Almost all yamim tovim have two days because of safek, but the days of Rosh Hashanna are not misafek, they’re called vadai and yomah arichta. Why is this so? There are, as always, two answers: a technically correct one, which is well known, and a deeper, perhaps truer, answer.
I believe that answer is as follows. What follows was inspired by the sefer Menachem Tzion (from Rav Menachem Sachs, Rav Tzvi Pesach Frank's son in law, founder of the Associated Talmud Torah in Chicago, and father in law of Rabbi Jack D. Frank z'l of KJBS.)
Ba’alei mussar say that the reason ‘pen’ is repeated is that the yetzer hara has two strategies of attack.
One is to find a crack in one’s faith; if a person just takes his emunah for granted, and does not reflect on how Hashem runs the world and hashgacha pratis, there may be a weakness in his emunah that he is not even aware of. This is the ‘"פן יש בכם...אשר לבבו פונה"”--the ‘pen’, the doubt and weakness in bitachon that is within the person himself. The Gematria of Amalek and of Sofeik is 240.
The other strategy is if the person’s emunah is good, the Yetzer Hara looks for a chance to convince the person that what is actually an aveira is not so bad, not really assur, maybe even a big mitzvah to do--this is the "pen" of a person who does not stay aware of what is muttar and what is assur, he has a “pen” about what the halacha is. While he may start out doing things that are arguably only maaaaybe a safek, it is a שורש פורה רוש ולענה of maizid gamur, it is a root that produces poisonous fruit. It's an easy ride from “eh, it’s probably muttar.” "not only is it muttar, it’s probably a mitzvah." This is the ‘Pen’ of “shoresh poreh rosh vela’ana.”
As an instrument of spiritual destruction, the ‘pen’ is mightier than the sword. It's easier to withstand an external threat to our lives for our faith than to withstand internal doubt hiding in unexamined faith, and a negligent lack of clarity in halacha.
We see now that this series of psukim lists the five most dangerous factors that lead to a life of aveiros. They are:
1. Vatir’u es shikutzeihem- ותראו את שקוציהם
2. Pen #1,
3. Pen #2,
4. Vehisbareich bil’vavo- והתברך בלבבו , and
5. leimor shalom yi’hiyeh li- לאמר שלום יהיה לי.
Vatir’u is exposure to anti-Torah immorality, especially when that bad behavior is celebrated in society, what I call “ha’ro’eh sotah be’hiddurah. Pen #1 is weakness in faith. Pen #2 is not caring enough to know for sure what the halacha is. Vehisbareich is intellectual arrogance, the attitude that whatever I do is fine, and nobody can tell me that I am wrong. Shalom yiheyeh li means that I don’t care how my behavior influences orther people because I don’t care what happens to other people, as long as sholom yiheyeh li, as long as I’m going to be alright.
1. Exposure to immoral behavior.
2. Uncertainty of faith.
3. Ignorance of halachah.
4. Intellectual arrogance.
5. Indifference to the well-being of the community.
If a person sees any of these characteristics or attributes in himself, it’s a good sign that needs to re-examine his lifestyle.
We cannot come into Rosh Hashanna with a ‘pen', with sfeikos. There are no "sfeikos" on Rosh Hashanna. You have to deal with your doubts before the day comes, because if you walk into shul unprepared on Rosh Hashanna, you have lost a tremendous opportunity. You have to prepare for the Yomim Noraim by examining where you stand, who you are, what you are proud of, what you are ashamed of, and then you can benefit from Rosh Hashanna. Chazal absolutely did not want a person to come and say, well, it’s a sfeika diyoma, maybe it’s not today, I still have tomorrow....chazal want us to know that this is not the case. Today is the day, and there is no tomorrow. The time to prepare for Rosh Hashanna is not when you walk into shul on Rosh Hashanna, it’s when we begin the slichos.
And here's a mashal about the great enemy of teshuva- procrastination.
In Europe, the chimney sweeps, the Koimenkerrers, were looked down upon. Their work left them filthy and covered with tar and soot, and besides the dirty layer of ash, their skin was stained and they smelled like wet ash and the residue of all the food that had been cooked in the fireplace. There was a man who needed to marry off his daughter, but he was a koimen kerrer, and nobody would look at his daughter. The Shadchan decided that he would try his luck in a neighboring town, where the father's trade was not known, and he was successful. As soon as the daughter became engaged, the father decided that he would do no chimney sweeping for a month before the wedding. A month would be enough time to scrape all the ash and tar off, and it would be enough time for the stains in his skin to go away, and he could come to the wedding as clean as anyone else, and cause no embarrasment to his daughter and to his family.
Sure enough, a few days into the month, he realized that he had to pay for the wedding, and money was tight, so he decided that two weeks of enforced vacation would be enough, and he could try to do a couple of jobs in order to get some money together. After the two weeks went by, of course, a friend came over and said, please, my chimney is blocked and really needs to be cleaned, could you please just do this one job? Well, for a friend...and anyway, two weeks is plenty of time. One week before the wedding, a long time customer came over and said, look, you've been doing my work for years, and I don't want to give the work to someone else, but I need the job done, and if you can't do it, I'll have to go to the competition. Sure enough, he decided that under the circumstances, he had to do the work, which took almost the entire week. But, he thought, I'll really scrub myself on the day of the wedding. The stains won't come off, and I might still smell a little, but a little scented soap will do the job, and I'll still look decent. Comes the morning of the wedding, and he is absolutely determined that the morning will be spent in the shvitz with a bar of fels naptha, and he'll be fine. On the way to the bath, there's an emergency. Someone comes over and says that if his chimney is not swept, his wife will leave him, he will be made to look like a fool, he'll die of shame, and he is willing to pay ten times the going rate for the job, but please, please, it's just two hours of work. Well, ten times the rate! And I'll be finished by noon, plenty of time to clean up enough for the wedding. So it's off to work. But this is a difficult job, and it's an old chimney, and as he's finishing up, ma'aseh sattan! He gets stuck in the chimney. It takes three men and two ropes, but after two hours, he is dragged out of the chimney, he's never been so filthy and smelly and tarred, and if he doesn't leave RIGHT NOW he'll miss the chupah, so he runs off to the wedding covered from head to foot in tar and wet ash and rancid grease, his clothing ripped, you can barely tell he's human. (From the sefer Kerem Tzvi, from Reb Tzvi Hirsh Farber of London in the 1930s.)
The story is only funny until you realize that it's really about how you yourself have spent the entire month of Ellul and what you're likely to look like on Rosh Hashannah.
(An earlier version of this post was published in 2007.)
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