In the fall of 1988, I began a new chapter in my life. It had been almost a year since I delivered my bar mitzvah speech in my family’s warm suburban synagogue and just a few months after I’d completed eighth grade at the Hebrew Academy of Cleveland – the Jewish day school I had attended since pre-kindergarten.

That fall, I was a freshman settling into the dormitory of the Wisconsin Institute for Torah Study (WITS) – a yeshiva high school in Milwaukee, where the next four years would pass far too quickly.

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I cannot adequately describe in these few lines the camaraderie, Jewish learning, and new experiences that were an integral part of my high school years on the shores of Lake Michigan. I would, however, like to share one episode of that first fall semester that I will never forget.

It was September, and we could all sense the rapidly changing season. The leaves were starting to color, and we watched deer gracefully dart through the yeshiva’s property and disappear into the woods. We had also enjoyed a Rosh Hashanah holiday unlike any we had known in our hometown synagogues. We had less than a week of yeshiva remaining until Yom Kippur – after which we would return to our homes across the country to celebrate Sukkot together with our families.

Aside from being the start of the Jewish year, Rosh Hashanah also begins the period known as Aseret Y’mei Teshuvah – the Ten Days of Repentance which culminate with Yom Kippur. Our ninth-grade Talmud instructor, Rabbi Powers, explained that while God, according to Jewish tradition, welcomes our sincere return to Him throughout the year, it is these ten days of the Jewish calendar that provide us an optimum opportunity to approach, reconnect, and rebuild our relationship with our Creator.

Although we had only known Rabbi Powers for a few weeks, my classmates and I felt a strong connection to him. He had an infectious smile, a sense of unbridled enthusiasm, and a palpable sense of concern for each of his young charges.

In the spirit of the Ten Days of Repentance, Rabbi Powers asked us each to take out a pen and a piece of paper so that we could embark on a learning experience together. He asked us to spend a minute or two in thought and then compile a private list of what we would each like to change about ourselves in the coming year in order to become a better Jewish person.

While I have no recollection of the items I came up with, I will never forget that day’s lesson. After a few minutes, Rabbi Powers asked us to look over our lists and cross off half the items. We were puzzled by his request. Why did he put us through the effort of compiling a lengthy New Year’s resolution list if we were just going to cross off half? Rabbi Powers had earned our trust, though, and we followed his instructions.

He then asked us to do the unthinkable: to again cross out half the remaining items. We were perplexed, and murmuring could be heard. Most of our lists were left with only one or two items of possible self-improvement. (One classmate from Chicago whispered to me that since his list was originally so short, he now had nothing left to improve about himself.)

Rabbi Powers quieted the room and went on to explain that our Talmudic sages had long ago taught: “Tofasta merubah lo tofasta – if one attempts to take hold of too much, he takes hold of nothing.”

The reason why most of us never carry through with our New Year’s resolutions is that we have taken on too great an assignment. While it is important as human beings to dream big, it is crucial that we remain realists.

More than 20 years have passed since that morning’s lesson, yet it is one I try to remember each year at this time. Self-improvement is a difficult business, and it goes against our basic nature. In order to experience the satisfying taste of success, our resolutions need to be realistic – and we need to be careful not to bite off more than we can chew.

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Rabbi Akiva Males began serving as rabbi of the Young Israel of Memphis in the summer of 2016. Prior to that, he served as a congregational rabbi in Harrisburg, Pennsylvania. He can be reached at: [email protected].