Increasing Tzedakah:
There is a common minhag to increase the amount one gives to tzedakah before Sukkos. The source for this is the Arizal (Pri Eitz Chaim, end of Shaar 28) who says that on Erev Shavuos one should give a lot of tzedakah. It is stated that his student, Rav Chaim Vital zy”a, would give away all of the money they collected for tzedakah on Erev Sukkos and he would say that giving charity on this day is very effective.
Making Other’s Happy:
It is stated in Siddur Hatanya (257:3) that true simcha is not being happy by oneself. Rather, it is to make others happy. He compares this to one who makes a wedding for his son and does all he can to make everyone else happy.
Therefore, he says that one should give as much tzedakah as he can on Erev Sukkos, in order to provide the poor people with a joyous yomtov. One should ensure that not only is he happy on Sukkos, but that others are happy as well.
The Sanzer Rov’s Avodah of Tzedakah:
The Sanzer Rov zy”a made sure to give a lot of tzedakah on Erev Sukkos. Although he lived in poverty and had very little money, he distributed quite a bit of tzedakah throughout the year. It is said that he wouldn’t go to sleep without giving away whatever he had to the needy. However, on Erev Sukkos he gave out even more. In addition to giving away whatever he had, he would take out loans and pawn his belongings to get more money to give.
One Erev Sukkos, one his sons said to him, “Tatte, I haven’t seen any sefer that says that there is a mitzvah of tzedakah after one gave away all of the money he has!”
The Rov got very upset at him and said, “I don’t know how a son of mine could want to kill his father! Can’t you see that I have almost no Torah or yirah. All I have is a bit of tzedakah, and you want to take that from me as well?”
