The Death Readiness Podcast: Not your dad’s estate planning podcast

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...

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 Smit...

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 c...

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 t...

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 y...

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...

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 sentenc...

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 a...

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...

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...

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 at...

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,...

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,...

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 aut...

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 ho...

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...

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 t...

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 means Why trusts are tools , not status symbols Two key reasons people use...

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 fi...

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 it Who can grant a power of attorney and...

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...

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 ag...

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 c...

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...

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 necessar...