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

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 actionable guidance to help you plan from a position of strength, for both growth and the unexpected.

What Jill discussed:

Agency and Planning

• Why estate planning is about taking ownership of your business and future.
• A client story that illustrates why having access to business agreements matters.

Business Foundations

• Ensuring you have your EIN letter and business entity governing documents.
• Why even solopreneurs need an Operating Agreement, and what it should cover.
• How to request copies of official filings from your Secretary of State.

Banking and Financial Preparedness

• Adding a second signer to your business accounts.
• Why access to cash flow is critical to keeping operations running in your absence.

Accounting and Bookkeeping

• Systems for tracking income and expenses.
• The benefits of outsourcing bookkeeping for peace of mind and continuity.

People and Relationships

• Identifying your key clients and team members.
• Adding a “death or incapacity” clause to client contracts.
• Keeping an accessible list of important contacts and roles.

Recurring Expenses and Digital Access

• Documenting subscriptions, accounts, and access credentials.
• Managing digital assets like domains, trademarks, and renewals.

Systems and Processes

• The importance of standard operating procedures (SOPs) for daily tasks.
• Using clear documentation to make your business resilient and scalable.

Content Management

• Organizing your content for easier repurposing and brand consistency.
• Creating a master file for branding and creative assets.

Insurance and Risk Management

Key types of coverage every business owner should consider:

• Businessowner’s policy for general liability
• Cybersecurity and digital media coverage
• Professional liability insurance

Advanced Planning Tips

• Using life insurance to maintain cash flow during transitions.

Final Takeaway

• Planning for your business isn’t just about preparing for the worst — it’s about creating systems and organization that make your business stronger and more valuable every day.

Resources and Links

• Learn more about Jill's Estate Planning Support Services

Connect with Jill:

• Website: DeathReadiness.com
• Email: [email protected]
• Subscribe to receive news and updates.
• Love this episode? Please rate and review in the Apple podcasts app!
• Submit 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.

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 Attorney:

• How these two tools differ and when each comes into play.
• Why guardianships (or conservatorships, in some states) should be the last resort.

Capacity and Timing:

• Why mental capacity is critical for signing a power of attorney.

Avoiding Probate Court:

• Proactive planning steps to reduce the chances of a guardianship proceeding.
• The importance of early conversations with your parents and transparency among family members.

Real-World Scenarios:

• Examples of how lack of communication or delayed planning can lead to confusion, conflict, or costly legal battles.

Action Steps for Listeners:

1. Start the conversation early. Talk with your parents about the importance of powers of attorney while they still have mental capacity. And if you don’t already have your own power of attorney, lead by example. Get one in place, and—if you’re comfortable—share whom you chose as your agent and why.

2. Share key information. When it’s possible and safe to do so, let other family members know that these documents are in place. Transparency helps reduce misunderstandings later on.

3. Keep the focus on care, not control. Powers of attorney aren’t about taking over someone’s life. They’re about protecting the people we love when they’re unable to protect themselves.

Resources and Links

• Parent Prep Plan: Personalized support to walk your parents through the estate planning process, from finding the right attorney to organizing assets and understanding legal documents.
• Episode 27: Judge Hedrick’s interview: What Really Happens with DIY Wills and other Lessons from the Bench
• Episode 17: How Powers of Attorney Work, When to Use Them, and When It’s Too Late to Get One.
• Episode 25: Why Naming the Caregiver Adult Child (instead of your Spouse with Dementia) as Beneficiary of your IRA Can Backfire
• Episode 26: Why Banks Reject Powers of Attorney for Trust Accounts

Connect with Jill:

• Website: DeathReadiness.com
• Email: [email protected]
• Subscribe to receive news and updates.
• Love this episode? Please rate and review in the Apple podcasts app!
• Submit 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.

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 Hedrick also shares insights on how the court works day-to-day, including what happens when families show up without a lawyer and why making your wishes clear is the best way to protect your loved ones.

What We Discussed:

What Probate Actually Means

• Why a will has no legal effect until it is admitted to probate.
• How the petition process works and what “pro se” (representing yourself) looks like in court.

Beyond Wills: Other Roles of Probate Court

• Guardianships for minors inheriting money.
• Emancipation proceedings for minors entering contracts (like young entertainers).
• Conservatorships for adults with disabilities or cognitive decline, and the conflicts that arise when family members disagree.

Challenges in Court

• Families surprised by estate outcomes that don’t match verbal promises.
• The risks of vague or conflicting instructions from a deceased loved one.

