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 know who has practice, rehearsal, or a field trip tomorrow.
And somewhere in the middle of all that, you're supposed to figure out estate planning.
The Death Readiness Podcast: Not Your Dad’s Estate Planning Podcast is an estate planning podcast for women juggling aging parents, growing children, family finances, and approximately a thousand things nobody else seems to know need doing.
From Wills and trusts to powers of attorney, probate, and the difficult conversations families tend to avoid, this podcast helps you understand the legal and practical decisions that come with taking care of the people you love.
Do your parents need a trust? What happens if someone dies without a Will? What does it actually mean to serve as agent under a power of attorney? How does probate work? And how do you help aging parents who insist they're perfectly fine when you can see that they're struggling?
Hosted by Jill Mastroianni, an estate planning and probate attorney with more than a decade of experience, The Death Readiness Podcast tackles the legal questions and family conversations that most of us would rather avoid.
Through real-life stories, practical explanations, and a healthy dose of humor, Jill helps you understand Wills, trusts, powers of attorney, probate, inheritance, and the decisions that come with caring for the people you love.
Whether you're creating your own estate plan, helping your parents get organized, or trying to figure out what to do after someone dies, you'll find information you can actually use.
You don't need to become an estate planning expert. You just need to understand enough to ask better questions, make informed decisions, and know where to start.
And if you're still waiting for your mom to give you the password to her computer, you're in good company.
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102: What to Ask Before Serving Under a Power of Attorney
Épisode 102
mardi 10 novembre 2026 • Durée 19:40
Your mom, dad, or another family member asks you to serve as their agent under a power of attorney. You want to help. But do you understand what you're agreeing to?
Serving as someone's agent under a financial power of attorney is more than helping them pay a few bills. You're accepting legal responsibilities, potential liability, and a job that could become much more demanding than you anticipated.
In this episode of The Death Readiness Podcast: Not Your Dad’s Estate Planning Podcast, estate planning attorney Jill Mastroianni shares seven things to consider before accepting an appointment under a power of attorney, including questions professional fiduciaries ask before agreeing to serve.
You'll learn what to look for in the estate planning documents, how to protect yourself, and why being asked to serve doesn't mean you have to say yes.
What You'll Learn in This Episode
When do your responsibilities under a power of attorney begin? Being named as an agent doesn't mean you've agreed to serve. Learn the difference between an immediate power of attorney and a springing power of attorney, which becomes effective upon incapacity, and why you need to understand when your authority and responsibilities begin.
What financial information should you have before agreeing to serve? A power of attorney gives you legal authority, but it doesn't tell you where Mom banks, which bills are automatically paid, or who manages her investments. Find out what information you should ask for before you're responsible for managing someone else's financial affairs.
Can you get paid for serving as an agent under a power of attorney? Managing someone else's finances can become a significant commitment. Learn why you should review the compensation provisions before accepting the appointment, even if you don't currently intend to charge for your time.
What records should you keep when acting under a power of attorney? Keeping accurate records is one of the most important responsibilities of an agent. Learn why you should document financial transactions, save receipts, keep the principal's money separate from your own, and understand your accounting obligations.
Can you be sued for decisions you make as an agent? Serving under a power of attorney comes with potential legal liability. Learn why you should review provisions addressing liability and indemnification, including whether the document provides protection for actions taken responsibly and in good faith.
Can you resign as an agent under a power of attorney? Your circumstances may change. Learn why you should understand the resignation process, notice requirements, and successor-agent arrangements before accepting the responsibility.
Can you make gifts using someone's power of attorney? Just because a power of attorney authorizes gifts doesn't necessarily mean the principal would approve of every gift you might make. Learn why it's important to discuss gifting authority, family expectations, and potential conflicts before you find yourself caught in the middle of a family disagreement.
What If You Don't Want to Serve?
Being named as someone's agent under a power of attorney doesn't mean you're obligated to accept the responsibility.
Jill also discusses why it's okay to decline a fiduciary appointment, what alternatives may be available, and why the attorney who prepared the estate planning documents isn't necessarily an attorney representing you.
The takeaway? You can love someone, want to help them, and still decide that serving as their agent under a power of attorney isn't the right job for you.
Resources & Links
The Death Readiness Playbook is an educational guide and hands-on workbook that helps you understand the legal, financial, and practical considerations involved in preparing for incapacity and death.https://www.deathreadiness.com/playbook
Estate planning, without the legal jargon or the lectures. Join attorney Jill Mastroianni for honest conversations about Wills, trusts, probate, aging parents, family dynamics, and all the things we'd rather put off until tomorrow. More at DeathReadiness.com.
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.
101: Why You Can't Just Refuse an Inheritance
Épisode 101
mardi 3 novembre 2026 • Durée 20:56
What happens when someone leaves you an inheritance you don't want? Can you simply refuse it? And if you do, who gets the money instead?
