How Wealthy Families Help Children Find Their Own Path
After three years of preparing to apply to colleges in the United States, Carol came to her parents in tears.
By any objective measure she had done everything right and should have been excited about what was to come. She attended a strong trilingual school in Rio de Janeiro, Brazil, achieved high grades, and had the academic profile to pursue higher education at universities in the United States, Europe, or South America. Her parents invested in helping her keep every option open.
“I don’t think I want anything from this,” she said. “This is your dream, not mine.”
As we talked further, it became clear that the sheer weight of the possibilities brought her to tears. Instead of feeling liberated by her choice, she felt paralyzed. She ultimately chose to stay in Brazil, but only after giving herself permission to seriously consider other avenues. The process was difficult and emotionally taxing, but in the end, her family realized that the greatest value wasn’t the decision itself—it was her entering into a process of true self-discovery and making an informed choice about who she really could be.
This moment captures a paradox I often see among highly successful families. Parents spend years believing that more luck leads to greater freedom. But at some point, the number of choices can be a burden in itself.
Months after speaking with the Carroll family, I attended a private meeting of New York’s highest net worth families to discuss education, family legacy and preparing the next generation.
A parent shares her experience growing up thinking she and her siblings would take over the family’s tech business. Instead, she chose to pursue a PhD in psychology. Her parents were so upset that they did not attend her graduation. Her husband eventually joins the company with her brothers—but only after years of trauma, frustration, and estrangement from the family.
The experience shook her deeply. As a mother herself, she is determined that her children will never think that her love depends on following a certain path.
And yet, years later, she found herself expressing a different struggle. Her children – now young children – had grown up with every opportunity imaginable, but now they felt directionless, unsure of what their lives meant.
How are families providing their children with unique benefits and helping them find real purpose?
The most successful families I’ve worked with don’t compromise expectations. Instead, they describe them in their own terms. Instead of expecting their children to follow a predetermined path, they expect them to engage in a deliberate process of exploration before making important decisions.
In many entrepreneurial families, for example, joining the family business is not considered. Children are encouraged to develop identities independent of the family organization before deciding whether or not to return.
One family explained that each of their children was expected to work in at least two different fields before making any long-term career decisions. When a boy announces that he wants to open a restaurant, his parents either reject his idea or don’t immediately give him money. Instead, they had a condition: “First, go to work in a restaurant.”
The same principle applies whether a child is considering joining the family business or not. These families resist the temptation to write their child’s future or let them figure it out entirely on their own. They notice new needs, create opportunities to explore them, and then create space for reflection. Because trying something is only half the job. What did you learn in real growth?
One of the most important practices that families can do is to create regular opportunities for reflection. In the face of pressure to achieve, young adults are not encouraged to stop and think, such as: What have I learned about myself in the past six months? What activities motivate me and feel more like a duty? The answers can often reveal more details about a young person’s future direction than ever before.
Of course, this process does not begin with college admissions. That is simply a time when a family’s values are tested. It starts very early, in the small moments when a parent notices a toddler’s interest and chooses to take it seriously.
I think of one family who asks their child to write down a few birthday goals each year – things they hope to learn, try, or become. On the next birthday, revisit the list together and reflect on what was true, what changed, and what you discovered. It’s a simple ritual, but it sends a powerful message: your needs are important, your growth deserves attention, and in one year, a lot can change.
Action is as important as meditation.
I remember a young man in middle school who was fascinated by cars. Not as a passing hobby, his parents helped him spend part of the summer shadowing an eighth-grade mechanic. They weren’t trying to steer him toward any particular career path or bolster a future college application. They were simply helping him test interest. That experience led to new questions, new skills, and ultimately an engineering major.
Another student developed an obsession with buying, selling and trading baseball cards. His parents saw him as an opening to help him think like an entrepreneur. They discussed pricing, inventory, and customer service, and eventually engaged their family accountant to help them form an LLC. What started as a hobby turned into a business that—and most importantly—helped shape his sense of identity, responsibility, and autonomy.
In both cases, parents recognized a spark, provided structure and created opportunities for the child to practice ownership.
So how do children build their own paths? Not a single moment of clarity, but a series of experiences. One interest, one reflection at a time, with parents who take their curiosity seriously and give them permission to explore where it might lead to help it grow.
