In this month's reading, "Sha'ar Lashon Ha-ra," which is translated by Rabbi Silverstein as "The Gate of Slander," there is a puzzling observation in the second (English) paragraph. The text reads,
Certainly, one who is given to slander removes from himself the yoke of Heaven, for he sins without pleasure and is worse than a thief or an adulterer, who pursue pleasure (Shochar Tov 120:3).First of all, the "yoke of Heaven," (ol shamayim). This phrase denotes the acceptance of the obligation to live in accordance with the Divine will. The image seems to be one of a painful burden and when we read it we might say, "What am I, an ox? What a drag (pun intended)." If you allow the image to play out you might see it as more meaningful and beautiful. One of the reasons an animal carries a yoke is to pull a plow behind it. The plow digs into the earth to make possible the planting of seeds that will ultimately grow into something beneficial. We uphold the Torah because our goal is to turn the fallow fields of earthly life into something that is abundant with life and sustenance.
What about this idea that this is a more serious sin because we don't derive pleasure from it? I don't actually accept the premise. One of the reasons that lashon ha-ra is so easy to do is that it brings immense pleasure to the one who speaks it. Part of the pleasure is taking the person down a notch or too, perhaps satisfying some deep insecurity we have. That we satisfy this insecurity by our worst impulses (dragging someone down) rather than with our best (elevating ourselves) is one of the signals of the harm of lashon ha-ra: we damage ourselves in the process (as the Talmud says in Arachin 15b, "Lashon ha ra kills three people: The one who speaks it, the one who hears it and the one about whom it is spoken").
There is another pleasure in lashon ha-ra, and our desire for it actually stems from holiness: lashon hara creates solidarity between the speaker and the listener. There is a kind of warmth, the comfort of a bond between one person confiding something that is mutually morally repugnant to another person. This desire for connection and sympathy with others is essential to human holiness, but of course this particular expression of that desire is evil.
The Aish Kodesh writes that every thought, desire and deed that we have can be revealed to have at its core a dimension of holiness. Even within an act as ugly as lashon ha ra is the potential for holiness to be revealed. Lashon Ha-ra is an ugly garment covering, as it were, a light of holiness. While the teshuvah (repentance) that we must do begins by refraining from lashon ha-ra and making a good faith effort to undo damage that we have caused, it should also include an examination of the desire for holiness, warped as it may have been, that might have been at its core.