The Death Readiness Podcast

The Death Readiness Podcast Honest conversations about estate planning, legacy, and preparing for life's hardest moments with clarity, compassion, and a little humor.

A podcast for women quietly carrying the weight of everyone else’s future. We talk about the hard stuff - aging parents, death, paperwork, legacy, guilt, and how to deal with it before it becomes a disaster. Real talk, practical tools, and permission to finally start. Hosted by Jill Mastroianni - Tennessee estate planning and probate attorney. Trusted guide for women like you. Giving voice to the

conversations your family’s been avoiding. Listen on Apple, Spotify, YouTube, or wherever you get your podcasts.

If you’re divorced and your parenting plan requires you to maintain life insurance for your children, here’s something I...
09/08/2026

If you’re divorced and your parenting plan requires you to maintain life insurance for your children, here’s something I want you to check.

Pull out three things:
1. Your parenting plan
2. Your life insurance beneficiary designation
3. Your estate planning documents

Now ask yourself: Are these three things actually telling the same story?

Because having the life insurance policy is only part of the plan.

Your parenting plan might tell you that you’re required to maintain a certain amount of life insurance for your children. But that doesn’t necessarily mean it gives you clear instructions for how to set up the beneficiary designation so the money actually gets to your children, and can be managed for them, if you die while they’re still minors.

And naming a minor child directly as the beneficiary can create its own set of problems.

That’s the issue I tackle in this week’s episode of The Death Readiness Podcast.

I actually pulled up my own life insurance company’s beneficiary designation form and worked through what would happen if I were a divorced parent trying to follow the language in Tennessee’s form parenting plan.

It turns out that something that sounds pretty simple on paper can get complicated very quickly when you’re staring at an actual beneficiary form wondering which box you’re supposed to check.

Today, I talk about:
→ Why naming a minor directly as a beneficiary can be a problem
→ What a custodian under UTMA is and when that might be useful
→ Why “trustee” and “custodian” aren’t necessarily interchangeable
→ How your Will can work together with your parenting plan and life insurance
→ And the question I think every divorced parent with a life insurance requirement should ask:

If I died tomorrow, would this money actually go where my parenting plan says it should go?

Watch the full episode here:

Your parenting plan may require you to maintain life insurance for ...

09/07/2026

Labor Day seems like an appropriate time to articulate my five-year plan.

A few years ago, I’m not sure I would have predicted that work would look like building my own law practice, talking about death into a microphone every week, spending summers working from my dad’s house in the Adirondacks, and regularly having to count the dogs in my house to remember how many currently live here.

But here we are.

I’ve spent a lot of my career thinking about what I was supposed to do next.

These days, I’m much more interested in building work, and a life, that actually feels like mine.

So on this Labor Day, I’m feeling pretty grateful for work I care about, the freedom to do it in a way that fits my life, and the fact that my commute occasionally involves stepping over a foster puppy.

The five-year plan may need some adjustments.

Mostly to accommodate more dogs.

09/06/2026

These two understand one of the most important parts of Labor Day weekend: gathering around the food.

Their version happens to involve sharing a dog bowl.

Ours might be burgers on the grill, a family recipe that shows up at every cookout, or everyone squeezing around a picnic table that isn’t quite big enough.

And it has me thinking about something we don’t talk about enough when we talk about “legacy.”

Your legacy isn’t just the house you leave behind or the money in your accounts.

It’s also the people who gather around your table, the person who always takes too many pictures, and the one who can’t resist sneaking food to the dogs.

Estate planning is about taking care of the people you love after you’re gone.

But your legacy?

You’re building that while you’re still here.

Happy Labor Day weekend. I hope yours includes good food, people you love, and perhaps slightly better table manners than these two.

P.S. The two dining companions featured here are Joxer and Callisto, my foster puppies. They’ll be available for adoption soon through Detroit Dog Rescue, which means they’ll be accepting applications for a lifetime of gathering around someone else’s table.

What is estate planning? Excellent question, tiny puppy.Estate planning is deciding what you want to happen if you can’t...
09/05/2026

What is estate planning? Excellent question, tiny puppy.

Estate planning is deciding what you want to happen if you can’t make decisions for yourself, and what you want to happen to your stuff after you die.

It’s answering questions like:
🏡 Who gets the things I own?
💰 Who handles the money and paperwork?
🏥 Who makes medical decisions for me if I can’t?
📋 Who can step in and manage things while I’m still alive?
👧 Who takes care of my children?
🐶 And yes, who takes care of my dog?

A good estate plan takes those answers out of your head and puts them into legally enforceable documents so the people you love aren’t left trying to figure out what you would have wanted.

Making decisions now so the people you love have fewer decisions to make later.

