Equality Isn’t Always Fair: Evaluating Multigenerational Wealth Decisions in Context of a Family’s Values
Parents do not always treat their children identically. Especially when children are still young and living under the same roof, most families do not think twice about it. One gets the video game console she’s been asking about. Another gets a telescope because he spent the summer talking about the moon landing. The same logic shows up in the activity budget every year: a $3,000 travel soccer league for the daughter who’s serious about it, a $200 day camp for the son who’d rather just be with his friends. Few would identify this as favoritism.
That instinct changes once children become grown adults living lifestyles shaped by their own decisions, with few specific costs left for a parent to respond to. The shift is pronounced when giving moves from a birthday budget into a will. This space is where feelings of indecision and anxiety about conflict with loved ones tends to take hold, which is why it deserves direct attention rather than avoidance.
We recently wrote about why families avoid the inheritance conversation altogether. This piece assumes that conversation is already happening and asks the harder question that builds from it: once parents are talking about how to divide what they’ve built, what do they do with the fact that their kids are different people with different needs?
This piece works through what is a fair decision when equal division doesn’t fit, what it takes for the people receiving an inheritance to be ready to hear it, and where a financial advisor for inheritance planning fits into getting the structure right.
Equal and Fair Are Not the Same Thing
Equal is a math problem. “Right” is a family problem.
When parents divide an estate three equal ways between their three children, that split often happens before anyone sits down to talk through what each child needs. An equal division can feel like the simplest starting point, particularly when children’s circumstances are relatively similar. However, circumstances can change over time, which may cause families to reconsider whether an equal division continues to reflect their intentions.
That default usually works as long as the children’s lives stay roughly similar. It becomes harder to sustain when circumstances vary. One child may be managing medical costs from a chronic health condition, another has built a business from the ground up and reinvested everything back into it, and a third has a child has a disability who will need financial support for the rest of their life. Fairness asks a different question: what does each child need to reach a similar starting point?
This is often where inheritance planning breaks down: nobody made a bad decision about how to divide the estate. Nobody may have made a decision at all. The equal split became the plan by default, not because a family sat down and agreed it was the fairest way to reflect what each of their children needs. Successful multigenerational wealth planning starts early and asks what fairness should mean for this specific family before the estate documents get drafted.
The Real Mechanism Behind Fair Inheritance Planning
Families often treat the choice between equal and equitable as a neutral, almost mathematical decision. It isn’t. Choosing to split an estate into identical shares is itself a statement about what a family values, not a default that avoids taking a position. The Portfolio Strategy Group (PSG) recently hosted a Family Capital conversation with Dr. Joe Schippa, PhD, MBA. During the webinar, PSG Wealth Advisor Natasha Hanan asked, “Get down into the values. What do you value? How does that play out in how you divide what you’re giving?”
The following scenarios were discussed:
The $200,000 Education Gap
Consider a hypothetical example of two grandchildren from the same family. One attends a four-year private university, and the other enrolls in a two-year community college closer to home. Over four years, the family spends roughly $200,000 more supporting the first grandchild’s education than the second. On paper, that looks unequal. Is it unfair?
Dr. Joe Schippa’s answer is no, and his reasoning gets at why: “I don’t think anything is that black and white. I would have to look at each individual situation and say, what does this person need?” Different amounts spent, same underlying intention: give each grandchild what their specific path really requires.
When Equitable Reasoning Gets Uncomfortable
Not every case resolves as cleanly as the one above. PSG Managing Director, Thomas Zottner, CFA walked a client through a harder version of the same question: does equal still mean fair when one child’s circumstances are far less stable than the other’s?
He asked to consider a family with two adult sons: one a schoolteacher who lived modestly and within his means, the other someone who had made a lot of money in business and then lost most of it. A parent’s first instinct may be to split their estate equally between them. But, they could reconsider, wanting to leave more to the son with the unstable finances out of concern that he would eventually run out of money without extra support. To the schoolteacher son, that choice could easily look like the estate rewarding the very instability he’d spent decades avoiding. He had made the careful decisions, saved consistently, and spent within his means. An uneven split in his brother’s favor could be seen as penalty for having done just that. There was no version of this decision that was going to feel fully comfortable to every person it touched, and Tom suggested that a parent has to decide what they could live with, not what would please everyone.
