Some of the most difficult conversations I have with families are not about tax rates, structures or returns. They are about fairness.
Someone will mention, “I know my parents didn’t mean anything by it, but over time, it started to feel uneven.” And what they are describing is rarely a single event. It is a pattern that developed slowly, often without anyone intending it.
In many families, favouritism does not come from preference. It comes from perceived need.
One child struggles in school or faces health challenges. Another goes through a divorce, or a business fails, or a mental health issue appears. In these cases, support naturally flows toward the person who seems most vulnerable. This may take the shape of more time spent, more financial help given, more accommodation made, more tolerance granted.
At the time, these decisions were reasonable. Often, they were necessary, and the assumption was usually that things would rebalance later.
But they rarely do.
Over time, extra support becomes part of the family system. The child who needs help continues to receive it. The capable child, on the other hand, becomes “the strong one.” The independent child becomes “the easy one.” No one announces this shift—it simply happens. Parents still care deeply about all their children. Nothing about that changes, but what changes is how attention, advocacy and resources are distributed.
From a planning perspective, this matters more than many families realize. Because by the time estate planning, succession or major transfers are being discussed, the emotional patterns are already well established.
Family dynamics continue into adulthood
If reasoning has never been explained, beneficiaries begin to interpret decisions through their own lens. Why did one sibling receive repeated financial support? Why was another expected to manage alone? Why were certain risks absorbed for one child and not another? These interpretations quietly shape expectations long before any documents are signed.
In family office work, this often shows up later as “surprise” conflict.
Parents are confused, saying, “We treated everyone the same.” Siblings are frustrated: “It never felt that way.”
Both perspectives can be true.
Most parents respond to urgency, not comparison. They manage crises, trying to stabilize situations and protecting whoever appears most at risk. They assume the resilient child is fine, and often that child confirms it. Over time, independence becomes expected rather than supported.
Many families equate fairness with equality. But fairness is not purely mathematical; it is experiential.
These dynamics tend to carry forward into adulthood. Support continues through down payment assistance, business bailouts, childcare help, housing arrangements or emergency funding. Each decision makes sense on its own. Taken together, they form a pattern. By the time families reach major transitions—business succession, liquidity events, estate freezes or intergenerational transfers—that pattern has become emotionally charged.
It ends up influencing how every decision is received.
Fairness vs. equality
Many families equate fairness with equality—the same amounts, the same structures, the same rules. But fairness is not purely mathematical; it is experiential. It is about whether each child feels seen, respected and considered in the process.
When those elements are present, families are far more resilient, even when outcomes differ. When they are absent, even equal distributions can feel deeply unfair.
The families who navigate this well tend to do something simple but uncommon: They talk about it. Not once, and not just at the end, and not through documents. They also:
- Acknowledge patterns early.
- Explain why certain support is being provided.
- Name the trade-offs.
- Make space for questions.
- Revisit decisions as circumstances change.
They say, in effect, “We know this may look uneven. Here is why we are doing it. This does not reflect our love or our confidence in you. We are paying attention to how this feels.” That transparency changes how decisions are experienced.
From a wealth planning perspective, this is not “soft.” It is structural risk management. After all, unspoken resentment can become legal risk. Misunderstood intent can become governance risk. Emotional distance can become succession risk.
Once more, with clarity
Support given without context often feels like preference. Support given with clarity feels like care. Over time, the difference is profound.
Strong families are not built on perfectly equal spreadsheets. They are built on trust, communication and a shared understanding of how decisions are made. They are built on children who feel secure enough to be honest, and adults who do not feel they have to perform to remain valued.
That kind of family culture does not happen by accident. It is shaped deliberately, through awareness, humility and ongoing conversation.
And in my experience, it is one of the most important investments any family can make.
Elke Rubach is a Certified Financial Planner with CLU and MFA-P designations. Her expertise lies in optimizing income and tax efficiencies, achieving cohesiveness in financial and estate plans, and providing ongoing asset management strategies that foster wealth accumulation and growth. Elke is a reformed lawyer who earned her graduate degree in law, with a focus on banking and finance, at the London School of Economics, where she studied on a Chevening Scholarship. She worked as an associate at the London (U.K.) and Toronto offices of the law firm McCarthy Tetrault. During a stint in banking, Elke observed the life-changing impact of good financial advice and decided to switch to a career in financial planning and wealth management. She founded Toronto-based Rubach Wealth in 2012. Today, Elke is a sought-after speaker on wealth management, estate planning and philanthropy. She’s the founder of Fashion Heals for SickKids, which has raised more than $500,000 for pediatric cancer care and research since 2016. She also gives back with board and volunteer commitments with the Professional Advisory Council for SickKids Foundation, the Investment Committee at the Office of the Public Guardian, the advisory board for Transpod Inc., and the board of Ronald McDonald House Charities in Toronto.
The Canadian Family Offices newsletter comes out on Sundays and Wednesdays. If you are interested in stories about Canadian enterprising families, family offices and the professionals who work with them, you can sign up for our free newsletter here.
Please visit here to see information about our standards of journalistic excellence.