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A listener in Michigan asks what happens when her Will leaves a lake house that she sold years ago. Jill breaks down how Michigan law treats the sale of specifically gifted property, why the gift doesn’t disappear the way it would under traditional ademption rules, and how that one missing update can unintentionally shift millions of dollars and destroy family relationships.
What You’ll Learn in This Episode
Resources & Links
Michigan Estates & Protected Individuals Code, Section 700.2606 (Specific devises; nonademption rules)
Purchase The Death Readiness Playbook: https://www.deathreadiness.com/playbook
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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.
A beautiful estate planning binder doesn’t mean your plan is complete, especially when business interests or stock grants are involved. In this Tuesday Triage episode, Jill Mastroianni unpacks a listener question about distributing a family business in a blended family and uses it to expose one of the most common estate-planning blind spots: assumptions about ownership.
Through real-world examples and practical guidance, Jill walks listeners through how to identify who actually owns a business interest, what that ownership really means, and why these details matter long before a crisis forces the issue.
What You’ll Learn in This Episode
Why business interests and stock grants are often the weakest link in an otherwise solid estate plan
How a “perfect” estate planning binder can still be full of gaps
Why contributing money to a business does not automatically mean you own the business interest
How to use tax documents like Schedule K-1s and Form 1099-DIVs to identify ownership
The difference between pass-through entities and C corporations, and why that matters
How buy-sell agreements work in family businesses and how life insurance funds them
A practical starting point for gathering reliable business information using the Secretary of State’s records
Resources & Links
The Death Readiness Playbook. A practical system to help you translate documents into real-world readiness and fill in the gaps that estate plans often miss. https://www.deathreadiness.com/playbook
Tennessee Secretary of State – Business Entity Search. Use this link to look up entity details and historical filings): https://tncab.tnsos.gov/business-entity-search
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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.
What really happened to the home of President James K. Polk? Jill revisits the fate of Polk Place in Nashville and walks through original deeds, wills, and trust language to explain how a presidential estate plan unraveled over decades. The result is a cautionary tale about life estates, unclear ownership, failed trusts, and how even “well-documented” plans can quietly erase a legacy.
What You’ll Learn in This Episode
Having documents isn’t the same as having an effective estate plan. James Polk had a will, and a trust but unrealistic assumptions and expectation still led to a will contest.
A life estate is not ownership. Sarah Polk had the right to live in Polk Place for her lifetime, but she did not own it. That distinction determined everything that happened next.
How property is titled controls what happens at death. The deed to Polk Place showed sole ownership in James Polk’s name, which gave him the power to dictate what happened at his death.
Trusts fail when trustees never agreed to serve. Polk assumed the State of Tennessee would act as trustee without evidence the state ever accepted that role.
Poor estate planning risks more than money. The real loss wasn’t just a house; it was history, continuity, and the ability to honor lived relationships.
Resources & Links
The Preamble Podcast, hosted by Sharon McMahon: Sarah Polk’s Power Behind the Presidency
Lady First: The World of First Lady Sarah Polk by Amy S. Greenberg
The Death Readiness Playbook. A practical guide to understanding what you have, how estate planning actually works, and where plans commonly fall apart: https://www.deathreadiness.com/playbook
Connect with Jill:
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.
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.
What You’ll Learn in This Episode
Resources & Links
Episode 19:Why You Need (or Don’t Need) a Trust. A deeper dive into when revocable trusts make sense—and when they don’t.
Episode 17:How Powers of Attorney Work, When to Use Them, and When It’s Too Late to Get One. A practical explanation of financial powers of attorney and how they function in real life.
The Death Readiness Playbook A step-by-step system to help you organize information, understand your documents, and identify gaps before a crisis forces decisions.
Learn more at deathreadiness.com/playbook
Connect with Jill:
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.
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.
What You’ll Learn in This Episode
Resources & Links
Connect with Jill:
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.
What You’ll Learn in This Episode
·What raising a child with special needs looked like in the 1970s, when there was no internet, limited resources, and little institutional support
·Why early intervention matters, and how one supportive professional can change the trajectory of an entire family
·How advocacy shows up in everyday moments, from fighting for inclusion in neighborhood schools to pushing back when institutions say “there’s no place for your child.”
·Why mainstreaming and community inclusion matter, not just academically, but socially, and how being known in a community can protect and empower a child.
