What Every Parent Needs to Know When Their Child Turns 18
Jillian Mastroianni Jillian Mastroianni

What Every Parent Needs to Know When Their Child Turns 18

When your child legally becomes an adult at age 18, a lot changes. 

You can still pay their tuition, keep them on your health insurance, pack their favorite snacks for the dorm. But in a medical emergency, you don’t have a right to their healthcare information.

Sadly, most parents don’t realize this until there’s an unexpected crisis.

Today on The Death Readiness Podcast, I share the stories of two young women whose families fought landmark legal battles because neither had signed an advance healthcare directive before tragedy struck. Their stories made national headlines, and they also left a legacy we can learn from.

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Why Prenups Aren’t Just for the Rich (or the Divorcing)
Jillian Mastroianni Jillian Mastroianni

Why Prenups Aren’t Just for the Rich (or the Divorcing)

Most people associate prenuptial agreements with cynicism, mistrust, or worst-case scenarios. But what if we’ve been looking at them all wrong?

In this week’s episode of The Death Readiness Podcast, we’re flipping the script. I sit down with family dynamics coach, Emily Bouchard, to talk about how hard, honest, ongoing conversations about money can actually strengthen relationships. 

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What You Need to Know About Medicaid and Protecting Your Mom’s House
Aging Parents, Caregiving Jillian Mastroianni Aging Parents, Caregiving Jillian Mastroianni

What You Need to Know About Medicaid and Protecting Your Mom’s House

I get asked this all the time: “Should we put mom’s house in a trust in case she needs nursing home care?”

In today’s Tuesday Triage episode, I answer that question through the story of a listener named Eileen. She’s 73, lives alone in upstate New York, and owns her home. Her son-in-law thinks she should put her house in a trust to “protect it from the government.” Eileen’s not so sure.

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Why You Need (or Don’t Need) a Trust
Probate, Aging Parents Jillian Mastroianni Probate, Aging Parents Jillian Mastroianni

Why You Need (or Don’t Need) a Trust

If you’ve ever been told, “You need a trust,” and didn’t quite know what that meant, you’re not alone.

It’s something people hear from well-meaning friends, financial advisors, or maybe even their parents. But rarely does anyone slow down and explain why you might need one or whether it makes sense for your situation.

That’s what this week’s Tuesday Triage episode is all about.

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Preparing for your Parent’s Cognitive Decline Before it’s too Late
Caregiving, Aging Parents Jillian Mastroianni Caregiving, Aging Parents Jillian Mastroianni

Preparing for your Parent’s Cognitive Decline Before it’s too Late

When a parent’s health starts to decline, the questions you never wanted to ask become urgent. Bills still need to be paid, decisions still need to be made. Are you legally allowed to step in?

This week on our first Tuesday Triage episode, I tackled a question from a listener named Molly. Her situation might sound familiar to you.

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Why I Turned Off Alex Hormozi’s Podcast
Personal Jillian Mastroianni Personal Jillian Mastroianni

Why I Turned Off Alex Hormozi’s Podcast

Like many small business owners, I’m always working and always learning.

Podcasts are one of my favorite ways to learn. They fit into dog walks, dishwashing, and school pickup lines—moments when I want my brain to stay active even if my hands are full.

This morning, while walking my dog, I pressed play on The Game with Alex Hormozi. I’m new to his show. This was maybe my third episode.

Alex was talking about what he called “exploitation mode,” his strategy for extracting the most value from the thing you already have. I was listening in, curious about how to apply that mindset to my business.

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How Our Favorite Movies Trained Us to Accept Less
Legacy Preservation, Personal Jillian Mastroianni Legacy Preservation, Personal Jillian Mastroianni

How Our Favorite Movies Trained Us to Accept Less

When you think about “estate planning,” old rom-coms probably don’t come to mind. But maybe they should. Because for many of us, the movies we grew up watching taught us more than we realized, especially about what we’re expected to accept.

These movies quietly trained us to accept less: less agency, less credit, less space, less support. And those lessons show up everywhere, from hospital rooms to attorney meetings, from caregiving roles to family finances.

In Episode 15 of The Death Readiness Podcast, I take a closer look at these cultural scripts, and how they still shape the way many women carry the emotional and logistical weight of family life.

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How to Succeed in the Caregiving Role No One Trained You For
Caregiving, Aging Parents Jillian Mastroianni Caregiving, Aging Parents Jillian Mastroianni

How to Succeed in the Caregiving Role No One Trained You For

Caregiving isn’t side work - it’s a leadership position. Host Jill Mastroianni talks with Jennifer O’Brien, author of Care Boss and The Hospice Doctor’s Widow, about the emotional labor, strategic thinking, and societal blind spots surrounding caregiving. Drawing from her experience leading healthcare organizations as well as caring for her husband and parents, Jennifer challenges the notion of caregiving as “soft” work and offers real-world tools to do it well. We cover everything from palliative care to “go bags” to how not to offer help to a caregiver.

