“ויקמו משם האנשים וישקפו על פני סדם ואברהם הלך עמם לשלחם.”
רש”י: “וישקיפו על פני סדום – כל השקפה שבמקרא לרעה חוץ מהשקיפה ממעון קדשך, שגדול כח מתנות עניים שהופך מדת רוגז לרחמים.”
The Mashgiach zt”l was not very fond of what we commonly refer to as “hashkafos”. In that regard, he would often quote the above Rashi, “כל השקפה לרעה”- Every hashkafa is for the bad. This was more than a clever play on words.
Why does the word “השקפה” always have a negative connotation in the Torah? Similar to the word “משקוף”, which refers to the beam which rests above the doorway, “השקפה” means to observe from above. Meaning that the observer examines the other person from his own position, at a distance; he makes no effort to enter the world of his subject. When the Malachim looked toward Sedom- “וישקיפו”, they were evaluating Sedom from the vantage point of a Malach: what is expected of a city, how a society is meant to function. Extenuating circumstances and justifications were not a part of the equation; either you meet up to expectations, or you don’t. Sedom did not. But not only Sedom- “כל השקפה שבמקרא לרעה”- everything in our world is “רעה” when measured against a towering, uncompromising ideal.
That is the defining characteristic of “hashkafos”- to approach life from an entrenched, self-possessed point of view. A person who is very taken with his own “hashkafos” will not learn from life. He has the “emes” already; there is nothing left to learn. All that remains is for him to evaluate the different things that are happening around him, according to that which he knows to be true. The Mashgiach held that a person has no right to observe the world from the “outside”, imposing his convictions upon it. No, the world speaks to the person and teaches him.
At times, the world also makes demands upon a person. An avreich is sitting and learning, but his bank account is empty and he cannot pay his bills. The Borei Olam is communicating to him, through the world, “I want something from you.” Perhaps the Borei Olam wants him to be a Rebbe out-of-town, but his “hashkafos” won’t allow him to hear that. “I’m young; I still need to learn.” So how does he respond? It’s all a test. And then the electric bill is the Yetser Hara, and the water bill is the Yetser Hara, and sometimes his wife is the Yetser Hara. But the truth is that Hakadosh Boruch Hu can also speak to us through money problems. We just have to be willing to listen.