·What independence can look like for an adult with special needs, including living in a group home, working, maintaining friendships, and making decisions about one’s own life.
·How group homes actually work, including funding, staffing, waitlists, and the realities families face as caregivers age.
·Why planning for the future is essential, especially when parents won’t always be around, and how special needs trusts fit into that picture.
·How individuals with special needs experience grief, relationships, and emotional loss, often more deeply than people assume.
·Why legacy isn’t just about money, but about advocacy, adaptability, and the quiet, persistent work of love over decades.
Resources & Links
Center for Disability Services: Residential Services
Center for Disability Services
314 South Manning Blvd.
Albany, NY 12208
518-437-5700
The Center for Disability Services is a nonprofit organization in New York that provides comprehensive support and services for individuals with disabilities. The Center played a crucial role in securing supportive housing and care for Dan. Through its commitment to inclusion and individualized care, the Center continues to provide essential resources that empower individuals with disabilities to lead fulfilling lives.
Gerald B. Healy, MD, FACS was an ear, nose, and throat specialist at Children’s Hospital in Boston who played a critical role in saving Dan’s life. Dan suffered from severe respiratory issues as a toddler—issues that local doctors were unable to diagnose. Dr. Healy identified that Dan’s airway was dangerously small due to enlarged tonsils and adenoids and recommended immediate surgery.
Kids Like These is a 1987 TV movie that tells the story of a couple who has a baby with Down syndrome. The script was co-written by Emily Perl Kingsley, a well-known advocate for individuals with disabilities, along with Allan Sloane. Kingsley, whose own son, Jason Kingsley, has Down syndrome, infused the film with real-life experiences to highlight the struggles and triumphs of parenting a child with special needs.
One notable detail from the movie was inspired by Dan’s mother, who once shared a story with Emily Perl Kingsley about Dan being denied a library card because he couldn’t sign his name. This real-life event was later referenced in the film, illustrating the systemic barriers faced by individuals with disabilities and the importance of advocacy.
Connect with Jill:
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.
What You’ll Learn in This Episode
Why gifts in the context of work relationships are generally taxable income to the recipient, even when labeled as “holiday gifts”
The key difference between gifting to family (federal gift tax rules) and gifting in an employment or business context (income tax rules)
Why holiday cash gifts do not qualify as de minimis fringe benefits, and why gift cards are treated as cash equivalents
What employee achievement awards are, why cash doesn’t qualify, and how strict the requirements really are, including dollar limits and “meaningful presentation” rules
How gifts to someone who is both family and employee are analyzed, and why intent and context matter more than labels
Why gifts tied to service, loyalty, or length of employment are treated as compensation, even when they feel heartfelt
How the Supreme Court’s decision in Commissioner v. Duberstein (1960) still governs whether a transfer is a true gift or taxable income
What can happen in estate planning when bequests to employees are framed as thanks for service—and how wording can change tax outcomes for beneficiaries
Resources & Links
Episode 46: How to Give Money Without Triggering Gift Tax
Commissioner v. Duberstein, 363 U.S. 278 (1960)
The Supreme Court case that established the “detached and disinterested generosity” test for gifts connected to business or employment relationships
The Death Readiness Playbook - A practical, guided system for organizing information, making decisions, and turning good intentions into real clarity www.deathreadiness.com/playbook
See Internal Revenue Code Sections below.
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Internal Revenue Code Sections
26 U.S. Code § 102(a) General rule. Gross income does not include the value of property acquired by gift, bequest, devise, or inheritance.
26 U.S. Code § 102(c) Employee gifts
(1) In general
Subsection (a) shall not exclude from gross income any amount transferred by or for an employer to, or for the benefit of, an employee.
(2) Cross references
For provisions excluding certain employee achievement awards from gross income, see section 74(c).
For provisions excluding certain de minimis fringes from gross income, see section 132(e).
26 U.S. Code §274(j) Employee achievement awards
(1) General rule
No deduction shall be allowed under section 162 or section 212 for the cost of an employee achievement award except to the extent that such cost does not exceed the deduction limitations of paragraph (2).
(2) Deduction limitations
The deduction for the cost of an employee achievement award made by an employer to an employee—
(A) which is not a qualified plan award, when added to the cost to the employer for all other employee achievement awards made to such employee during the taxable year which are not qualified plan awards, shall not exceed $400, and
(B) which is a qualified plan award, when added to the cost to the employer for all other employee achievement awards made to such employee during the taxable year (including employee achievement awards which are not qualified plan awards), shall not exceed $1,600.
