The Death Readiness Podcast: Not your dad’s estate planning podcast
You’re the one prepping for your child’s IEP meeting while trying to talk your aging dad out of getting a puppy. You’re booking medical appointments, managing the money, juggling work emails during school pickup and still expected to keep the fridge stocked and know who has practice, rehearsal, or a field trip tomorrow. Your parents are struggling, but they still insist they’re fine. You see the mobility issues, the memory slips, the unopened mail, but every offer to help feels like an argument. You’re scared to push. You’re scared to wait. And there’s no clear roadm...
Why Your Teen’s Brain Can’t Outrun the Algorithm
Jill explores one of the most urgent parenting challenges of our time: the dangers hidden inside our kids’ devices. From algorithm-driven eating disorders to sextortion scams run like global businesses, today’s threats don’t hide outside the house; they live inside apps, platforms, and anonymous accounts. Inspired by the podcast Left to Their Own Devices, Jill shares four essential insights every parent needs to understand, plus why talking about these uncomfortable realities is now part of true death readiness.
What You’ll Learn in This Episode
Our Kids Are Growing Up in a Completely Differen...
How to Stop the Family Camp from Splitting Siblings
Jill breaks down why family camps, cottages, and vacation homes become the most emotionally charged and conflict-prone assets families try to pass down, and how to prevent them from tearing siblings apart. Using stories from her own Adirondack upbringing and recent travels, Jill explores the tension between nostalgia, financial reality, sibling dynamics, and unspoken expectations. She outlines clear steps families can take to avoid disaster: understanding real costs, clarifying fairness, addressing governance, confronting entitlement, and creating a legally sound structure before a crisis hits.
What You’ll Learn in This Episode
Why Family Properties Create Ou...
How to Give Money Without Triggering Gift Tax
This Tuesday Triage episode breaks down how gift tax actually works, when a gift must be reported to the IRS, and why most people won’t owe gift tax but may need to file a gift tax return anyway. Using a real listener scenario, Jill explains what counts as a gift, what doesn’t, four major exceptions, and common year-end mistakes that can accidentally trigger IRS reporting rules. And, as always, she reminds us that not all gifts come wrapped. Sometimes the most meaningful gift is showing up.
What You’ll Learn in This Episode
What legall...Can you Inherit from Someone You Killed (or Tried to Kill)?
In this episode, Jill explores one of the most fascinating intersections of true crime and estate law: the slayer statute. She dives into a real 2025 Michigan Court of Appeals case involving a trust, an unexpected beneficiary, an alleged murder-for-hire plot, and two deaths by natural causes. The big question: Can you inherit from someone you planned—but failed—to kill? The answer reveals just how narrow the slayer statute really is and why understanding your estate plan matters more than you think.
What You’ll Learn in This Episode
The Case Background
The trust Donald...Avoiding the Hidden Tax Trap in Lifetime Gifts
Jill unpacks one of the most misunderstood estate-planning tools: the irrevocable trust. Using a real-world scenario, she explains how transferring assets too soon can backfire, especially when it comes to capital-gains taxes. If you’ve ever wondered whether your trust is helping or hurting your long-term plan, this episode will help you make sense of what you really need (and what you don’t).
What You’ll Learn in This Episode:
Revocable vs. Irrevocable Trusts. How control, flexibility, and tax treatment differ between the two.
When to Use an Irrevocable Trust. Situations where it can p...
How Hosting This Podcast Taught Me to Face Grief
This week’s Tuesday Triage isn’t about someone else’s question—it’s about Jill’s.
After losing her Uncle Charlie, Jill reflects on how a previous guest, Jamie Sarche, taught her that grief isn’t something we can “opt out” of. In Episode 18, Jamie explained why ceremony matters, not for the person who died, but for the people left behind. In this episode, Jill shares how she had to live that lesson, honoring her uncle by showing up, feeling the loss, and remembering the man who quietly held his family together.
What You’ll Learn in This Epi...
How to Talk to Your Parents About Getting Help at Home
Talking with your aging parents about getting help at home, or possibly moving, can feel impossible. How do you bring it up without overstepping, causing conflict, or stripping them of their independence?
In this episode, I sit down with Laura Lynn Morrissey, founder of Silver Savvy, to discuss how families can successfully navigate aging, home safety, assisted living, and long-term care decisions.
