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The Death Readiness Podcast: Not your dad’s estate planning podcast: Daily Summaries Delivered
by Jill Mastroianni - Estate Planning & Probate Consultant 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, 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 actionable guidance to help you navigate aging parents, estate planning, and family dynamics with confidence and compassion.
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- 3 days ago18 min
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 several young friends, Jill explains why estate planning isn't just for retirees. You'll learn why powers of attorney and healthcare advance directives may be more important than a Will when you're young, how the famous Nancy Cruzan case changed the conversation around end-of-life decision-making, and what a recent Michigan court decision means for pregnant individuals and advance directives. Most importantly, you'll learn why estate planning doesn't have to be perfect; it just has to start. What You’ll Learn in This Episode Why Young Adults Often Avoid Estate Planning Most people in their twenties and thirties aren't ignoring estate planning because they're irresponsible. They're avoiding it because no one has ever explained it to them. Estate planning feels expensive, complicated, and irrelevant—until life proves otherwise. The Four Core Estate Planning Documents Jill explains the four foundational documents that make up a basic estate plan: Last Will and Testament Financial Power of Attorney Healthcare Power of Attorney Healthcare Advance Directive (Living Will) She also shares which of these documents she actually had when she was thirty years old. Why Powers of Attorney Matter More Than You Think A financial power of attorney allows someone you trust to manage financial matters if you're unable to do so yourself. Jill explains the difference between immediate and springing powers of attorney and why she chose to put one in place long before she thought she would ever need it. Bad Things Happen to Young People Too Estate planning isn't just about death. Jill reflects on the loss of former teammates, friends, and family members whose lives changed unexpectedly due to illness, accidents, and catastrophic medical events. Those experiences taught her an important lesson: A tragedy may be unlikely, but it's never impossible. What Nancy Cruzan Can Teach Us Nancy Cruzan was only 25 years old when a car accident left her in a persistent vegetative state. Because she hadn't left clear instructions about her wishes, her family spent years in court, including a case before the United States Supreme Court, trying to answer one heartbreaking question: What would Nancy have wanted? Michigan's New Advance Directive Ruling A recent Michigan court decision struck down a state law that prevented patient advocates from carrying out certain end-of-life decisions for pregnant patients. Jill explains: What the law previously said Why it was challenged How the ruling affects Michigan residents Why pregnancy-related restrictions on advance directives still exist in many states This discussion also connects to the story of Adriana Smith, the Georgia nurse whose case sparked a national conversation about pregnancy and end-of-life decision-making. Do You Need a Will at 30? Jill shares her own situation as a 30-year-old attorney: Single No children Two retirement accounts A checking account A house She explains why she didn't have a Will at that stage of life and why beneficiary designations and account titling can sometimes accomplish much of what young adults need. Estate Planning Isn't a Pass-Fail Test One of the biggest mistakes people make is believing they need to do everything perfectly. Instead, Jill encourages listeners to think of estate planning as a series of small steps: Sign a healthcare power of attorney Complete an advance directive Create a financial power of attorney Add beneficiaries to accounts Organize key information for loved ones Every step makes life easier for the people who may one day need to help you. Resources & Links Watch this episode on YouTube: https://youtu.be/Nde4fFp5Hmk The Death Readiness Playbook: https://www.deathreadiness.com/playbook Important Information Sheets: https://www.deathreadiness.com/resources/important-informati
- 1 weeks ago37 min
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; it’s about starting with what you know, organizing your spending, and creating a flexible plan for the future. They also cover required minimum distributions (RMDs), consolidating accounts, and strategies to involve adult children responsibly in financial decisions. Key Takeaways Retirement readiness is a spectrum, not a single “finish line.” Start by understanding your current spending habits rather than just your savings. Track spending effectively: Financial advisors can help do the heavy lifting: They can consolidate statements, analyze tax returns, and build an initial plan collaboratively. Plan for “tent pole” expenses: Big, irregular expenses (roof repairs, new cars, house renovations) should be accounted for in long-term financial planning. Required Minimum Distributions (RMDs): Consolidating accounts simplifies management: Having accounts spread across multiple institutions