I have been privileged to be writing my financial column for this esteemed newspaper for about 18 months and greatly enjoy sharing my knowledge and expertise in investing and wealth management. At this time of year I would like to share with you some loftier ideas and ideals as the holiday season fast approaches. As I am sure you appreciate, my religious observance helps shape the way I conduct my professional and personal life in manifold ways. Just as important as it is to achieve professional success, it is equally critical to harmonize that success with the ethical practices that are demanded from us from our Torah. And there is no better time than the new year to take stock of our lives and determine ways that we can continually reinvent and improve ourselves.

I will preface my thoughts by plainly confessing that I am in no position to use this platform to deliver mussar. We are all in this boat together. We are flawed and have personal shortcomings. No matter how much we accomplish in life, there is always ample room for improvement. The rewards for making positive changes in behavior and attitude can have a profound impact on every aspect of our lives and relationships, not to mention our share in the world to come!

Let me begin by quoting the words of the Ramchal in his magnum opus, Mesilat Yesharim. The introduction of this profound work of Jewish literature states the following:

“I have composed this work not to teach people what they do not know, but to remind them of what they already know and which is very familiar to them….But according to their familiarity and to the extent that their truth is evident to all, so too is their neglect very prevalent and forgetfulness of them very great.”

I believe that these words resonate with all of us at this time of the year. Unfortunately, we tend to get caught up in the dizzying pace of our lives, with nary a thought of what we can do to improve our situation. So, I would like to suggest a couple baby steps, albeit important steps, in order to achieve our desired atonement for our sins and to enjoy this blessed holiday season.

Entering the High Holiday
Season with the Proper Mindset

First, I would like to broach the subject of the proper attitude toward the High Holiday season (or Shabbos, or any of the holidays). This year will undoubtedly be particularly challenging as we are quickly transitioning from vacation mode to Rosh Hashana with little time to mentally shift gears. I am sure many of us would prefer to have a couple extra weeks to facilitate a smoother transition. But we are all accustomed to facing daily challenges that we need to address in order to move ahead. And in the spirit of the overarching themes of the season, we should be embracing the holidays with a sense of great anticipation and gratitude. In our prayers, we thank Hashem for giving us the holidays to raise us up and strengthen us. Sometimes I wonder how we can sincerely express thanks to Hashem in our amidah while begrudging the fact that Yom Tov presents a number of stresses. These include the many hours in shul, preparation of numerous meals and arranging the children’s babysitting and play dates.

When we expend our mental energy on all the worries, we tend to lose focus on the real purpose for our observance of the holidays. So, rather than getting overly focused on the challenges, we should at least conserve some of our energy on endeavoring to fulfill the key mitzvot of the holidays. More specifically, even a nominal but highly focused act of teshuva or tefillah can have a profound impact. As Rabbi Yaakov says in Pirkei Avos (4:22):

“One moment of teshuva and good deeds in Olam Ha’zeh is greater than all of existence in Olam Haba.”

Rabbi Yaakov is not suggesting that we should minimize or limit our efforts. Rather, I believe the message is that we should focus our religious practice on intensive and meaningful “moments of truth.” I know some Rabbis who embrace the “less is more” philosophy when it comes to our prayers. A heartfelt and meaningful prayer is more effective than just showing up to shul with a negative attitude.

Ending the High Holidays On a High Note

There is another idea that I would like to share regarding teshuva more specifically. While we bang our chests during selichot and the Yom Kippur davening, I do not view this merely as an act of self-flagellation. Rather, see the teshuva process as an essential way to bring us to a higher spiritual level each year. Several years ago I wrote a parable regarding the crucial closing moments of Yom Kippur:

“On January 5, 2015, the Arroyo High School girls’ basketball team defeated Bloomington High School girls’ basketball team by a score of 161-2. About 10 days later Arroyo’s coach, Michael Anderson, was suspended for two games for “mercilessly running up the score.” One of the unwritten rules of etiquette in athletic competition is that when one team is so far ahead of the other, the winning team should be charitable, take their foot off the gas and to just let the clock run out.

So here we are at the close of the High Holiday season, the season primarily focused on teshuva. During the month of Elul we began our mission by davening with increased intensity. We took notice of the meaning of the sound of the shofar in shul each morning. Later in the month we began reciting selichot in the wee hours of the morning. We took stock of our deeds and considered meaningful positive changes for the coming year. We called our friends and family, asked them for forgiveness and wished them well. We fulfilled the mitzvah of hearing the 100 sounds of the shofar on Rosh Hashanah. We recited tashlich, symbolically ridding ourselves of our sins. We increased our charitable giving. We increased our prayer during the aseret yemai teshuva. We performed the kaparot ceremony as an atonement for our sins. We immersed ourselves in the mikvah to achieve a higher level of purity. We chanted the Kol Nidre to help innoculate ourselves from breaking vows in the coming year. On Yom Kippur we have fasted, and davened with even greater intensity.

In sum, we have been attempting to run up the score with our good deeds so that we can receive a favorable judgment. But how far should we attempt to run up the score? Why don’t we just run out the clock now? One way or another, Yom Kippur will end and we will return to the daily lives to which we are accustomed.

The answer is that we Jews never have the mindset that we are capable of keeping score of our deeds. This is not an athletic competition with a flashing scoreboard. Our prospects for the coming year are completely dependent on Hashem’s judgment of how our good deeds match up against our transgressions.

The Gemara in Kiddushin (40B) says that a person should view himself as half guilty and half meritorious such that if one performs one mitzvah, one can tip the scale in favor of a positive judgment.

So, as we commence the final prayer of Neilah on Yom Kippur, it is incumbent upon us to view our future as precariously hanging in balance. We should view the ebbing moments of the Yom Kippur holiday as the perfect opportunity to improve our prospects for the coming year by davening this last prayer with even more intensity. Let us all join together in taking advantage of this opportunity. And if in G-d’s judgment we have run up the score, then the only thing that will be suspended are the evil decrees that may have originally been our fate.”

A Final Bracha

In the zechut of our prayers and our resolve to elevate ourselves to progressively higher spiritual heights, may we all be blessed with a happy, healthy and prosperous new year.

The views presented are those of the authors and should not be construed as personal investment advice or a solicitation to purchase or sell securities referenced in this market commentary. The authors or clients may own stock or sectors discussed. All economic and performance information is historical and not indicative of future results. Any investment involves risk. You should not assume that any discussion or information provided here serves as the receipt of, or as a substitute for, personalized investment advice. All information is obtained from sources believed to be reliable. However, we do not guarantee the accuracy, adequacy or completeness of any information and are not responsible for any errors or omissions or from the results obtained from the use of such information.

Jonathan D. Caplan, a former Wall Street executive, is president and founder of wealth management firm Caplan Capital Management, Inc., with offices in Highland Park and Hackensack. He holds a BA from Yeshiva University and an MBA in finance from New York University Stern School of Business. You can find other recent investment articles by Jonathan at www.caplancapital.com/blog.