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The Gates of Repentance

The Third Principle of Teshuvah: BEING SAD

One practical way of assessing our own personality is to ask ourselves what makes us happy. For by determining that, we're essentially determining our values and inner convictions. If we're gladdened by coarse, small, and wrongful things, we're essentially coarse, small, and wrongful; whereas if we're gladdened by holy, majestic, and G-dly things, we're essentially holy, majestic, and G-dly. And the same goes for what saddens us.

Rabbeinu Yonah offers that we'd do well to be saddened by our lapses into spiritual mediocrity. And to sigh and mourn for the loss of the chance for spiritual excellence and closeness to G-d the way an investor would be saddened, sigh and mourn for the chance he or she had lost to become rich. Simply because we value spiritual excellence and closeness to G-d as much as another soul might value wealth (though there's really no comparison).

Of course Rabbeinu Yonah wouldn't be advocating growing depressed or dolorous. He seems to be alluding to the sort of sadness that lies somewhere between the kind of wistful sadness we'd feel recalling a past loss; and the deeper-blue sort of sadness we'd feel ruminating about what "might have been", and might have made our lives better. He certainly wouldn't be advocating an ongoing self-castigating sort of deep sadness. After all, it's hard to strive for spiritual excellence if you're that sad all the time.

Nonetheless, Rabbeinu Yonah asserts that the sort and degree of sadness he's advocating is in fact a sign of a pure soul, a clear mind, and seeing eyes. For as we indicated, it would be based on a sudden realization that you'd lapsed into spiritual mediocrity and suddenly turned away from G-d. Only "a refined, sublime soul", as Rabbeinu Yonah puts it, would be saddened by that.

This section ends with a rather touching quote from an ancient holy supplicant, who addressed G-d thusly: "Since I sigh in awe of You, dear G-d, please remove my other sighs; and since I worry about my shortcomings in Your service, please remove my other worries."

What this holy person was implying so pointedly is that it's so very human to sigh and worry. In fact, we spend much more time sighing and worrying than we'd like to imagine (though it seems that some of us are more "gifted" with those skill than others). As such, it would do us well to channel those natural inclinations into our pursuit of spiritual excellence. That is, to sigh perhaps over a chance we'd overlooked to do good, or to pray especially well; and to worry, for example, about whether or not our children will dream of growing close to G-d.

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