Raising grounded children in a world of abundance requires leaving room for responsibility, disappointment and independence. The harder question is what that looks like in practice when parents can solve almost any problem.
One of the questions I hear most often from affluent parents is where to draw the line. Paying for university is rarely in question. The harder decisions come later: Should they buy each child a first home or fund a new business? Support a lifestyle their child’s income cannot sustain? Or use family relationships to advance a career?
For parents with more than one child, every decision raises another question: If we do this for one, what should we do for the others? These are exactly the questions families should be asking. The challenge is that none can be answered by a fixed rule or dollar amount alone. Each decision requires parents to consider what the support will make possible, what expectations it may create and whether it is helping a child develop independence or protecting them from something they may need to experience for themselves.
Kids figure it out on their own
Recently, I was speaking with parents who had done everything they could to help their daughter find a job. They used their connections, made introductions and secured an opportunity that appeared to be a very good fit. Then it began to look as though the position might not work out.
Before her parents could find another solution, their daughter decided to pursue the job she really wanted. She found the number, cold-called the organization and explained why she was interested. That call led to an interview, and the interview led to an offer.
When her parents told me the story, we laughed about the lesson it had been for all of them. Their original help had been thoughtful and came from exactly the right place. There was nothing wrong with using their relationships to create an opportunity for their daughter. But when that plan fell apart, she had the space to create one for herself.
The outcome was better than anything they could have arranged, not only because she landed her dream job, but because of everything she learned before she even started it. She identified what she wanted, advocated for herself, risked being told no and discovered that she could make something happen without waiting for someone else to open the door.
Her parents could help her find a job. They could not give her the confidence that came from making that call herself.
That distinction sits at the heart of so many decisions families of significant wealth face. Support and independence are not necessarily opposites. Parents can provide education, access, capital, relationships and security while still leaving room for children to take ownership. The challenge is recognizing when support is creating possibility and when it is replacing something a child needs to do for themselves.
Those decisions become more consequential as children move into adulthood.
The quiet expectations
Not long ago, I was speaking with parents who wanted to buy their daughter her first home. It was a gift they could comfortably afford and one they were genuinely excited to give. As we talked, however, the conversation quietly shifted. They were no longer discussing the house itself. They were wondering what would come next.
If the carrying costs exceeded their daughter’s income, would they cover them indefinitely? If she later wanted a larger home, would the original gift become the expected starting point? If her siblings made different choices, would they receive an equivalent amount? And if the home established a lifestyle their daughter could not maintain independently, had they given her security or created an expectation of continuing support?
But the family’s approach reflects an important principle: Different treatment does not have to mean unequal treatment.
What appeared to be a conversation about buying a home was, in reality, a conversation about expectations.
Wealth rarely presents itself as one dramatic decision. It arrives through hundreds of thoughtful and well-intentioned ones. A home is purchased. A business is funded. A position is created within the family enterprise. A loss is quietly absorbed. Financial support increases as a child’s expenses grow.
Individually, each decision may be entirely reasonable. Together, they quietly shape what becomes normal. Every act of generosity has the potential to become tomorrow’s baseline.
The home itself was not necessarily the problem. It could provide security and give their daughter choices unavailable to most people. The more important question was what the gift would set in motion. Would it expand her possibilities or establish a life that required continuing support? Did everyone understand whether the gift represented a beginning, a limit or the first of many interventions?
Long before children inherit wealth, they are developing a relationship with it. They are learning whether family money is a source of possibility or an answer that appears whenever circumstances become uncomfortable. They are learning whether setbacks require adaptation and whether choices still involve trade-offs when the family can afford almost anything.
The effect will not be the same for every child.
Wealth affects each child differently
Children raised in the same home, by the same parents and with access to the same resources can develop remarkably different relationships with money. One may be cautious, reluctant to spend even when doing so would create a meaningful opportunity. Another may assume that almost any desired lifestyle can be supported. One may instinctively seek independence, while another experiences family support as reassurance and security.
