Introduction: Why I Wrote This Book

The family that fell apart over a $50 vase

The vase was turquoise. Art glass, maybe 1970s, the kind of thing you'd find in a thrift store for ten dollars on a good day. It sat on a bookshelf in a split-level house in a neighborhood I'd sold four or five houses in already. I was there to list the property. The listing appointment was supposed to take forty-five minutes.

I was there for six hours.

Here is what happened. The mother had died eighteen months earlier. The father had died eleven weeks before I walked through the door. They had three adult children — two sisters and a brother — and they had no will, no trust, no letter of instruction, no personal property memorandum, nothing. Just a house full of forty years of stuff, and three siblings who had not spoken to each other without tension since a disagreement at Thanksgiving 2014 that none of them could quite remember the start of.

The house was straightforward. One-third, one-third, one-third. Sell it, split the money, done. That part took about twenty minutes of conversation and a handshake. I thought I was going to be pulling comps and photographing bedrooms by ten o'clock.

Then the older sister pointed at the turquoise vase and said, "Mom promised me that."

The younger sister said, "She promised me that."

The brother, who did not care about the vase, made a joke about it. The older sister started crying. The younger sister called her a liar. The brother stopped joking. I sat on a couch I had not been invited to sit on and watched fifty-two years of birthdays, Christmases, graduations, a wedding, a divorce, a funeral for a golden retriever, and every single slight that had ever been exchanged between these three children come pouring out into the living room their parents had decorated in 1978.

They did not sell the house through me. They did not sell the house for eleven more months. The vase got broken — nobody will say by whom — in month four. The older sister does not speak to the younger sister anymore. The brother speaks to both of them but has stopped going to family events because he cannot handle being the messenger. Their children, who grew up as cousins, do not text each other.

The vase was worth maybe fifty dollars. The fight was worth fifty years.

I have been a licensed realtor for fifteen years. I have listed probably four hundred properties. Maybe sixty of those were estate sales — a parent died, the adult children are selling the house. I have watched this exact scene play out, with different props and different names, so many times that I cannot count them anymore. Different vase. Different sibling. Different thanksgiving. Same fight.

The fight is never about the vase.

What fifteen years in the room actually teaches you

When I started in real estate, I thought estate sales were going to be about real estate. They are not. They are about family systems, old wounds, guilt, birth order, money, shame, and the particular American refusal to talk about death until we are in the middle of it.

The house — the thing I was ostensibly hired to sell — is almost always the simplest part of the estate. It has a market value. You price it, you list it, you close it, you wire the money to three accounts. Done.

The hard parts, the parts that can take eighteen months and destroy a family, are the parts that nobody thinks to plan for:

• The ring that was promised to three different granddaughters at three different times.
• The 1968 Mustang in the garage that the oldest son restored with his father every Saturday for three years when he was in high school, which the will leaves to all three children equally.
• The dining room set that Mom told the in-laws was "going to you," but which the biological son's wife has her eye on, and which the will does not mention at all.
• The savings account with one name on it that Dad "meant to put all of you on" but never got around to.
• The boyfriend from the last five years, whom Mom introduced as "the love of her life," and who is now sleeping on the couch in the house that the adult children own and are trying to sell.
• The adult son who was "loaned" $40,000 in 2011 that was never paid back and was never put in writing, and whose siblings believe must come off his share.
• The executor, named in the will, who is the least organized person in the family and is also going through a divorce.

Every one of these is a landmine. Every one of them can be prevented — not perfectly, but largely — by work that takes a few hours and a few hundred dollars, done while everyone is still alive and still speaking.

Almost no family does that work.

This book is my attempt to explain, in the plainest language I can manage, what the work actually is. Not the legal theory. Not the tax code. The work. The conversations. The documents. The lists. The order of operations. The parts that nobody ever tells you about because the people who know are lawyers who charge by the hour and have no incentive to make it simple.

Not a lawyer — and that is exactly the point

Every lawyer I respect will tell you to hire a lawyer. I will too, and I will tell you in Chapter 19 exactly when to do it and in Chapter 20 how to pick one who is not going to waste your money.

But a lot of what families need to do first is not legal work. It is not even particularly complicated. It is work that any competent adult can do with a weekend, a printer, a fireproof box, and the willingness to have one or two uncomfortable conversations. Lawyers are not trained for that work, and they do not want to do it at $450 an hour. They want you to show up with your family already aligned, your assets already inventoried, and your decisions already made. Then they draft the documents.

