The Midrash quotes an often-used pasuk relating to the mitzvah of tzedakah, charity: Ashrei maskil el dal, b’yom raah yimalteihu Hashem, “Praiseworthy is he who contemplates the needy, on the day of disaster Hashem will deliver him” Tehillim 41:2. David HaMelech enjoins us to give tzedakah with understanding: delving into who stands before us and why; making an attempt to put ourselves in his shoes. The above pasuk addresses the needs of one who has not yet hit rock bottom. He is faltering and needs assistance to prevent him from falling into the abyss of abject poverty. We are admonished to support him: give him a loan; a job; an investment in his endeavor that demonstrates we believe in him. At times, such encouragement can have a greater effect than a check. Money can quickly be spent, while encouragement can catalyze one to strive harder, achieve independence. When one gives money, he should be maskil, contemplate his actions. Thinking can make the major difference between a handout that might be quickly spent and support that can transform someone’s life.
Kehillas Yitzchak observes that this pasuk which enjoins us to employ seichel, common sense, in supporting our brother follows shortly after the laws of shemittah, yovel, the paradigmatic laws which underscore the importance of maintaining everything, our sole manner of earning a livelihood, by letting our fields lay fallow for a year. It takes great bitachon to adhere to this mitzvah. Since bitachon is so important, and every person should strive to develop his own level of bitachon, one might mistakenly feel that it is his responsibility to teach others the importance of bitachon. For example, a poor man approaches someone who is able to help him and asks for a loan – or even an “investment.” The well-to-do would-be benefactor responds, “Why should you turn to mortals for assistance? You should have bitachon and turn to Hashem for help. Pray, and He will help you!” This is obviously the benefactor’s manner of avoiding an act of kindness. It is his “frum” cop-out. To him, David HaMelech asserts, “Praiseworthy is the one who contemplates the needy.” You (the benefactor) can be a believer, and you worry about your bitachon. When it involves another Jew, a poor man in need who turns to you for assistance, do not play the “bitachon card” on him. Help him! Do not preach to him about bitachon. One does not tell someone else who is in need that he must have bitachon; use some seichel – be maskil el dal and give him a check to cover his needs.
A well-known scholar once asked the Rosh Yeshivah of Novordok in Mezritch, Horav Avraham Zelmans, zl, a scholar who was well-known as one of that period’s chachmei ha’mussar, masters of ethical discourse, the following sheilah, question: Is it permissible for one to borrow money from another Jew, knowing fully well that in the foreseeable future he has no way of paying back the loan? Is he permitted to rely on bitachon, his trust in Hashem, that some way, somehow, he will procure the necessary funds to pay back the loan? Is he allowed to rely on his bitachon in order to borrow the money from someone?
The Rosh Yeshivah gave an insightful reply which addresses the crux of bitachon and defines our relationship vis-à-vis others. “If you are prepared to lend money to a person solely upon his bitachon,” he began, “in other words, he has no money and, for all intents and purposes, he has no means for obtaining sufficient funds for paying back the loan, then, you, too, are permitted to borrow under similar conditions. If, however, you are unwilling to part with your money based solely upon the borrower’s bitachon, you may not borrow either.”