"become a lawyer"
Aristotle would say that Henry was not living the good life. The good life, according to Aristotle, is a life of eudaimonia, which is often translated as "happiness" but is more accurately understood as "human flourishing." Eudaimonia is achieved through the exercise of virtue, and virtue is a disposition to act in accordance with reason.
Henry did not act in accordance with reason when he attended law school. He did it for the wrong reasons: to please his father and to get financial support. He did not do it because he thought it was the right thing to do, or because he thought it would lead to a life of happiness.
Aristotle would advise Henry to follow his own path and to do what he thinks is right. He would tell Henry that he should not be afraid to be different, and that he should not let other people's expectations dictate his life.
Sue and Henry differed in their reasons for attending law school. Sue wanted to go to law school because she was interested in the law and she thought it would be a fulfilling career. Henry went to law school because he felt he had to, not because he wanted to.
Sue was acting in accordance with reason when she decided to go to law school. She was doing what she thought was right, and she was doing it because she thought it would lead to a life of happiness. Henry, on the other hand, was not acting in accordance with reason when he decided to go to law school. He was doing it for the wrong reasons, and he was not doing it because he thought it would lead to a life of happiness.
A person can be happy if the reason they do a task is for some other reason then itself, but only if the reason is good. For example, if Sue went to law school because she thought it would be a way to help people, then she could still be happy even if she did not enjoy the work itself. However, if Sue went to law school because she thought it would make her rich, then she would not be able to be truly happy unless she actually enjoyed the work.
In the end, Henry was able to find happiness by following his own path and doing what he thought was right. He was able to achieve eudaimonia, or human flourishing, by living a life of virtue.