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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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