(And I Won)
Why Simple Estate Plans Sometimes Create the Exact Problems Families Were Trying to Avoid.
One of the things I say often is that estate planning problems rarely come from bad intentions. They usually come from plans that were meant to be simple.
This story started only a few weeks after a grandmother named Margaret passed away. My client was a widowed father named David, and his 18-year-old daughter, Samantha, who had just lost her grandmother. Samantha’s mother had already passed on years earlier, and now Margaret’s estate was being settled. Samantha had just graduated from high school and wanted to use part of her inheritance to pay for college.
That’s when the problem surfaced.
Margaret had what looked, on the surface, like a very straightforward estate plan — a simple Will combined with pay-on-death (POD) and transfer-on-death (TOD) designations on most of her financial accounts. The family believed everything had been set up to be easy, avoid probate, and make sure Samantha didn’t receive money outright until she was older.
What actually happened was very different.
The “Simple” Will That Created a Complicated Problem
The Will said that any inheritance for grandchildren would be held until age 40. The trustee and executor was Margaret’s son — Samantha’s uncle, Robert. The Will itself was extremely basic. There were no provisions allowing distributions for education, health, or support before age 40. No flexibility. No discretion. Just a hard age requirement.
Robert did exactly what he was supposed to do. He took the Will to an attorney, the attorney read it, and the conclusion was straightforward: nothing could be distributed to Samantha before age 40.
That meant no college money. No support. Nothing.
From a legal standpoint, Robert wasn’t wrong. He was following the document exactly as written. But it was also fairly obvious that this probably wasn’t what Margaret intended. Most grandparents who delay inheritance until age 40 aren’t trying to prevent their grandchildren from going to college — they’re trying to prevent an 18-year-old from blowing through an inheritance.
Unfortunately, intent doesn’t control. The documents do.
Where the Estate Really Went Off the Rails
When I reviewed the estate, the bigger issue became clear almost immediately.
The Will only controlled probate assets.
And almost nothing was in probate.
The house was still titled in Margaret’s name, so that asset went through probate. But the life insurance policy, the bank accounts, and the IRAs all had POD or beneficiary designations. Those assets passed outside the Will entirely.
The beneficiary designations named Margaret’s son, Robert, and her deceased daughter “equally, per stirpes.” Because Samantha’s mother had already passed away, Samantha stepped into her mother’s place.
Which meant half of the financial accounts went directly to Samantha — outright — with no trust at all.
About $1.1 million. At age eighteen.
Meanwhile, the only asset actually controlled by the Will was the house. Half of that value now had to remain in a testamentary trust until Samantha turned 40, requiring court supervision, annual reporting, and ongoing probate involvement for the next twenty-two years.
The irony was unavoidable. Margaret likely wanted to avoid probate and protect her granddaughter.
Instead, the plan did the opposite.
The Conflict That Followed
At this point, Robert intended to enforce the Will strictly. He was going to hold everything he controlled until Samantha turned 40. Again, legally speaking, he was on solid ground with respect to the house.
But he did not have authority over assets that passed by beneficiary designation.
Once that became clear, Samantha had the right to make claims directly with the financial institutions. If Robert interfered with those transfers, litigation was going to follow. I made that clear.
Ultimately, Samantha received the financial assets directly, which allowed her to pay for college without needing permission from anyone.
The only portion remaining in trust was half of the house value, locked into a testamentary trust that will remain under court oversight for decades.
The Lessons From This Situation
There are several lessons here, and none of them are unusual. I see versions of this scenario regularly.
First, Robert wasn’t the villain. He sounded harsh, but he was following the instructions in the Will. When estate planning documents are rigid, the people administering them often have no flexibility, even when everyone agrees the outcome doesn’t make sense.
Second, avoiding probate using TOD or POD designations is often far too simplistic. These designations have almost no contingencies built into them. When something unexpected happens — like a beneficiary passing away first — the results can be completely different from what the person intended.
Third, this is exactly the type of situation where a properly drafted revocable living trust would have helped. Margaret could have avoided probate entirely, kept assets in trust for protection, and still allowed a trustee to pay for education, housing, or other reasonable expenses before a certain age.
Finally, flexibility matters. The trusts we draft typically allow a trustee to make earlier distributions if the beneficiary demonstrates maturity and responsibility. That allows protection without creating unnecessary hardship.
The Uncomfortable Reality
Samantha can now afford to go to whatever college she wants. In the short term, that’s a good outcome.
But there’s an uncomfortable truth here as well. Giving more than a million dollars outright to an 18-year-old is rarely ideal. Margaret probably intended to prevent exactly that scenario.
The problem is that even flawed estate plans are legally binding. Once someone passes away, we don’t get to rewrite the documents based on what we think they meant to say.
We have to follow what they actually said.
If you want to see the full breakdown of how this situation unfolded — and why “simple” estate plans often create complicated problems — you can watch the full explanation on the Plain English Attorney YouTube channel here: https://youtu.be/BcyffIkUcsI?si=JoEBcrSDcNCJC4jy
The goal of estate planning isn’t simplicity; it’s clarity, flexibility, and making sure the plan actually works for the people you leave behind.