100 episodes about preparing for death. Who knew that could teach you so much about living? In this special 100th episode of The Death Readiness Podcast, estate planning attorney Jill Mastroianni takes a break from tax calculations and trust provisions to reflect on the unexpected lessons she's learned since launching the podcast in January 2025. From recording conversations with her dad about his childhood and military service to asking her brother questions she'd never thought to ask, Jill shares how creating the podcast has changed her understanding of family, legacy, and the things we pass along to the people we love. And sometimes, the memories that matter most are the ones we least expect, like singing One Direction in a parking lot with your teenage daughter and a foster dog. Estate planning isn't supposed to take over your life, but give you more peace of mind so you can spend more time enjoying it.
What You’ll Learn in This Episode
Why recording your family's stories matters. You don't need professional equipment or a published podcast to preserve meaningful conversations with your parents or grandparents. Sometimes all it takes is asking a question and pressing record.
What happens when we ask questions we've never asked before. Jill shares how interviewing her dad and her brother, Dan, helped her understand two people she thought she already knew so well.
Why we need to listen to the people we're planning for. When Jill asked Dan about his experience growing up with Down syndrome, his answer challenged her assumptions and offered an important lesson about understanding what makes someone else's life meaningful.
How our children learn from watching us navigate uncertainty. Building an estate planning podcast and a business hasn't always gone according to plan. Jill reflects on what she hopes her daughter April has learned from watching both the successes and setbacks.
Why your legacy is about more than money and possessions. Family stories, shared experiences, traditions, and everyday moments can be just as meaningful as the assets we leave behind.
How preparing for death can help us appreciate life. Estate planning and getting your affairs organized isn't about dwelling on what might happen someday. It's about making things easier for the people you love and spending more time enjoying the life you're living right now.
Resources & Links
Related Podcast Episodes
Episode 7 — What it Takes to Raise a Child with Special Needs
One of Jill's favorite episodes, featuring conversations with her dad about raising her brother Dan and with Dan about his own experiences, relationships, and memories of their mother.
https://www.deathreadiness.com/podcast/what-it-takes-to-raise-a-child-with-special-needs
Episode 11 — Start Your Own Family Podcast with these Simple Steps
Learn how to record conversations with your parents, grandparents, or other loved ones to preserve their stories for future generations.
https://www.deathreadiness.com/podcast/start-your-own-family-podcast-with-these-simple-steps
The Death Readiness Playbook
https://www.deathreadiness.com/playbook
Estate planning and preparing for death doesn't have to feel overwhelming or depressing. The Death Readiness Playbook combines approachable explanations of estate planning with a practical workbook to help you organize the information your family may someday need.
Halloween Special: Save $10 with code BOO through October 31, 2026, while supplies last.
Connect with Jill:
· Website: DeathReadiness.com
· Email: jill@deathreadiness.com
· Learn more about Jill’s solutions
· Subscribe to the Death Readiness Dispatch!
· Ask a question for Tuesday Triage
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Today is my 100th episode of The Death Readiness Podcast, the 100th episode talking about death, dying, estate planning, probate, and all the things most people would rather not think about. Which, when I put it that way, doesn't sound like much of a celebration. But today is a celebration.
So we're doing something a little different. There won't be any estate-tax calculations or complicated trust provisions. Instead, I want to share some of the things these 100 episodes have taught me about what it really means to leave a legacy, why some of the most important things we pass along have nothing to do with money, and how thinking about death can actually help us appreciate the lives we're living right now.
Welcome to The Death Readiness Podcast. This is not your dad's estate planning podcast. I'm Jill Mastroianni, estate planning attorney, death readiness guide, and your translator for wills, trusts, probate, and the conversations most families avoid.
If you've been wondering things like, "Can a trust protect what I leave to my children?" "What happens if I give someone power of attorney over me?" and "How can I help my parents while respecting their independence?" You're in the right place.
