“Once Again” is in the title here because I’ve already written several blog posts about fairness in the context of family; this is one of the repeating topics arising with the enterprising families I work with.

It is understandable that families often ask me for the best way to be fair in their situation. It makes complete sense that they ask this. If there was a rule book or definitive guide, I’d share it freely. Of course, there is no such thing. There can’t be. Fairness is subjective and requires communication, flexibility, and compromise. What is fair is specific to each family and its circumstance.

Take the picture included with this blog: does this represent fairness or lack of fairness? Here are some potential scenarios that could be behind this image:

  • The parent cutting the cake was in a rush trying to balance making dinner, completing an important work assignment with a looming deadline, and paying attention to the birthday of one of her sons. She simply did not have the wherewithal to pay careful attention to piece size as she was cutting. Maybe the birthday boy has the larger piece. Maybe the birthday boy has the smaller piece. Is either fair?


  • The older brother is in charge of the younger brother while their parents take a walk around the neighborhood. The older brother, who was told he could cut the cake, decided that the size of the slice each would get depends on years alive. Is this fair?


  • The younger brother threw a temper tantrum because he was jealous about his older brother’s birthday. Out of anger, he slammed his fist into the cake on the table. Half the cake was unscathed and the older brother was given a large slice of it by parents while the younger brother received none due to his inappropriate behavior. The older brother, feeling sad for his younger brother, sliced off part of his piece to share with the upset younger brother. Is this fair?

I could go on, but you get the idea: fairness can be complicated. Fairness is not always a 50/50 split of the assets under consideration. Usually there are several ways to consider fairness.

All families struggle with how to share or not share the resources of the family—whatever those are. The decisions are often complex. In some ways, poor and working-class families have harder choices because limited resources often permit them to help only one family member at the direct expense of others. For example, I know of financially struggling families in which several siblings work hard to put one sibling through college, graduate school, and beyond. Is this fair? Does the sibling who received the education owe the others anything? If so, what?

Frequently in this blog I use examples from my own family life to demonstrate concepts. While my wife and I possess usually a tiny fraction of the financial resources of the clients I work with, there is relevance to our family story since, as we just explored, all families face questions of fair sharing.

My older son, Jeremy, graduated engineering school and immediately upon graduating networked himself into a job with a large company with great benefits. He received a company car that included gas, tolls, insurance—even for personal use—and great health insurance. His coverage was far better than the insurance my wife and I pay an arm and a leg for each month for ourselves—with a huge family deductible and high copays . . . don’t get me going. When Jeremy got injured playing soccer and needed screws put into his wrist, his insurance covered almost all of it.

Our younger son, Matthew, was in his freshman year of college when Covid hit, sending him home for the rest of that year and all the next. Classes he needed for his major were not offered yet somehow, with grit and hustle, he graduated on time despite all that. His first job upon graduating was a “character-building experience” (my description—I can’t share his precise words here). It did include a very competitive salary for a recent grad and health benefits. However, he was treated poorly and was caught up in a mismanaged family business generational transition. All the stuff he has heard me talk about for years. His compensation was not handled in accordance with employment law and he was put into some awful situations. It was great stuff for growing and learning about life, but it was also painful.

This led to some soul-searching, and he connected with what has been a passion of his for many years: physical fitness and a wish to be a personal trainer for elite athletes. But stepping away from his job and getting certified would be a financial sacrifice, and he’d lose his health insurance. My wife and I discussed possibilities and agreed to offer to add him to our health insurance as long as he completed his personal training certification within a specified time frame and, when a health issue arose, and he had significant expenses, we agreed to help him pay for the amount not covered by insurance.

I then asked our older son if he felt any resentment or unfairness over the amount of money going to his brother without a similar amount going his way. I could understand feeling perhaps somehow punished if getting a good job with great benefits was somehow tied to less parental generosity. Another version of this I have seen several times with very wealthy family clients trying to find their “fairness” is when one child goes to college, then medical school, and becomes a prominent surgeon, for example, who creates significant wealth. The parents then leave their wealth to a different sibling who did not put in as much effort; the parents worry the less financially successful child will not be able to care well for themselves. The surgeon child, in this example, may not need the parents’ assets, but often feels unfairly treated or even less loved.

When I brought all this up to Jeremy, his reply was, “Dad, I am totally fine. You and mom let me live at home rent free for two years after college while I worked and saved for a down payment on my first home. I could never have done that without you letting me live with you. Now I’m a homeowner at twenty-five. And Matthew is living with friends and paying rent. You could make the case that he lost on that one. I am fine and this all feels very fair. You and mom are there for us and help when it is needed or you want to. It is not like we need a tally sheet tracking the amounts given to each of us.”

My wife and I had wondered about feelings of fairness or lack thereof, but rather than wonder silently, a simple conversation gave us insight into Jeremy’s experience. We also spoke with Matthew, who struggled with accepting the health insurance and funds for healthcare expenses. We told him we could set up a time frame after which he’d be responsible to pay us for the cost of his health insurance or keep a running balance if he could not afford that until he started working again. He found some relief in this. As parents we could not be prouder of both his concern over wanting to make sure he pulls his own weight and his ability to graciously accept help from loving parents who want to help and can afford to.

As I hit publish on this blog post, Matthew has just started his new job working in a boutique gym as a personal trainer, having passed his certification a couple of weeks ago.

The message is not that other families should handle these situations the way we do. It is that the sharing of family resources is powerful and deeply meaningful in idiosyncratic ways. Without open communication and a willingness to understand fairness from a variety of viewpoints, there can be forceful misunderstandings and dramatic rifts. As with so much related to family and money, early transparency and intentional communication go a very long way.