Why There Is No Perfect Estate Plan,
Just a Really Good One

William Bissett has told this particular story many times over the years.

A wealthy family.

Old money.

A grandmother who got sick with dementia.

A grandfather who grew tired of the situation and eventually started seeing someone else.

Kids who were furious.

And when the grandmother passed and the grandfather remarried, a decision that disinherited the children and grandchildren entirely, leaving everything to the new wife and her family.

Despite the fact that the original wealth came from the first wife’s side of the family.

It’s the kind of story that makes every parent and every business owner sit up straight. It’s a cautionary tale about what can happen when assets are left without protection and life takes an unexpected turn.

But recently, William found himself checking that story against a couple of experiences that told a different side of the same coin.

When Leaving It Open Is the Right Call

A client whose husband of 50 years passed away a couple of years ago has since grown into her own vision for charitable giving. She has been supporting causes and organizations that she and her husband never prioritized together during his lifetime. Because the assets were left to her outright, she has the freedom and the power to make those decisions. And she is doing it beautifully.

Another client, a 92 year old widower whose wife passed away a couple of years ago, has updated his estate documents to direct a little more toward a charity they both supported during their marriage. It’s exactly the kind of decision his wife would almost certainly have endorsed wholeheartedly.

Both of these outcomes are the result of assets being left open rather than tied up. And both of them are exactly right for the families involved.

There Is No Right Answer. There Is Just a Really Good One.

This is the tension at the heart of every estate planning conversation. When you tie up your assets through trusts and structured documents, you make the decisions. You control what happens after you are gone. When you leave assets open, you trust the people you leave behind to make those decisions wisely.

Neither approach is universally correct. The right answer depends entirely on your family, your circumstances, your values, and frankly, the people who might be around your heirs when those decisions get made.

William makes a point that is worth holding onto. If you have been a great parent for 40 or 45 years, your kids almost certainly know how to make good decisions. The real question isn’t whether they will do the right thing. It’s whether the people around them will influence them in the right direction.

Getting Comfortable With Not Knowing

One of the harder truths William shares in this episode is that we will never truly know whether we made the right estate planning decisions. By the time that question gets answered, everyone involved will be long gone.

That’s uncomfortable.

But it is also liberating in a way, because it means the goal isn’t perfection. It’s just making the best possible decision with the information and the values you have right now. Getting it out of your head and into your documents. Trusting that the people you have spent a lifetime loving and guiding will carry it forward the way you intended.

Estate planning doesn’t have to be paralyzing. It just has to be thoughtful.

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[00:00:00] I’ve had a lot of meetings recently, and for one reason or another, they’ve circled around estate planning. And so I used to tell a story, or I guess I still tell a story, about a family that I used to know where we’ll say grandmom and grandpop, um, grandma and granddad, were wealthy. And technically speaking, the money came from grandmom’s side of the family.

And, uh, they had a beautiful house, small town, place down at the beach, too. Uh, just a, a nice old school wealthy family. And Grandma got sick, um, dementia, Alzheimer’s, and for a long time, and Granddad kind of got tired and ended up starting dating some- somebody else. [00:01:00] Kids didn’t like that and, um, were mad at Grand- or their dad, and, um, ended up, uh, getting in a fight.

And when the, when the grandmother passed away, uh, he ended up remarrying, and obviously, kids didn’t like that at all. Um, he didn’t really care. He was doing what he wanted to do and, um, ended up disinheriting their kids and his grandkids, um, and leaving the money to the new wife and her family, so despite the fact that the money came from his original, previous, first wife.

Um, and so I tell that story a lot in terms of protecting assets, right? Like, you never know. And, um, I mean, it’s a great story because you don’t know. But I’ve had a couple instances recently that kind of caused me to check that, right? We’ve got, um, a family that we’ve worked with for a number of years.

Husband unfortunately passed away, but they were married for 50 years, and s- he’s been gone now for a couple years, and [00:02:00] his wife has really gr- grown into their charitable giving, um, and where she wants to make an impact around the community. And some of those are things that they didn’t support while he was still alive.

But because the money was left outright to her in this instance, she’s got the, the power to make those decisions. And, um, and the same thing goes with, uh, another husband and wife that we work with, have been married for 40-plus years. He’s 92 years old. Uh, she passed away a couple years ago. Um, no strings attached.

He’s updated the, the, the documents. He’s leaving a little bit money to, a little bit more money to a charity that they both supported. And, um, she’d probably, given the nature and intent of what he’s doing, I’m sure she’d be 100% supportive. And so, you know, estate documents are funny because you, you can want to control, um, sometimes you can need to control, and other times you, you don’t want to.

And there’s no right answer, [00:03:00] right? I started thinking about the fact that there is– And we’re always seeking what’s the right answer. Um, and there’s– I’ve gotten to the point in life where oftentimes there’s not a right answer. There’s just a really good answer. Sometimes there’s a really bad answer, too, right?

But, um, so when you’re thinking about estate planning and, and how to leave assets and how to tie them up. Um, you know, realize that when you tie it up, that’s you’ve made the decision, and when you don’t tie it up, you leave it behind for others to make decisions. Um, and there are right instances to do it and there are wrong instances to do it, and we really won’t know what the right answer was until everybody’s long gone, which is a painful decision.

But it is one that you have to grow and get comfortable with. And I was talking to another client, um, last night actually, and we were talking about their kids, and their kids are 45 [00:04:00] and, and 40 and, and they asked, you know, how, how they should do things, how they know their kids will make responsible decisions and how they can kind of ensure that in their estate documents.

And I asked them how old their kids were, and they told me, and I said, “Look, you’ve been great parents for the last 40 and 45 years for these kids. You know they’re going to make good decisions.” Um, so it’s not about their decisions, it’s about the folks around them. Um, and I mean, again, it goes back, there is no right answer.

We won’t know the right answer until it’s long past knowing the right answer, and at that point in time, they’re all gonna be gone. So anyways, just take that into consideration as, as you go through your business, um, your life, whatever it is. There, there is no right answer. Um, there’s just, uh … There’s not oftentimes right answers, right?

There are just really good answers and, um, oftentimes you know what that is. It’s in your heart of hearts, it’s just a matter of getting it out there. So if you like the video, um, hit [00:05:00] subscribe. Um, would love to have you, um, tune in to more, um, nor- more of our Little Portus Perspectives going forward.​

ORIGINAL MEDIA SOURCE(S):

William Bissett: Tie It Up or Leave It Open: The Estate Planning Decision Nobody Talks About | Portus Perspectives

Originally Recorded on May 22, 2026

Portus Perspectives: Episode 18