Beit Midrash
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Answer: It is important to understand that ma’aser kesafim (which you are blessed with the wherewithal to perform and bodes well for your financial future – see Ta’anit 9a with Tosafot) is not an independent mitzva but rather a mode of fulfilling the mitzva of tzedaka (see Shulchan Aruch, Yoreh Deah 249:1). There are various opinions whether ma’aser kesafim is required from the Torah, required Rabbinically, or a recommended practice (Shut Chatam Sofer II:231), with the latter being the more accepted opinion (see Living the Halachic Process, G-8). Poskim say that the practice has the potential of become binding as a repeated mitzva practice. Therefore, one should begin ma’aser kesafim with a stipulation that it not become a neder, or at least that he not be bound to follow the more stringent opinions (see Chatam Sofer ibid.; Ahavat Chesed II:18). It should not be too surprising that this less structured and halachically fluid practice has fewer classical sources and analysis than one might have expected.

Bemare Habazak - Rabbis Questions (626)
Rabbi Daniel Mann
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Let us discuss principles of preference and suggest a basic approach that will work well for many people. First, realize that ma’aser kesafim adds two stages to the basic action of tzedaka: calculating and setting aside the money. It is generally worthwhile to do these in proximity to each other, as once one has determined how much he "owes," he should act with diligence.
One principle of tzedaka is that quantity of actions counts. The more chesed-related acts one does (even "smaller" ones), the better it is for developing positive attributes (Rambam to Avot 3:15). While the Rambam refers to giving money to the ani, this should apply to setting aside money as well. Ma’aser kesafim, after all, separates the experience of tzedaka, as one "takes money out of his pocket" at a different time from when he gives it to the poor person. Therefore, it is good to actively set aside money periodically, even if exact calculation is only done once yearly. One may estimate the amount due and adjust later, including downward (see two opinions in Ahavat Chesed ibid. and the lenient ruling in Tzedaka U’mishpat 5:11 and Living the Halachic Process I, F-5).
Some people’s style and finances make it wise to set aside money as it comes in (for most, from salary), and some set up a hora’at keva (standing order) to ensure consistency. However, this is not necessary and may not even be preferable according to the above Rambam. It is perfectly acceptable to time contributions when you have extra income (e.g., bonuses, help from parents, investment sales).
Nowadays, when much finance is done through bank accounts and electronic payments, it is usually wise to set aside funds in forms that make contributing sizable sums efficient. While there is logic to disbursing money diligently, for many there is great wisdom in keeping significant funds on hand. This makes sense when one wants to be prepared for large needs among family or friends or is waiting for campaigns of favorite charities. Placing such "donations in waiting" in a gemach that guarantees return of funds as needed is ideal to both keep tzedaka money in use and remain prepared.
May we always have the ability to give to others.

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