Today is the 100th episode of The Death Readiness Podcast. And, I'm pretty excited about that. When I started this podcast in January of 2025, I had recently lost my job. I was living in Michigan, having moved there from Tennessee, where I'd spent most of my legal career. And I was trying to figure out what came next.
I knew a couple things for certain. I loved estate planning and I believed that people wanted and needed to understand it better. My mom was an elementary school teacher, and she was a really good one. I think I inherited my mother’s love of education. In fact, when I was little, before I was old enough to go to school, I was jealous of my older siblings because they had homework and I didn't. So my mom made up homework assignments for me.
And now, decades later, I spend a substantial portion of my time explaining things like the difference between a revocable trust and an irrevocable trust, and why the words “per stirpes” matter in a Will. And actually, that love of teaching is also what led me to create both this podcast and The Death Readiness Playbook.
With the Playbook, I wanted to create something that would make estate planning and getting your affairs organized feel less intimidating. And I wanted it to be something people would actually enjoy opening.
So the Playbook isn't some drab, black-and-white manual full of legal jargon. It's beautifully designed, in full color, with illustrations and explanations that make complicated topics easier to understand. And it comes with a separate workbook to help you organize the information your family might need someday.
And, I want to remind you about a little Halloween treat. Through October 31st, you can take $10 off the Playbook with code BOO, B-O-O. That brings the digital version down to just $17, and the printed version, which also includes access to the digital version, to just $27.
You can find it at deathreadiness.com/playbook. That's deathreadiness.com/playbook. Use code BOO, B-O-O, at checkout. The offer is good through Saturday, October 31st, while supplies last.
Okay, back to how this whole podcast adventure got started.
I didn't know anything about microphones or recording software. I didn't know what made audio sound good or bad. I didn't even know whether I would enjoy hosting a podcast. So I started experimenting. And I recruited two people to help me, my daughter, April, and my dad, Carmen.
April and I started interviewing my dad. Initially, we were just trying to figure out how to record a conversation. We were testing equipment and figuring out where to put the microphone. And something really wonderful happened. We started learning things. Not just about podcasting equipment, but about my dad. My dad is a storyteller. Anyone who has met him knows that. But there is a difference between hearing a story that someone tells at the dinner table and sitting down with that person, asking questions, and really listening to the answers.
April and I asked my dad about growing up in Schenectady, New York. We asked about his family, his childhood, and his service during the Vietnam War. And we learned things I didn't know, like about the little gifts from his mother delivered to Vietnam that reminded him of home. Here’s a little bit of that conversation:
Jill: What did your parents think about you getting the draft notice?
Carmen: My parents—my father didn't quite understand it, because I remember—he asked me, “is Pat going with you?” And I just shook my head. My mother did. She would send me care packages and she’d write me letters.
Jill: What kind of care packages did grandma send? She sent food?
Carmen: She would send raviolis and cans. Everybody in my unit would go nuts when the package would arrive because it was delicious stuff.
Jill: Arrive in Vietnam?
Carmen: In Vietnam. Yup.
Now, I don't know how many people listening have ever had canned ravioli, but I imagine that receiving a package of it from your mother when you're serving in a war on the other side of the world must have been pretty special.
We also learned about a transfer my dad received during the war that he credits with saving his life. And we learned more about his best friend, Donnie Brewer, who is still technically missing in action.
And I was grateful that April was there to hear these stories, too. Because as her grandfather, the relationship my dad has with April is different from the relationship I have with him. She gets to know him through her own experiences. And these interviews gave her an opportunity to learn about the person he was long before she was born.
We eventually turned one of those recordings into Episode 11 of this podcast, which was about how to create your own family podcast. If you've ever thought about recording conversations with your parents or grandparents, I encourage you to listen to the rest of that episode, which I’ll link to in the show notes. You don't need professional equipment and you don't need to publish anything. You don't even need to call it a podcast.
You can simply sit down with someone you love, ask questions, and record the conversation. You might be surprised by what you learn. And someday, you’ll be very grateful that you did it.
