Let’s begin by thinking about some curious aspects of the High Holidays. We’ll discuss three different questions and then try to resolve them with the help of our three clues.

What is Rosh Hashanah all about? In addition to its meaning as the “head of the year”, we also refer to it as the “Day of Judgment”. Every single person in the world is judged individually on Rosh Hashanah.

In fact, the Talmud tells us that three different books are opened on Rosh Hashanah: The Book of Life — for those judged to be completely righteous, the Book of Death — for those judged to be completely wicked, and the Middle Book for all who are judged to be in between.

If Rosh Hashanah is really the day when every single person is evaluated for life or death, how would we expect people to act on that day? Wouldn’t we expect people to spend the day fixing up past mistakes, pleading their personal cases, and praying for G-d to give them all good judgments?

What, in fact, did the Rabbis tell us to do on Rosh Hashanah? Curiously, there is virtually no mention of our own personal judgment in the Rosh Hashanah prayers. Instead, the prayers are all about the general condition of the world. We pray that the world will recognize G-d is its exclusive King, that He is aware of everything that occurs, and that the shofar of Mt. Sinai will demonstrate G-d’s love and concern for all of mankind. These are certainly beautiful and meaningful prayers. The difficulty is why we would focus exclusively on the overall world situation just at the time when our lives are on the line? This is our first difficulty.

Now let’s think about Yom Kippur. Why is it such a significant day? It is the “day of kapara” — the time of spiritual cleansing. It is the day that we are able to fix up the damage caused by our various past mistakes. That being so, wouldn’t it be much more logical for Yom Kippur to come first, i.e., for the “day of cleansing” to precede the “day of judgment”? This is our second difficulty.

The third question arises from a discussion in the Talmud tractate Rosh Hashanah on the nature of the judgment of Rosh Hashanah. The Torah reading for the first day of Rosh Hashanah presents the story of Yishmael (the father of the Arab nation) pleading for his life (on Rosh Hashanah). The verse tells us that “G-d heard the voice of the lad where he was.” The Talmud explains that the words “where he was” do not refer to Yishmael’s physical location. That would be completely superfluous. Where else would G-d be answering him other than the specific place he was in? Rather, the verse is speaking in terms of time. Based on this, Rebbe Yitzchak (in the Talmud) said, “A person is not judged (on Rosh Hashanah) except according to his actions of that exact moment.”

The commentaries explain that Yishmael was saved at that time even though his descendents were destined to hurt the Jewish people throughout later history. In other words, the negative future deeds of his descendents did not change his judgment at that time.

There is a different source quoted by the Jerusalem Talmud, however, which seems to go much further than this. It tells us that even if an individual was not pure and straight in the past, as long as he is pure and straight in the present, on Rosh Hashanah itself, then he will have a positive judgment. 

These two different sources together (i.e., the positive judgment of Yishmael on Rosh Hashanah despite his descendents hurting the Jewish people later in history, and ignoring the fact that the person being judged was not pure and straight in the past) teach us a remarkable fact. It sounds like the judgment of Rosh Hashanah does not have to do with either the past or the future, but rather exclusively with one’s situation on the day of Rosh Hashanah. This would seem to be telling us that even if the one being judged was evil during the entire previous year, as long as he was righteous on Rosh Hashanah, he would be judged as a righteous person. This, of course, runs counter to any notion of logic and fairness in the nature of judgment. This is our third difficulty.

To summarize, the three questions are:

1. Since we are all being judged for life and death on Rosh Hashanah, why don’t we do teshuva or plead our personal case?

2. Why doesn’t Yom Kippur — the “day of cleansing” — precede Rosh Hashanah — the “day of judgment”?

3. How can the judgment of Rosh Hashanah be exclusively a function of the day of Rosh Hashanah itself, irrelevant of the future and even of the past?

We mentioned previously that every holiday has three clues that help us to unlock its hidden meaning. Let’s begin with the first one, its historical significance, to try to resolve these various difficulties.