The same assistance can therefore produce very different outcomes. A financial gift may give one child the confidence to take a thoughtful risk. For another, it may reinforce the expectation that the family will absorb every consequence. One child may need encouragement to use the family’s resources. Another may need clearer limits because learning to make trade-offs is what will help them develop.
This creates a genuine tension for parents. They want to respond to each child as an individual, but they also want to remain fair. Different forms of support may be appropriate, yet differences between siblings can easily be interpreted as differences in love, confidence or value.
Equalization methods vary by family
One family I know has approached this thoughtfully. They accept that their children will require help in different forms and at different times. One may receive assistance purchasing a home. Another may receive capital for a business. A third may not need significant support until much later.
Rather than forcing every child into the same arrangement, the parents maintain an equalization ledger recording the major financial assistance provided to each of them. When one child receives additional support, they consider how an equivalent amount might be set aside or eventually provided to the others.
They do not account for every gift, vacation or ordinary family expense. The ledger is simply a discipline that allows them to respond to an individual child’s needs without losing sight of fairness over time.
In some cases, they may provide an equivalent amount to the other children. In others, they may add it to an investment account, preserve it for a future opportunity or reflect it in their estate planning. The support remains equal in value even when it is not identical in form, purpose or timing.
No system can eliminate every disagreement, and a ledger cannot resolve the emotional complexity of fairness. But the family’s approach reflects an important principle: Different treatment does not have to mean unequal treatment.
This requires clarity. Decisions that seem reasonable to parents can feel arbitrary or deeply personal to children, particularly when they are made privately or explained only after resentment has developed. Families may reach different outcomes for different children, but the principles informing those decisions should be consistent and clearly understood.
An outsider’s perspective
This is where a trusted third-party advisor can be valuable. The role is not to make parenting decisions or impose a standard formula. It is to act as a sounding board, help families identify what is driving a decision and create space for conversations about different needs, personalities and ideas of fairness before they become sources of conflict.
Those conversations should extend beyond who receives what and when. They can help children understand what the family’s wealth makes possible, the responsibility that comes with being a custodian of it and the power it can have to improve the lives of others.
The question is not only how wealth should be divided—it’s what is the wealth for?
The answer may look different for every child. One may feel connected to philanthropy. Another may want to build a business, support a community or contribute through their professional life. The goal is not to prescribe a single path. It is to help each child develop a relationship with wealth that reflects their own personality and values while remaining connected to the values of the family.
Families can give equally without giving identically. They can honour each child’s individuality without losing sight of fairness, responsibility or purpose.
Wealth creates freedom, but then what?
None of this means parents should manufacture hardship or deny their children the benefits of family success. Significant wealth creates extraordinary freedom. It can allow children to pursue education without debt, take entrepreneurial risks, contribute meaningfully to society and make choices based on purpose rather than immediate financial necessity.
Those are advantages worth sharing.
But generosity is most powerful when it strengthens a child’s capacity rather than substituting for it. Sometimes that means making an introduction. Sometimes it means providing capital with clear expectations. Sometimes it means helping one child now while deliberately preserving an equivalent opportunity for another. And sometimes it means allowing a plan to fall apart long enough for a child to imagine a better one.
Over time, I have come to believe that the greatest advantage wealth offers is not simply the ability to provide more. It is the freedom to be intentional.
The freedom to ask not merely whether something can be afforded, but what that support will make possible, what expectations it may create and how it will affect each child differently. The freedom to consider whether help is building confidence or dependence, and whether it can be offered fairly without being offered identically.
The line moves with every child, every family and every stage of life. Parenting has never been about applying the same answer to every situation. It has always been about judgment. Wealth simply asks more of it.
Lindsay Hollinger is the vice-president and co-founder of Granite Family Office. She began her career as a tax lawyer at McCarthy Tétrault LLP and remains a member of the Québec Bar. Since 2022, Lindsay has served as a lecturer at McGill University’s Desautels Faculty of Management and is a frequent speaker on financial literacy, investing and strategic philanthropy.
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