The Rise of DIY and Internet Wills

• Why homemade wills often create confusion and costly cleanup.
• Missing provisions (like residuary clauses) that cause unintended gaps.
• Examples of ambiguous language and why precision matters.
• Why fixing problems after death is far more expensive than doing it right from the start.

Inside the Courtroom

• Open access to the public and how hearings can often be observed (sometimes even via Zoom).
• Court culture and expectations around dress, conduct, and participation.
• Judge Hedrick’s perspective on keeping the court accessible to all.

Resources & Links

• Parent Prep Plan – If you’re worried your parents may try the DIY will route, Jill can help walk them through the estate planning process with the right attorney and keep things moving forward: Parent Prep Plan — Death Readiness

Connect with Jill:

• Website: DeathReadiness.com
• Email: [email protected]
• Subscribe to receive news and updates.
• Love this episode? Please rate and review in the Apple podcasts app!
• Submit 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.

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 attorney don’t apply to trust accounts, and what you can do to avoid roadblocks when helping aging parents.

What Jill discussed:

• Lindsey’s story: Why her father’s power of attorney worked at the bank for checking and savings accounts, but not for trust accounts.
• The basics of a financial power of attorney: What authority it gives, and its limits.
• Why banks sometimes hesitate: Knowledge gaps, fear of liability, and extra review layers.
• Tips to smooth the process: Submitting powers of attorney before capacity is lost, and consolidating accounts at cooperative institutions.
• The bigger picture: A power of attorney covers personal assets; trust assets follow the trust agreement.

Resources & Links:

• Episode 17: How Powers of Attorney Work, When to Use Them, and When It’s Too Late to Get One
• Episode 19: Why You Need (or Don’t Need) a Trust
• Parent Prep Plan – Hands-on support to help your parents start (and finish) their estate planning 

Connect with Jill:

• Website: DeathReadiness.com
• Email: [email protected]
• Subscribe to receive news and updates.
• Love this episode? Please rate and review in the Apple podcasts app!
• Submit 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.

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, and offers guidance on safer ways to ensure assets are available for care when they are needed most.

What Jill discussed:

• The central question: Should Molly’s father name her as IRA beneficiary to help care for her mother?
• Three major problems with naming a child as beneficiary in this context:
• A Michigan Court of Appeals case illustrating breach of fiduciary duty by an agent under a power of attorney
• The fiduciary duties of an agent: good faith, loyalty, prohibition against self-dealing, and meticulous record-keeping
• Practical advice: If you’re managing someone’s finances, keep accurate records from the start and get help if needed.

Link

• Tuesday Triage episode on powers of attorney: How Powers of Attorney Work, When to Use Them, and When It’s Too Late to Get One

Connect with Jill:

• Website: DeathReadiness.com
• Email: [email protected]
• Subscribe to receive news and updates.
• Love this episode? Please rate and review in the Apple podcasts app!
• Submit 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.

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, resilience, and legacy, and how it inspired her life and work through Good Name Advisors.

What We Discussed

• Emery’s idyllic childhood in Transylvania and the close-knit community he grew up in
• How scarlet fever and a delayed hospital discharge upended the family’s chance to hide from the Nazis
• Life in the ghettos and the horrific conditions aboard cattle cars to Auschwitz
• Slave labor at Auschwitz, including the senseless task of building walls to be torn down each day
• Emery’s separation from his parents, and the small moments of reconnection with his mother through a fence
• A narrow escape from death thanks to Kari’s father following a group of Polish boys to another barracks
• The brutal death march and train transport to Mauthausen
• Liberation on his 13th birthday, and the train journey back to his village
• The miraculous survival of Emery’s family dog
• The journey to the United States, including fake passports, a six-week visa, and overstaying to build a life in Detroit
• How Kari’s father’s values, humor, and resilience live on in her family, and inspired her business, Good Name Advisors
• A brief explanation of the Claims Conference and symbolic reparations for Holocaust survivors

Resources & Links

• The Zekelman Holocaust Center in Michigan
• Aunt Clara’s video interview
• Emery Grosinger’s family dog

Connect with Kari Alterman:

• Website: GoodNameAdvisors.com
• Email: [email protected]
• Subscribe to Kari’s email newsletter here. 

Connect with Jill:

• Website: DeathReadiness.com
• Email: [email protected]
• Subscribe to receive news and updates.
• Love this episode? Please rate and review in the Apple podcasts app!
• Submit 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.

