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.
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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.

09/02/2026
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...

08/31/2026

Tomorrow, I’m talking with my longtime friend Alex Fisher about what actually happens behind the scenes when a professional trustee is managing the assets you leave behind.

We often name the “responsible child” as trustee because we know they can handle it.

But just because they can do the job doesn’t mean we should automatically ask them to.

There can be a cost in time, stress, mental load, and relationships with siblings.

We get into all of that tomorrow.

As for my co-host, Joxer is one of our newest foster puppies from Detroit Dog Rescue and will be available for adoption in about two weeks. ❤️

So you have two things to stay tuned for:
🎙️ A new episode of The Death Readiness Podcastt tomorrow.
🐾 And Joxer looking for his forever family very soon.

My dad told me this was the best summer of his life.And I can see why.My daughter had her first job across the lake and ...
08/30/2026

My dad told me this was the best summer of his life.

And I can see why.

My daughter had her first job across the lake and took a little purple boat back and forth to work. My brother spent lots of time with us, playing ping pong and pool and watching Mamma Mia far too many times.

It was one of those summers that makes it very easy to look at a family vacation home and think: Of course we should keep this in the family.

But that’s where I want families to be careful.

A place can hold some of your family’s very best memories and still not be an asset your children want to own together.

Maybe one child wants to spend every summer there while another lives 1,000 miles away. One can comfortably afford the taxes, insurance and repairs; the other can’t.

Maybe everyone loves visiting, but nobody wants to be responsible for maintaining it.

Or maybe they really do want to keep it but they have very different ideas about what co-ownership should look like.

You don’t have to guess.

Ask them.

That’s why I created my Keeping the Camp worksheets. They’re designed to help family members think through the questions that are easy to avoid while everyone is happily sitting by the lake.

Find out what your kids actually want.

Then create an estate plan around the family you have, not the family arrangement you’re hoping will somehow work itself out.

08/29/2026

We got home from the Adirondacks last night after an 11-hour drive.

So obviously, this morning, we picked up two foster puppies from Detroit Dog Rescue.

They’ve already made it through the full first-day itinerary:
Pickup.
Car ride home.
Exploring every corner of the house.
Playing.
More playing.
And now… complete exhaustion.
For them, anyway.

Next on our list: back-to-school shopping because April starts 10th grade on Monday.

Apparently, we’re going straight from Adirondack summer to full-speed Michigan life.

And in case you’re keeping track, these two bring the current dog count in our house to five.

Which feels like plenty.

These little ones will be available for adoption through Detroit Dog Rescue in about two weeks. Stay tuned. I have a feeling you’ll be seeing more of them before then.

08/28/2026

There’s leaving.

And then there’s the kind of leaving that comes at the end of an Adirondack summer.

Today, I’m packing up my little summer branch office at my dad’s house and heading back to Michigan.

The laptop is packed, the dogs are loaded, and we’re officially on our way home.

Leaving is always a little bittersweet.

But I’m also incredibly grateful that I’ve built a career that lets me spend my summers here—working from my childhood bedroom, having coffee with my dad, running on the trails, and still showing up for my clients.

Building my own law practice has come with plenty of uncertainty.

But this part?

This is exactly what I hoped I was building toward.

Michigan, here we come.

Although judging by the view from the passenger seat, not everyone is ready to go.

My daughter hung this skeleton on the doorknob of my summer office at my dad’s house.Her explanation?“It goes with your ...
08/27/2026

My daughter hung this skeleton on the doorknob of my summer office at my dad’s house.

Her explanation?

“It goes with your Death Readiness theme.”

So he’s been hanging there all summer, welcoming me to work every morning and apparently serving as the unofficial mascot of The Death Readiness Podcast.

And maybe there’s something fitting about that.

I spend a lot of time talking about death—not because I’m particularly morbid, but because pretending it isn’t going to happen isn’t a particularly good estate planning strategy.

Talk about it. Plan for it. Then get back to living your life.

Preferably with a tiny plastic skeleton guarding the office door.

This is what happens when you start your own law firm and your family is willing to humor you.Matching sweatshirts.My da...
08/26/2026

This is what happens when you start your own law firm and your family is willing to humor you.

Matching sweatshirts.

My dad. My brother. My daughter. Two of my dogs. And a whole lot of Mastroianni Legacy Law representation in one photo.

But there’s something else I like about this picture.

This is my “why.”

Estate planning includes documents and beneficiary designations and probate and trusts.

But it’s really about people.

The people we love, the people we worry about, the people we want to make things easier for, and the people who will someday have to figure things out when we’re not there to help.

That’s true when I’m working with clients.

And it’s true in my own family.

This summer, while staying with my dad in the Adirondacks, I sat down with him and reviewed his estate plan. We checked accounts and beneficiary designations and found one that still listed my mom, who died almost 14 years ago.

So we fixed it.

I don’t enjoy talking to my own dad about what happens when he dies. Being an estate planning attorney doesn’t make that conversation any less personal.

But I practice what I preach.

We have the conversations, check the accounts and fix what needs fixing.

And then we put on matching sweatshirts, wrangle the dogs for a family photo, and get back to living.

If you created a revocable trust to avoid probate, I have some homework for you.Make a list of what you own.Your house.C...
08/25/2026

If you created a revocable trust to avoid probate, I have some homework for you.

Make a list of what you own.
Your house.
Checking account.
Savings account.
Brokerage account.
Retirement accounts.
Life insurance.

Then, next to each one, answer this question:
What happens to this asset when I die?

Maybe it’s owned by your trust, has a beneficiary or payable-on-death designation, or maybe you own it jointly with someone else with survivorship rights.

But if the answer is, “It’s just in my name, and I haven’t done anything else with it,” you’ve found a probate asset.

And here’s where having a revocable trust can create a false sense of security.

Your trust only controls the assets that actually make it into the trust.

Yes, your pour-over Will can act as a safety net and direct an asset you missed into your trust after you die.

But the safety net doesn’t eliminate probate.

That’s the distinction I dig into today on The Death Readiness Podcast.

I walk through exactly how a pour-over Will works, what “funding” a trust actually means, and what happens when an asset is accidentally left outside your trust.

The most important question isn’t “Do I have a trust?,” but “How does each of my assets pass when I die?”

Check out the full episode here:

You created a revocable trust to avoid probate. So why did your att...

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