Perek 58 (the Haftara we read on Yom Kippur morning) includes Yeshaya`s reminder to the people to ensure that their fasting and teshuva moves beyond external actions, and is actualized by caring for the poor.
The Alshich comments on the double command of the Navi, who encourages the people to “Give bread to the poor, and bring them into your house.” He explains that merely giving bread to the poor is symbolic of giving a person charity without investigating what the specific needs of that person are. In addition to the immediate giving of tzedaka (charity), one should bring the poor person into the home, symbolic of coming into close proximity with the poor person, to identify and attend to the person’s specific needs.
We can take the Alshich`s stress on the importance of close proximity to the receiver of tzedaka a step further. It is emotionally more comfortable to give tzedaka to a poor person from afar, to so to speak “use the poor person as one’s Lulav,” and do the mitzva of charity without ever having to emotionally sympathize or more importantly, empathize, with the poor person. Bringing the poor person into the home is a way of breaking down that barrier, of ensuring that not only does a person give the poor person the money, but he connects to and empathizes with, the receiver of his charity. Similarly the Rambam in Avos writes that it is better to give one coin a thousand times, rather than a thousand coins in one go, because it makes one into a more giving, empathetic person. Tzedaka is not necessarily about the amount given, but it is about caring for the poor person.
This finds its expression in fast days, as the Gemara in Brachos 6b says: “The main reward one receives for a fast, is for the tzedaka he gives afterwards.” The Ben Ish Chai explains that the experience of a fast should help one empathize with the poor person who lacks food, and this understanding will lead to the giving of tzedaka. We should make efforts to empathize with those going through difficulties, and not merely help them from afar.