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 autonomy, abortion law, and what happens when healthcare decisions collide with unclear legal guidance.

What Jill covers in this episode:

• The story of Adriana Smith, who was declared brain dead when she was 9 weeks pregnant
• How Georgia's abortion and advance directive laws might have affected her care
• The 2013 case of Marlise Munoz and Texas’s pregnancy restrictions on end-of-life care
• The Dobbs  United States Supreme Court decision: what it actually did, and what the dissent said
• Georgia’s advance directive statute and its impact on end-of-life care for pregnant women
• A 2019 JAMA study showing how 31 states restrict advance directives during pregnancy
• Reflections on what it means to feel powerless and why kindness matters in hard conversations

Connect with Jill:

• Website: DeathReadiness.com
• Email: [email protected]
• Subscribe to receive news and updates.
• Love this episode? Please rate and review in the Apple podcasts app!
• Submit a question for Tuesday Triage

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.

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 home, Jill walks you through the essential documents and conversations that can protect your child’s autonomy and give your family peace of mind.

What We Cover in This Episode:

• Why the law treats your child differently the moment they turn 18
• The story of Nancy Cruzan, and how a lack of documentation led to a prolonged legal battle all the way to the U.S. Supreme Court
• The story of Terri Schiavo, the national debate that followed, and what it revealed about end-of-life decision-making
• What “persistent vegetative state” and “clear and convincing evidence” mean
• The difference between a guardian and a guardian ad litem
• Why advance healthcare directives and healthcare powers of attorney matter, not just for older adults, but for your 18-year-old
• Conversation starters for talking to your child about medical wishes
• Jill’s personal story and why she chose her husband as her agent

Resources + Links:

• State-by-State Advance Directive Forms
• Tuesday Triage Submission

Connect with Jill:

• Website: DeathReadiness.com
• Email: [email protected]
• Subscribe to receive news and updates.
• Love this episode? Please rate and review in the Apple podcasts app!

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.

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 marriage, this conversation offers tools for more honest, compassionate dialogue around money.

Jill also shares a real-life story from my legal practice about how one couple’s lack of communication led to unintended and heartbreaking consequences, and how it could have been different.

If you've ever felt uncomfortable talking about money with someone you love, this episode is for you.

Listen to learn:

• Why a prenup isn't planning for divorce; it's planning with intention
• What financial infidelity looks like and how it erodes trust
• How childhood money experiences shape adult relationships with money
• The difference between the “context” and “content” of a prenup
• Tips for starting prenup and money conversations with empathy and intention
• What to do if red flags surface before the wedding
• Why these conversations matter, even if you're already married (or never plan to be)

Resources & Links:

• Get a free digital copy of The Beginner’s Guide to Purposeful Prenups by contacting Emily Bouchard
• Seinfeld clip: Ask her to sign a prenup

Connect with Emily:

• Website: www.emilybouchard.com
• Listen to Emily’s podcast, Wealth Coherence
• Connect with Emily on LinkedIn

Connect with Jill:

• Website: DeathReadiness.com
• Email: [email protected]
• Subscribe to receive news and updates.
• Love this episode? Please rate and review in the Apple podcasts app!

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.

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 the property. 

This episode is a must-listen if you’ve ever panicked about Medicaid’s five-year lookback or felt pressure to “act fast” without knowing what you're really signing up for.

Listen to learn:

• What Medicaid is, and how it differs from Medicare
• What it actually means for the government to “take the house”
• What Medicaid Estate Recovery is and how it plays out in real life
• How a Medicaid Asset Protection Trust works (and when it might backfire)
• What the five-year lookback is and how the penalty period is calculated
• Why giving away control could cause more problems than it solves
• The question every family should ask: Does this plan serve the person at the center of it?
• What to consider before putting your parent’s house in a trust

Resources & Links

• Episode 10 of The Death Readiness Podcast: How to Start the Senior Care Conversation
• Episode 19 of The Death Readiness Podcast: Why You Need (or Don’t Need) a Trust
• U.S. Department of Health and Human Services 2019 Research Brief: What Is the Lifetime Risk of Needing and Receiving Long-Term Services and Supports?

Connect with Jill:

• Website: DeathReadiness.com
• Email: [email protected]
• Subscribe to receive news and updates.
• Love this episode? Please rate and review in the Apple podcasts app!
• Submit a question for Tuesday Triage!

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.