PODCAST · education
The Death Readiness Podcast: Not your dad’s estate planning podcast
by Jill Mastroianni - Estate Planning & Probate Attorney/Lawyer for Women
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 roadmap for how to do any of this without losing your mind or your family.Hosted by Jill Mastroianni, an estate planning and probate attorney and trusted guide for women holding it all together, this podcast is your space to untangle the mess. With more than a decade of legal experience, Jill brings clarity to the hardest conversations most families avoid until it’s too late.Each episode offers honest stories, practical tools,
Episodes
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What to Expect When Hiring an Estate Planning Attorney
Hiring an estate planning attorney shouldn’t require you to figure out your estate plan before you walk through the door. You don’t need to know whether you need a Will or a trust. You don’t need to have every fiduciary selected or every beneficiary designation figured out. And you definitely…
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What Divorced Parents Need to Know About Life Insurance
Your parenting plan may require you to maintain life insurance for your children. But does your beneficiary designation actually accomplish what the court order requires? In this episode of The Death Readiness Podcast, Jill looks at a life insurance provision in Tennessee’s form parenting plan…
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Why Your Responsible Child Might Be the Wrong Trustee
What actually happens after a professional trustee takes over a trust and a beneficiary asks for money? In this episode, Jill sits down with longtime friend and trust advisor Alex Fisher for a behind-the-scenes look at how professional trustees actually do the job. They walk through how...
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Why Your Pour-Over Will Won’t Avoid Probate
You created a revocable trust to avoid probate. So why did your attorney also give you a Will? That Will is a pour-over Will, designed to catch assets that are still in your individual name when you die and direct them into your trust. But there’s an important catch: those assets have to go…
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Why Turning 18 Changes Everything in a Medical Crisis
What You’ll Learn in This Episode What really changes when your child turns 18. Being Mom or Dad no longer necessarily means you’re entitled to healthcare information or automatically have authority to make medical decisions. Why a HIPAA authorization matters. Once your child is an adult, their...
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Why Reading the Will Looks Nothing Like in the Movies
You’ve seen the scene in movies: the family gathers in a lawyer’s office, the Will is dramatically read aloud, and everyone discovers who inherited what. Real life looks very different. In this episode, Jill Mastroianni explains what actually happens to a Will after someone dies, who receives a...
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Why You Shouldn't Add Your Child to Your Deed or Bank Account
Should you add your child to your deed or bank account? It sounds like a simple way to avoid probate or make things easier if you need help later in life. But that estate planning shortcut can create risks you never intended, from exposing your home to your child's creditors to accidentally...
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Why Your Original Will Matters More Than You Think
Have you ever wondered whether a photocopy of your Will is enough? In this episode of The Death Readiness Podcast, estate planning attorney Jill Mastroianni explains why the answer is often no. You'll learn what happens when an original Will can't be found, why courts may presume it was...
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How to Overcome Estate Planning Jargon and Overwhelm
The biggest obstacle to estate planning isn't procrastination. It's confusion and overwhelm. In this episode, Jill shares why she changed the way she practices law, the surprising lesson a surgeon taught her about communication, and why helping clients understand their estate plan is just as...
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How to Avoid Costly Mistakes After a Death
Losing someone you love is hard enough. Figuring out what to do next can feel overwhelming. In this episode, estate planning attorney Jill Mastroianni sits down with estate administration expert Mollie Lacher to discuss the practical realities of settling someone's affairs after death. From...
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Why I Won't Leave My Kids Cash
If your children inherited a million dollars tomorrow, would you want them to receive a check—or a trusted guide? In this episode, Jill pulls back the curtain on her own family's estate plan and walks you through exactly what would happen if she and Jeremy died while their children were still...
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What You Need to Know Before Editing Your Will
What happens if you simply cross out part of your Will, write “VOID” above it, and initial the change? The answer is more complicated, and riskier, than most people realize. In this episode, estate planning attorney Jill Mastroianni explains why making handwritten changes to your estate planning...