In this episode of The Death Readiness Podcast, estate planning attorney Jill Mastroianni takes a closer look at a surprising estate planning problem inspired by And Just Like That, the sequel to Sex and the City. When Mr. Big leaves his ex-wife Natasha a million dollars, she tells Carrie Bradshaw she doesn't want the money and asks her to give it to charity.
But refusing an inheritance isn't that simple. Jill explains how qualified disclaimers work, why beneficiaries cannot decide where disclaimed property goes, and how estate planning laws in different states can produce dramatically different outcomes. She also shares a real-life estate administration story about a beneficiary who wanted nothing to do with his inheritance.
What You’ll Learn in This Episode
What You'll Learn About Estate Planning and Refusing an Inheritance
Why you can't simply refuse an inheritance. Saying “no, thanks” to an inheritance is not the same as legally disclaiming it. There are formal requirements and deadlines that must be followed.
What a qualified disclaimer is and how it works. A disclaimer allows a beneficiary to legally refuse an inheritance, but federal tax law and applicable state law impose specific requirements. For federal tax purposes, a qualified disclaimer must be completed within nine months.
Why you can't choose who receives a disclaimed inheritance. If you refuse an inheritance through a qualified disclaimer, you cannot direct the money to a particular person or charity. Instead, the property passes according to the estate planning documents and applicable state law.
How estate planning laws differ between states. New York and Tennessee have different anti-lapse statutes, which affect who inherits property when a beneficiary dies before the person making the Will or is treated as having died first after disclaiming an inheritance.
What happens when a beneficiary dies before receiving an inheritance. Anti-lapse statutes can preserve gifts for a beneficiary’s descendants, sometimes producing results the person who created the Will never anticipated.
100: How Talking About Death Changed the Way I Live
Épisode 100
mardi 27 octobre 2026 • Durée 16:41
100 episodes about estate planning, preparing for death, and the things we leave behind. Who knew that could teach you so much about living?
In this special 100th episode of The Death Readiness Podcast: Not Your Dad's Estate Planning Podcast, estate planning attorney Jill Mastroianni takes a break from tax calculations and trust provisions to reflect on the unexpected lessons she's learned since launching the podcast in January 2025.
From recording conversations with her dad about his childhood and military service to asking her brother questions she'd never thought to ask, Jill shares how creating an estate planning podcast has changed her understanding of family, legacy, and the things we pass along to the people we love.
And sometimes, the memories that matter most are the ones we least expect, like singing One Direction in a parking lot with your teenage daughter and a foster dog.
Wills, trusts, and other estate planning documents are important. But there's more to preparing for death than deciding what happens to our money and possessions. There are stories worth preserving, relationships worth nurturing, and conversations worth having while we still can.
Estate planning should help us prepare for the future without losing sight of the lives we're living right now.
What You’ll Learn in This Episode
Why recording your family's stories matters. Your estate planning documents can address what happens to your property, but they won't preserve the stories behind it. You don't need professional equipment or a published podcast to record meaningful conversations with your parents or grandparents. Sometimes all it takes is asking a question and pressing record.
What happens when we ask questions we've never asked before. Jill shares how interviewing her dad and her brother, Dan, helped her understand two people she thought she already knew so well.
Why we need to listen to the people we're planning for. When Jill asked Dan about his experience growing up with Down syndrome, his answer challenged her assumptions and offered an important lesson about understanding what makes someone else's life meaningful. It's a reminder that good estate planning begins with understanding the person, not simply deciding what to do with their assets.
99: Why Your Parents' Trust Could Cost You Thousands
Épisode 99
mardi 20 octobre 2026 • Durée 18:03
Your parents may have created an irrevocable trust years ago as part of their estate planning to protect family assets and reduce estate taxes. But what if that same trust could leave you with a substantial capital gains tax bill when you inherit their property?
In this episode of The Death Readiness Podcast: Not Your Dad's Estate Planning Podcast, estate planning attorney Jill Mastroianni uses her father's lake house in the Adirondacks to explain an often-overlooked issue in estate planning: how the type of trust you create can affect the taxes your family pays after your death.
Using a $3 million house as an example, Jill explains the difference between revocable and irrevocable trusts, how a step-up in tax basis works, and why an estate plan designed to reduce estate taxes could instead result in $2.5 million of taxable gain when inherited property is sold.
You'll also learn why estate planning strategies that made sense twenty years ago may deserve another look today, how certain irrevocable trusts can be modified or planned around, and what to ask your estate planning attorney before making changes to an existing trust.
What You'll Learn in This Episode
Why choosing the right type of trust matters in estate planning. A revocable trust allows its creator, known as the grantor, to retain control of the assets. Assets held in a revocable trust are included in the grantor's taxable estate. Certain irrevocable trusts, on the other hand, are designed to remove future appreciation from the grantor's taxable estate. That distinction can have significant income-tax consequences for beneficiaries.
The difference between estate taxes and capital gains taxes. Estate taxes may apply when someone dies with an estate exceeding applicable exemption thresholds. Capital gains taxes may apply when inherited property is sold for more than its income-tax basis. An estate planning strategy that reduces one type of tax can sometimes increase exposure to the other.