We explore how to start the conversation before crisis hits, identify the family “influencer,” and make informed decisions about everything from home modifications to long-term care insurance. Whether your parents are fiercely independent or a...
Why Losing Your Original Will Could Cost Your Family Everything
This week’s Tuesday Triage question comes from Jazmine in New Jersey. She believed she had “filed” her Will with her attorney until she discovered he’d been disbarred and her original Will was missing. In this episode, Jill unpacks what it really means to “file” your Will, how to protect it, and what happens if your original goes missing. She also shares a true Tennessee case that shows how critical proper Will storage can be and the surprising twists that followed.
What You’ll Learn in This Episode
“Filing” your Will isn’t an official legal act...
Can You Leave Money to Your Dog?
Your dog might run your home, your heart, and your schedule, but legally, he’s still property.
In this episode, Jill explores how to make sure your beloved pets are cared for after you’re gone. From Diane Keaton’s rumored estate plan for her dog, Reggie, to Jill’s own story of Oliver—the “best dog in the universe”—this episode walks through what pet trusts are, how they work, and how to decide if you need one.
What You’ll Learn in This Episode
What a Pet Trust Is. A legal arrangement that sets aside mon...
Why Jane Goodall’s Lessons Matter More Than Ever
In this episode, Jill reflects on the life and legacy of Dr. Jane Goodall, exploring what it means to “do your little bit” in a world where not everyone starts from the same place. From Jane’s courage in defying gender norms to the continuing conversation around affirmative action, equity, and opportunity, this episode weaves together stories of perseverance, purpose, and the quiet power of small, determined acts. Jill connects Jane’s story to her own lessons from running cross-country, a mother’s unwavering support, and what it means to lift the next generation when we can’t always lift ourselv...
Why you need (or don’t need) a Will
Most people think a Will is the foundation of an estate plan but not everything you own is controlled by it. In this episode, Jill Mastroianni breaks down what a Will actually does (and doesn’t) cover, how to tell which of your assets are “probate assets” controlled by your Will, and why understanding the distinction between probate and non-probate assets could change the way you approach your estate plan.
What You’ll Learn in This Episode
The difference between probate and non-probate assets, and why it matters.
The three ways assets pass at death...
Why You Don’t Have to Take the Executor Job
Jill unpacks a common misconception: that you have to serve as Executor just because your name appears in a Will. She explains when, and how, you can decline the role while still protecting family relationships and yourself.
What You’ll Learn in This Episode
You Have a Choice. Just because you’re named in a Will doesn’t mean you’re required to serve. Each state has a process to determine who can step in if you decline.
Executor vs. Personal Representative. Understand the difference between these roles and why “personal representative” is the broader te...
When Deeds Promise to Avoid Probate but Create Chaos
Thinking about using a Ladybird deed (also known as a transfer-on-death deed) to keep your house out of probate? It may sound like the perfect shortcut but it can create more problems than it solves. In this episode, Jill is joined by Minnesota attorney Jen Gumbel to unpack the good, the bad, and the unintended consequences of these deeds. Together, they explore why they’re tempting, where they go wrong, and how they fit (or don’t fit) into a thoughtful estate plan.
Key Takeaways
Deeds: A deed proves ownership of real estate and transfers property. A tra...Why Your Old Will Might Leave Out Your New Baby
Leslie signed her Will five years ago when she had one child. Last year, she had twins. Does her old Will still work—or does it need to be updated? In this episode, Jill answers Leslie’s question and dives into the legal concept of “pretermitted children.” Jill looks at how different states handle this issue and unpacks what happened in the high-profile estates of Heath Ledger and Anna Nicole Smith when their Wills didn’t account for new children.
What You’ll Learn in This Episode
When a Will may still work with more children. Som...
How Small Gaps in Your Will Become Big Problems
What happens if you forget to list something in your will, or if two people end up entitled to the same item, like a piece of jewelry? In this episode, Jill takes on two smart questions from her daughter, April, and unpacks the legal rules around tangible personal property, specific bequests, and residuary estates. Along the way, she shares practical takeaways to help you keep your family out of conflict.
What You’ll Learn in This Episode
The role of a will. A will directs the distribution of your probate assets, the property titled in your na...Why Your Aging Parents Aren’t Planning and How to Change It
So many of us in the sandwich generation can see our parents’ challenges—mobility issues, memory lapses, financial disorganization—yet struggle to help our parents move beyond the problem to actually finding a solution. In this episode, I share my guest appearance on The Legacy of Love Podcast with Sara Ecklein, where we explore how to guide aging parents through estate and life planning in ways that are compassionate, collaborative, and empowering.