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Why Your Power of Attorney Can't Do Everything
When someone you love names you as agent under a power of attorney, it can feel like you'll be able to step in and handle whatever needs to be done. But what happens when the law says otherwise? In this episode, I share the story of a Tennessee woman who discovered that even a broad financial…
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What You Need to Know About Corporate Trustees
Michael thought he had done everything right. He created a revocable trust, avoided probate, and named a neutral third party to serve as trustee after his death. But when the corporate trustee declined to serve, his family spent fourteen years trying to untangle the consequences. In this episode,...
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How Creditors Can Delay a Probate Estate
Can you open a probate estate, distribute the assets, close the file, and move on without worrying about creditors? Not quite. In this episode of The Death Readiness Podcast, Jill answers a listener's question about why probate sometimes feels painfully slow. Using Tennessee law as an example…
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What You Need to Know About Estate Planning at 30
What estate planning documents does a healthy 30-year-old actually need? In this episode of The Death Readiness Podcast, Jill answers a question from a young listener who wondered what someone her age should be doing about estate planning. Using stories from her own life, including the loss of...
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How to Prepare for Retirement Without Panic
Jill Mastroianni is joined by her close friend and financial advisor, Blair Coffman Martin, to discuss how to approach retirement planning, long-term care, and helping adult children without feeling overwhelmed. Blair emphasizes that financial planning isn’t about having all the answers upfront;...
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How Do You Know If Mom Can Still Sign
What happens when someone with memory changes needs to sign a will, trust, or power of attorney? Who actually decides whether they’re “competent” enough to sign, and what happens if people disagree? In this episode, Jill Mastroianni share personal stories involving her own mom, a deathbed signing...
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How to Update Estate Planning After a Dementia Diagnosis
What happens when a parent develops dementia and an attorney tells your family it’s “too late” to update estate planning? In this week’s Tuesday Triage episode, Jill walks through a real-life scenario involving outdated trusts, powers of attorney, probate versus non-probate property, and the…
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How to Take Your Estate Plan Off Script
You can follow all the estate planning rules and still end up with the wrong plan. In this episode, Jill walks through a question from a young attorney who’s been handed traditional estate planning forms and is wondering whether they actually serve her clients. Jill break down how a standard…
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Why your life insurance trust might not work
New clients came in with two life insurance trusts—professionally drafted, signed, notarized, and organized in beautiful binders. There was just one problem: the trusts didn’t do anything. In this episode, Jill breaks down what an irrevocable life insurance trust (ILIT) is, when it actually makes...
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How Living Wills and Last Wills Get Confused All the Time
A living will and a last will and testament sound similar but they do completely different jobs. In this episode, Jill breaks down the difference in plain English so you know what goes where and why it matters. She also walks through a recent Michigan court decision that changes how advance...
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How assets get lost after death and what to do
When someone dies, there’s no master list of what they owned and no automatic system that pulls it all together. In this episode, Jill walks through what actually happens when families try to track down assets, why unclaimed property isn’t the safety net people think it is, and how a lack of...
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Why saying yes to serving as agent under a POA can backfire
Agreeing to serve as an executor, trustee, or agent under a power of attorney often feels like the right thing to do but it’s also one of the most overlooked risks in estate planning. In this episode, Jill flips the perspective and walks through what you need to evaluate before you say yes to a...
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What You Can and Can’t Do with the Trust You Inherited
Can you stop your child from inheriting money, even if the trust says they should? In this estate planning episode, we walk through a real-life scenario where a mother is trying to protect her son from receiving a large inheritance at the wrong time. Along the way, we break down how estate…
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Why That Retirement Account May Not Go Where You Think
What happens if you don’t name a beneficiary on your retirement account? Most people assume it goes to the estate. But that assumption can be dangerously wrong. In this episode, Jill walks through a real case where getting this wrong would have cost a surviving spouse more than $300,000, and...
