Look down (hashkifa) from thy holy habitation, from heaven, and bless thy people Yisra᾽el, and the land which thou hast given us, as thou didst swear to our fathers, a land flowing with milk and honey. (Devarim 26:15)

Chazal tell us that whenever the torah uses the word “hashkifa”, it has a negative connotation – except in this week’s parsha, where it is used positively in connection with giving maaser properly. (See Rashi Bereishis 18:16.)

The Divrei Malkiel (Rabbi Malkiel Tzvi HaLevi Tenenbaum 1847-1910) explains this anomaly. Why would “Hashkifa,” usually associated with something unfavorable, suddenly become positive?
When certifying food for kashrus, we use the term “hashgacha”, which implies intentional, careful oversight. “Hashkifa” is similar – looking from above, observing what is going on – but with a significant difference, which he explains as follows:

The world generally runs according to nature, yet at times Hashem deviates from nature and performs miracles. The gemora in Shabbos (53b) provides an example. A man’s wife died, leaving behind an infant. The man prayed to Hashem to be able to produce milk to feed his baby, and Hashem granted his request. The gemora debates whether this man was a great person, worthy of such a miracle, or the opposite – demanding that Hashem change nature for him shows a lack of greatness.

We commonly speak of “hashgacha pratis” – Hashem guiding events through natural means. But we never use the phrase “hashkafa pratis,” because hashkafa implies something out of the ordinary. Since Hashem constantly showers us with His goodness, anything “off” indicates something negative. This raises the question: why does the Torah use the typically negative word “Hashkifa” regarding the person who gives maaser?

The Divrei Malkiel answers with an insight familiar to many. When someone collects for a penniless widow or a father who lost his job, people understand the obvious need. But when someone collects for a kollel or Torah institution, people often respond, “Why don’t they just get a job and earn a respectable living?!” Thus, there two categories of charity: One that people naturally view as a mitzvah; and one they struggle to appreciate – giving only from a sense of hashkafa, in a begrudging way.

Yet the Torah tells us why we give maaser to the Levi and the Kohen: They cannot earn a living in the usual way, because they are devoted to serving Hashem. When we remember this, our perspective shifts from an attitude of hashkafa – a negative, skeptical view – to hashkafa litov – seeing our support of them in a positive light.

About 20 years ago, a friend of mine, a distinguished rosh kollel, made a siyum in his Jerusalem kollel. Rav Tuvia Weiss, the gaavad of the Eida Hachareidis, was invited to speak. At that time, a single individual was supporting the entire kollel. Rav Weiss quoted the pasuk: “Eitz chayim hi la’machazikim bah, v’tomcheha me’ushar.” He explained: There are people immersed in the world and the way that they remain sane is by maintaining a connection to Torah. For them, Torah is an eitz chayim – like a drowning man holding onto a branch to survive. Others, however, feel that since they give money to support Torah, the Torah exists because of them. Such people are also meushar (fulfilled) – blessed from Hashem – but it cannot compare to those who recognize that it is Torah that sustains them, not the other way around.

As we prepare for the Yomim Noraim, one mitzvah in which people overextend themselves is Tzedakah. When supporting Torah, we should try to see ourselves as those whom Dovid Hamelech refers to as “eitz chaim…” – people upheld by the Torah, rather than people who imagine they are upholding Torah. If we internalize this, we fulfill the words of the Divrei Malkiel as Hashkifa, which is usually negative, is transformed in the context of maaser into hashkifa litov.