Key Insights You’ll Learn
Problem-aware vs. solution-aware: Parents may know they’re struggling (with mobility, memory, or paperwork), but that doesn’t mean they know wh...6 Steps to Finding the Right Estate Planning Attorney for Your Situation
Finding the right estate planning attorney can feel overwhelming and choosing the wrong one can cost you time, money, and peace of mind. In this Tuesday Triage episode, I walk you through six practical steps to help you identify the right fit for your needs, avoid common pitfalls, and trust your instincts throughout the process. Whether your estate is simple or more complex, these tips will give you clarity and confidence in choosing the attorney who can best serve you and your family.
What Jill discussed
·Why referrals are a great starting point but not t...
Why Medical Aid in Dying and Assisted Suicide are not the same thing
Charles just turned 90, and he’s asking a question many of us wonder about but rarely say out loud: “What are my options if I want to die with dignity?”
In this Tuesday Triage, Jill unpacks what medical aid in dying really means, how it differs from assisted suicide, and what the law says for families navigating these difficult conversations. With legal insights and examples from California’s End of Life Option Act, this episode shines a light on a topic often tucked away in silence.
What We Discussed
A personal connection: Jill shares h...
Why an Innocent Woman Spent 27 Years in Prison
Imagine spending 27 years in prison for a crime you didn’t commit. That was the reality for Joyce Watkins, a woman wrongfully convicted in 1989 of the rape and murder of her four-year-old great-niece. Joyce and her longtime partner, Charlie Dunn steadfastly maintained their innocence. But flawed medical testimony, prosecutorial missteps, and systemic biases led to their conviction and life sentences. Charlie tragically died in prison after 27 years, while Joyce was paroled in 2015, branded as a registered sex offender. Even in the face of wrongful conviction, parole restrictions, and decades of injustice, Joyce never gave up her agency.
Jil...
Why Your Business Needs an Estate Plan, Too
Whether you’re a solopreneur, a small-business owner, or running a growing team, your business needs an estate plan. In this episode of Tuesday Triage, Jill walks through the practical steps to protect your business, your income, and the people who depend on you. From organizing legal and financial documents to creating systems that make your business more resilient, this episode is packed with actionable guidance to help you plan from a position of strength, for both growth and the unexpected.
What Jill discussed:
Agency and Planning
Why estate planning is about taking ownership of...How to Protect Your Aging Parents and Avoid Probate Court
Guardianship. Probate court. Powers of attorney. These terms can feel intimidating but they don’t have to be. In this episode, Jill Mastroianni breaks down the differences between powers of attorney and guardianship, and shares actionable steps to help you protect your aging parents, and yourself, from unnecessary stress, cost, and court involvement.
What Jill discussed:
Guardianship vs. Power of Attorney:
How these two tools differ and when each comes into play.Why guardianships (or conservatorships, in some states) should be the last resort.Capacity and Timing:
Why mental capacity is critical fo...What Really Happens with DIY Wills and other Lessons from the Bench
Jill talks with Judge Andra Hedrick, the first female probate court judge in Davidson County, Tennessee, to pull back the curtain on what really happens when DIY wills, internet forms, and quick-fix estate plans land in probate court. They discuss the rise of homemade documents, the conflicts they leave behind, and what families should know about probate, guardianships, and conservatorships. Judge Hedrick also shares insights on how the court works day-to-day, including what happens when families show up without a lawyer and why making your wishes clear is the best way to protect your loved ones.
What...
Why Banks Reject Powers of Attorney for Trust Accounts
In this Tuesday Triage episode, Jill unpacks a common source of frustration for families: why a power of attorney works for some accounts but fails when it comes to trust assets. Using listener Lindsey’s real-life question, Jill explains the crucial distinction between acting as an agent under a power of attorney and serving as trustee. You’ll learn how banks view these documents, why powers of attorney don’t apply to trust accounts, and what you can do to avoid roadblocks when helping aging parents.
