Promised safe passageway out of the beleaguered town of Sodom, Lot's wife must, in turn, accept that there will be no last looks, no last licks, and no watching the destruction of her hometown (19:17). Her apparent inability to keep the deal sealed her fate, and she joined her fellow sedomites, albeit "buried" out of town.
How are we to understand Hashem's deal? If she was worthy of surviving Sedom, why did one look back rob her of her rightful destiny? According to Rashi, she was indeed not worthy but in Avrohom's merit, possibly to allay Avrohom's suffering over the loss of a niece, she could have a future. Perhaps walking away, clearly embarrassed, would demonstrate to all that she knew well that "there but for the grace of Avrohom Avinu go I". Yet if so, why was Avrohom fated to suffer even more as she looks over her shoulder?
What possessed her to look back? If it was no more than a natural habitual response, would she be turned into salt?
Furthermore, just two pesukim after Lot's wife looks back and is punished for it, we read that Avrohom takes in the view of the smoldering remains of the Sodom and Amora (19:28). What is the significance of reporting and recording Avrohom's visual review of the destruction?
It does not take much study to note that the Torah carefully distinguishes between Lot's wife's look which brought about her death, and Avrohom's view, which on its own merited record in the Torah. Lot's wife was told to refrain from "haboto" (19:17). She is told "al tabeit acharecho - don't look behind you". Unfortunately "vatabeit ishto - She looked back" (19:26). On the other hand, "vayashkeif Avrohom - Avrohom looks towards Sodom and amora ... He (vayare) sees smoke rising up..." (19:28).
Vatabeit is punishable by death and vayashkef is the righteous act of Avrohom! Though translated similarly, they clearly must convey different ideas, and indeed the two synonyms appear in Tanach in very different contexts.
Perhaps the most instructive context is that of the selection of Dovid Hamelech. Shmuel is sent by Hashem to Yishai's home, only to find that once inside, he is on his own to choose one of the seven sons. After evaluating son by son, and erring over and over again, Hashem tells Shmuel: "al tabeit" - don't look at the outward appearances, for that is the limited and inadequate insight that can best be expected of people. Rather rely only on Hashem's ability to see into one's heart. Hence "haboto" refers to the shallow and undiscerning abilities of people.
Similarly, Avrohom in last week's parsha (15:5) is asked "habet no hashomeimo" - please look upward and as you appreciate that the stars are too many to count, understand that so will you children be too many to count. Avrohom was to take in the breadth of the galaxies and their imposing numbers and to realize that any attempt to study them is well beyond him. Once again "haboto" refers to the limited grasp that distance can impose.
That is why the song of Haazinu, in describing the love that Hashem harbors for His children, notes "lo hibit - He does not see the sins of His children". Surely it is the brief cursory glance that He allows Himself, which protects us and His love for us. Haboto does not catch our ugly side.
Thus the instruction, "al tabeit - don't look back" in fact informed her that she does not have the distance from the culture of Sodom to look in a discerning or studied manner. Her gaze would reconnect her to her friends and their evil behaviors rather than evaluate the vulgarity that she merited to leave behind. Her uncritical and even unrepentant moment would sever any potential connection to the legacy of her husband's uncle, and she no longer merited his protective shade.
Contrast this to Avrohom about whom it is said, "vayashkef - that he looked at the burning cities." That is how Avimelech is described when he discovers that Yitzchak is Rivka's husband, not her brother. It was a studied look evaluating their relationship and concluding that they were indeed married to each other.
That is probably what leads the Seforno to comment that during Avrohom's mountain top review, he became enraged with their evil and their decadence. Accordingly it is the moment that he accepted the futility of his own prayers. Thus "vayashkeif Avrohom" is a penetrating study with conclusive thinking.
Thus Hashem made the deal with Lot's wife that if she associated with Avrohom, and grew in her commitment to his moral lifestyle, his merit could rescue her. Yet if she would look back with naivete and undiscerning shallowness, and squander a moment of possible growth, she would be fated to become a memorial for unrepentant stubbornness.
The charge to Lot's wife is a resounding call to all of us, as suggested by Rav Zilberstein in his book aleinu leshabeach. "Al tabeit acharecho ve'al taamod" - if you don't look back at yourself, your talents and your accomplishments, with smugness and acceptance, but instead look with critical introspection, than you won't stand in one place and will continue to grow in the service of Hashem.