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 have done.
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 instead.
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.
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