Silence
2 June 2026
First published in Substack, June 2026.
I have spent most of my working life around other people's money at the moments it matters most: when it is being given away, and when it is being passed on.
A decade of that was in philanthropy, advising families on what they wanted their giving to mean. The work I do now sits a little further along the same line, at the point where wealth, law, tax, family and mortality meet at once.
Wills. Testamentary trusts. Superannuation. Family trusts. The structures families use to carry what they have built into the lives of the people who come after them.
You learn things in that seat that are written down nowhere.
One of them is this: the estates that come apart are rarely the ones you would have picked from the balance sheet.
I was asked recently what I thought was the single biggest indicator of potential conflict in estate planning and the transfer of wealth between generations.
The person asking expected, I think, something technical.
A blended family. A business with one capable child and three who are not. A second marriage. A vulnerable beneficiary. A farm that cannot be divided four ways.
Those situations are real, and they are difficult.
But they are not what I have come to fear most.
My answer was one word.
Silence.
The estates that fracture are almost never the ones where too much was said. They are the ones where almost nothing was.
The man who planned everything except the conversation
A colleague described a matter to me some years ago.
The man at the centre of it, call him Peter, was in most respects a careful man. He had spent 40 years building something modest into something substantial. By the end, he owned the family home in one of Sydney's older suburbs, worth more on its own than everything else he held combined, along with a holiday house, a share portfolio and the usual superannuation.
He had three children.
In his final years it was his eldest daughter, I will call her Anna, who moved back in. She gave up a good deal to do it. She managed his medication, his moods, the slow administrative grind of a long decline, and she did it for the better part of five years while her brothers visited when they could.
Peter made what he thought was a fair decision.
He left Anna the family home and divided the rest of the estate equally between the three of them.
He understood exactly what he was doing and why. He was not confused, and he was not unduly influenced. He had simply weighed five years of a daughter's life against the convenience of an equal split, and decided the equal split was the lie.
The documents were faultless. The advice was sound. The will did precisely what he wanted it to do.
He never told his sons.
He meant to. He told his solicitor he would. But the conversation was the one thing in the whole exercise he could not bring himself to have.
So he did what a great many otherwise courageous people do.
He signed the documents, filed them away, and trusted that his children would understand once he was gone.
They did not understand.
What the sons saw, when the will was read, was that their sister had been given the single most valuable asset in the estate and they had been left to divide the remainder.
They knew she had cared for him. They had not been told that her care would be recognised in this way, or why, or that their father considered it a debt the estate owed her.
The recognition arrived as a fact in a document, rather than as something their father had said to them while he was alive to be questioned about it.
Within months there was a family provision claim. The estate funded senior counsel on both sides. To pay the legal costs and the settlement, the house had to be sold.
So in the end Anna did not keep the home she had been left.
Three children who had grown up close to one another no longer speak.
Peter's will was faultless. His silence was fatal.
Why it is silence, not money
People assume money is what drives families apart.
Money is certainly present at the scene. But money is often the subject of the dispute, not its cause.
The cause is the gap between what people assumed and what turned out to be true. And that gap is manufactured by silence.
Silence does not mean nothing is happening inside a family. It means the opposite.
It means every person is building their own version of the plan, in their own head, in the absence of any other information.
And because human beings are human beings, each version tends to be the one most favourable to the person constructing it.
The child in the business assumes the business.
The child who stayed close assumes the house.
The child who has struggled assumes the estate will be weighted to even things out.
None of them are necessarily unreasonable. They have simply been left to guess.
And people guess in their own favour.
Then the will is read, and every private version collides with the single real one at the same moment.
The distance between assumption and reality becomes visible all at once. That distance is the dispute.
It did not begin at the reading of the will.
It had been there for years.
Probate merely turned on the light.
The comfort of good documents
There is a belief, common in my profession and entirely understandable, that good documents prevent disputes.
A watertight will. A carefully drafted testamentary trust. A binding death benefit nomination that leaves nothing to chance.
These things matter. I spend a great deal of my time getting them right.
But I want to be careful about the weight we ask them to carry.
A perfect document delivered into a silent family does not prevent a fight. It postpones one. Sometimes it sharpens it.
The structure performs exactly as designed. It is the relationships around the structure that fail.
I have seen flawless drafting tear a family apart. I have also seen the reverse.