What is it that actually occurred on the very first Rosh Hashanah? Although in the davening (prayers) of Rosh Hashanah it is referred to as “yom harat olam” (the birthday of the world), it was not actually the day of creation of the world, but rather the creation of mankind. The first Rosh Hashanah was day number six of creation, and the day upon which the first man, Adam, was created.

Rosh Hashanah — The birthday of free will

Let’s ask what may seem like an odd question — What is the great significance of the creation of mankind? Prior to day six, the Torah tells us that G-d had already created the entire physical world as well as a vast number of different forms of life. What, then, did mankind bring to the world that had not previously existed?

When the Torah describes the creation of mankind, it tells us that man was created “b’tzelem Elokim” (in G-d’s image). One of the most central meanings of this fundamental concept is that human beings have the ability to exercise free will in relation to moral decisions.

To properly understand this, we need to appreciate the Jewish view of a human being. Every person has a body and a soul. The body desires physicality, the soul wants spirituality; the body is interested in short-term gratification, the soul in eternity. What is it that decides which side will prevail?

Judaism understands that there is a third component in the system — free will. Free will is what arbitrates this existential tug-of-war between the body and the soul. It is specifically the creation of free will, which epitomizes our very humanity, that we celebrate and relive every Rosh Hashanah. As Rav Berkowitz, a teacher of mine, once expressed it — Rosh Hashanah is the birthday of free will.

Free will exists only in the present

It is significant that of these three different components within every human being — the body, the soul, and the free will — it is specifically the free will which exists exclusively in the present moment. For example, a person could live his life by a particular set of moral guidelines for many years and then, in an instant, decide to completely shift course. The state of one’s free will is, by definition, whatever he chooses at that particular moment.

In contrast to free will, which exists only in the present, the state of both the body and the soul are almost entirely a function of the past. A person’s physical health at any given time, for example, is mostly determined by their past diet and exercise even if they happen to deviate from that at the present. Similarly for the soul, it is generally the cumulative past behavior that determines one’s spiritual health, not occasional changes afterwards.

Focus of Rosh Hashanah — our free will in the present

Now if we put this point – that free will exists exclusively in the present, together with the cryptic statement in the Talmud that: “A person is not judged (on Rosh Hashanah) except according to his actions of that exact moment,” we come to a remarkable insight — the judgment of Rosh Hashanah is specifically on the state of our free will. Let’s try to understand what that means.

We generally assume that the focus of Rosh Hashanah is on the state of our soul — i.e., the spiritual repository of our actions of the previous year, not on what our free will is choosing at that particular time. This would explain why it seems so obvious that the judgment of Rosh Hashanah would be a cumulative evaluation based on our actions of the previous year.

The spiritual health of one’s soul as a result of one’s past behavior is obviously of critical importance, it just happens not to be the focus of Rosh Hashanah.

Everything that we have ever done, both positively and negatively, has affected our souls. And if this is left as is, these various impacts will be with us forever, in both this world and the next. Fortunately Judaism says that there is a way to minimize or even to eliminate the negative impact of our past mistakes on our eternity. This mechanism is “teshuva” (return) and the result is called “kaparah” (a spiritual cleansing). This goal of kaparah is so important that we have a holiday devoted exclusively to its attainment — Yom Kippur (the “day of kaparah“). It is on Yom Kippur that we try to address our actions of the previous year and fix up all of our mistakes.

Since it is specifically Yom Kippur that addresses our behavior and situation of the previous year, what, then, is the purpose of Rosh Hashanah? We mentioned earlier that one of the clues to uncovering the essence of a holiday is to examine its name. The way that Rosh Hashanah is often understood, it would seem more appropriate for it to have been called “Sof Hashanah” (the “end of the year”), and for it to have been placed at the end of the previous year. However, it is actually called Rosh Hashanah (the “head of the year”), and, of course, it is situated at the very beginning of the brand new year. Besides reinforcing that the focus of Rosh Hashanah is not on our actions of the previous year, what else does the name teach us?

