Who should get mom's ring?

But most of the time, those transfers don't happen successfully. There's this one thing that seems to keep tripping families up every time. A focus on assets, not relationships.

And I'm Sally Herships. Thanks for having me back. Today on the show, we look at the uncomfortable side of estate planning and what happens when it's overlooked.

Mary says she always made more money than her second husband. We're not using her full name because Mary's worried about damaging her relationship with her family. But here's how she sees things. Her first husband passed away and she married her second husband 25 years ago. They own a house together. But she's not sure exactly what she wants to happen to the house when she's gone. She has two stepdaughters and also a son from her first marriage.

But this is where Mary keeps getting stuck. She feels like she's been a generous Grammy and stepmom and mother in law. So she's been toying with all these different options, like maybe everything goes to

Wait, you think, what do you think he would recommend? I think he's going to think he

Mary says she feels a knot in her stomach even talking about this. And she's not alone. Amy Castoro knows how hard talking estate planning can be. It's hard her job to make those conversations easier. She is CEO and president of the Williams Group. They do what you might call relationship planning.

Think about it. Amy says a will is a legal document. It's designed to take care of assets, I. E. Who gets what and when. Not to explain why you gave your grandmother's blue and gold Dresden porcelain dessert plates with the angels to one of your kids rather than the more deserving one.

I'm not going to discuss this.

Oh, I know the guy who founded Amy's company, did a 20 year field study looking at where things break down and how to make things right. And he's got a formula for the money to go where it's supposed to and to keep everyone happy.

Only 5% of your time should be spent on the mechanical side of estate planning, like figuring out those interest rates, mortgages, investment accounts, that kind of thing.

In other words, most of the time, we have got it backwards. Louis Osterman has seen this firsthand. He's a lawyer in Denver who specializes in estate planning. Like a couple of years ago, he had some clients, a brother and sister.

Wait a minute, wait a minute. A vacuum cleaner?

Like a Hoover? Like the kind you clean your house with?

Listen, some of those older appliances, they are worth their weight in gold.

So what was the bill for the vacuum transfer?

Wow, that is nuts.

And when it comes to dividing up assets, Lewis says folks often get stuck trying to figure out this one what's fair versus what's equal. And in economics, equal means everyone gets the same slice of the pie. But fair could mean bigger slices for the hungriest. So he says the question becomes, do

Lewis says a question a family shouldn't have to ask is, how much fighting can they afford?

Wow.

So Mary says she did talk to her son. We don't know the details yet. And you know what? I hope we don't find out for a very long time.