5. Remind him that you are proud of both his personal and artistic accomplishments. Express a deep hope that he can one day make a living as an artist, and express admiration for his bravery and courage. Making a living as an artist is one of the most challenging endeavors one can take on. It stems from a deep passion within, which is often difficult to explain or erase. Once an artist, always an artist. Your son is figuring out how to negotiate his dreams with real world responsibilities. He is no doubt filled with anger over not being able to succeed quickly enough, consistently questioning his talent and fearful about the future. His possible disdain for a profession such as yours could be a coping skill to handle these pressures. It could also be a defense mechanism, in order to shield him from the shame of taking his "daddy's money." It might be even be a natural rebellion against his father's lifestyle...and the list goes on! If you want to teach him something, explain to him that this is the profession you have chosen. Acknowledge and share with him your talent as a successful financial analyst. Tell him of the value it brings to your life, including the financial rewards and personal fulfillment you have attained. Your son needs to understand the meaning behind your professional choices, so he can continue to monitor and challenge his own. I would have this conversation sooner than later. Have the conversation today. You don't want to continue providing him with financial resources indefinitely. It serves neither of you individually, and does nothing to strengthen your relationship. I also caution you against removing your financial backing immediately. It is best to ease him into taking part in earning his own living. However, don't be mistaken, a carefully drawn out time frame is needed. Your son will begin to feel much better about himself as he becomes an earner. He will grow in leaps and bounds as he empowers himself. Your bond will strengthen as well, as he remembers your encouragement.