on Rebecca’s block. The mailman and Rebecca would interact on a consistent basis when she received her mail. Each small interaction added up and prompted the mailman to ask Rebecca out. Rebecca and the mailman were engaged and married later in the year.

At Rebecca’s wedding, her former HASC and Camp Simcha counselors had traveled near and far to celebrate with her. During the ceremony Rebecca needed physical help to walk down the aisle and stand up straight under the chuppah. Yet, her partner stood by her side. The simcha dancing later contained more energy and excitement than a rock concert. Carl deemed Rebecca’s marriage a miracle from God and inspiration for the wedding guests to never give up on their hopes and dreams.

Over Elul and beyond pray for your hopes and dreams to come true. Pray for the hopes and dreams of others to come true. No matter how unlikely the odds seem, no matter what the statistics predict. With God in our corner, I’m telling you there’s a chance.