adds complexity and risk; consolidation helps both clients and advisors. Including adult children in the conversation: Long-term care planning: Incorporate potential future healthcare needs into financial plans early, even for those not yet in retirement, to reduce uncertainty later. Financial planning is dynamic: Plans should evolve over time to accommodate changing priorities, unexpected events, or new goals. It’s okay to feel unprepared: No one is expected to know all the answers before meeting with a financial advisor. Initial conversations often help clarify next steps and provide peace of mind. Resources & Links Watch this episode on YouTube: https://youtu.be/JsqlbeG8SCk Learn more about Blair Coffman Martin and the team at Robert W. Baird and Co. Incorporated: https://lexingtondt.bairdwealth.com/team/blair-c-martin Blair's email: bcmartin@rwbaird.com Blair's phone number: 859-514-0183 Connect with Jill: Website: DeathReadiness.com Email: jill@deathreadiness.com Learn more about Jill’s solutions Subscribe to the Death Readiness Dispatch! Ask a question for Tuesday Triage Did you enjoy this episode? Share it with someone you care about. This podcast provides estate planning guidance for women and discusses real, practical issues, from caregiving, pre-planning a funeral, how to avoid probate using beneficiary designations, planning for individuals with special needs (and special needs trusts), whether you need a professional fiduciary (trustee or executor), how the estate tax works and how to preserve your legacy. Tuesday Triage episodes answer questions from listeners like you, from powers of attorney, healthcare advance directives (and whether they work when you’re pregnant), what a Last Will and Testament really is, whether you need a trust, how Medicaid works and how to have senior and elder care conversations and how to care for aging parents. Disclaimer: This podcast and all related content are for educational purposes only and do not constitute legal advice. No attorney-client relationship is established here. Use of this information without careful analysis and review by your attorney, CPA, and/or financial advisor may cause serious adverse consequences. For legal guidance tailored to your unique situation, consult with a licensed attorney in your state.
- 2 weeks ago14 min
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 that never happened, and what the law actually says about mental capacity and estate planning. We talk about why competency is not an all-or-nothing question, who acts as the initial gatekeepers during a signing, and why families often begin asking “Can Mom still sign?” when they’re already standing in the middle of a crisis. Most importantly, we talk about why estate planning works best when decisions are made from a place of choice, not urgency. What You’ll Learn in This Episode Why “competent” is not a simple yes-or-no determination The difference between testamentary capacity and contractual capacity Why someone may be able to sign a will but not a power of attorney The four things a person generally needs to understand to sign a will Why dementia does not automatically mean someone lacks legal capacity Why attorneys sometimes refuse to let a client sign documents The risks and concerns that can arise when adult children request standalone powers of attorney The role of notaries and witnesses as gatekeepers, but not final decision-makers What courts look at when capacity is challenged after a signing Why moments of lucidity matter in capacity determinations Why families often wait too long before starting important conversations The hidden systems we all carry in our heads—passwords, finances, routines, healthcare information, and family details Why timing matters more than most families realize Resources & Links Watch this episode on YouTube: https://youtu.be/coX3guCoFMI The Death Readiness Playbook: https://www.deathreadiness.com/playbook Connect with Jill: Website: DeathReadiness.com Email: jill@deathreadiness.com Learn more about Jill’s solutions Subscribe to the Death Readiness Dispatch! Ask a question for Tuesday Triage Did you enjoy this episode? Share it with someone you care about. This podcast provides estate planning guidance for women and discusses real, practical issues, from caregiving, pre-planning a funeral, how to avoid probate using beneficiary designations, planning for individuals with special needs (and special needs trusts), whether you need a professional fiduciary (trustee or executor), how the estate tax works and how to preserve your legacy. Tuesday Triage episodes answer questions from listeners like you, from powers of attorney, healthcare advance directives (and whether they work when you’re pregnant), what a Last Will and Testament really is, whether you need a trust, how Medicaid works and how to have senior and elder care conversations and how to care for aging parents. Disclaimer: This podcast and all related content are for educational purposes only and do not constitute legal advice. No attorney-client relationship is established here. Use of this information without careful analysis and review by your attorney, CPA, and/or financial advisor may cause serious adverse consequences. For legal guidance tailored to your unique situation, consult with a licensed attorney in your state.
