I built a plan years ago that held up. Every piece of it. The trusts funded on schedule. The tax savings materialized. Nobody challenged anything. When the client died, the administration was clean. The assets moved exactly where they were supposed to move.
And the family fell apart anyway.
Not because of anything the plan did. Because of everything the plan didn’t touch. The sibling who had always felt less-than discovered that the structure confirmed it. The sibling who had quietly resented the controlling parent found that the trust perpetuated the control from beyond the grave. The one who had hoped the inheritance would finally let him feel settled discovered that it didn’t, and now had no more runway of “when I have it, then I’ll feel it.”
The plan worked. By every technical measure, it was a success. By every measure that mattered to the people it was built for, it wasn’t.
I’ve been thinking about that case for a long time. What it taught me is that we have a definition of “working” in this profession that is almost entirely technical, and almost entirely unexamined.
Science and Art
Tony Robbins distinguishes between the science of achievement and the art of fulfillment. The science of achievement is real. There are patterns, methods, repeatable processes. If you want to build a business, a portfolio, a career, a body of work — there are people who’ve done it and can show you how. Study them. Apply what they did. Most of the time, with enough time and effort, the results show up.
Fulfillment doesn’t work that way. It’s not a science. It’s an art. It’s subjective, internal, and doesn’t come with a checklist. Two people can achieve the same thing and feel completely differently about it. One feels alive. One feels empty. The achievement didn’t change. The person carrying it did.
The estate planning profession is almost entirely in the science column. We know how to transfer assets efficiently. We know how to minimize tax. We know how to structure trusts that hold up under scrutiny. We know how to document decisions so they survive challenge. These are real skills and they matter.
But the reason a client builds a plan is almost never in the science column. It’s in the art column. I want my family to be okay. I want what I’ve built to mean something. I want the people I love to thrive. None of those outcomes are guaranteed by the technical work. They’re downstream of it — sometimes way downstream — and they depend on human variables the plan can’t touch.
Robin Williams
I don’t want to belabor it, because the example has been used a lot. But it’s worth naming.
Robin Williams was one of the most achievement-successful people of his era. He had the awards, the resources, the recognition, the family, the career most people in his field would have traded anything for. He was also, by every account, profoundly unfulfilled at the end. Achievement was not the problem. The presence of achievement didn’t solve the problem.
This is not a sad story about a celebrity. This is a warning about a category error most of us make. We assume that enough of the achievement column will, eventually, resolve the art column. It doesn’t. The art column has to be worked on directly. It doesn’t show up as a byproduct.
Our clients are often achievement-successful in ways that have never touched the art column. The estate plan, framed the right way, can be one of the rare forcing functions that asks them to look at the art column. Framed the wrong way, it’s just another line item in the achievement column.
Ikigai
There’s a Japanese concept — ikigai — that’s been overexposed lately, but I’ll use it anyway because it’s useful. The framework asks four questions: what do you love, what are you good at, what does the world need, and what can you be paid for? The overlap of those four is where a meaningful life is supposed to live.
You can use it as a planning diagnostic. Not for the client’s career — for the plan itself.
Does this plan reflect what this family actually loves? Or does it reflect what they think they’re supposed to care about?
Does this plan play to what this family is actually good at? Some families are good at building, some are good at preserving, some are good at giving, some are good at teaching. Plans that ignore the family’s actual strengths tend to underperform even when the structure is flawless.
Does this plan address something the world — or at least the family’s world — actually needs? Or does it optimize for a problem no one is really trying to solve?
Does this plan sustain itself financially? Meaning the numbers still have to work. This is the column we’re fluent in. It’s just not the only column.
When all four are in the room, the plan has weight. When one or more is missing, the plan is brittle in a way that’s hard to see from inside the technical work.
What Plans Work Actually Means
I’ve started, when I’m closing out a planning engagement, to ask a different question than the one I used to ask. I used to ask whether we’d accomplished the goals we set at the beginning. Most of the time, the answer is yes — because the goals we set at the beginning were almost entirely technical, and technical work is tractable.
Now I ask: five years from now, what would it look like for this plan to have actually worked? Not legally. Not technically. Actually.
Some clients have answers ready. They’ve thought about it. Some clients have never been asked. They go quiet for a long moment and then say something like, “I want my kids to still be talking to each other.” Or, “I want my wife to feel taken care of without feeling like she’s been managed.” Or, “I want my business to still mean something to whoever takes it.”
None of those outcomes come automatically from the plan. But once they’ve been said out loud, the plan has a different job. The structure is in service of something. The technical work is the means, not the end.
A Note on AI
Some of you are watching the transactional layer of this work get automated. Document assembly is getting faster. Intake is getting more structured. Pattern-matching across precedent is getting better. You’re right to notice it.
Here’s what I think about it. The parts of our work that can be automated are largely in the science column — the repeatable, teachable, testable parts. The parts in the art column — reading a room, asking the question that changes the frame, noticing what’s not being said, helping a family articulate what they actually want the money to do — those are much harder to automate. Not because AI won’t get better. Because those conversations require presence, and presence is a different category than intelligence.
The planners who survive what’s coming will be the ones fluent in both columns. Not just technically excellent. Also able to sit in a room where the hard thing is unspoken, and help the family find language for it.
Over to You
If you imagine a plan you built five years ago, and you asked the family today whether it actually worked — not legally, not technically, but actually — what would they say?
And how much of what they’d say depends on conversations you had, versus conversations you didn’t?
Originally published on LinkedIn on 2026-06-05. View the LinkedIn version.