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Chol HaMoed, the weekday of a Festival, is the term used to describe the five days sandwiched between the first two days and the last two days of Sukkot or Pesach.

The word chol by itself means weekday, on which work is permitted. The word moed by itself means a Festival day, on which most work is prohibited. The phrase Chol HaMoed seems a contradiction in terms. What are these five days – festivals or weekdays?

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The blessing we make at Havdalah to distinguish between the first two days of Sukkot or Pesach and the onset of Chol HaMoed, “Baruch hamavdil bein kodesh lechol,” suggests that Chol HaMoed is weekday. Yet the Torah refers to Chol HaMoed by the term moed, which is reserved for days on which work is forbidden. Then again, the Torah declares, “On the first [and second, outside Israel] day [of Sukkot], you shall not do any work,” clearly implying that on the five days of Chol HaMoed one may perform work. Nowhere, perhaps, is the confusion more visible than in the matter of tefillin on Chol HaMoed; those who consider it chol wear tefillin, and those who consider it moed do not.

In fact, the truth is somewhere in the middle. On Chol HaMoed some work is prohibited and some is permitted. According to some opinions, the work prohibition is biblical; according to others, it’s rabbinical. Whatever the source of the prohibition, all agree that the rabbis decide what work may and may not be done on Chol HaMoed.

For the Chayei Adam, the starting point for prohibited work on Chol HaMoed is Yom Tov itself. With a few exceptions, including lighting a fire, the Chayei Adam lists the melachot as being prohibited both on Yom Tov and Chol HaMoed. Others maintain that it is impossible to define what work is prohibited on Chol HaMoed. All agree, however, on what work is permitted on Chol HaMoed.

Before considering the various permitted categories of work on Chol HaMoed, one should be cognizant of the special status the rabbis ascribe to it, which is best summed up by the phrase “One who disrespects Chol HaMoed is compared to an idol worshipper.” The overriding principle is that work becomes prohibited if it has the effect of rendering Chol HaMoed as just another workday.

Work permitted on Chol HaMoed falls within one of five categories.

The first and perhaps broadest permitted category is known as “Tzorach HaMoed,” meaning work that enhances the joy of Chol HaMoed. Examples of activities that are permitted if they are performed in order to enhance the enjoyment of Chol HaMoed include driving, turning lights on and off (which according to the Chayei Adam was never prohibited on Chol HaMoed in the first place), repairing a leaking roof, erecting a sukkah, sewing torn clothes needed for immediate wear, and writing shopping lists required for Chol HaMoed.

Indeed, the determination of what falls into the first category is quite subjective and dependent on individual tastes and preferences. The only restrictions that apply to the first category are that work (other than work involved in preparing food) must not be performed in an artisan fashion and may not be deliberately postponed to Chol HaMoed.

The second permitted category is “Davar Ha’aved,” meaning work which, if not performed on Chol HaMoed, would result in financial or other loss. This important category includes conducting business or going to work when failure to do so would cause irretrievable loss of principal. Whether loss of profit is considered Davar Ha’aved is a point of debate. Clearly, if such profit is required for and used to cover Chol HaMoed expenses, work generating such profit would be permitted. Again, any work deliberately postponed to Chol HaMoed does not qualify as Davar Ha’aved. According to those who maintain that the source of prohibited work on Chol HaMoed is rabbinical, any doubt about whether a desired activity falls within either of these two permitted categories should be resolved in favor of permitting such work.

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Raphael Grunfeld received semicha in Yoreh Yoreh from Mesivtha Tifereth Jerusalem of America and in Yadin Yadin from Rav Dovid Feinstein. A partner at the Wall Street law firm of Carter Ledyard & Milburn LLP, Rabbi Grunfeld is the author of “Ner Eyal: A Guide to Seder Nashim, Nezikin, Kodashim, Taharot and Zerayim” and “Ner Eyal: A Guide to the Laws of Shabbat and Festivals in Seder Moed.” Questions for the author can be sent to [email protected].