- 3 weeks ago24 min
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 estate planning opportunities that may still exist even after incapacity enters the picture. This episode explores how understanding asset titling, existing estate planning documents, and revocable trusts can help families creatively adapt an older estate plan to current realities. What You’ll Learn in This Episode Estate planning is not always “all or nothing.” Even if someone can no longer sign new estate planning documents, meaningful planning opportunities may still exist. Revocable trusts only control assets that are actually transferred into the trust. If the revocable trust was never funded, families may have more flexibility than they realize. A pour-over will acts as a safety net by directing probate assets into the revocable trust after death. Understanding how assets are titled is critical when incapacity becomes part of the estate planning picture. Joint ownership, beneficiary designations, and payable-on-death designations can dramatically affect what estate planning options remain available. Existing durable financial powers of attorney may allow a spouse or agent to continue planning on behalf of an incapacitated individual. Probate property and non-probate property work differently. Probate property requires court involvement after death. Non-probate property transfers automatically by operation of law, contract, beneficiary designation or trust agreement. Families should periodically revisit older estate plans. Estate plans that made sense 20 years ago may no longer fit current finances, health concerns, or family dynamics. Updating powers of attorney for a healthy spouse after the other spouse develops dementia can help make sure both spouses are protected in an emergency. Estate organization matters. Gathering account information, contacts, passwords, beneficiary designations, and legal documents before a crisis can significantly reduce stress for adult children and caregivers. Sometimes good estate planning is less about perfection and more about creatively adapting the tools already in place to the realities of life today. Resources & Links Watch this episode on YouTube: https://youtu.be/6i-C-_q6Mqc Estate Plan Audit: https://www.deathreadiness.com/audit Mollie Lacher and Sunny Care Services: https://sunnycareservices.com/about-us/ Episode 17: How Powers of Attorney Work, When to Use Them, and When It’s Too Late to Get One: https://www.deathreadiness.com/podcast/episode-17-how-powers-of-attorney-work-when-to-use-them-and-when-its-too-late-to-get-one Episode 19: Why You Need (or Don’t Need) a Trust: https://www.deathreadiness.com/podcast/episode-19-how-to-know-if-you-need-a-trust Episode 68: Why Good Powers of Attorney Still Fail: https://www.deathreadiness.com/podcast/68 Probate v. Non-Probate Asset Infographic: https://static1.squarespace.com/static/67427098ef10a8326b64eba9/t/694b2f436198f33cd2adcf08/1766534979768/Probate+and+Non-Probate+Assets+educational+representation.png Connect with Jill: Website: DeathReadiness.com Email: jill@deathreadiness.com Learn more about Jill’s solutions Subscribe to the Death Readiness Dispatch! Ask a question for Tuesday Triage Did you enjoy this episode? Share it with someone you care about. This podcast provides es
- May 5, 202617 min
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 trust structure can limit flexibility for families who don’t need estate tax planning, and how small adjustments can make a big difference. Estate planning isn’t about checking boxes. It’s about building something that works. What You’ll Learn in This Episode What a traditional Family Trust / Marital Trust estate planning structure is and why it’s so commonly used Why many families today don’t need estate tax planning, even though their documents assume they do The tradeoff between tax planning and flexibility for a surviving spouse A simple rule: the more control you have over an asset, the more likely it is to be included in your taxable estate Why an estate plan can technically “work” and still miss your actual goals How directing assets to a Marital Trust can provide more flexibility in certain situations What a Disclaimer Trust is and how it can build in estate planning flexibility for future law changes Why estate planning should account for human behavior, not just legal theory The best estate plans are designed to adapt over time, not just work on day one Resources & Links Watch this episode on YouTube: https://youtu.be/Ad7ZkN6sX6I Estate Plan Audit: https://www.deathreadiness.com/audit Episode 19: Why You Need (or Don’t Need) a Trust: https://www.deathreadiness.com/podcast/episode-19-how-to-know-if-you-need-a-trust Episode 38: Why You Need (or Don’t Need) a Will: https://www.deathreadiness.com/podcast/why-you-need-or-dont-need-a-will Connect with Jill: Website: DeathReadiness.com Email: jill@deathreadiness.com Learn more about Jill’s solutions Subscribe to the Death Readiness Dispatch! Ask a question for Tuesday Triage Did you enjoy this episode? Share it with someone you care about. This podcast provides estate planning guidance for women and discusses real, practical issues, from caregiving, pre-planning a funeral, how to avoid probate using beneficiary designations, planning for individuals with special needs (and special needs trusts), whether you need a professional fiduciary (trustee or executor), how the estate tax works and how to preserve your legacy. Tuesday Triage episodes answer questions from listeners like you, from powers of attorney, healthcare advance directives (and whether they work when you’re pregnant), what a Last Will and Testament really is, whether you need a trust, how Medicaid works and how to have senior and elder care conversations and how to care for aging parents. Disclaimer: This podcast and all related content are for educational purposes only and do not constitute legal advice. No attorney-client relationship is established here. Use of this information without careful analysis and review by your attorney, CPA, and/or financial advisor may cause serious adverse consequences. For legal guidance tailored to your unique situation, consult with a licensed attorney in your state.
