A husband and wife sat in my conference room last month, both of them successful, both of them reasonable, neither of them willing to sign the plan.
The technical work was done. The trusts were drafted. The structure was sound. What they couldn’t agree on had nothing to do with tax. It was whether their three kids — now in their thirties, doing well — should receive outright distributions at forty, or whether the trust should hold back until fifty-five.
He wanted the kids to build something on their own first. If we hand it to them too early, what did we build all this for? They’ll coast.
She wanted them to have it while they still needed it. What’s the point of having it if we can’t help them when it matters? We have enough. Let them live.
Neither of them was wrong. Both positions were reasonable, consistent, defensible. The problem was that they had been married for thirty-two years and had never — not once — sat down and said out loud what they wanted the money to do. What it was for. What they were trying to pass along beyond the balance sheet.
The estate plan was just the first place the disagreement had nowhere to hide.
The Rallying Cry
Patrick Lencioni has a line that I think about a lot. He said that if his corporate clients ran their companies the way most people run their families, they’d be out of business inside a year. No shared mission. No defined priorities. No review cadence. Just reacting to whatever shows up in the inbox.
He wrote a short book called The 3 Big Questions for a Frantic Family. The three questions are simple enough that you can read them in ten minutes, and hard enough that most families never actually answer them.
What makes your family unique? Not what makes you impressive. Not what you’d put on a holiday card. What actually distinguishes this family — its rhythms, its humor, its commitments, the way it shows up when things get hard. Most couples have never articulated this. They feel it. They’ve never said it.
What is your rallying cry right now? Not your long-term vision. Not your values statement in perpetuity. What matters this year — this season of life, this stage of the kids, this phase of the work? Rallying cries are temporary by design. They change as the family changes.
How do you keep it alive? The standing check-in. The Sunday night conversation. The weekly fifteen minutes where you look at what’s actually happening and whether it matches what you said mattered.
None of this requires a family office. None of it requires nine figures. It requires willingness to have a conversation most couples have successfully avoided for thirty years.
The Rules Problem
Tony Robbins has a framework I come back to when couples describe the same value and mean completely different things. He distinguishes between values and rules — the specific conditions that have to be met before you get to feel the value.
Two people can both say they value security. One of them, when you dig in, believes they’ll feel secure when they have enough set aside to weather five years of expenses, the house is paid off, and the kids’ educations are funded. Achievable. Finite. The rule has an end.
The other will feel secure when they have enough for ten years, plus their aging parents have enough for any eventuality, plus the kids have trusts that protect against everything that could go wrong, plus the spouse never has to worry about anything at all, plus nothing external — the market, tax law, politics — ever changes unfavorably. The rule, in practice, can never be satisfied. Security, for this person, is permanently out of reach.
Same word. Same stated value. Completely different rules. And the plan you build will feel right to one of them and wrong to the other, and neither of them will know why.
This is what spouses often mean when they say they can’t agree. They’re not disagreeing about the value. They’re disagreeing about the rule — the conditions under which the value gets to be real. And until someone names the rule, the plan will keep hitting a wall nobody can describe.
A Note on Each Other’s Histories
Morgan Housel opens The Psychology of Money with a line that should be the first slide of every couples’ estate planning session: “No one’s crazy.”
Everything a client thinks about money — how much is enough, what feels safe, what feels generous, what feels reckless — makes perfect sense through the lens of their own life. The decade they grew up in. What their parents did or didn’t do with money. The first financial shock they lived through. Whether they watched someone lose everything, or watched someone never have to worry.
When spouses can’t agree about an estate plan, they’re often not disagreeing about the plan. They’re importing two different financial autobiographies into the same decision. One of them watched a parent go bankrupt. The other watched a parent give generously and feel whole doing it. They’re not debating. They’re each re-living a lesson.
The work isn’t to resolve whose history is right. It’s to name that both histories are in the room, and to let the plan account for both.
In Practice
This doesn’t have to be a weekend retreat. It can be forty-five minutes in your conference room, or at their kitchen table, with three questions written on a single piece of paper.
What do you want the money to do for the people you love?
What do you not want it to do?
What would it look like, five years from now, if this plan had gone well — not technically, but actually?
I’ve watched couples stare at the third question for a long time. I’ve watched spouses hear each other answer it for the first time in a marriage and quietly reach for each other’s hand. I’ve watched the plan change, sometimes substantially, once the answers were in the room.
And I’ve watched plans move forward — technically correct, financially optimized — without those questions ever being asked. Some of those plans held. Some of them didn’t. The ones that didn’t usually failed for reasons that looked, in hindsight, entirely predictable.
Over to You
When was the last time you asked a client what their family’s top priority is right now — not their estate planning priority, their family priority — and let the answer shape the plan?
And when you did, how many of them had actually thought about it before you asked?
Originally published on LinkedIn on 2026-05-08. View the LinkedIn version.