Some people get angry at the Jewish calendar. It takes away their ability to decide when they want to rejoice, when they want to mourn and when they want to repent. While narrowing our choices is true of halacha in general, there is something about the calendar that can feel especially oppressive.
But even without the anger, who has not experienced the discomfort of not feeling spiritually ready for a holiday? And of all the holidays, I imagine that we are most likely to experience this with Rosh HaShanah. Besides the greater difficulty that teshuva entails, Rosh HaShanah’s date may feel negotiable. What I mean is Pesach, Shavuot, Purim and Chanukah all celebrate events that happened specifically at that time of year. Rosh HaShanah however does not really celebrate a historical event. And if you tell me that it celebrates the creation of man, I will remind you that the Talmud (RH 10b) relates to the date of man’s creation as an unresolved debate. The Talmud (RH 16a) also tells us that there are different days of judgment for different things scattered throughout the year, not to mention the more intuitive approach of Rabbi Natan that our judgment by God is actually constant.
Yet precisely because we would be so likely to delay the observance of Rosh HaShanah, it is the most important not to delay. I would go even further and say that this may well be its most central teaching. You see, deadlines are a tricky thing. Though they are usually self-created, they are also a key element in making sure we get the job done. When it comes to teshuva, it is trickier still, since it only really needs to be done once in our lifetime. Like anything really, our lives can only be fully evaluated once they are complete. (Of course, there are immediate benefits to doing teshuvah regularly, which is another reason why we are instructed to do it yearly at this time.) Yet if we choose to wait until the last minute in our lives to put our lives in order, it is not just that we might suddenly die or be incapacitated and never actually get the chance. It is also that we will simply be unprepared and not know how to go about it. Hence if we do not do teshuvah now and every year, it is more than likely that we will never do it.
This makes Rosh HaShanah a tricky exercise indeed, all the more so when life expectancy is high and danger from war, pestilence and the like are – even at the height of the Covid pandemic – relatively low. Yet it is clear that people have always procrastinated. Why else would the Talmud (Shabbat 153a) have pointed out that we must constantly repent, since we never know when we are going to die, or Rabbenu Yonah (Sha’arei Teshuvah 1:2) have pointed out the great moral failure that comes with not repenting for sin at the earliest possible moment? But neither of these teachings is enough by themselves. The Torah anticipated the critical need for a time of year dedicated to buckling down and fighting our all too human tendency to procrastinate even the most important things.
Keeping the above in mind allows us to fully appreciate what Rosh HaShanah is all about and why it is so important. This yearly day of judgment is meant to truly maximize our chances of a favorable judgment after concluding our time on Earth. As such, it is not meant to just be good advice. It is meant to make us realize just how much is truly at stake.
To reinforce this, Jewish tradition constantly and advisedly conflates our yearly deadline on Rosh HaShanah with our ultimate deadline (ever wondered why it is called a deadline?). For example, it is no coincidence that we speak about Rosh HaShanah as Yom HaDin (the day of judgment), even though the term is also – and technically more correct – used for the day of our ultimate judgment. This also explains the power and impact of the famous UNetaneh Tokef prayer, as well as why some Jews wear shrouds that are otherwise only used for burial. But more than anything else, it is this holiday’s very existence that serves to remind us that just like we cannot prevent the smaller day of judgment from coming, so too can we not prevent the ultimate day of judgment from coming as well.
This is presumably why the month of Elul is singularly associated with preparation. Whether saying selichot or simply listening to the shofar, the traditions of this month are all about taking the deadline of Rosh HaShanah seriously. As taking it seriously means we may not delay.