How a step-up in tax basis can reduce taxes on inherited property. Property included in someone's estate for federal estate-tax purposes generally receives an income-tax basis equal to its fair market value at death. This adjustment, commonly called a step-up in basis, can substantially reduce capital gains taxes when heirs sell inherited property.
98: Why You Shouldn’t Give Your Kids the House Yet
Épisode 98
mardi 13 octobre 2026 • Durée 15:56
If you inherit a house, there’s one number you may not realize you need: what was the house worth on the date the owner died?
In this episode, Jill uses a fictional house from HBO’s Somebody Somewhere to explain what happens to tax basis when you inherit property, why getting a date-of-death appraisal can matter years after someone dies, and why receiving a house as an inheritance can have very different income-tax consequences from receiving that same house as a lifetime gift.
You’ll also hear why avoiding probate shouldn’t be the only consideration when deciding how to transfer property, and how solving one estate planning problem can sometimes create an entirely different tax problem.
What You’ll Learn in This Episode
The different ways you might inherit a house. A transfer-on-death deed, revocable trust, Will, or state intestacy law can all affect who ultimately receives real estate after someone dies.
What tax basis actually means. Jill breaks down tax basis using simple numbers and explains why it matters when you eventually sell an asset.
How the step-up in tax basis works. Inherited property generally receives a new tax basis based on its fair market value as of the owner's date of death, which can dramatically reduce the taxable gain when appreciated property is eventually sold.
Why you should consider getting a date-of-death appraisal. You may have no intention of selling an inherited house today, but you could need to establish its tax basis ten, fifteen, or twenty years from now. Documenting the value shortly after someone dies can be much easier than trying to reconstruct it years later.
What happens if you move into an inherited house. The principal-residence exclusion may allow a qualifying homeowner to exclude up to $250,000 of gain from federal income tax, or up to $500,000 in certain circumstances for married couples filing jointly.
Why your parents shouldn't necessarily put the house in your name now. Property received as a lifetime gift generally carries over the donor's existing tax basis for purposes of determining gain. If your parent bought a house decades ago for substantially less than it's worth today, that difference can matter enormously.
97: Why Jane Goodall’s Message Matters Right Now
Épisode 97
mardi 22 septembre 2026 • Durée 19:36
In this episode, Jill reflects on the life and legacy of Dr. Jane Goodall, exploring what it means to “do your little bit” in a world where not everyone starts from the same place. From Jane’s courage in defying gender norms to the continuing conversation around affirmative action, equity, and opportunity, this episode weaves together stories of perseverance, purpose, and the quiet power of small, determined acts. Jill connects Jane’s story to her own lessons from running cross-country, a mother’s unwavering support, and what it means to lift the next generation when we can’t always lift ourselves.
Key Takeaways
Starting Lines Aren’t Equal. Just like in a race, life’s starting points differ. As Dr. Martin Luther King Jr. wrote in Why We Can’t Wait, centuries of inequity can’t be erased by pretending the race is fair.
Affirmative Action as Fairness, Not Favoritism. President Kennedy’s 1961 executive order introduced “affirmative action” to open doors long kept closed, not to advantage one group, but to create opportunity where opportunity was denied.
The Double Tax. Economist Anna Gifty describes the “double tax” faced by women of color, the compounding burden of racism and sexism that leaves them underpaid, overcharged, and underestimated.
Jane Goodall’s Courage and Conviction. When the British government told Jane she couldn’t travel alone, her mother didn’t argue — she packed a bag. Together they faced malaria and isolation so Jane’s dream could take root. It’s the truest example of lifting someone by standing right beside them.
Say What You Mean, Mean What You Say. A lesson from Jill’s high school English teacher and one Jane Goodall embodied throughout her life — integrity, honesty, and consistency of purpose matter more than comfort.
Doing Your Little Bit. Jane reminded us that every person makes an impact every single day. Even small, imperfect actions move the world forward.
Death Readiness as Peace. Jane’s view of death as her “next great adventure” reframes readiness; it’s about living with purpose and peace, not fear.
96: What to Expect When Hiring an Estate Planning Attorney
Épisode 96
mardi 15 septembre 2026 • Durée 22:07
Hiring an estate planning attorney shouldn’t require you to figure out your estate plan before you walk through the door.
You don’t need to know whether you need a Will or a trust. You don’t need to have every fiduciary selected or every beneficiary designation figured out. And you definitely don’t need to know what provisions should go into your documents. That’s part of what you’re hiring an attorney to help you determine.
In this episode, of The Death Readiness Podcast: Not Your Dad's Estate Planning Podcast, estate planning attorney Jill Mastroianni takes you behind the scenes of the estate planning process and explains three things you should understand before hiring an estate planning attorney: scope, cost, and process.
She also walks through her own estate planning process, from the first conversation through drafting, document review, signing, implementation, and an optional Family Estate Planning Meeting—so you know what questions to ask when choosing an attorney and what a thoughtful estate planning process can look like.
