The Hardest Thing About Money Is Giving It Away

For most of my career, I have had a front-row seat to one of the most intimate acts a person can perform: deciding what to do with their wealth before they leave it behind.

As head of a foundation, I sat alongside people at the moment they were trying to turn money into meaning. Some had built it themselves over decades of discipline and sacrifice. Others had inherited it, carrying the particular weight that comes with receiving something they did not earn.

All of them, at some point, had to answer a question that sounds simple and is anything but: Who gets this, and why?

What I came to understand is that money, when it moves between generations, rarely travels alone. It carries history, expectation, guilt, love, and sometimes a quiet kind of grief. Giving it away - whether in life or through a will - is also a way of reckoning with what you built and whether it meant something.

We are living through the largest transfer of wealth in human history. Trillions of dollars are moving, or about to move, from one generation to the next. But behind each of those transactions is a family, a conversation, and a set of assumptions about fairness, obligation and care. Most of those conversations are not happening the way they should.

The part no one talks about

The giving often starts before anyone thinks of it as a transfer at all. A house deposit here. School fees there. A loan that becomes a gift. A crisis absorbed without fanfare. Over time, money flows from parents to children in ways that are responsive and full of love, but rarely deliberate.

One child buys into the property market early with a helping hand. Another does not need help yet. A third is supported in ways the others do not fully see. No one is keeping score. Except, of course, everyone is.

This is where the tension sits. Not in formal structures or strategy discussions, but in the gap between what families assume is understood and what is never actually said. Parents believe they are giving equally because their intentions are equal. Children absorb very different messages about what they are worth to the family.

Money does not just fund things. It tells people what you think of them.

Where philanthropy becomes something else

Not every wealthy person comes easily to philanthropy. I have sat with people who felt conflicted about it, worried that giving publicly was a form of performance, or that they did not know enough about the causes they cared about to give wisely. These are not trivial concerns. They are honest ones.

But I have also seen the opposite. People for whom giving became the most clarifying thing they ever did with their money. Not because it was easy, but because it forced them to articulate what they actually believed, what problems they thought were solvable, and what kind of world they wanted to invest in.

What looks like a question about generosity is often a question about control. And control, in this context, is not just about who decides - it is also about whether the people making those decisions are the right ones at all.

There is an assumption, often unspoken, that wealth should remain within the family's sphere of influence. But that is not always where it is best deployed.

Not all capital is best deployed by the people who hold it.

The question is not just whether the next generation should have a voice. It is whether they should have control. And more broadly, whether retaining control is the point at all.

The will is not the beginning

By the time we reach the will, most people feel like they have thought it through. The structure is considered, the percentages allocated, the executor chosen. On paper, everything looks orderly.

But what the document rarely captures is everything that has already happened. The gifts given, and to whom. The support that was invisible. The different paths each child has taken, and how those paths were shaped along the way.

I have seen estates where the will was carefully equal and the lifetime giving was nothing of the sort. Not out of favouritism, but out of circumstance. And I have watched adult children sit with that after a parent's death, trying to work out whether they were loved the same.

A will is a final statement. But it is always read against a much longer context.

What actually works

The families who navigate this well do not treat giving as a moment. They treat it as a practice. They talk about money while they still hold it. They explain the decisions they are making, and why. They ask questions early, rather than leaving them to surface later.

They understand that fairness is not a formula. It is something that needs to be paid attention to over time.

The transfer of wealth is not just a financial event. It is a social one. It determines what moves within families, and what flows beyond them. It reinforces some futures, and constrains others.

The transfer is already happening, whether you shape it or not.

Rachael Rofe is an estate planning lawyer and wealth transfer specialist. She has spent her career helping families navigate the transfer of wealth in life and at death - legally, and everything beyond the legal.