I do most of my grocery shopping at Trader Joe’s. Not because it saves me money, but because the people who work there are kind. And that matters to me.

Tuesday Triage
December 9, 2025

 
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Hi there,
 
I do most of my grocery shopping at Trader Joe’s. Not because it saves me money, but because the people who work there are kind. And that matters to me.
 
A few weeks ago, I was checking out in a Death Readiness Podcast sweatshirt when the cashier, Ron, asked what the show was about. We chatted briefly, and then, in the parking lot, he walked over with a follow-up question:
 
“If I want to leave everything to my brother, can I just write it down and sign it?”
 
The technical answer is yes.
The practical answer is more complicated.

Why People Turn to a DIY Will 

Ron’s question is extremely common and totally reasonable. Lawyers are expensive. The legal system is confusing. And most people assume that if their situation is “simple,” their Will should be, too.
 
Enter the handwritten, DIY, last-ditch estate document: the holographic Will. In Michigan, where Ron and I live, they’re legal. But legal and advisable are not synonyms.

Why DIY Wills Blow Up Later

On paper, holographic Wills seem easy.  In real life, they’re a minefield:
  • They get challenged
  • They get misinterpreted
  • They get weaponized in family disputes
  • And they often distribute property in ways you never intended
Why? Because documents written in a rush, without legal guidance, still have to function in the complex machinery of probate, and probate has no patience for “I know what they meant.”

If You Absolutely Must Write a Holographic Will

I am not recommending anyone do this. I spent years untangling handwritten Wills that created more conflict than clarity. But people write them anyway, usually in a hospital room, a crisis, or a moment when there isn’t time to wait for a lawyer.
 
So in today’s episode, I walk through how to draft a handwritten Will that is:
  • Coherent
  • Valid in Michigan
  • And less likely to send your family into litigation
We talk through:
  • How to structure the document so a court can interpret it
  • Which words actually matter
  • Why defining “Property” with a capital P can simplify everything
  • And the six traps to avoid at all costs: gifts to minors, gifts that jeopardize benefits for a person with special needs, multiple beneficiaries, DIY “trusts,” splitting one item between multiple people, and poetic final speeches
A Will is a legal instrument, not a final monologue. Clarity beats catharsis every time.
 
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Curious what Ron’s handwritten Will
actually looks like? 

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The Death Readiness Playbook is getting ready to launch.

If you’ve ever thought, “I need a plan, not just paperwork,” that’s exactly what The Death Readiness Playbook is designed to provide—a guided system to help you organize information, make decisions, and communicate them clearly.
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Thanks for being here.
Jill
 

 
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