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

When someone dies, their bills don’t generally become yours, but the wrong step can make them yours. In this episode, Jill Mastroianni breaks down what really happens to debt after death, when you can walk away, when you can’t, and why the order in which you pay bills matters more than the amount you owe. Using a real client story, listener Tracy’s question from Virginia, and clear legal examples,...

What happens when someone is killed by a federal officer—and no criminal investigation follows? In this episode, Jill connects Dr. Martin Luther King, Jr.’s final words to the modern-day death of Renée Good, then walks through the legal doctrines that shape accountability in the United States. You’ll learn how immunity works, why investigations matter, and what legal paths, however limited, may st...

A listener in Michigan asks what happens when her Will leaves a lake house that she sold years ago. Jill breaks down how Michigan law treats the sale of specifically gifted property, why the gift doesn’t disappear the way it would under traditional ademption rules, and how that one missing update can unintentionally shift millions of dollars and destroy family relationships.  What You’ll Learn in...

A beautiful estate planning binder doesn’t mean your plan is complete, especially when business interests or stock grants are involved. In this Tuesday Triage episode, Jill Mastroianni unpacks a listener question about distributing a family business in a blended family and uses it to expose one of the most common estate-planning blind spots: assumptions about ownership. Through real-world examples...

What really happened to the home of President James K. Polk? Jill revisits the fate of Polk Place in Nashville and walks through original deeds, wills, and trust language to explain how a presidential estate plan unraveled over decades. The result is a cautionary tale about life estates, unclear ownership, failed trusts, and how even “well-documented” plans can quietly erase a legacy. What You’ll...

What happens when an estate plan is technically correct—but doesn’t quite work in real life? In this Tuesday Triage episode, Jill shares a moment from a client meeting where one simple, common-sense question changed an entire estate plan. Through a personal story and a real client scenario, she breaks down the differences between trusts and powers of attorney, and explains why questioning the expe...

Disinheritance is often viewed as a clean solution to a painful family problem—but in reality, it can create far more conflict, litigation, and long-term harm than people expect. In this Tuesday Triage episode, Jill Mastroianni unpacks what disinheritance actually means, when it tends to arise (often after emotionally charged family gatherings), and why cutting someone out entirely is frequently t...

What You’ll Learn in This Episode · What raising a child with special needs looked like in the 1970s , when there was no internet, limited resources, and little institutional support · Why early intervention matters , and how one supportive professional can change the trajectory of an entire family · How advocacy shows up in everyday moments , from fighting for inclusion in neighborhood schools to...

What You’ll Learn in This Episode Why gifts in the context of work relationships are generally taxable income to the recipient, even when labeled as “holiday gifts” The key difference between gifting to family (federal gift tax rules) and gifting in an employment or business context (income tax rules) Why holiday cash gifts do not qualify as de minimis fringe benefits, and why gift cards are treat...

What You’ll Learn in This Episode Why housing risk is common in blended families and cohabitation situations What a life estate actually is How life estates can be created (by deed, will, or trust) The difference between ownership and the right to live in a home Why many people are uncomfortable blending ownership, even in committed relationships How a lease can provide housing security without li...

What You’ll Learn in This Episode What Andrea Gibson’s “biggest tiniest dreams” teach us about presence, attention, and finding meaning in ordinary moments. How a poet can name experiences we didn't realize we were carrying , from nervous parental love to loving complicated rescue animals. Why agency rarely looks dramatic and how a simple phone call can be an act of courage. What it means to creat...

What You’ll Learn in This Episode What a Holographic Will Is A handwritten Will, entirely, or mostly, in the testator’s handwriting , signed and dated Allowed in some states, including Michigan Often valid on paper, messy in reality Michigan’s Requirements (for validity) A handwritten Will is valid in Michigan if it: Is dated Is signed by the testator Has material portions in the testator’s handwr...

Divorce doesn’t just end a relationship; it leaves a tangle of legal documents, beneficiary forms, and estate planning decisions that need follow-up. In this episode, Jill answers a listener question from Amy in Tennessee, who just finalized her divorce and wants to know whether she needs to update her Will. Jill explains how Tennessee treats estate planning documents after divorce, why beneficiar...

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...

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 cle...

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, sh...

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...

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). Wha...

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 lesso...

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 decisio...

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 critic...

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...

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,...

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 est...

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...