This post is dedicated in memory of Etya Sarah bat Yitzchak ha-Levi. May it be an aliyah for her neshama.

In Judaism, each of us are like our own private corporation. Instead of being held accountable to stockholders, we are held accountable by G-d how we spend the money. Each dollar we earn is scrutinized, perhaps none more so than the money we give away to those in need. It says in the Gemara, every year our total net income for the year is decided on Rosh Hashanah. If this is the case, why work hard after Yom Kippur? The answer is, because we have some control over this money. Say you are slated to earn $70,000, but only are allowed to keep $60,000 - what about that other $10,000. Well, you can give it away in the form of tzedakah, or you can have it pried from your fingers in unpleasant ways, such as speeding tickets (which are a double punch because now your auto insurance is going up), doctor's appointments, broken items around your home, etc. Tzedakah is very powerful. Our Sages say it saves from death (along with repentance and prayer). Every year on Rosh Hashanah we say during the prayer service as a reminder to ourselves that the way to be judged favorably and be inscribed in the Book of Life is through repentance, prayer, and tzedakah. Friends of mine have often remarked that they know they have not been giving their required 10%-20% of their income to tzedakah when they suddenly start getting parking tickets or other annoying and unexpected expenses. This is why my friends jump into action and quickly up their giving when they notice they are having a lot of surprise expenses. Better to part with your money on your terms and feel good that it is going to help people, than filling the coffers of tax collectors or your insurance company!
The first question you may have is, what is the difference between tzedakah and chesed. Of course you get mitzvah points for doing acts of chesed, beneficial and kind acts for others, but there isn't an obligation to do a certain amount each year. With tzedakah, it is written out quiet explicitly in the Torah that we have to give at least 10% - and as much as 20% if you are very comfortable (we learn out the 20% amount from the story of Yosef HaTzaddik. When he was viceroy in Egypt and the land was bountiful, the people were required to give 20% of their abundant crop to the country as a tax). There is no way in skirting this responsibility. Even those who must receive tzedakah are still required to give a portion of that money to others in need. Through this perpetual giving we have the opportunity to be reminded to be thankful for what we do have, as well as do our part to help our fellow brothers and sisters improve their lot. It is perhaps for this reason that our Sages say giving tzedakah is equivalent to doing all of the mitzvot in the Torah.
Additionally, there is a method for how to give. First, notice that 10% is all that is expected of you - you are not supposed to go broke through giving to others. Next, you are supposed to give first to those immediately around you in need: parents, siblings, and other family members, in this order. Only after you have ensured your family's needs are met, then you can expand and give to your community. After that, you can expand to those in need throughout your country. When it comes to Israel, no matter where in the world you live, Israel is considered to be a priority for giving, coming in after or alongside of giving to your own community. This is because Israel belongs to all Jews, so all Jews have an obligation to help out those who try to make their life in the land.
At the same time, people are supposed to work very hard to not need tzedakah. If a job is available, even if you don't like it, it is better to take it than to rely on handouts. The Rabbis in the Gemara are very clear that if someone makes themselves a burden on their community, they can lose their share in the World to Come. This is because the ultimate purpose of tzedakah is to give people the ability to get themselves to a place where they are once again self-sufficient with as much grace and dignity as possible. When giving to someone in need you are supposed to give according to their accustomed standard of living. That is, if someone lives a very simple life, then you can donate to them in order to maintain that lifestyle. However, if someone has become accustomed to a very luxurious lifestyle, and for some reason unfortunately loses their income, you are required to donate in order to help them maintain their high standard of living. This may seem unfair - you could help two or three families for the same price! But this is where we must remember to be sensitive to others and protect their dignity. It is very hard to go from one lifestyle to a much more modest one very quickly. What is most important in this situation is to ensure the person maintains his dignity in the process, otherwise it will be that much harder for him to lift himself up by the bootstraps and start over. The flipside of this is the reminder to try not to become too comfortable in an opulent lifestyle, so as not to be a burden on others if you happen to lose your income and need to start over with a much more modest income.
Now that we understand our obligation in tzedakah and what to give, in our next post on tzedakah we will learn how to give.
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