I have been giving Chomesh for almost two years now and I am losing money. I have followed the rules about giving to a family member who studies Torah and who really needs it because they don’t have any other source of income. On June 30th I had a certain amount in my savings, and today I have $586.51 less than what I had on June 30th. The promise of Chomesh is that it’s the only thing where we can test G-d to see if he will send us a fortune (in money, not in other things). This is obviously not happening with me and it’s in fact going the opposite way. I feel like I was falsely led to believe that I would increase my monetary wealth by giving Chomesh but that never happened. I feel desperate and I feel like a fool. I don’t regret helping my relative because they really need it, but this is causing me not to be able to save money for my old age or in case I lose my job. I am 56 and there are not that many job opportunities for someone my age. I have enquired about this with several rabbis but nobody has an answer. I beg you to please help me make sense of this and if you don’t know the answer please refer me to someone who does. The promise of wealth is very clear that it is for monetary wealth, not health or other things. Those are wonderful blessings which I appreciate very much, but I started giving Chomesh to increase my monetary wealth. Thank you.
You sound pretty upset, and to be honest about it, I also give chomesh and I have not (yet) become rich. Nevertheless, we have to know clearly, that Hashem knows what He is doing, and He will pay us back for all the mitzvos that we do. Not always will it necessarily be in the form that we expect. The Navi says, the same way the heavens are above the earth, likewise the ways of Hashem are above us, (and superior to our ways) and thoughts, and expectations. Therefore, a Jew never regrets ding a mitzva, especially when it comes to tzedakah. Chazal say that a person never loses out from giving tzedakah. The money that you gave to your children as tzedakah will be given back to you. You might not notice it, because Hashem is not going to send us an itemized accounting how he has paid us back for you mitzva. (IY”H one day we will be able to see the accounting… but and we aren’t in a rush to get to the place where we’ll see it).
One other point before addressing your actual question, the poskim say that when a person gives maaser, it shouldn’t all be to one person, rather part should be given to other poor people (ע’ ערה”ש יו”ד ס’ רנ”א סע’ ד’ וה’) .
Getting back to the actual issue. Your question is asked by a number of Rishonim and Achronim, actually, there is a sefer called B’orach Tzedaka (R’ Y. Feinhandler) and he devoted an entire chapter (in his second introduction) to addressing your question. He brings the Chida (Bris Olam on sefer Chasidim 395) who specifically asks this, and then the author (in B’orach Tzedakah ibid) brings a number of answers. Here are some of them.
- If the money (or even part of it) was not earned honestly. (Chida ibid).
- If the person does things that cause one to lose their money, (not paying workers on time, taking ribbis, stepping on bread, etc.) by giving tzedakah the person will not lose his money. (Chofetz Chaim Ahavas Chesed 2 Chap. 19 in comment. The Chofetz Chaim says there, that chazal say “עשר בשביל שתתעשר עשר בשביל שלא תתחסר” , give maaser so you should be come rich, give maaser so you won’t become poor”. If one will get rich, obviously he won’t become poor? He explains that the latter is to prevent the person from becoming poor because of things that he did which cause one to become poor.
- If the person has large aveiros, that are blocking the merit of the tzedakah to take effect. (Nevertheless, the mere fact that the person gave tzedakah and didn’t become rich, can serve as an atonement for some aveiros). (See B’orach Tzedakah ibid footnote 12 for further discussion in this.)
- The Chofetz Chaim (Al Hatorah pg. 259) says that there are times that person will give tzedakah and specifically become poor! The reason for this is, because this person was really supposed to die, r”l, and because of the tzedakah he gave, Hashem switched that decree, and instead he only lost money, but not his life. As a side point I also heard this idea in the name of R’ Eliyashiv zt”l. He said that there are times when Hashem will switch the money and “riches” the person was supposed to get, and he pays him back with something that is worth a lot more! Such as if the person was supposed to get sick, or a calamity was supposed to happen to this person’s relative, Hashem will switch the money, for good health, and spare the person the calamity. This indeed not a monetary payment, but the person is not now a lot richer than he would have been without Hashem switching the two. (From a different angle; being saved from having to do an expensive operation, or some other major financial expense, is no less than earning that money.)
- If the person used his maaser, to perform his own mitzvos with it, instead of giving the money to poor people. (This doesn’t apply to the chomesh part that was given), or if the person didn’t give maaser correctly, such as not giving maaser from the original principle money, but only from the profits. (As a side point it is a good idea to buy a sefer that will help you learn all the halachos of giving maaser correctly.)
- Rabeinu Yona (Sharei Teshuva 3-9, see sources) asks your question, and answers, (based on a number of verses in Mishlei), that there are times when not getting the money is actually to the person’s benefit. Because Hashem wants to give the person a larger, everlasting reward for his mitzva in Olam Haba. (This is the best retirement investment you can make.)
As a closing point, as we have seen, giving chomesh is quite worthwhile, and very profitable, even if it isn’t in the form of “greenbacks”, and is in our “best interest” to keep it up. Especially since some of the reasons why the person didn’t become rich until now (because of a certain decree, or as an atonement for certain aveiros), and when that issue is taken care of due to previous maaser or chomesh, the person might actual get rich. Therefore, we have to keep it up, and trust the one who knows best, that he has our best interests in mind.
Best wishes, and Hashem should send you a great fortune in this world and the next.
P. S. Don’t underestimate the great fortune that it is, to have a relative learning in kollel, and raising a fine family of Torah observant Jews. We take it for granted, but it is a true fortune.
 ספר שערי תשובה לרבינו יונה שער ג אות ל וז”ל “ואמרו רבותינו זכרונם לברכה (תענית ט א) כי במצות המעשרות בלבד הותרה הבחינה, שנאמר (מלאכי ג, י): “הביאו את כל המעשר אל בית האוצר ויהי טרף בביתי ובחנוני נא בזאת”. ואמר שלמה עליו השלום (משלי ג, ט – יא): “כבד את ה’ מהונך ומראשית כל תבואתך”. וימלאו אסמיך שבע ותירוש יקביך יפרוצו. מוסר ה’ בני אל תמאס ואל תקוץ בתוכחתו. פרוש: אם לא יהיה לך כן להמלא אסמיך שבע, בתתך מהונך ומראשית כל תבואתך לעבודת הצדקה, אבל יאחזוך ימי עוני, אל תמאס מוסר ה’, ודע כי גם זה לטובתך, “כי את אשר יאהב ה’ יוכיח” (שם פסוק יב) – להיטיב באחריתו, להיות תמורת שכר העולם הזה ותחת כבודו, שכר אמת והטוב הצפון העומד לעד לעולם”.