Over the weekend, my daughter and I spent five hours at a Detroit Dog Rescue adoption event with our foster puppy, Boots. Four puppies found their forever homes that day. Boots wasn’t one of them.

Death Readiness Dispatch

March 18, 2026

Hi there,

 

Over the weekend, my daughter and I spent five hours at a Detroit Dog Rescue adoption event with our foster puppy, Boots. Four puppies found their forever homes that day. Boots wasn’t one of them.

 

By the time we got home, I was exhausted, and starting to come down with something, so I crawled into bed, and pulled up YouTube. That’s when I came across a viral story about a 78-year-old DoorDash driver who received nearly $1 million through a GoFundMe campaign after someone noticed him struggling to complete a delivery.

 

It’s a classic feel-good story but it also highlights a problem I’ve seen firsthand in my work as an estate planning attorney: Sometimes the very thing meant to help someone can create a bigger problem.

In this week’s Tuesday Triage episode, I walk through what can happen when financial help intersects with means-tested government benefits. Giving someone money can affect their eligibility for programs like Medicaid.

 

 I share real examples from my practice, including:

• How a $10,000 gift can temporarily disqualify someone from benefits,
• How that same $10,000 gift can turn into a $20,000 liability,
• How public fundraising campaigns can create unexpected legal exposure, and
• Why “just trying to help” isn’t always enough

 

My goal isn’t to discourage generosity, but to make sure your generosity actually helps.

At the end of the episode, I come back to a phrase from medical ethics that I think applies just as much here: First, do no harm.

 

We need to slow down long enough to understand the full picture before we give. If you’ve ever helped (or thought about helping) a parent, friend, or neighbor financially, this episode will give you a different lens to look through.

The second edition of The Death Readiness Playbook is officially heading to the printer this week. I’ll be sharing more soon, including a closer look at co-branded versions for professionals.

 

And if you ordered the first edition, you’ll automatically receive a digital copy of the second edition at no cost.

Thanks for being here. If this sparked a thought or question, I’d love to hear from you.

PS: Boots is still available for adoption. If she’s meant for you or someone you know, reach out to Detroit Dog Rescue.