Few things gnaw away at our being as much as musing about what might have
happened had we done "that" instead of "this" -- taken that job rather
than the one we have, moved there instead of here, etc. But the real harm
done from that comes when we have second thoughts about all the good
things we'd done and dwell instead on other, less lofty things we might
The yetzer harah will fill you with "with anxiety", as Ibn Pakudah points
out, when it comes to such thoughts. It will "make you skittish all the
time, and have you regret all the good you've done" in retrospect
and "have you ... relish" all the more mundane things you could have done
Obviously, though, all the good you'd done has fulfilled your larger,
ultimate dream of achieving spiritual excellence. And your fantasies about
more mundane pleasures would be on par with the whimsical ideas successful
people sometimes have about living "simpler" lives (which really aren't
simpler so much as less stirring and fulfilling).
Other times the yetzer harah will try to persuade you to regret spending
time delving into various intellectual pursuits, and it will try to
persuade you to keep your curiosity in check. It will advise you to settle
either for what others tell you or for knowing only down-to-earth,
practical things. But while that would be "wise" for those willing to
accept a life of utter, not just spiritual mediocrity (or for those
with limited capacity), it would be foolish for the serious student of G-d
and His ways in the world.
And finally, the yetzer harah will sometimes have you lament your choice
of spiritual goals and have you envy others' lesser options. Lapse into
that and not only will you inevitably come to "despise those others, ...
find fault with them, insult them, and speak of them spitefully", but
you'd also come to be unduly "proud of yourself" after you realize the
wisdom of your own choices. And all that would do is demean you and your
spiritual achievements in the end.
This series is dedicated to the memory of Yitzchak Hehrsh ben Daniel z"l,
and Sara Rivka bas Yaakov Dovid, z"l.