Rosh Hashanah — Potential in the present for the future

The essence of Rosh Hashanah is specifically this point — that it is the very beginning of the new year. Just as G-d originally created mankind as a completely blank slate on the very first Rosh Hashanah, similarly He creates every one of us anew with a similarly blank slate at the beginning of each new year. Rosh Hashanah is our once-a-year opportunity to establish a fresh new direction and reality in our lives. Don’t get stuck in the past. Ask yourself: “If I was born this very instant, without the constraints of my various past habits and patterns, what would I do? How would I ideally want to live this brand-new year?“

This is what it means that the judgment of Rosh Hashanah is a judgment on our free will, or in other words, on the choices and values that we express on the day of Rosh Hashanah itself. Since the new year is a completely blank slate for every one of us, G-d presents all of us with the opportunity to set up whatever values and parameters we would like to govern our brand new year. And then G-d gives us the type of a year that we ourselves actually chose. In other words, G-d gives us for this coming year as much as we want to do, not as much as we have done.

The fear and trepidation that is commonly felt on Rosh Hashanah isn’t only a fear that G-d will be tough on us, but also because the opportunity of the day is so enormous. Imagine winning a contest which allows you to have five minutes inside of a department store where you can keep whatever you carry outside. The fear you would be likely to feel just before those five minutes begin is that you will not get all that you can out of this enormous opportunity.

Let’s now return to our three original questions. Our first question was — “Why shouldn’t we be spending the day fixing up past mistakes in order to receive the best possible judgment?” That was clearly based on our assumption that the judgment of Rosh Hashanah was a judgment on our actions of the previous year.

The key to understanding this actually comes from the third question — the puzzling statement in the Talmud that the judgment of Rosh Hashanah is exclusively on the day of Rosh Hashanah itself. This told us that the judgment of Rosh Hashanah is not on the state of our souls, but rather on our free will choices. Once we understand that the judgment of Rosh Hashanah is basically an assessment of what we ourselves want for our coming year, it is obvious that our past behavior is not the point here. The relevant issue is whether we will appreciate what is truly valuable and make the proper choices for the coming year. This also explains why our prayers on Rosh Hashanah are that the entire world will come to a deep appreciation of G-d’s existence, awareness and supervision. By making these the prayers of Rosh Hashanah, the Rabbis are teaching us the following critical lesson: Recognizing the needs of others, seeing ourselves as responsible for others, and understanding that the greatest need any of us have is to appreciate reality more deeply — are the most important values to base our upcoming year on.

The decision to change for the future must precede fixing up past damage

This leaves us with just the second question — Why Yom Kippur, the day of cleansing, didn’t precede Rosh Hashanah, the day of judgment. On a simple level, this question was also based on the mistaken assumption that the judgment of Rosh Hashanah is a judgment on our actions of the previous year. It, therefore, seemed logical that G-d should allow us the chance to cleanse ourselves from our previous mistakes before He would actually judge us on them. However, even now that we recognize the judgment of Rosh Hashanah to be on the choices we will make on this first day of the upcoming year, the logic of Rosh Hashanah preceding Yom Kippur still needs to be understood.

Everyone is capable of choosing a new path in life, independent of their situation up until that point, anytime they really want to. This could be done anytime throughout the year, and all the more so on Rosh Hashanah. How likely is this, however, to occur? We are all carrying around a lifetime full of past habits and patterns. In light of this, how many people will be strong enough to simply make a decision to carve out a brand new direction in their lives? It would seem, therefore, that it would still make more sense for the purification of Yom Kippur to come first, and thereby help our choices on Rosh Hashanah for the coming year to be less impeded by all of our past mistakes.