What Jill discussed:
Lindsey’s story: Why her father’s power of a...Why Naming the Caregiver Adult Child (instead of your Spouse with Dementia) as Beneficiary of your IRA Can Backfire
In this Tuesday Triage episode, Jill answers a listener question from Molly in Washington, whose father is considering naming her as the beneficiary of his IRA to help care for her mother, who has dementia. Jill explains the potential pitfalls of naming the “helpful child” as a beneficiary, shares a real-life cautionary case from the Michigan Court of Appeals about mishandling a power of attorney, and offers guidance on safer ways to ensure assets are available for care when they are needed most.
What Jill discussed:
The central question: Should Molly’s father name her as IRA be...How One Boy Survived Auschwitz and Found His Dog
Jill speaks with Kari Alterman about the extraordinary life of her father, Emery Grosinger, a Holocaust survivor who lost his parents and his home in the Holocaust. Born in a small village in Hungary, Emery survived Auschwitz, endured a death march, and was ultimately liberated from Mauthausen just before his 13th birthday, May 8, 1945, Victory in Europe Day. Kari shares the story of his survival, resilience, and legacy, and how it inspired her life and work through Good Name Advisors.
What We Discussed
Emery’s idyllic childhood in Transylvania and the close-knit community he grew up inHow sc...What Happens When a Pregnant Woman Is Declared Brain Dead?
When a woman is declared brain dead, but still pregnant, who decides what happens next? And what if she made her wishes clear, but the law says they don’t matter?
Jill explores the tragic case of Adriana Smith, a young nurse from Georgia whose body was kept on life support for four months after brain death because she was nine weeks pregnant.
This episode tackles uncomfortable questions about autonomy, abortion law, and what happens when healthcare decisions collide with unclear legal guidance.
What Jill covers in this episode:
The story of Adr...What Every Parent Needs to Know When Their Child Turns 18
Your child becomes a legal adult at 18, but what if something happens, and they can’t speak for themselves? Would you be allowed in the room? Would you know what they’d want?
In this episode, Jill shares the powerful real-life stories of Nancy Cruzan and Terri Schiavo, and explores the legal right to terminate life-sustaining treatment.
Whether your teen is heading to college or still living at home, Jill walks you through the essential documents and conversations that can protect your child’s autonomy and give your family peace of mind.
What We Cov...
Why Prenups Aren't Just for the Rich (or the Divorcing)
What if a prenup could actually strengthen your relationship?
In this episode, family dynamics coach Emily Bouchard joins Jill Mastroianni to challenge the stigma around prenuptial agreements. They explore how prenups, and the conversations that come with them, can deepen connection, build trust, and clarify expectations in relationships. Whether you’re engaged, remarried, or already decades into marriage, this conversation offers tools for more honest, compassionate dialogue around money.
Jill also shares a real-life story from my legal practice about how one couple’s lack of communication led to unintended and heartbreaking consequences, and how it c...
What You Need to Know About Medicaid and Protecting Your Mom’s House
Are you worried that the government might “take the house” if your parent ever needs nursing home care? A listener named Eileen is facing this exact question, and her son-in-law thinks a trust is the answer. But is it?
In this episode, Jill unpacks how Medicaid works, what a Medicaid Asset Protection Trust actually does, and why good estate planning starts with the person at the center, not just the property.
This episode is a must-listen if you’ve ever panicked about Medicaid’s five-year lookback or felt pressure to “act fast” without knowing what you're really...
Why You Need (or Don't Need) a Trust
Most of us don’t understand what a trust is or what it does. In this bite-sized Tuesday Triage episode, Jill breaks it down in plain language: what a revocable trust is, what it can and can’t do, and how to know whether it’s the right tool for your situation.
What Jill Discusses:
What a trust is and what a revocable trust meansWhy trusts are tools, not status symbolsTwo key reasons people use revocable trusts: (1) to simplify management of assets during life and after death, and (2) to avoid probate after death.Common situations where a revo...What to Do with a Dead Body, Who’s in Charge, and Who Pays
What do you actually do when someone dies? Call 911, the coroner, or Google “funeral homes near me”? In this episode, director of pre-planning at Feldman Mortuary in Denver, Colorado, Jamie Sarche, returns to The Death Readiness Podcast to demystify what really happens behind the scenes after a death. We discuss how a lack of planning can leave your family vulnerable to grief, manipulation, and financial strain, why skipping a funeral can backfire, and how pre-planning can be the ultimate act of love.