What You’ll Learn in This Episode
The three things to understand before hiring an estate planning attorney: scope, cost, and process.
What “scope of representation” actually means. Before focusing only on the price, understand exactly what the attorney has agreed to do. Does the fee include a Will or trust? Powers of attorney? Revisions? Signing? Trust funding? Beneficiary designation assistance?
What to ask about legal fees. Whether an attorney charges hourly, a flat fee, or some combination, you should understand how you’ll be charged, what is included, and when additional fees might apply.
Why process matters almost as much as the documents. Ask what happens after you hire the attorney. How many meetings will you have? When will you receive drafts? Will the attorney explain them? Can you request changes? What happens after signing?
You don’t need to know whether you need a revocable trust or exactly what should happen in every possible scenario. Bring information about your family, assets, concerns, and goals. Your estate planning attorney can help you work through the legal solutions.
95: What Divorced Parents Need to Know About Life Insurance
Épisode 95
mardi 8 septembre 2026 • Durée 25:38
How Divorce Affects Life Insurance and Estate Planning: If you're divorced with minor children, your parenting plan may require you to maintain life insurance to provide financial support for your children if you die. But does your life insurance beneficiary designation actually accomplish what the court order requires?
In this episode of The Death Readiness Podcast, estate planning attorney Jill Mastroianni explains why divorce, life insurance, and estate planning need to be considered together, especially when minor children are involved.
Using the life insurance provisions in Tennessee's form parenting plan, Jill walks through what happens when you try to translate a court order into an actual life insurance beneficiary designation. She explains why naming minor children directly can create problems, the difference between a custodian and a trustee, and how a trust created under a Will may help ensure that life insurance proceeds are managed for your children as intended.
You'll also learn why updating your estate plan after divorce involves more than changing your Will, and why a life insurance policy, parenting plan, and estate planning documents should all work together.
Having the required life insurance policy is only part of the plan. The money also needs a clear path to the children you're trying to protect.
What You'll Learn About Estate Planning, Divorce and Life Insurance
Why divorce should trigger an estate planning review. If you're divorced with minor children, your parenting plan or divorce agreement may require you or your former spouse to maintain life insurance. That obligation should be reviewed alongside your Will, any trusts, and your life insurance beneficiary designations. A divorce can change who you want managing your children's inheritance and how you want those funds distributed.
Why a parenting plan's life insurance requirement may not be enough. Tennessee's form parenting plan can require a minor child to be named as the beneficiary of life insurance with an adult serving as “trustee.” But the language in a divorce-related court order may not translate neatly onto an insurance company's beneficiary designation form. Additional estate planning may be necessary to carry out the intended arrangement.
94: Why Your Responsible Child Might Be the Wrong Trustee
Épisode 94
mardi 1 septembre 2026 • Durée 40:52
How do professional trustees manage trusts? Estate planning attorney Jill Mastroianni and Alex Fisher explain fiduciary duties, trust administration, beneficiary distributions, and how to choose a trustee.
What actually happens when a beneficiary asks a trustee for money? And who would you rather have making that decision: your responsible adult child or a professional trustee?
Choosing a trustee is one of the most important decisions you'll make during the estate planning process. But many people don't fully understand what they're asking someone to do or how complicated trust administration can become.
In this episode of The Death Readiness Podcast: Not Your Dad's Estate Planning Podcast, estate planning attorney Jill Mastroianni sits down with longtime friend and trust advisor Alex Fisher for a behind-the-scenes look at how professional trustees manage trusts, evaluate distribution requests, and navigate the fiduciary responsibilities that come with managing someone else's assets.
They discuss what happens when a beneficiary requests money for tuition, medical expenses, a car, or home improvements, why a trustee sometimes has to say no, and how those decisions can affect family relationships.
You'll also learn what professional trustees consider before agreeing to serve, why naming your “responsible child” as trustee may come with hidden costs, and how thoughtful estate planning can give future trustees the flexibility to respond to circumstances you can't predict today.
What You’ll Learn about Trustees and Trust Administration in this Episode
What a professional trustee actually does. Alex explains the different roles a trust advisor may play, from helping families with estate planning questions to overseeing trust administration and serving as executor or trustee after someone dies. Learn what professional trust administration involves and why the job requires more than managing investments.
What happens when a trust beneficiary requests money. A beneficiary's request for tuition, a car, medical expenses, or home improvements isn't necessarily answered with a simple yes or no. During trust administration, a trustee may need to review the trust's distribution provisions, invoices or estimates, investment performance, prior distributions, and how long the trust is expected to last before deciding whether to approve a request.
93: Why Your Pour-Over Will Won’t Avoid Probate
Épisode 93
mardi 25 août 2026 • Durée 21:13
Why a Revocable Trust Still Needs a Pour-Over Will
You created a revocable trust as part of your estate planning to avoid probate. So why did your attorney also give you a Will?