The gap between "nothing planned" and "ready to see a lawyer" is where most families live, and where most families die. This book is trying to close that gap.

A lawyer can draft you a beautiful trust, and then your family will fight over the engagement ring anyway because nobody wrote down who was getting it. A lawyer can tell you that California has a $184,500 small estate exemption, and then your mother's brokerage account will go through probate for eighteen months anyway because nobody updated the beneficiary designation on it. A lawyer can explain the step-up in basis, and then your siblings will still not speak to each other at your father's funeral because you never had the conversation about the house while he was alive.

Lawyers do legal work. This book does everything else.

And some of the book is, frankly, stuff a lawyer cannot do. A lawyer cannot make your sister forgive your mother for liking you better. A lawyer cannot make your stepfather tell your biological siblings what he actually plans to do with the lake house. A lawyer cannot sit on the couch on a Tuesday afternoon and watch a family cry over a turquoise vase and gently say, so what do we do about this one?

That part is what fifteen years in the room taught me. And that part is most of what is actually going to save your family.

What makes this book different

Every estate planning book I have read — and I have read a lot of them, some of them very good — has one of two problems. Either it is written by a lawyer for lawyers, in which case it is accurate and thorough and completely unreadable. Or it is written by a personal finance author who has never sat on a couch with a grieving family at three in the afternoon, in which case it is readable but it is not telling you what actually happens.

I wrote this book because I could not find the book I wanted to hand to my own clients. I kept writing the same email fifteen times a year — here is what I wish you had known six months ago, here is what to do first, here is the conversation you need to have tonight with your brother before you take another step. At some point I realized I was writing a book in pieces, and I should just write the book.

So: this book has the legal stuff, simplified. It has the tax stuff, in English. It has the paperwork, in checklists. But it also has the parts I actually talk to families about — the stepmother, the sibling who is not speaking to anyone, the adult child with a drug problem, the vase.

If you are a lawyer, financial advisor, or CPA, this book is not for your clients instead of you. It is for your clients before they get to you, so that when they do they are ready. You will get better clients. Your work will be cleaner. You will close more deals and have fewer meetings that end in tears. Please recommend it freely.

If you are a family member — a son, a daughter, a spouse, a sibling, a parent, a grandparent — this book is for you. It will not make you a lawyer. It is going to make you the person in your family who understands what is happening, who can ask the right questions, and who can keep the fight from happening in the first place.

A word about how I got here

I am not going to write a memoir. But you should know, because it matters for the book, that I have been sober for twenty-one years. I am a recovery sponsor. Most of what I know about how families actually operate — who is carrying what resentment, what the real issue under the surface issue is, how to sit with someone who is scared and not try to fix them — I learned in recovery rooms, not in real estate school.

Estate planning and recovery have more in common than you would think. Both of them require you to tell the truth about things you have been avoiding. Both of them require you to make amends while you still can. Both of them require you to let go of things you cannot control and take responsibility for the things you can. Both of them are easier with a sponsor, a program, or a very good friend.

The families who do this work well tend to be families that have already done some version of emotional work somewhere else. They have been in therapy. They have been in twelve-step. They have been through a divorce and come out speaking to each other. They know how to sit in a hard conversation without running out of the room.

The families who do this work badly tend to be families where nobody has ever said the hard thing. Where "we don't talk about that" has been the rule for forty years. Where love is real but language has never been built for it.

Both kinds of families are going to show up in this book. Both kinds are going to be okay — if they do the work. You do not have to be a perfect family to plan your passing well. You just have to be willing to have one more uncomfortable conversation than you would prefer to have.

What I want you to walk away with

If you read this book and do nothing else, I want three things to stick:

One. The mechanics of estate planning are not complicated. They are specific. They are a list of documents, a list of conversations, a list of accounts, and a list of decisions. Nobody in your family has to be a genius. Somebody has to be willing to do the list.

Two. The fights that destroy families after a death are almost always fights that could have been prevented by a conversation before the death. The conversation is hard. The fight is harder. Pick the hard thing that ends.

Three. The person reading this book — probably you — is very likely going to be the person who has to drag your family through this. Not because you want to be. Because nobody else is going to. That is okay. This book is the instruction manual for that job. You can put it down when you are done. You do not have to carry it forever. But for now, you are it. Welcome to the job.

Turn the page.

Let's start with the hardest thing, which is not a document. It is a conversation.