Recently, a successful entrepreneur approached me for advice about his daughters, who are both in their 20s. They had attended the best schools and had every advantage, but he saw them as fearful of failure and hesitant to take initiative.

It struck me that this quandary was just as much about the father as his daughters – and that it is a common intergenerational challenge.

The father’s success was hard-won. He lost his own father when he was young, and all through university he waited tables in his mother’s small restaurant. He started a business with no family resources. He had no choice but to forge his own path in life.

His daughters, by contrast, were born into a world of peace and prosperity. I told him that he might need to accept that his children are more interested in happiness and fulfilment than in driving their careers and proving themselves.

A fortunate upbringing can have its downsides. I’ve observed executives from privileged backgrounds hitting a career roadblock in their 30s or 40s, revealing their fragile self-esteems. Adversity in their early years might have made them more resilient.

Bringing up my own nine-year-old son, I wonder if I, too, am depriving him of opportunities to fail that might provide important lessons for his future. For example, I recently considered enrolling him in an advanced Mandarin programme, but worried it might be too tough, and so chose a lower level.

Being a parent is a humbling experience. As the poet Kahlil Gibran wrote: “Your children are not your children… You may give them your love but not your thoughts, for they have their own thoughts.”

While we may need to let our children forge their own paths, we also need to ask them about their hopes for their careers and legacies. That might inspire them to try, to fail, and to learn – and so make a difference in a world in much need of their ideas and energy.

This article appeared in the Classified Post print edition as Is tough love best ?