That Will is probably a pour-over Will, designed to catch assets that are still in your individual name when you die and direct them into your trust. But there's an important catch: assets passing under a pour-over Will have to go through probate first.
In this episode of The Death Readiness Podcast: Not Your Dad's Estate Planning Podcast, estate planning attorney Jill Mastroianni explains how pour-over Wills work, why creating a revocable trust and funding a revocable trust are two very different things, and how the way you own your assets determines whether they'll avoid probate when you die.
You'll learn why having a revocable living trust doesn't automatically mean your estate will avoid probate, how beneficiary designations and account ownership affect what happens to your property, and why a pour-over Will remains an important backup in many trust-based estate plans.
The takeaway? If avoiding probate is one of your estate planning goals, don't just ask, "Do I have a trust?" Ask, "What happens to each of my assets when I die?"
What You’ll Learn About Revocable Trusts, Pour-Over Wills, and Probate
Why you still need a Will when you have a revocable trust. A pour-over Will is commonly included in estate planning packages that use a revocable living trust. It serves as a backup, directing assets that are subject to probate and haven't been transferred into your trust during your lifetime to the trust after your death.
Why a pour-over Will doesn't avoid probate. Although a pour-over Will directs assets into your revocable trust, it doesn't automatically transfer them there. Assets passing under the Will must go through probate before they can be distributed to the trustee. The Will tells us where the assets should go, but it doesn't eliminate the legal process required to get them there.
Why the residuary clause in your Will matters. The residuary estate receives property that isn't otherwise effectively distributed, including gifts that are disclaimed.
Why an ex-spouse might receive an inheritance. Estate planning after divorce sometimes involves financial obligations that survive the marriage, including obligations established in a marital dissolution agreement.
The difference between probate and non-probate assets. Your Will doesn't necessarily control everything you own. Assets with beneficiary designations or survivorship arrangements pass outside probate.
What to do before refusing an inheritance. Accepting money or exercising control over inherited property prevent a later qualified disclaimer. Understanding your options before taking action is essential.
How to avoid unintended consequences in your own estate plan. Thoughtful estate planning addresses not only who should inherit your property, but also what should happen if that person dies before you or chooses not to accept the inheritance.
Resources and Links
Related Episodes of The Death Readiness Podcast
Episode 91 – What really happens to a Will after someone dies, and why the dramatic Hollywood-style reading of the Will isn't how probate actually works. https://www.deathreadiness.com/podcast/91
Episode 95 – Estate planning for divorced parents, including life insurance obligations intended to protect minor children. https://www.deathreadiness.com/podcast/95
The Death Readiness Playbook – A practical resource for organizing important information, documenting decisions, and helping your loved ones understand your wishes. https://www.deathreadiness.com/playbook
The Death Readiness Dispatch – Get practical estate planning information, helpful resources, behind-the-scenes stories, and more delivered to your inbox every Wednesday morning. https://www.deathreadiness.com/subscribe
Take the Next Step with The Death Readiness Playbook
Estate planning can feel overwhelming, especially when you don't know what you don't know.
The Death Readiness Playbook is an educational guide and hands-on workbook that helps you understand the legal, financial, and practical considerations involved in preparing for incapacity and death.
Through plain-English explanations, real-life examples, and practical worksheets, you'll learn what questions to ask, what decisions to consider, and how to organize the information your loved ones may someday need.
Whether you're just beginning to think about estate planning or already have documents in place, the Playbook helps you take the next step.
Estate planning, without the legal jargon or the lectures. Join attorney Jill Mastroianni for honest conversations about Wills, trusts, probate, aging parents, family dynamics, and all the things we'd rather put off until tomorrow. More at DeathReadiness.com.
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.
How our children learn from watching us navigate uncertainty. Building an estate planning podcast and a business hasn't always gone according to plan. Jill reflects on what she hopes her daughter April has learned from watching both the successes and setbacks.
Why your legacy is about more than money and possessions. Estate planning often focuses on how we transfer assets after death. But family stories, shared experiences, traditions, and everyday moments can be just as meaningful as the things we leave behind.
How preparing for death can help us appreciate life. Estate planning and getting your affairs organized isn't about dwelling on what might happen someday. It's about making things easier for the people you love and spending more time enjoying the life you're living right now.
Episode 11 — Start Your Own Family Podcast with these Simple Steps Learn how to record conversations with your parents, grandparents, or other loved ones to preserve their stories for future generations.
Estate planning and preparing for death doesn't have to feel overwhelming or depressing. The Death Readiness Playbook combines approachable explanations of estate planning with a practical workbook to help you organize the information your family may someday need.
Halloween Special: Save $10 with code BOO through October 31, 2026, while supplies last.
Digital Playbook: $17 with discount
Printed Playbook (includes digital access): $27 with discount
Estate planning, without the legal jargon or the lectures. Join attorney Jill Mastroianni for honest conversations about Wills, trusts, probate, aging parents, family dynamics, and all the things we'd rather put off until tomorrow. More at DeathReadiness.com.