We discuss:
Whom to call when someone dies at home
Why calling 911 is o...How Powers of Attorney Work, When to Use Them, and When It’s Too Late to Get One
Your parent’s health is declining. The bills keep piling up. Are you legally allowed to step in? In this first Tuesday Triage episode, Jill explains how powers of attorney really work, who can use them, and what you can do now to prepare for your parent’s cognitive decline before it’s too late.
What We Discussed
What a power of attorney is and when to use itWho can grant a power of attorney and when mental capacity mattersImmediate vs. springing powers of attorneyWhy successor agents can’t act until the primary agent can’tPractical steps to pr...How to Prevent your Estate Plan from Becoming a Family Battlefield
What happens when no one agrees on who should manage a loved one’s care—or their money? Jill talks with Sara Ecklein, a professional fiduciary in California, to talk about what goes wrong when we don’t plan ahead. From costly legal fights to irreparable family breakdowns, they unpack how a neutral third party can step in before conflict becomes a catastrophe.
They also explore what it means to be a mindful fiduciary, how family dynamics get complicated when siblings are put in charge, and why planning isn’t just about documents; it’s about legacy.
What...
How our favorite movies trained us to accept less
What if the movies we loved growing up were quietly teaching us to settle for less credit, less rest, and less power? In this episode, Jill Mastroianni unpacks the messages in movies like Groundhog Day, Three Men and a Baby, and Miss Congeniality, and how those messages still echo today in hospitals, law offices, and family conversations about caregiving and estate planning.
Jill talks about agency, consent, emotional labor, and how the women who keep everything afloat often lack the tools and support they deserve. This episode is both a breakdown and a wake-up call. And, it’s...
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.
If you're juggling caregiving responsibilities, this episode is...
What You Need to Know About Embalming, Cremation, and Eco-Friendly Funerals
What happens to your body after you die—and who decides? Jill sits down with Jamie Sarche, Director of Pre-arranged Funeral Planning, at Feldman Mortuary, to explore embalming, cremation (both fire and water), green burial, body composting, and the emotional and logistical weight of making funeral plans. Jill even begins her own funeral planning on-air, offering listeners a firsthand look at what these conversations involve.
If you've ever wondered what’s inside an urn, whether you can be composted, or why so many cremated remains end up forgotten in a closet, this is the episode for you.
Why Talking About Your Parent's Death Can’t Wait
As a daughter, a sister to a brother with special needs, and a mother herself, Jill Mastroianni knows firsthand what it feels like to carry the weight of future planning. This episode offers an intimate glimpse into her own family’s story—one filled with heartbreak, hesitation, and ultimately, the strength to move forward. Because sometimes death readiness doesn’t feel brave—it just feels necessary.
We explore:
The mental load women carry when they’re the ones holding it all togetherThe emotional weight of estate planning conversations with aging parentsPlanning for a sibling with special needs—and...Start Your Own Family Podcast with these Simple Steps
In this special episode, we step away from legal mechanics and into something deeply personal: the power of capturing family stories. Jill and her daughter April share an episode from their private family podcast, featuring Carmen Mastroianni—Jill’s father and April’s grandfather.
Carmen reflects on his childhood in Schenectady, New York, his unexpected path to college, and his unforgettable experience serving in the Vietnam War. Nicknamed “Macaroni” during basic training, Carmen’s stories are full of humor, heartbreak, and history. Along the way, Jill offers listeners a behind-the-scenes look at how you can create a podcast to p...
How to Start the Senior Care Conversation
In this real and relatable episode, Jill explores the often-avoided topic of senior living and long-term care. She’s joined by senior care consultant Mikelle Rappaport, who breaks down the various types of senior living and care options and how to plan for them—both practically and financially. Jill also speaks with Bob Stanton, who shares the journey of moving his wife of 54 years into a skilled nursing facility. Together, they unpack the real challenges families face when navigating aging, caregiving, and the difficult decisions that arise at their intersection.
What We Discuss
What long-term care real...How to Choose the Right Special Needs Estate Planning Team
In this episode, host Jill Mastroianni continues her conversation with Kristen Lewis, a special needs estate planning attorney. They explore how to build the right team of professionals to support your child’s future. From trustees to life care planners, disability care managers, and legal guardians, they discuss who should be on your team and how to choose the right people for these critical roles.
Kristen also shares key mistakes to avoid—such as disinheriting a child with special needs—and explains how tools like special needs trusts and ABLE accounts fit into a well-rounded planning strategy. Whethe...