Those early recordings also led to my favorite episode of the entire podcast, Episode 7, which I’ll also link to in the show notes. In that episode, I interviewed my dad about raising my older brother, Dan, who has Down syndrome. Dan was born in 1977. And the world was a very different place for people with intellectual disabilities then. My parents had to figure out how to advocate for him, how to make sure he received an education, and how to give him opportunities to participate in the world around him.
But I also wanted to hear Dan's side of the story. So April and I sat down with him separately and asked him about his life. It was a chance to ask some very candid questions that I’d never asked my brother before. Take a listen.
Jill (18:24):
"How do you think having Down syndrome has impacted your life?"
Dan (18:25):
"Me having Down syndrome. I mean, Down syndrome to me, you know, it's like a chromosome. I mean, it doesn't really affect me, because I still have a great life."
I remember being surprised by Dan’s answer. Because when I think about Dan's life, I think about all the things my parents had to fight for. I think about the challenges he faced and the ways the world wasn't always designed to accommodate him. But that's my perspective.
Dan's perspective is different. He thinks about the life he's lived, the friends he's made, the things he's enjoyed, and the people who love him. And he's had a great life.
And it reminded me of something I think we sometimes forget when we're making plans for the people we love. We can become so focused on protecting someone from what might go wrong that we forget to ask them what makes their life good. That matters in estate planning, particularly when we're planning for someone with a disability. But it matters in our everyday relationships, too. I also asked Dan about our mom, who died in 2012.
Here's a little bit of that conversation.
Jill: "Do you want to talk about mom at all?"
Dan: "Yeah, I’d love to talk about my mom. Yeah."
Jill: "Okay. What was your relationship like with mom?"
Jill: "Do you remember her as a happy person before then?"
Dan: "Oh yeah."
Jill: "Laughing a lot."
Dan: "Laughing a lot, being happy a lot. Her laughter was so contagious, which you and I both know. That she had a hearty, hearty laugh."
Jill: "And did dad talk to you about what was going on with her health?"
Dan: "Yes. Losing a parent is difficult, which you and I both know. There was no cure. There was no, there was no medication. And that's really it."
My conversation with Dan was a reminder that sometimes we assume a family member doesn’t want to have a difficult conversation, so we don't have it. But when we actually ask, they may want to share something important.
Episode 7 remains my favorite interview because I learned so much about my dad and my brother, two people I already thought I knew very well. And April was part of that experience. That's a very special thing to have come out of a podcast I originally started because I wanted to teach people about estate planning.
I talk about my dad a lot on this podcast. And that's because he and my mom are such an important part of who I am. They gave me opportunities, supported me, and taught me things, sometimes intentionally and sometimes simply by the way they lived.
And now I'm a parent. My daughter April has been part of this podcast almost from the beginning. She's watched it grow from something I wasn't even sure I knew how to do into something that people actually listen to. Every once in a while, one of her friends' moms will mention the podcast to her, which I think she finds amusing.
But April has also seen what goes on behind the scenes. And it hasn't all been pretty. She's watched me start a business and build something from scratch. She's seen me excited about opportunities that worked out. And she's seen me disappointed when things didn't.
There have been times when I've been very uncertain about what comes next. I still am. I hope April has learned something useful from that. And it’s not that everything always works out exactly as we planned. Because it definitely doesn't. But that when things don't work out, we can make another plan. We can ask for help or try something different. And we can keep going.
So, after 100 episodes, what have I learned about legacy?
Well, I still think estate planning documents are important. And organizing your information, communicating with the people you've named to help you, and understanding how your assets will pass at death are all very important. But we also sometimes define legacy too narrowly. We think about what we're going to leave behind. Our house, our investments, and our personal belongings. And those things matter.
For example, my dad's house in the Adirondacks matters enormously to our family. But it’s not because of its monetary value. It matters because of what we've experienced there, like the summers April has spent with her grandfather.