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.
How a $3 million house could create $2.5 million in taxable gain. Jill compares two estate planning scenarios involving a house with an original tax basis of $500,000. In one, the house receives a stepped-up basis when its owner dies. In the other, an irrevocable trust preserves the original basis, potentially creating $2.5 million in taxable gain when the property is sold.
Why an irrevocable trust may have been a good estate planning decision years ago. Federal estate-tax exemptions have increased dramatically over time. In 2026, the federal estate and gift-tax exemption is $15 million per person, although some states impose their own estate taxes with lower exemption amounts. A trust designed to minimize estate taxes decades ago may no longer provide the same benefits.
Why not all irrevocable trusts are the same. Irrevocable trusts can serve different estate planning purposes, including reducing estate taxes, addressing long-term care concerns, and protecting assets for children or grandchildren. The appropriate planning depends on the family's goals and the trust's provisions.
What a power of substitution can accomplish. Some irrevocable trusts allow the grantor to exchange, or swap, personally owned assets for trust assets of equivalent value. When properly structured, this provides an opportunity to bring appreciated property back into the grantor’s taxable estate to obtain a step up in tax basis at death.
Why reviewing an older estate plan matters. Changes in tax laws, asset values, and family circumstances may mean that a trust created decades ago deserves another look. Reviewing an existing estate plan with a qualified estate planning attorney can help identify whether an older irrevocable trust still accomplishes its intended goals or whether other strategies should be considered.
Three Questions to Ask Your Estate Planning Attorney About an Existing Irrevocable Trust
If you or your parents created an irrevocable trust years ago, consider discussing these questions with your estate planning attorney:
Why was the trust originally created? Was the goal to reduce estate taxes, plan for long-term care, or protect assets for future generations?
Does the trust still accomplish what your family's estate planning goals? Have changes in tax laws, asset values, or family circumstances affected the benefits of the original plan? Are there options for modifying the trust or addressing potential tax problems?
What are the income-tax consequences of the trust? Does the trust hold highly appreciated real estate or other assets?
An irrevocable trust isn't necessarily a mistake simply because it creates income-tax consequences. But understanding those consequences is an important part of evaluating your family's estate plan.
Resources & Links
Related Episodes
Previous episode: Episode 98: Why You Shouldn’t Give the Kids the House Yet: The income-tax consequences of giving your children your house during your lifetime versus leaving it to them at death. https://www.deathreadiness.com/podcast/98
Get started organizing the information, decisions, and wishes your loved ones may need someday with The Death Readiness Playbook, available in printed and digital formats.
Halloween Special: Save $10 with code BOO through October 31, 2026, while supplies last.
Estate planning, without the legal jargon or the lectures. Join attorney Jill Mastroianni for honest conversations about Wills, trusts, probate, aging parents, family dynamics, and all the things we'd rather put off until tomorrow. More at DeathReadiness.com.
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.
Why this isn't just about houses. The same basic tax-basis issue can arise with appreciated stock, family businesses, closely held companies, valuable collections, and other assets.
Why avoiding probate isn't the whole estate plan. Putting your name on Mom's house or having Dad give you appreciated stock might accomplish one goal while creating an income-tax consequence you hadn't considered.
Resources & Links
Episode 44 – The Hidden Tax Traps in Lifetime Gifts Learn more about why giving appreciated property away during your lifetime can produce a very different tax result from leaving that property to someone at death.
Transfer-on-Death Deeds. Listen to Jill's earlier episode explaining how transfer-on-death deeds work and how they can allow real estate to pass at death without going through probate.
Revocable Trusts. Explore earlier episodes of The Death Readiness Podcast discussing revocable trusts, trust funding, and how trusts can be used to transfer assets outside of probate.
Take the Next Step with The Death Readiness Playbook
Estate planning can feel overwhelming, especially when you don't know what you don't know.
The Death Readiness Playbook is an educational guide and hands-on workbook that helps you understand the legal, financial, and practical considerations involved in preparing for incapacity and death.
Through plain-English explanations, real-life examples, and practical worksheets, you'll learn what questions to ask, what decisions to consider, and how to organize the information your loved ones may someday need.
Whether you're just beginning to think about estate planning or already have documents in place, the Playbook helps you take the next step.
Estate planning, without the legal jargon or the lectures. Join attorney Jill Mastroianni for honest conversations about Wills, trusts, probate, aging parents, family dynamics, and all the things we'd rather put off until tomorrow. More at DeathReadiness.com.
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.
Take the Next Step with The Death Readiness Playbook
Estate planning can feel overwhelming, especially when you don't know what you don't know.
The Death Readiness Playbook is an educational guide and hands-on workbook that helps you understand the legal, financial, and practical considerations involved in preparing for incapacity and death.
Through plain-English explanations, real-life examples, and practical worksheets, you'll learn what questions to ask, what decisions to consider, and how to organize the information your loved ones may someday need.
