When you choose to be a generous person there will be times you hesitate. There will be times you resist. There may be times you regret. That will not change the fact you are a generous person. However, that will effect how you give.
When you give to many people and to many organizations, you will most likely be burned at some point. Perhaps you give to an organization and they change their mission. Maybe you give to a person and the next week they go on a lengthy vacation. No matter the result of your giving, you still choose to be a generous person. You may, however, reassess your giving.
When you give there does need to be a certain amount of accountability. There will certainly be times that the giving doesn’t necessarily align perfectly with your desires and intentions. However, if your giving to certain organizations or individuals consistently evolves into results you do not agree with then you should re-assess your giving. You will inevitably be misled or misinformed here and there but if there is a consistent issue that pulls at your heart and thoughts then you should immediately reassess things and potentially stop giving to that organization or individual.
When it comes to giving to individuals this becomes magnified. Giving to individuals in your life may provide some of the highest impact that you can experience. However, you should ensure that your giving does not ultimately inhibit that person or contribute to bad money habits. Giving some people money may only serve as a band-aid approach and that doesn’t help them, you, or other causes you could otherwise help. If you know of an individual that you believe could benefit for your generosity it is appropriate for you to ask them questions about their financial situation and you should offer to provide them coaching about their money habits, budget, savings, background, etc. If they refuse to engage in honest, engaging conversations about their situation perhaps your generosity is not best for them. You should trust your intuition. Also, only give when you are okay with it being a gift. Never loan money to an individual. If they choose to pay you back some day that’s fine but always structure it as a gift and nothing else.