Forty-Three Calls
Tuesday
In 22 years of doing this work, I have met exactly one client who made me genuinely consider a career change.
His name was Richard. He was 68, recently retired, and had just inherited his mother’s estate — a modest house, two bank accounts, and a life insurance policy. Straightforward. I’ve closed more complicated estates in an afternoon.
Richard, however, had done his research.

He had read three books about estate law. He had watched, by his own count, “about forty hours” of YouTube videos on the subject. He had a spreadsheet. He had a second spreadsheet that cross-referenced the first spreadsheet. He had printed out several articles — some of which were from states where neither he nor his mother had ever lived.
He arrived at our first meeting with a binder. The binder had tabs. One of them was labeled “Contingencies (General).”
Over the following six weeks, Richard called me forty-three times. I know this because I counted. He emailed me 91 times. Several of his emails were follow-ups to previous emails asking why I hadn’t responded to the previous emails — sent, in one memorable instance, four hours after the original.
He disputed the probate timeline because he had read that it should take “six to eight weeks” and we were on week nine. I explained that the county courthouse had a backlog. He asked if I had tried calling them.
I had called them.
He asked if I had tried calling again.
He wasn't difficult because he was a bad person. He was difficult because he was scared.
His mother had died, he was dealing with something he didn’t understand, and the only thing he knew how to do with fear was turn it into preparation. The binder wasn’t about the estate. The binder was about feeling like he had some control over something that was completely out of his hands.
I’ve seen this a hundred times. The person who asks the same question fourteen different ways isn’t being difficult — they’re trying to find an answer that makes them feel okay. Sometimes there isn’t one.
We closed the estate in week eleven. Richard sent me a very formal thank you email. He attached a feedback form he had designed himself.
I gave him top marks on everything. He deserved them.
— Martin, Cincinnati OH