- Apr 28, 202621 min
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 sense, and how it fails when no one follows through. This is a real-life look at the gap between having documents and having an estate plan that actually works. What You’ll Learn in This Episode What an irrevocable life insurance trust (ILIT) actually does Why ILITs are primarily used to address estate tax The current federal estate tax exemption and why most people don’t need an ILIT The difference between estate tax and estate income tax (Form 706 vs. Form 1041) Why “setting up” a trust is not the same as “funding and administering” it The key questions to ask about any life insurance policy: Who owns it? Who is the beneficiary? Why an ILIT that isn’t connected to the policy is just a stack of paper What’s actually involved in creating and maintaining an ILIT How gift tax rules apply when funding a life insurance trust What Crummey letters are and why they matter Why serving as trustee is a real job, not just a title How the “trust recession” is changing the way people approach estate planning Resources & Links Watch this episode on YouTube: https://youtu.be/JaE0tkaacoU Episode 5, Why you shouldn’t worry about the estate tax: https://www.deathreadiness.com/podcast/why-you-shouldnt-worry-about-the-estate-tax Get your copy of The Death Readiness Playbook: www.deathreadiness.com/playbook Connect with Jill: Website: DeathReadiness.com Email: jill@deathreadiness.com Learn more about Jill’s solutions Subscribe to the Death Readiness Dispatch! Ask a question for Tuesday Triage Did you enjoy this episode? Share it with someone you care about. This podcast provides estate planning guidance for women and discusses real, practical issues, from caregiving, pre-planning a funeral, how to avoid probate using beneficiary designations, planning for individuals with special needs (and special needs trusts), whether you need a professional fiduciary (trustee or executor), how the estate tax works and how to preserve your legacy. Tuesday Triage episodes answer questions from listeners like you, from powers of attorney, healthcare advance directives (and whether they work when you’re pregnant), what a Last Will and Testament really is, whether you need a trust, how Medicaid works and how to have senior and elder care conversations and how to care for aging parents. Disclaimer: This podcast and all related content are for educational purposes only and do not constitute legal advice. No attorney-client relationship is established here. Use of this information without careful analysis and review by your attorney, CPA, and/or financial advisor may cause serious adverse consequences. For legal guidance tailored to your unique situation, consult with a licensed attorney in your state.
