Charity

I always learned that one who gives tzedaka is supposed to be blessed with more parnassa. Well, for decades, I have given lots of tzedaka to the best of my ability, and despite all that, I have almost always struggled to pay my bills. I am currently in mountains of debt with no hope of ever getting out of it for the foreseeable future. Most years of my adult life, I have struggled in poverty. I have tried my best to do well, but I have limited skills. As I mentioned, I have always given tzedaka when I can, whether it be minimal amounts or more. For several years of my adult life, I have done well and earned lots of money. These periods have been very limited. And when I did, I was very generous with my tzedaka, giving at least 10% of my income. These were times when I was able to afford to. So what reward did I get? The answer is my success dried up very soon after and I sunk back into poverty. I have never desired to be super wealthy. I only wish to be able to pay all my bills on time and to live without the anxiety of wondering where my next month’s rent or next meal are coming from. It also bothers me that my failure to earn a sufficient income has hurt others, others who are very dear to me, as I have often caused them to be disappointed in me and to have to bail me out. Often I wonder if my failures in life are punishments for my imperfect deeds or my imperfection at reciting my daily prayers. Then again, I see there are lots of people out there whose deeds and prayers are comparable to mine and they don’t struggle like this. And of course I have prayed numerous times in many different ways for an improved parnassa, but G-d has still not granted me that. And no, I have not lost faith in G-d. I just fail to understand why G-d has withheld this reward from me almost my entire life that I have learned about again and again. I have asked many rabbis about this in the past and they have told me this is not a punishment but a test. Well if that’s the case, then why has this test never ended? Why has it gone on for more than half of my life? Why has it not been temporary? I know that in reality, my job skills and prospects and my abilities to gain new skills are limited, but I know there are people out there who have more limited skills than I do, and they do much better than me. I have tried my utmost best, trying out a variety of lines of work, mostly with little or no success. I am nearing traditional retirement age, after which I expect to be living on a fixed income, and that which is due to me is by far insufficient to pay my rent or bills. Time is running out and I won’t know what to do then. So, if G-d is supposed to grant an improved parnassa to those who give tzedaka, why has it never happened to me after so many years?

I know I am supposed to give 10% of my income to charity. But I am currently in a mountain of credit card debt that accumulated when I was unemployed. The longer I go without paying it off in full, the more interest I am charged. Therefore, the wisest thing to do is to pay as much as I can until the balance is zero. This is likely to take several years. Am I still obligated to give tzedaka at this time if it’ll cause me to end up paying more interest?

If a person only has enough money in the bank to pay rent, should they still give maaser first? Or wait till they can pay it without it compromising other expenses?

Does paying for one's children for things like food, clothes, school etc count towards the 10% of charity?

I am scrupulous to give at least 10% of my income to tzedaka. There are a few local Jewish charities I like to support. I have been giving all my donations once a month on a single day in order to make things simple, plus I have some autopay donations. But I recently heard that one is supposed to give tzedaka daily except on Shabbat and Yom Tov. Is that really true? Or are the monthly donations sufficient?

Suppose a person claims they need money for a particular reason and you donate them money. Then you find out later they were deceptively lying and didn’t need the money. Have you still fulfilled the mitzvah of giving tzedaka?

This question revolves around the Second Tithe and Tithe for the Poor summarized in Deut 14:22-29. For the sake of clarity, let's assume we live in the Land. In Deut 14:22-27, the Torah indicates that every year of the 7-year shemittah cycle, we should observe the Feasts (Pesach, Shavuot, Sukkot) in the place G-d chooses i.e. Jerusalem if residing in the Land. Deut 14:28-29 is unclear on how one is to use their Festival (Second) Tithe and go to Jerusalem each year and how to distribute the Poor Tithe in Years 3 and 6. I've searched the Mishnah and other sources but could not find any real-world examples of how this was done and how we could use the principles for observing the Feasts and Tithing to the Poor in Years 3 and 6 today. To summarize the Question: During the Maaser Ani years, if the tithes were given to the poor, how did the pilgrims pay for their travel and eat when they went to Jerusalem? Or, is the Poor Tithe an additional tithe aka Third Tithe in Years 3 and 6? Any resources that would help explain how this was applied would be greatly appreciated as I am working on a Teaching on this subject.

There is a custom that some people have when they travel to take along a dollar bill with them that someone gave them and donate it to tzedaka upon their return. When you do that, are you required to give the exact same dollar bill that someone gave you before your trip? Or can you give any dollar?

If a Jewish organization approaches an individual begging for tzedaka to support their operations, but the one who has been approached does not agree with their philosophy or their practices and would rather give tzedaka to someone else who is a better match, are they required to give to that organization? I am asking because this happens to me all the time. I am constantly barraged with mailings, phone calls, and door knockings from Jewish organizations I am not comfortable giving to because what they stand for does not match my personal values. I do give a lot of tzedaka, but to those individuals, organizations, and causes I feel comfortable with.