A woman I will call Beth left a will so rough that any solicitor would have winced at it. Two pages, drafted at her kitchen table, with one of her three children plainly favoured over the other two.
On paper, it had every ingredient of a dispute.
There was none.
Beth had spent her last years telling all three children exactly what she intended and exactly why, more than once, at the same table where the will was written.
By the time she died, there was nothing left to discover.
The uneven share had been raised, questioned and absorbed while she was alive to answer for it.
The document was almost beside the point.
The conversation had done the work years earlier.
A trust deed without a conversation is just precise instructions for a fight nobody knew they were in.
Why families choose silence
If silence is so dangerous, the obvious question is why so many careful, loving people choose it.
The reasons are rarely cynical. They are human.
To explain an estate plan to your children is to do several uncomfortable things at once.
It is to confront your own mortality in front of the people most affected by it.
It is to differentiate between the people you love most, and to defend that judgement to their faces.
It is to invite the conflict now, while you are alive to absorb it, rather than leave it for a time when you will not have to watch.
Set against all of that, silence can feel like the kind option.
It feels like protecting the children from a hard conversation.
It feels like keeping the peace.
Silence feels like keeping the peace. More often, it is borrowing peace from the next generation, at an interest rate they never agreed to.
I do not say this to judge anyone.
The instinct to avoid the conversation is one of the most natural instincts there is.
I only say that it is almost always the wrong one.
And the cost of indulging it does not fall on the person who chooses silence. It falls on the people left behind, who are made to reverse-engineer a parent's reasoning from a document, at the precise moment they are least equipped to be generous about it.
The work the will cannot do
The most useful thing I do for a family is often not legal at all.
It is helping them say the thing they have spent years avoiding.
Sometimes that means a family meeting that is excruciating for an hour and saves a decade of litigation.
Sometimes it means a letter of wishes sitting alongside the trust deed, written in plain language, explaining the reasoning the legal instrument is incapable of carrying.
Sometimes it is simply persuading a parent to tell two of their three children, in person, why the third is receiving more, before that decision has to be explained by a barrister to a court.
The recurring word in all of this is why.
An estate can be unequal and the family may hold, provided the reasoning was spoken out loud, by the person responsible, while they were alive to be asked about it.
What families cannot forgive is finding out.
The shock is rarely the decision itself.
The shock is that it was kept from them.
Unequal is survivable. Unexplained rarely is.
What I would say to a family sitting across the table
Say the difficult thing while you are alive to explain it.
The conversation you are dreading is the one your children will otherwise have without you, in a lawyer's office, reconstructing your intentions from paper.
You are the only person who can give them the reasons. Do it yourself.
Treat the letter of wishes as part of the plan, not an afterthought.
The will says what happens. The letter says why.
The second document is often the one that holds a family together, and it is the one most frequently left unwritten.
Tell people about decisions that will surprise them, especially the unequal ones.
An uneven split delivered with a reason and a warning is a decision a family can absorb. The same split delivered as a posthumous surprise is a grievance with a court date.
Accept that the conversation will be uncomfortable, and have it anyway.
Comfort now is purchased at the expense of the people who survive you.
That is a poor trade, and it is one they did not consent to.
And choose advisers who will push you toward the conversation, not around it.
It is easier to simply draft the documents and send the bill.
The adviser worth keeping is the one who asks whether your family actually knows what you have decided, and does not let the question go.
The danger sign
Good structures protect families. But only the parts a conversation has already settled.
Where the conversation never happened, the structure becomes the battleground rather than the shield.
The danger sign in a family is not conflict.
Conflict, oddly, is a form of health. It means people are still talking, still testing their assumptions against one another, still close enough to argue.
The danger sign is silence.
The smooth and peaceful surface under which every person is privately rehearsing a different ending.
Peter, whose story I began with, did almost everything right.
He thought clearly. He took advice. He made a fair and considered decision and committed it faultlessly to paper.
The single thing he could not do was the one thing that may have saved his family.
He could not say it out loud to the people it concerned.
If there is something in your estate that your family would be surprised to learn after you are gone, that surprise is the dispute.
It already exists.
It is simply waiting to be collected.
The most generous thing you can do for the people you love is also the hardest.
Tell them now.
Tell them why.
Then they never have to guess.