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Why Giving Money Can Do More Harm Than Good
A viral GoFundMe campaign for a DooDash delivery driver reminds us that generosity, while beautiful, can have unintended consequences. In this episode, Jill walks through real-life examples from her law practice to explain how giving money, especially to someone receiving government benefits, can...
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Why Estate Plans Fail Adult Children
Your parents paid thousands of dollars for a revocable trust but none of the assets were ever transferred into it. Did their estate planning attorney make a mistake? In this episode of The Death Readiness Podcast, Jill Mastroianni explains what it actually means to fund a trust, why this step is...
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Why Good Powers of Attorney Still Fail
Most people think signing a power of attorney is the hard part but the real challenge is making sure it actually works when someone you love needs to use it. In this episode, Jill shares a real-life story of a daughter trying to help her mother and running into unexpected roadblocks with a bank,...
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How to Give Without Jeopardizing Government Benefits
A grandmother wants to divide her wealth equally among her grandchildren — but one grandchild has Down syndrome, and a simple gift could unintentionally jeopardize eligibility for important government benefits. In this Tuesday Triage episode, Jill walks through required minimum distributions...
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Why Small Acts of Care Matter More Than You Think
In this Friday episode, Jill shares the unexpected lessons she’s learning from fostering a puppy named Boots, and how chaos, inconvenience, and small acts of care reveal what agency really looks like. Through stories about raising a guide dog puppy as a child, parenting, and estate planning, this...
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Why You Should Beware of Tax Advice Via Social Media
A viral Instagram reel claims California’s Proposition 19 “hijacks your kids’ inheritance.” In this Tuesday Triage episode, Jill walks through the facts behind the fear. Using a real-world example, she explains how California property taxes actually work, what changed under Proposition 19, and…
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How to be Fair to Your Children in Your Estate Plan
What happens when you give one child a house during your lifetime but want to keep your estate plan “equal” later? In this Tuesday Triage episode, Jill answers a listener question about lifetime gifts, equalizing inheritances, and how beneficiary designations can complicate even the best...
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Why Knowing Your Rights Isn't Enough
After her daughter attends a student-organized ICE protest at school, Jill steps back to examine the legal framework behind immigration enforcement, protest, and constitutional rights. This episode walks through what ICE can and cannot legally do, how the Fourth, Fifth, Sixth, and Second…
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How Geography Can Wreck Your Estate Plan
Where you live can cost, or save, your estate hundreds of thousands of dollars. In this Tuesday Triage episode, Jill Mastroianni breaks down a listener question about estate taxes, domicile, and owning property in multiple states. Using a real-world scenario involving Washington, D.C., Maine,...
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How to Avoid Mistakes with Debt After Death
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...
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What You Need to Know When Justice Feels Out of Reach
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....
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Why Selling the Lake House Can Rewrite Your Will
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...
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How Business Interests Create Estate Planning Blind Spots
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…
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How Poor Estate Planning Cost a First Lady Her Home
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...
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Why You Should Question the Estate Planning Expert
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...
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Why Disinheritance Can Be the Riskiest Estate Plan
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...
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How to Build a Legacy That’s Not About Money
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...
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Why that holiday “thank you” might be taxable
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...
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Why Housing Security Gets Overlooked in Blended Families
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...
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How a Poet Helped Me Face What I Feared
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...
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How to write your own Will (and why you shouldn’t)
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…
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How to Keep Your Ex Out of Your Estate Plan
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…
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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...
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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...
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ABOUT THIS SHOW
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 roadmap for how to do any of this without losing your mind or your family.Hosted by Jill Mastroianni, an estate planning and probate attorney and trusted guide for women holding it all together, this podcast is your space to untangle the mess. With more than a decade of legal experience, Jill brings clarity to the hardest conversations most families avoid until it’s too late.Each episode offers honest stories, practical tools,
HOSTED BY
Jill Mastroianni - Estate Planning & Probate Attorney/Lawyer for Women
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