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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