The Death Readiness Podcast: Not your dad’s estate planning podcast
Jill Mastroianni - Estate Planning & Probate Consultant for Women
57 episodes
3 days ago
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, a former estate planning attorney turned 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, and bite-sized steps you can actually take, even if you’re overwhelmed, even if you’re grieving, even if you’re still waiting for your mom to give you the password to the computer. You don’t need a perfect plan. You just need a place to start.
Death readiness isn’t about control. It’s about love and the courage to face what’s next with open eyes and a steady hand.
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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, a former estate planning attorney turned 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, and bite-sized steps you can actually take, even if you’re overwhelmed, even if you’re grieving, even if you’re still waiting for your mom to give you the password to the computer. You don’t need a perfect plan. You just need a place to start.
Death readiness isn’t about control. It’s about love and the courage to face what’s next with open eyes and a steady hand.
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 expert can lead to a plan that actually works when it matters most.
This episode is about trusting your instincts, understanding your options, and remembering that estate planning is supposed to serve real people, not just legal theory.
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 the riskiest estate-planning move. Through a realistic scenario involving addiction and sibling dynamics, Jill explains how trusts, professional fiduciaries, and no-contest clauses can offer protection without tearing families apart. This episode is about slowing down, thinking clearly, and making estate-planning decisions that protect all of your children.
This episode revisits the most-listened-to episode of The Death Readiness Podcast in 2025. Jill sits down with her dad, Carmen Mastroianni, to talk honestly about raising a child with Down syndrome over a lifetime—from the shock of diagnosis in 1977 to decades of advocacy, inclusion, planning for independence, and learning to live with worry that never fully disappears.
This is not a story about flawless estate planning or financial success. It’s a story about showing up, adapting when systems fall short, and building a legacy quietly through everyday decisions that most people never see.
The holidays are a season of generosity but when gifts are given in a work context, good intentions don’t always lead to the outcome people expect. In this episode, Jill breaks down how the IRS treats cash gifts, bonuses, gift cards, and other “thank yous” given to employees and independent contractors, and why those rules are very different from gifting to family. Using real-world examples, Supreme Court case law, and a few cautionary stories from her years as an estate and tax attorney, Jill explains what’s taxable, what’s deductible, and where people commonly get tripped up when generosity meets the tax code.
Housing security is one of the biggest risks families don’t talk about until it’s too late, especially in blended families and long-term relationships where love and legal ownership don’t line up. In this Tuesday Triage episode, Jill answers a question from a listener named Sarah, who’s worried about her father living in a partner’s home he doesn’t own. Using that real-life scenario, Jill breaks down life estates, leases, and estate planning options in plain English, with a focus on tradeoffs, clarity, and reducing surprise before a crisis forces decisions.
Jill shares how a documentary about poet Andrea Gibson collided with her own avoided medical uncertainty — and why the smallest acts of agency often matter more than the big, dramatic gestures we imagine. Through Andrea’s “biggest tiniest dreams,” parental nervous love, three sweater-wearing rescue dogs, and a long-overdue doctor’s appointment, this episode explores what it means to stay awake to your own life, even when it feels overwhelming. It’s about fear, tenderness, and the luminous beauty tucked inside ordinary days.
This episode starts with a real-world question from a Trader Joe’s cashier in Michigan:
“If I want to leave everything to my brother, can I just write it down and sign it?”
The short answer in Michigan is yes — it’s called a holographic Will. The long answer is complicated.
In this episode, Jill explains what a handwritten Will is, what it legally controls, what the state requires, and how to draft one in an emergency without accidentally creating chaos for the people you love. She also walks step-by-step through a sample holographic Will and breaks down six specific pitfalls that turn “simple” DIY planning into expensive, painful litigation.
This is a practical crash course for anyone wondering whether they really need a lawyer, what handwritten Wills can and can’t do, and how to avoid the disasters that happen when “I’ll just jot this down” intersects with probate.
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 roadmap for how to do any of this without losing your mind or your family.
Hosted by Jill Mastroianni, a former estate planning attorney turned 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, and bite-sized steps you can actually take, even if you’re overwhelmed, even if you’re grieving, even if you’re still waiting for your mom to give you the password to the computer. You don’t need a perfect plan. You just need a place to start.
Death readiness isn’t about control. It’s about love and the courage to face what’s next with open eyes and a steady hand.