Whether you're just beginning to think about estate planning or already have documents in place, the Playbook helps you take the next step.
Estate planning, without the legal jargon or the lectures. Join attorney Jill Mastroianni for honest conversations about Wills, trusts, probate, aging parents, family dynamics, and all the things we'd rather put off until tomorrow. More at DeathReadiness.com.
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.
Why you don’t need to arrive with all the answers.
What actually goes into drafting an estate plan. Jill explains why she doesn’t start every Will with a blank Word document and how forms developed, used, and revised over approximately 14 years of practice provide a vetted foundation that can then be customized for each client’s circumstances.
Why understanding your documents matters. Receiving a stack of legal documents shouldn’t be the end goal. Jill explains how she reviews documents with clients so they understand what happens at death, who is in charge, what authority they’re giving someone under a power of attorney, and how any trusts will work.
Why signing doesn’t necessarily mean you’re finished. An estate plan may also require changes to asset ownership, beneficiary designations, or trust funding. Beautifully drafted documents may not accomplish what you intended if the implementation is never completed.
How much should your adult children know? Jill introduces her optional Family Estate Planning Meeting for estate planning clients, which can help adult children understand the big picture of their parents’ plan, where to find important information, who is in charge, and which professionals to contact, without requiring parents to disclose financial information they want to keep private.
Remember that you’re evaluating the attorney, too. Do you feel comfortable asking questions? Does the attorney explain things in a way you understand? Do you know what you’re paying for and what happens next? Do you feel heard? Choosing an estate planning attorney is a two-way decision.
Take the Next Step with The Death Readiness Playbook
Estate planning can feel overwhelming, especially when you don't know what you don't know.
The Death Readiness Playbook is an educational guide and hands-on workbook that helps you understand the legal, financial, and practical considerations involved in preparing for incapacity and death.
Through plain-English explanations, real-life examples, and practical worksheets, you'll learn what questions to ask, what decisions to consider, and how to organize the information your loved ones may someday need.
Whether you're just beginning to think about estate planning or already have documents in place, the Playbook helps you take the next step.
Estate planning, without the legal jargon or the lectures. Join attorney Jill Mastroianni for honest conversations about Wills, trusts, probate, aging parents, family dynamics, and all the things we'd rather put off until tomorrow. More at DeathReadiness.com.
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 you name a minor child as a life insurance beneficiary. Life insurance companies generally cannot simply distribute a substantial death benefit directly to a minor child. Depending on state law and the circumstances, a court may need to appoint someone to manage the funds. That can mean additional expenses, delays, and court involvement at an already difficult time.
The difference between a custodian and a trustee. A custodian under the Uniform Transfers to Minors Act (UTMA) can manage assets for a minor without establishing a separately drafted trust. A trustee, however, manages assets according to the terms of a trust. Understanding the distinction is especially important when a parenting plan requires life insurance proceeds to be managed for minor children.
Why UTMA may not be the best long-term solution for life insurance proceeds. Naming a custodian can be a relatively simple way to arrange for someone to manage a minor child's inheritance. But the child generally receives control of the funds at the age specified by applicable state law. Depending on the state and the type of transfer, that could be much earlier than you'd want a child to receive a substantial life insurance benefit.
Why selecting “trust” on a life insurance beneficiary form may not solve the problem. If your insurance company asks for the name, date, and other identifying information for a trust, you'll generally need an actual trust. Simply naming someone as a “trustee” in a parenting plan doesn't necessarily establish the trust arrangement needed to receive and manage the life insurance proceeds.
How a trust under your Will can help protect minor children. A properly drafted Will can create a trust that takes effect at death and provides instructions for managing life insurance proceeds. The trust can identify the trustee, explain how money may be used for your children, establish when distributions occur, and address what happens if the original trustee cannot serve.
Why your estate planning documents and life insurance beneficiary designations must work together. After divorce, it's important to review more than the names listed on your policies. Your parenting plan, Will, trusts, and beneficiary designations should be coordinated so that the life insurance proceeds are distributed and managed consistently with your legal obligations and estate planning goals.
Why state law matters when you're divorced with minor children. Jill discusses how she may coordinate life insurance beneficiary designations with a trust created under a Will in Tennessee. But divorce requirements, insurance beneficiary rules, trusts, and the treatment of assets left to minors vary by state. This is an area where state-specific legal advice matters.
Resources & Links
Watch This Episode on YouTube Watch Jill explain how divorce, life insurance, and estate planning intersect when minor children are involved. https://youtu.be/vmCCII-x5AU
Episode 49 – How to Keep Your Ex Out of Your Estate Plan Divorce is an important reason to review your estate planning documents. Listen to Jill's earlier episode about estate planning changes to consider after divorce. https://www.deathreadiness.com/podcast/49
Work With Jill If you live in Tennessee and want to review how your estate planning documents, life insurance beneficiary designations, and parenting plan work together after divorce, learn more about Jill's estate planning services. https://www.deathreadiness.com/estate-planning-solution
Take the Next Step with The Death Readiness Playbook
Estate planning can feel overwhelming, especially when you don't know what you don't know.
