The Jewish tradition’s levels of generosity — from public giving to anonymous giving to giving where nobody knows — maps to a deeper principle: the depth of generosity corresponds to how much it disintegrates the ego. When nobody knows about it and you’re still giving, the self-defining quality drops away and what remains is pure generosity.
“The depth of the generosity is in how much you are self-defining on it or how much your ego is cracking.”
This is why generosity “cracks you open” — it literally breaks down the boundaries of self-interest. Giving from a position of superiority (“I’ll help those poor people”) actually reinforces ego rather than dissolving it, which is why it often creates unhelpful dynamics. Joe describes Canadians bringing clothing to Nicaragua without asking for anything in return, inadvertently teaching recipients they can’t care for themselves. True generosity includes respect — it sees the other person as capable and dignified.
The most ego-dissolving generosity may not feel like generosity at all. Joe notes that his work no longer feels generous to him — it feels like living on purpose. When generosity becomes your natural mode, it stops being something special you do and becomes who you are.