I think about the fact that I now have recordings of my dad talking about his childhood, his military service, and his experiences raising my brother. And now it’s part of what I'm passing along to April. Legacy isn’t just something that happens after we die. We're creating it all the time in the way we treat people, the things we teach our children, in the traditions we create, and the conversations we have. And sometimes in the things we do together that seem completely unimportant at the time.
Which brings me to last weekend. April and I went to a Detroit Dog Rescue event along the Detroit riverfront. We brought Kobi, our foster dog. And it was really cold. After a few hours, April looked at me and said, "I'm frozen."
And I decided we'd done enough for the day. Kobi hadn't found his forever family, but we'd given it a good try. So we packed up and headed to the car. And then we discovered that the exit to the parking lot was closed, and it wasn't going to open for another hour.
We sat in the car and listened to April's playlist and sang along. And one of the songs was One Direction's "What Makes You Beautiful." Now, I only really learned about One Direction and Harry Styles this summer. I know, I'm a little late. April found this quite entertaining. And she added the song to her playlist for me. So there we were, sitting in a parking lot with a foster dog who hadn't been adopted, singing along to a boy band from 15 years ago that I had only recently discovered. And I think those are the kinds of moments we sometimes overlook when we talk about legacy.
I hope April remembers the big things we've done together like the summers in the Adirondacks and the trips to California. But I also hope she remembers some of the smaller things like sitting in a parking lot with her mom and a foster dog, singing along to One Direction. I know I will.
Getting Death Ready isn't supposed to take over your life or become another overwhelming responsibility. It's supposed to give you some peace of mind, so you can spend less time worrying about what might happen someday and more time enjoying what's happening right now.
And that's really the whole idea behind The Death Readiness Playbook.
And I made it beautiful, too. Because I don't think preparing for death has to look or feel depressing. So if you've been putting this off, here's a little encouragement to get started. Through October 31st, you can use code BOO, B-O-O, to save $10 on the Playbook.
That means the digital version is only $17, and the full-color printed version, which includes digital access, is just $27.
Head to deathreadiness.com/playbook and use code BOO, B-O-O, before Saturday, October 31st. The offer is available while supplies last.
But I don't want to end this episode talking about getting organized. I want to end it talking about living.
And if there's one thing I'd encourage you to do after listening to this episode, it's this. Spend some time with someone you love. Ask a question you haven't asked before. Record a family story. Or just do something fun together. You don't even need to leave the parking lot.
When I started The Death Readiness Podcast, I thought I was creating something to help other people. And I hope I've done that. But I didn't anticipate how much creating this podcast would mean to me. I didn't know it would give me a reason to sit down with my dad and ask questions I'd never thought to ask. Or that it would lead to conversations with my brother that helped me understand him better.
I didn't know how much April would become part of the process, or how meaningful it would be to build something together. And I certainly didn't know that 100 episodes later, I'd still be here, talking about death. But here we are. And I'm really grateful. To everyone who's listened to an episode, shared one with a friend, sent me a question, or told me that something I explained finally made sense, thank you.
To the guests who've shared their stories and expertise, thank you. And to my family, especially April, my husband, my dad, my brother, my cousin Nora and my sister-in-law Bethany, thank you for being part of this.
I started this podcast because I believed people wanted and needed to understand estate planning. I still believe that. But after 100 episodes, I think I understand something else a little better. The purpose of getting Death Ready isn't to spend all our time thinking about death. It's to make things easier for the people we love, so that we can spend more of our time living. And that's a pretty good reason to keep going.
Thanks so much for listening today, and for helping me celebrate Episode 100.
This is Death Readiness, real, messy and yours to own. I'm Jill Mastroianni and I'm here to help you sort through it, especially when you don't know where to start.
Hi, I'm April, Jill's daughter. Thanks for listening to The Death Readiness Podcast. While my mom is an attorney, she's not your attorney. The Death Readiness Podcast is for educational and entertainment purposes only. It does not provide legal advice. For legal guidance tailored to your unique situation, consult with a licensed attorney in your state. To learn more about the services my mom offers, visit DeathReadiness.com.