(3) Definitions
For purposes of this subsection—
(A) Employee achievement award
(i) In general
The term “employee achievement award” means an item of tangible personal property which is—
(I) transferred by an employer to an employee for length of service achievement or safety achievement,
(II) awarded as part of a meaningful presentation, and
(III) awarded under conditions and circumstances that do not create a significant likelihood of the payment of disguised compensation.
(ii) Tangible personal property
For purposes of clause (i), the term “tangible personal property” shall not include—
(I) cash, cash equivalents, gift cards, gift coupons, or gift certificates (other than arrangements conferring only the right to select and receive tangible personal property from a limited array of such items pre-selected or pre-approved by the employer), or
(II) vacations, meals, lodging, tickets to theater or sporting events, stocks, bonds, other securities, and other similar items.
26 U.S. Code §74(c) Exception for certain employee achievement awards
(1) In general
Gross income shall not include the value of an employee achievement award (as defined in section 274(j)) received by the taxpayer if the cost to the employer of the employee achievement award does not exceed the amount allowable as a deduction to the employer for the cost of the employee achievement award.
(2) Excess deduction award. If the cost to the employer of the employee achievement award received by the taxpayer exceeds the amount allowable as a deduction to the employer, then gross income includes the greater of—
(A) an amount equal to the portion of the cost to the employer of the award that is not allowable as a deduction to the employer (but not in excess of the value of the award), or
(B) the amount by which the value of the award exceeds the amount allowable as a deduction to the employer.
The remaining portion of the value of such award shall not be included in the gross income of the recipient.
(3) Treatment of tax-exempt employers. In the case of an employer exempt from taxation under this subtitle, any reference in this subsection to the amount allowable as a deduction to the employer shall be treated as a reference to the amount which would be allowable as a deduction to the employer if the employer were not exempt from taxation under this subtitle.
(4) Cross reference. For provisions excluding certain de minimis fringes from gross income, see section 132(e).
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 You’ll Learn in This Episode
Resources & Links
Connect with Jill:
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.
What You’ll Learn in This Episode
What Andrea Gibson’s “biggest tiniest dreams” teach us about presence, attention, and finding meaning in ordinary moments.
How a poet can name experiences we didn't realize we were carrying, from nervous parental love to loving complicated rescue animals.
Why agency rarely looks dramatic and how a simple phone call can be an act of courage.
What it means to create a life with “stretch marks on your heart,” and how that frames the work of death readiness.
Why noticing small joys matters, whether it’s a dog in a tiny t-shirt or kindness you weren’t expecting.
How estate planning and poetry unexpectedly intersect, both reminding us that life is finite and luminous at the same time.
Resources & Links
Come See Me in the Good Light — Documentary about poet Andrea Gibson (Apple TV).
Things That Don’t Suck — Andrea Gibson’s Substack newsletter.
Connect with Jill:
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.
What You’ll Learn in This Episode
What a Holographic Will Is
Michigan’s Requirements (for validity)
A handwritten Will is valid in Michigan if it:
That’s the bare minimum, not a guarantee that the document will do what you think.
What a Will Actually Controls
Not everything you own is governed by your Will. Some assets bypass probate entirely.
Assets controlled by your Will:
Assets that bypass your Will:
Example: A 401(k) will follow the beneficiary designation, even if your Will says otherwise.
If you want a change, update the form. Your Will does not override it.
How to Structure a Handwritten Will (in an Emergency)
Jill walks through a step-by-step handwritten format, including:
Plus a final affirmation sentence to prevent challenges to handwriting authenticity
When Notarizing Helps
Why Complexity Is the Enemy of DIY Wills
The episode offers six pitfalls that almost always blow up handwritten Wills:
DIY Wills explode when they try to do too much.
If you must write your own, keep it brutally simple.
Resources & Links
Visual guide: Probate vs. Non-Probate Assets
Sample language for a Michigan handwritten Will
Episode 36: When Transfer-on-Death Deeds Promise to Avoid Probate but Create Chaos
Episode 38: Why You Need (or Don’t Need) a Will
Estate Plan Audit — Translate your lawyer-written Will into English and verify whether it does what you think: www.deathreadiness.com/audit
Connect with Jill:
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.
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