Question

Is it proper to avoid sleeping during the day on Rosh Hashanah?

 
A) The Rema (583:2) writes that “the custom is not to sleep during the day on Rosh Hashanah, and it is a proper custom.” He notes that its source is from the Jerusalem Talmud, where it says, “Whoever sleeps at the beginning of the year, his fortune sleeps.”
And its common translation is: “Whoever sleeps on Rosh Hashanah, his fortune sleeps.” Some have newly explained that the reason one should not sleep is because of the dread of the Day of Judgment (the Ari and Pri Chadash): how can a person sleep when he is being judged Above?!
 
B) Many later rabbis mention this custom, among them: the Ari, the Vilna Gaon, Shulchan Arukh HaRav, Arukh HaShulchan, the Taz, the Magen Avraham, the Mishnah Berurah, the Ben Ish Chai, and others.
 
C) However, there is room to question the custom of avoiding sleep during the day on Rosh Hashanah for several reasons:
 

1. The source in the Jerusalem Talmud has never actually been found… It is a quotation whose true origin is unknown, and it may have been collected from some midrash. In addition, there is no mention at all of this custom among our medieval authorities (Rishonim).
2. On the contrary, Rabbi Hezekiah da Silva (Land of Israel and Italy, 1656-1696) brings that Maharam of Rothenburg, the father of Ashkenazic customs, was accustomed to sleep on Rosh Hashanah just as on other holidays, and he noted, “and so we practice.” And in fact there is a commandment of holiday enjoyment on a Jewish holiday, and Rosh Hashanah is a Jewish holiday, so there is a commandment to enjoy it through sleep.
3. Rabbi Baruch Epstein (1860-1942, Pinsk) noted that the later rabbis were not precise in translating the saying “Whoever sleeps at the beginning of the year, his fortune sleeps.” “Damikh” means “death,” not “sleep,” meaning the correct translation is: “Whoever dies on Rosh Hashanah is a sign that his fortune worsened to the point that he was judged immediately” (Torah Temimah on Ecclesiastes 8, note 57).
4. “Israel is not subject to mazal” (Babylonian Talmud, Shabbat 156a), and therefore there is not really any connection between sleeping on Rosh Hashanah and one’s fortune during the rest of the year, because the constellations have no control over a person’s fate. Indeed, Rabbi Mordechai Yaffe (1530-1612) omitted this custom in his book Levush, despite being a student of the Rema (who did mention this custom favorably).

 
E) In conclusion: in light of the reasons above, it seems to me that one may sleep during the day on Rosh Hashanah as usual, just as on other holidays, and thereby fulfill holiday enjoyment.

 
Wishing you a good and blessed year,