All parents want happy and fulfilling lives for their children. At the same time, young people want the approval of their parents. Promoting only career paths with a higher chance of monetary wealth and discounting the expressed interests and passions of a young person can lead to broken relationships and career dissatisfaction over time. The good news is that people can have meaningful and joy-filled lives at a wide range of incomes. Parents can play a crucial role in their children’s future happiness by listening well, encouraging often, and remaining open-minded about the paths their teens will choose.