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What I Learned from Planning My Own Funeral
Funeral Planning Jillian Mastroianni Funeral Planning Jillian Mastroianni

What I Learned from Planning My Own Funeral

If you’ve ever wondered what’s really in an urn, whether cremation is actually “green,” or what happens when no one claims the ashes? You’re not alone. I’ve worked in trusts and estates for more than a decade, and even I didn’t know the full story behind funeral planning until recently.

That changed when I sat down with Jamie Sarche, Director of Pre-Arranged Funeral Planning at Feldman Mortuary in Denver, Colorado for Episode 13 of The Death Readiness Podcast - What You Need to Know About Embalming, Cremation, and Eco-Friendly Funerals. Jamie walked me through planning my own funeral. And I learned a lot.

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The Digital Blind Spot in Your Estate Plan: A $750 Million Reminder
Digital Assets Jillian Mastroianni Digital Assets Jillian Mastroianni

The Digital Blind Spot in Your Estate Plan: A $750 Million Reminder

Imagine standing on top of a landfill, fully aware that your $750 million fortune is buried below — but barred by law from taking a single shovel to the ground.

That’s the reality for James Howells, a 39-year-old man who says his ex-partner accidentally threw away a hard drive containing 8,000 bitcoins back in 2013. Today, his story is the subject of a new documentary series: The Buried Bitcoin: The Real-Life Treasure Hunt of James Howells.

But beyond the headline-grabbing numbers and media spectacle, his experience surfaces a quieter, more relatable issue that’s often overlooked in estate planning: digital asset readiness.

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It’s Going to Be Okay
Personal, Probate, Aging Parents Jillian Mastroianni Personal, Probate, Aging Parents Jillian Mastroianni

It’s Going to Be Okay

In this episode of The Death Readiness Podcast, I’m not speaking as an estate attorney or a podcast host. I’m showing up as a daughter, a sister, a mother. A woman in the thick of the sandwich generation—caring for a child, walking alongside a father, and quietly planning for the day I’ll be the one who has to tell Dan again: “It’s going to be okay.”

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R-E-S-P-E-C-T Your Legacy: Lessons from Aretha Franklin’s Will
Probate Jillian Mastroianni Probate Jillian Mastroianni

R-E-S-P-E-C-T Your Legacy: Lessons from Aretha Franklin’s Will

I’m new to the Metro Detroit area—and I’m loving it here.
There’s a lot of pride in Detroit. People here wear Detroit T-shirts, Detroit hats—everything Detroit. We don’t need to go anywhere else when we have Detroit.

And one of Detroit’s greatest heroes—the Queen herself—is Aretha Franklin.
She’s still nearby, too: Aretha is interred at Woodlawn Cemetery, just down the road from where I live.

Aretha Franklin passed away on August 16, 2018, at the age of 76. She was unmarried at the time and left behind four adult children, including a son with special needs.

Initially, it was believed that Aretha died without a Will.

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Macaroni’s Story: Why We Hit Record—and Why You Should, Too
Personal, Legacy Preservation, Aging Parents Jillian Mastroianni Personal, Legacy Preservation, Aging Parents Jillian Mastroianni

Macaroni’s Story: Why We Hit Record—and Why You Should, Too

If you’ve been listening to The Death Readiness Podcast for a while, you know we often get into the legal mechanics of estate planning, end-of-life documents, and the practical steps that make life easier for the people we leave behind. But death readiness isn’t just about having the right paperwork. It’s about preparing your family for the day when you’re no longer here. It’s about preserving who you were—what you believed, what you lived through, what mattered to you.

And that kind of preparation doesn’t come in the form of a checklist. It comes in the form of stories. That’s why this episode - Macaroni’s Story: A Granddaughter Records Her Unknown Hero - is special. We’re sharing an excerpt from The Mastroianni Family Podcast—and giving you the tools to create a private family podcast of your own.

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Put Yourself in a Box: Why the Harmless Error Doctrine Is No Excuse for Poor Planning
Probate Nora Faherty Probate Nora Faherty

Put Yourself in a Box: Why the Harmless Error Doctrine Is No Excuse for Poor Planning

A plan is only as good as the paper it’s written—and properly signed—on. A valid, signed, witnessed and properly executed Will still matters. Yet time and again, people delay. They plan to go back to their lawyer, plan to sign next week, plan to finalize their intentions when life slows down. But life doesn’t slow down. And the result? Confusion, conflict, and sometimes devastating cost.

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