When Equal Division Isn’t Possible
There are situations where equal division is not just uncomfortable; it is not functionally possible. Dr. Schippa worked through one such estate with a family of five adult siblings, one of whom required lifelong care in a residential facility, funded entirely by the family’s assets. Splitting everything five equal ways would have left nothing to sustain that sibling’s necessary medical care for the rest of their life. Several of the siblings had never been told what was in the family trust before the conversation happened. Once it did, the family spent several months building a structure that protected their sibling without anyone being blindsided by how the estate had ultimately been allocated.
The Caregiving Nobody Counts
Caregiving can become an important consideration in families, but can go unnamed when financial gifting decisions get made. In many families, responsibility for aging parents is unevenly split among beneficiaries: managing appointments, coordinating with doctors, being the person who shows up when something goes wrong. Whether that imbalance belongs in the calculation is a question wealth transfer planning conversations tend to skip entirely, even though the labor is real and almost never distributed evenly among siblings.
Dr. Schippa has worked directly with clients who feel guilty for considering anything other than an equal split, including one who hadn’t spoken to several of his children in years and still felt obligated to divide his estate evenly among them. His response to that client applies just as directly here: “Your kids don’t have to get every penny that you have. It’s your money.” Every version of this decision comes back to the same underlying question, and it was never about dividing something evenly. It’s about what a family wants its approach to multigenerational wealth management to say about what mattered to them.
What Readiness Looks Like for the Person Receiving It
Everything so far has been about the person writing the plan. The harder half of this equation belongs to the person receiving it, and readiness has almost nothing to do with the sharing of a number.
Dr. Schippa draws a clear line between two very different children asking about family money. One wants to know because they’re calculating what’s coming to them. The other is simply curious, with no agenda beyond understanding their own family better. Dr. Schippa’s advice for telling them apart comes down to what they’re asking about in the first place: “You’re interested in them and their process. People like to know you’re interested in them.” Questions about how parents built their wealth may provide an opportunity for broader conversations about the family’s values, decisions, and intentions.
That kind of thinking rarely develops from one direct conversation. Dr. Schippa calls the alternative “seed planting”: smaller, low-stakes conversations, spread out over time, that build enough trust to make the bigger conversation possible later. “Going direct sometimes is not your best play… you’re planting the seed for further conversations.”
Readiness is part of generational wealth transfer that rarely gets planned for, but it matters as much as the plan itself. A values-driven inheritance may only hold up when the person receiving it can meet it with real judgment. Entitlement doesn’t get you there.
Where The Portfolio Strategy Group Fits
The Portfolio Strategy Group (PSG) doesn’t draft your will or estate documents or file your taxes with the IRS. An estate attorney and a tax professional handle those. PSG works alongside them as financial advisors for your inheritance planning, often surfacing the questions a family has never said out loud, clarifying what each person intends, and helping build a financial structure around a family’s real goals and circumstances. PSG has watched enough of these decisions play out to recognize where the predictable mistakes happen, and can help a family think through their own decision with that pattern in view.
This work picks up where our last piece left on why families avoid the inheritance conversation left off. Getting a family to start talking about inheritance planning is one part of that conversation, already covered. Helping that family build the structure once the conversation is happening is what this piece has been about. This, combined with ongoing dialogue is a reason why we believe this work matters.
Before You Divide Anything
A few questions worth sitting with before anything gets formalized into a document:
- Have we talked honestly about what fairness means in our family, or did we make default decisions without ever discussing it?
- Does our plan for dividing what we leave behind, or for giving while we’re living, account for the real differences between and circumstances that surround our children?
- Have we given our heirs enough context to understand the reasoning behind this plan?
- Are we planning only for the transfer itself, or also for what happens after it?
Every family will answer these questions differently, shaped by circumstances only that family understands. That’s the conversation worth having with someone who has sat across the table from families asking the same things.