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Answer: The two major categories of situations in which doing melacha is permitted are: 1. When the purpose of the work is appropriate for Chol Hamo’ed, e.g., it enhances the chag, it is for a mitzva or communal needs. 2. Davar ha’aved – i.e., if the work will not be done on Chol Hamo’ed, a loss will be incurred. While davar ha’aved permits even to perform "expert work" (Mishna Berura 545:35), it is forbidden to purposely set up the situation whereby the work will be needed specifically on Chol Hamo’ed (Shulchan Aruch, OC 538:1) While the classic cases are of loss to possessions (see ibid. 537-8), poskim posit that defying an employer’s work policy in a way that will likely result in firing or disciplinary steps is also davar ha’aved (see Shemirat Shabbat K’hilchata 67:11), which seems to be your case.
All things being equal, it is proper to arrange matters so that one’s yearly vacation time includes [as much of] Chol Hamo’ed [as possible]. Halacha is aware that in practical life, often "all things are not equal," including in regards to choosing vacations (see Zichron Shlomo, ruling #18 of Rav Moshe Feinstein; Shemirat Shabbat K’hilchata 67:14). To deal with the many "moving pieces" in such matters, it is best to discuss borderline cases with one’s personal rav. We will focus on what you asked: assuming you may work because of davar ha’aved, can you receive payment for it, or is the payment gain rather than preventing loss?
The primary problem with working on Chol Hamo’ed is any melacha you must do, but you are correct that being paid complicates matters. The gemara (Mo’ed Katan 12a) says that the workers in the Exilarch’s house were allowed to benefit from their work on Chol Hamo’ed because it was not in the form of classical pay. The Rosh (Mo’ed Katan 2:9) infers from this that it is forbidden to pay the worker even when his actions are permitted on Chol Hamo’ed because the pay makes it "like mundane matters."
The problem of receiving reward differs from the parallel issue on Shabbat and Yom Tov, which is even when the person is inactive. Here it is a problem only if the pay relates to activity with a problematic element, with the pay tipping the scale towards stringency (see Noda B’yehuda II, OC 104; Chut Shani, OC 542:1). Some sources focus their requirements on the Jewish employer who employs a Jew, (see language of the Shulchan Aruch, OC 542:1 and Be’ur Halacha ad loc.). While one might think that there would not be a problem if the employer is not Jewish, there are indications that there is a problem from the worker’s perspective (see discussions in Chol Hamo’ed K’hilchato, p. 307, Shemirat Shabbat K’hilchata 66:(164)).
Bemare Habazak - Rabbis Questions (657)
Rabbi Daniel Mann
627 - Ask the Rabbi: Erev Pesach That Falls on Shabbat
628 - Ask the Rabbi: Not Taking Vacation Time on Chol Hamo’ed
629 - Ask the Rabbi: Anonymous Return of Stolen Money
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In any case, since you have a set job, it is permitted to receive the pay because it is b’havla’ah ("swallowed up" by inclusion with other earning – see Shulchan Aruch, OC 306:4), even if you are paid per hour (Shemirat Shabbat K’hilchata 28:65). According to most poskim (ibid. 66:40; Moadim U’zmanim IV:301, against Chut Shani, OC 242:21), this works also for Chol Hamo’ed.
In the final analysis, you may get paid.
Rabbis in Midrash
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