Fifty years ago on Yom Kippur, just hours before the shofar was to be blown signaling the end of the fast, sirens went off in Israel, alerting the nation to the beginning of a war that would forever change the country. Despite clear warning signs and intelligence indicating that hostilities were going to break out, the head of AMAN (military intelligence) Major General Eli Zeira advised the Israeli leadership that the chances of war were very low. Following this advice precautions were not taken until the very last minute. Only on the morning of Yom Kippur did the mass mobilization of reservists commence, but by that time, it was too late to employ them in the initial containment battles. The price of this mistake and delay was paid in human life.

How could such a mistake have occurred? Why did Zeira maintain his assessment despite seeing evidence to the contrary? While much has been written about the “concept” and its impact on Zeira and his team of analysts, I would like to focus on a comment Zeira made in 2013, at a conference commemorating the 40th anniversary of the war…

While Zeira always downplayed his personal responsibility, claiming he was just an advisor and the leadership did not have to listen to him, among the errors he did admit to was the following: He related that whenever one of his officers would present him with an opinion or projection, he would push them by asking them, “What if they’re wrong?” In fact, he told the audience that this was such an important part of his routine, he always carried in his pocket a piece of paper with two Hebrew words written on it: “Ve’im lo—And if not?”

Zeira always challenged his subordinates to question their assumptions and judgments by considering what would happen if reality was not what they thought. With that piece of paper in his pocket, he would challenge himself as well. Ruefully, Zeira admitted that in the tension-filled days in the first week of October 1973, he had forgotten to check that piece of paper and question his own judgments and evaluate the potential consequences if he were mistaken.

It is not only generals and political leaders who need to question themselves. In these days leading up to the Yemei Hadin, it is something we all need to do. The Rav, Rabbi Joseph Soloveitchik, in one of lectures on teshuva, repentance, (Al HaTeshuvah, page 64) asks why in our confessional must we state that we have sinned, rebelled and erred as generalities, if we have to, anyway, confess our specific sins. These generalities seem to be superfluous. The Rav resolves this query by explaining that while we are capable of listing our sins, we are less capable of accurately determining whether they were accidental or intentional, or whether they were examples of human frailty or human rebelliousness. We, therefore, confess that we did all three types of sins, but we leave it to God to figure out which sins fit into which categories and forgive us accordingly.

By way of example, the Rav relates a very sad, but all too common story. A man had asked him his opinion regarding whether to send his daughter to a very prestigious college. The Rav demurred and advised him that it wasn’t a good idea. The spiritual challenges would be too great. The man, convinced of the strength of his daughter’s religious beliefs and infatuated with the honor of sending his daughter to such a school, told the Rav that his daughter would be fine. A year later, the man returned to the Rav crying. His daughter became engaged to a non-Jew she had met in the dorm. He insisted that had he realized this would happen he would never have sent her. The Rav concludes this story by asking, “What was the status of this man’s sin? Seemingly, it was unintentional and accidental. But was it really?” After all, had the man not been cognitively-blinded by the prestige of sending his daughter to that school, he might have looked at the evidence more carefully and objectively and, like the Rav, come to the conclusion that it was not a good idea to send his daughter to that college.

For the Rav, complete teshuva requires us to ask ourselves these painful questions, as we review our actions of this past year. We must perform an honest reckoning and do our best to assess our level of culpability. Moving forward as we set our goals for next year, we should bear in mind Eli Zeira’s mea culpa and always question our decisions before we act. To be clear, asking ourselves, “Ve’im lo?” will not make us inactive and it will not immobilize our creative and constructive spirit. But it will help prevent us from making some big mistakes, and serve as an insurance policy that the decisions we make stand the best chance of succeeding in making the world a better place, and making us better people in the process.

Rabbi Dr. David Hertzberg is the director of the Yeshivah of Flatbush William S. Levine Family Shoah Institute. He has a weekly podcast on “Israeli History on the Nachum Segal Network.” He can be reached at [email protected]