Let’s use an analogy to point out the mistake in this way of thinking. Imagine that you know someone who is an alcoholic or a drug addict. This addiction has damaged every aspect of his life — his family, his job situation, his friendships, etc. One day he comes to you and tells you that he has decided to fix up all of the damage he has caused. He has compiled a comprehensive list of all the mistakes he has made during the past number of years. And he is planning to go to every person that he hurt with these mistakes and ask for their forgiveness. As admirable as this certainly is, there is one obvious circumstance in which you would be likely to strongly discourage him — if he has not yet begun to work on the alcoholism or the drug addiction itself. You would tell him to direct his energy first and foremost to his personal life situation and direction. Not only because it is so much more fundamental, but also because if he doesn’t address this first, it is likely that he will end up hurting many of these same people again in the future. As important as it is that he go to all of the people he has hurt and ask them for their forgiveness, it only makes sense for him to do this once he has straightened his life out first.

Let’s try a second analogy to make this even clearer. Imagine a person whose car is full of dents and scratches because he has been such a poor driver. He goes to a body shop to get all of the dents and scrapes fixed up. The man in the body shop, however, tells him not to bother because this would likely end up being a waste of money. He recommends that this lousy driver first work on becoming a better driver. To merely fix up the damage to his car without first changing his poor driving habits would be pointless; it is inevitable that he will end up damaging his car all over again. Only once he has improved his driving, will it make sense for him to get his car fixed up.

Every human being makes mistakes. At least once a year we all need to take stock of ourselves and work on improving. Our spiritual improvement must occur in two different parts of ourselves — our free will and our soul. We need to examine our free will, meaning our values as well as how those values translate into a vision and direction for the future. In addition, we must assess the damage which our previous values and direction have caused to our souls as well as to others around us. Both tasks are critical. Working on our values and choices will determine the quality of our upcoming year, while working on the damage from our mistakes of the past will determine the nature of our soul. By the Torah placing Rosh Hashanah before Yom Kippur, it is telling us very clearly that the first step must be to work on our values and our vision. Only then can we be sure that the work we do to fix up the damage from our past mistakes will end up lasting.

New direction requires the most time and effort

It is interesting that people usually assume that the effort required to fix up their soul (i.e., repairing the damage from their mistakes of the previous year) will be much more time consuming than what will be necessary to work on their free will (i.e., improving their values and direction for the coming year). After all, to repair their soul will require first identifying and then rectifying every single mistake they have made during the past year. In contrast to this, we might imagine that improving our free will merely requires some basic introspection and making a few different resolutions for the new year.

Judaism, however, tells us that the reality is exactly the opposite. We have an entire month of Elul to prepare ourselves for Rosh Hashanah, and only one week after Rosh Hashanah to get ourselves ready for Yom Kippur. Think back to the two previous analogies. Isn’t it obvious that the work involved in breaking an addiction is enormously greater than rectifying the damage that resulted from that addiction? And, similarly, with changing how one drives versus having the dents taken out of one’s car? Changing our values and our vision involves changing who we are. Fixing up past mistakes, on the other hand, is basically a mechanical process. It is critically important, but it is mechanical nonetheless. Additionally, the more that we are able to make ourselves into brand new people for the upcoming year, the easier it will be to rectify our past mistakes through this process.

We could summarize the essence of Rosh Hashanah with a well-known expression — “Today is the first day of the rest of your life.” One of the biggest mistakes we all make is to allow our past to govern and determine our future. The defining quality of our free will, which is really what defines us as human beings, is that it is free and unencumbered. And it is the past, perhaps more than anything else, which is specifically what it is free of. While, as this expression itself spells out (and as Judaism would certainly agree), this is an obviously relevant consciousness for one to have the entire year, Rosh Hashanah is the time which is most ideal for its implementation. At least once a year, at its very beginning, we must take the time to think, not about what we have already done, but rather what we want to do; not about where we have already been but, instead, where we really want to go with our lives. This should give us the ability not only to fix up the damage from our past mistakes, but also to allow us to live an upcoming year which is truly new, not only in name but in reality.