In my Daily Dvar, today’s reading in Ahavas Chesed brought a very poignant Gemara in Bava Basra (10a).
There it says that just like one’s income is determined on Rosh Hashana, similarly the expenditures (or losses) one will encounter are determined on Rosh Hashana. If the person merits, they can be ‘lost’ by being given to the poor. If not, the money will be taken forcibly.
Rabban Yochanan Ben Zakkai had a dream where he saw that his sister’s children were to lose seven hundred dinars (an ancient currency) that year. Without telling them about the dream, he convinced them to give him a total of six hundred and eighty three dinars over the year. He wasn’t successful in getting the last seventeen from them.
It came Erev Yom Kippur, and the Caesar sent his henchman to grab money from them. On that day they took seventeen dinars. Rabban Yochanan reassured them that they need not worry that more would be taken. When his nephews asked how he knew that no more would be taken, he told them about his dream.
They proceeded to ask him why he hadn’t told them of the dream, so they could have given the full amount to charity instead of losing it to the Caesar! To this he responded and told them that he wanted them to be able to have the reward of giving the charity altruistically, without an ulterior motive.
For a deeper understanding of this, please listen there to episode 200.