Your son may not be taking the easy way out. It is most important that he be challenged and have ambition, which can be endangered by growing up in an affluent environment. Your son might see following in your footsteps as "the easy way out." He is choosing a course that will certainly be challenging and require discipline and motivation. You should be proud that he is seeking his own challenges.

Even if you are disappointed, keep all doors open to him. Remember that the prodigal son came home! Your son could change his mind sometime in the future and want to join you in the family business. If so, it is quite possible that his outside experiences will cause him to gain additional insights and a breadth of vision that will benefit not only him, but also your family business.

Bruce Stone, estates attorney, Goldman Felcoski & Stone, Coral Gables, Fla.

The differences between you and your son are created by conflicting and competing values. Your son feels the freedom to take the "follow your dreams" approach to work, and your attitude comes from another part of the spectrum, knowing the character building that is inevitable in successful entrepreneurial endeavors.

You don’t want him to miss one of life’s most precious rites of passage to maturity, yet clearly you have allowed him to follow his dreams to some extent in his studies. You can encourage him in both priorities: yes to graduate school and yes to developing his academic achievements into a career. He is young, and assuming that you still hold the keys to his financial freedom, it is likely that you will be able to gain his cooperation.

Encourage him to develop his talents to the highest degree he can. Applaud his successes. At the same time, require that he develop the expertise and responsibilities of financial literacy. Remember, the strongest families are those in which the individual members are encouraged and supported in developing human capital based on their inherent gifts.

Thayer Willis, family counselor and author of Navigating the Dark Side of Wealth, Lake Oswego, Ore.

Start by discussing with your son his motivation for going to grad school. If it is to pursue his passion, challenge himself and find his own way to contribute to society, then it could be the best path for him. At that point, you might discuss as a family how you can support this path to further develop his character.

If grad school is merely a way to avoid growing up, as with so many students I see, then I would be far less inclined to enable him to use the family’s wealth for it. He would just be avoiding testing his mettle and finding out who he is and what he stands for. This helps no one.

Think less about exactly which path he chooses and more about his motivation, the family’s support (without enabling) and the consequences of either path. Good, honest communication that includes expressing your family’s values and concerns, as well as the parameters of your support, is essential.

Greg McCann, director, Family Business Center, Stetson University, Deland, Fla.

Rather than convincing your son that he needs to work, explore various options.

A full-time job can open up exciting possibilities. It can lead to connections and exposure to situations that he will never encounter otherwise. Talk about what he enjoys, and help him investigate what jobs might be a good fit for him. Suggest that he try one out, for the experience. He might discover he likes it.

Explore with him why he wants to study philosophy on the graduate level. If he truly has a passion for this field and has a plan to earn an advanced degree, conduct research and teach at the collegiate level, then it might be better to be supportive of his career aspirations.

Trudy Steinfeld, executive director, Wasserman Center for Career Development, New York University

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