P.S. Today’s very thoughtful question comes from my foster puppy, Joxer, who will have a big decision of his own coming up soon: choosing his forever family. He’ll be available for adoption through Detroit Dog Rescue when he’s old enough, in about a week. 🐾

09/04/2026
Yesterday, I was grocery shopping at Trader Joe’s when the tornado siren started blaring.The store manager announced tha...
09/04/2026

Yesterday, I was grocery shopping at Trader Joe’s when the tornado siren started blaring.

The store manager announced that we had two choices: head to the back of the store to shelter or leave immediately.

I left.

I had just picked up my daughter, April, from school, and she was waiting in the car with our entourage of two foster puppies.

We were only three miles from home.

Those three miles felt VERY long.

The sky behind us was getting darker. There were road closures. Stop signs. Red lights that suddenly seemed to last in perpetuity.

And I was panicking.

There were also a lot of expletives.

But somewhere in the middle of all that panic, I had one reassuring thought:

I have life insurance.

My husband was already safely at home in our basement. And if something happened to me, I knew he would be financially okay. I knew where everything would go. I knew there was a plan.

It didn’t make me any less desperate to get home. But in a moment when almost everything felt completely outside of my control, it was one thing I didn’t have to worry about.

Thankfully, we made it home safely.

And then we all piled into the basement: humans, resident dogs, foster puppies, dog beds, crates and all.

Estate planning can feel like something you’re doing for some distant, hypothetical future.

Until the tornado siren goes off.

Then you realize that maybe the real gift of having a plan is knowing, in the moments when you’re scared and can’t control what happens next, that you’ve already taken care of the things you could.

Two years ago, April started 8th grade in a new school, in a new state.Around that time, I happened to see a list she ha...
09/03/2026

Two years ago, April started 8th grade in a new school, in a new state.

Around that time, I happened to see a list she had made of her goals and things she wanted for her first year in Michigan.

One of them was very specific:
Get a snack at McDonald’s once a week.

Her new school was right around the corner from a McDonald’s.

And so, McDonald’s Wednesday was born.

Yesterday was the first Wednesday of 10th grade.

April’s high school is nowhere near a McDonald’s. And our lives look a little different, including the two foster puppies who came along for the ride.

But McDonald’s Wednesday continues.

It means a little more driving now. But that also means more time to talk, more time to sing loudly to her music, and more time when neither of us is looking at a screen or trying to get somewhere else.

I can’t say I’m a particularly big fan of McDonald’s.

But I am a very big fan of McDonald’s Wednesdays.

I spend a lot of my professional life talking about what we leave behind and how we take care of the people we love.

And I know that when April grows up, she won’t remember how many podcast episodes I released or how many estate plans I completed.

But I think she’ll remember McDonald’s Wednesdays.

I’m grateful that gets to be part of my legacy, too.

Friend to friend, I may have overextended myself. These two little troublemakers came home with me from Detroit Dog Resc...
09/02/2026

Friend to friend, I may have overextended myself.

These two little troublemakers came home with me from Detroit Dog Rescue on Saturday.

There have been worms, lots of laundry, and so, so many trips outside. And there has been very little respect for traditional sleeping hours.

But there have also been puppy snuggles, ridiculous little personalities emerging, and the satisfaction of watching them get healthier and more comfortable every day.

So yes, I may have overextended myself.

But also?

10/10 would foster again.

And if you’ve ever thought about fostering, Detroit Dog Rescue has plenty of dogs who could use a temporary place to land while they wait for their people. ❤️

If you have more than one child, you probably know exactly which one is the “responsible one.”The one who gets things do...
09/01/2026

If you have more than one child, you probably know exactly which one is the “responsible one.”

The one who gets things done, the one you can count on, and the one whose name you’re tempted to put in the blank next to Trustee.

But before you do, ask a different question: What am I actually asking my child to take on?

A trustee has to:
• Manage investments and other assets
• Review requests for distributions
• Decide when a sibling gets money and when they don’t
• Keep records and handle administrative work
• Interpret the instructions you left behind
• Make decisions that could affect family relationships for years

And even if your child agrees to do all of that without taking a fee, that doesn’t mean the job is free.

There’s the time they’re not spending on their career, their own family, sleep, exercise, or everything else already filling their days.

And then there’s the emotional cost.

Imagine telling your brother that the trust Mom created isn’t going to pay for something he wants.

A professional trustee can say no and go home. Your daughter may have to see him at Thanksgiving.

That doesn’t mean you should never name a child as trustee. Sometimes a family member is absolutely the right person.

But “she’s the responsible one” isn’t enough of a reason.

Today, on The Death Readiness Podcast, I sit down with my longtime friend and trust advisor Alex Fisher to talk about what the job of trustee actually looks like behind the scenes.

We talk about how trustees decide whether to make distributions, what happens when the answer is no, how professional trustees make those decisions, what they look for before agreeing to serve, and why the trust you create today needs enough flexibility to still work decades from now.

And if you’re deciding whom to name as trustee, I hope it gives you a few more questions to ask before you fill in that blank.

Check out the full episode here:

What actually happens after a professional trustee takes over a tru...

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