- Apr 21, 202612 min
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 directives work and raises a bigger question: who gets to decide in a medical crisis? What You’ll Learn in This Episode Why these documents get confused. “Living will” and “last will” sound similar, but they operate at completely different times and serve different purposes. What a living will actually does Covers medical decisions when you’re alive but unable to speak Addresses questions like life support and end-of-life care In Michigan, this is part of an advance directive, not a standalone document The role of a patient advocate The person you name to make healthcare decisions for you Can act any time you’re incapacitated, not just at end of life What changed in Michigan law (April 2026) A court struck down a rule preventing patient advocates from honoring a pregnant patient’s end-of-life wishes The case centered on reproductive freedom under Michigan’s constitution What a last will and testament does Takes effect after death Controls distribution of probate assets, appointment of a personal representative, and guardianship for minor children Does not control medical decisions The simplest way to think about it Living will = medical decisions while you’re alive Last Will = financial and administrative decisions after death Why this matters for your family A living will gives direction in a hospital room A last will gives structure after death Resources & Links Watch this episode on YouTube: https://youtu.be/N4in8DLF7Mw Related Episode: How to Write Your Own Will and Why You Shouldn’t: https://www.deathreadiness.com/podcast/50 Submit a Question for Upcoming Guest Blair Martin (Financial Advisor): Email: jill@deathreadiness.com Connect with Jill: Website: DeathReadiness.com Email: jill@deathreadiness.com Learn more about Jill’s solutions Subscribe to the Death Readiness Dispatch! Ask a question for Tuesday Triage Did you enjoy this episode? Share it with someone you care about. This podcast provides estate planning guidance for women and discusses real, practical issues, from caregiving, pre-planning a funeral, how to avoid probate using beneficiary designations, planning for individuals with special needs (and special needs trusts), whether you need a professional fiduciary (trustee or executor), how the estate tax works and how to preserve your legacy. Tuesday Triage episodes answer questions from listeners like you, from powers of attorney, healthcare advance directives (and whether they work when you’re pregnant), what a Last Will and Testament really is, whether you need a trust, how Medicaid works and how to have senior and elder care conversations and how to care for aging parents. Disclaimer: This podcast and all related content are for educational purposes only and do not constitute legal advice. No attorney-client relationship is established here. Use of this information without careful analysis and review by your attorney, CPA, and/or financial advisor may cause serious adverse consequences. For legal guidance tailored to your unique situation, consult with a licensed attorney in your state.
- Apr 14, 202612 min
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 organization can turn estate administration into a frustrating, years-long scavenger hunt. This is where estate planning meets real life and where most plans break down. What You’ll Learn in This Episode There is no central database of your assets. Death doesn’t come with a built-in inventory. When you die, your fiduciary has to piece everything together manually. Finding assets is one of the hardest parts of estate administration. Executors often start with tax returns to identify income-producing assets but that’s only a partial picture. Even professionals don’t have perfect tools. Asset-search platforms (like Trustate) can help, but they rely on incomplete databases and still require human follow-up. People, not systems, are often the biggest bottleneck. Accessing information frequently depends on whether someone is willing (or able) to respond, not whether the information exists. Unclaimed property is not a reliable backup plan. Assets only end up there if institutions know someone has died and can’t locate an owner and even then, it can take years. Estate planning isn’t just documents; it’s information sharing. Having a will or trust is not enough if no one knows what you own or where to find it. Your fiduciary can’t guarantee they’ll find everything. Even the most diligent executor can only follow leads. They can’t recover what they don’t know exists. Preparation reduces emotional and administrative burden. Organizing your assets now is one of the most practical ways to support your family later. Resources & Links Watch this episode on YouTube: https://youtu.be/_fNqrE306C8 The Death Readiness Playbook. A practical guide + worksheets to help you organize your assets and make estate administration easier for your family: https://www.deathreadiness.com/playbook Sunny Care Services (Mollie Lacher). Professional executor and personal representative services: https://sunnycareservices.com/ Trustate: https://www.trustate.com/ Pet Information Sheet: https://www.deathreadiness.com/pet-important-info-sheet Connect with Jill: Website: DeathReadiness.com Email: jill@deathreadiness.com Learn more about Jill’s solutions Subscribe to the Death Readiness Dispatch! Ask a question for Tuesday Triage Did you enjoy this episode? Share it with someone you care about. This podcast provides estate planning guidance for women and discusses real, practical issues, from caregiving, pre-planning a funeral, how to avoid probate using beneficiary designations, planning for individuals with special needs (and special needs trusts), whether you need a professional fiduciary (trustee or executor), how the estate tax works and how to preserve your legacy. Tuesday Triage episodes answer questions from listeners like you, from powers of attorney, healthcare advance directives (and whether they work when you’re pregnant), what a Last Will and Testament really is, whether you need a trust, how Medicaid works and how to have senior and elder care conversations and how to care for aging parents. Disclaimer: This podcast and all related content are for educational purposes only and do not constitute legal advice. No attorney-client relationship is established here. Use of this information without careful analysis and review by your attorney, CPA, and/or financial advisor may cause serious adverse consequences. For legal guidance tailored to your unique situation, consult with a licensed attorne
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About 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 actionable guidance to help you navigate aging parents, estate planning, and family dynamics with confidence and compassion.
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