The Death Readiness Playbook is an educational guide and hands-on workbook that helps you understand the legal, financial, and practical considerations involved in preparing for incapacity and death.
Through plain-English explanations, real-life examples, and practical worksheets, you'll learn what questions to ask, what decisions to consider, and how to organize the information your loved ones may someday need. Whether you're just beginning to think about estate planning or already have documents in place, the Playbook helps you take the next step.
Estate planning, without the legal jargon or the lectures. Join attorney Jill Mastroianni for honest conversations about Wills, trusts, probate, aging parents, family dynamics, and all the things we'd rather put off until tomorrow. More at DeathReadiness.com.
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.
Why a trustee's discretion comes with fiduciary responsibilities. Having discretion to make distributions doesn't mean a trustee can simply distribute money whenever a beneficiary asks. Trustees have fiduciary duties and must exercise their authority in accordance with the trust's terms and applicable law. That can mean balancing a beneficiary's immediate needs with the trust's purpose and long-term financial health.
How professional trustees make difficult distribution decisions. Alex describes how professional trustees may use trust committees to evaluate distribution requests and why she sometimes prepares beneficiaries for the possibility that their requests won't be approved. Learn how professional trust administration can involve multiple layers of review and judgment.
Why saying no may be easier for a professional trustee than a family member. When a sibling serves as trustee, a denied distribution request can become a family conflict. A professional trustee may be better positioned to make difficult fiduciary decisions without the same personal history or emotional complications.
The hidden costs of naming your “responsible child” as trustee. Your daughter may be willing to serve as trustee without charging a fee, but that doesn't mean the responsibility comes without a cost. Trust administration can require significant time, attention, and emotional energy. Serving as trustee may take time away from work, family, and personal responsibilities, while also creating tension when decisions involve siblings or other relatives.
How a professional trustee and family member can work together. Naming a professional trustee doesn't necessarily mean excluding your family from trust administration. A co-trustee arrangement may combine professional expertise with the personal knowledge and perspective of someone who understands the beneficiaries and family dynamics.
Why a professional trustee may decline to serve. Naming a bank or professional fiduciary in your estate planning documents doesn't guarantee that the institution or individual will accept the appointment. Professional trustees may review the trust's terms, assets, and family circumstances before agreeing to take on fiduciary responsibilities. Discussing the appointment in advance can help avoid surprises later.
Why different trust assets require different expertise. Managing a trust that holds stocks and bonds can look very different from administering one that owns real estate, farmland, mineral interests, or other specialized assets. When choosing a trustee, consider whether that person or institution has the resources and experience to manage the assets your trust may hold.
Why flexibility matters when drafting a long-term trust. A family lake house may be a treasured gathering place today. Decades from now, family members may live across the country, insurance costs may become unaffordable, or the property may no longer serve its original purpose. Estate planning documents that are too restrictive can leave future trustees with limited options, potentially requiring expensive court involvement to address circumstances no one anticipated.
What matters most when choosing a trustee. A trustee needs more than financial knowledge. Good judgment, empathy, communication skills, and the ability to make difficult decisions are all important. Whether you choose a family member or a professional trustee, consider who will be capable of carrying out the trust's purpose while managing the legal, financial, and personal responsibilities involved.
Resources & Links
Alex Fisher Trust Advisor, Regions Bank Alex shares her perspective and experiences in this episode in her personal capacity and is not speaking on behalf of Regions Bank.
Take the Next Step with The Death Readiness Playbook
Estate planning can feel overwhelming, especially when you don't know what you don't know.
The Death Readiness Playbook is an educational guide and hands-on workbook that helps you understand the legal, financial, and practical considerations involved in preparing for incapacity and death.
Through plain-English explanations, real-life examples, and practical worksheets, you'll learn what questions to ask, what decisions to consider, and how to organize the information your loved ones may someday need.
Whether you're just beginning to think about estate planning or already have documents in place, the Playbook helps you take the next step.
Estate planning, without the legal jargon or the lectures. Join attorney Jill Mastroianni for honest conversations about Wills, trusts, probate, aging parents, family dynamics, and all the things we'd rather put off until tomorrow. More at DeathReadiness.com.
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.
The difference between creating a revocable trust and funding it. Signing a trust agreement establishes the legal structure, but funding the trust means transferring ownership of assets into it or otherwise arranging for assets to pass to it. This is one of the most important distinctions in trust-based estate planning. Simply signing the documents doesn't guarantee that your assets will avoid probate.
How to keep a bank account out of probate. Depending on your circumstances and estate planning goals, you may be able to retitle a bank account into your revocable trust or designate the trust as the account's payable-on-death (POD) beneficiary. These approaches can allow the account to pass outside probate, but they don't work in exactly the same way.
Why trust ownership and beneficiary designations aren't interchangeable. When a bank account is owned by your revocable trust, your successor trustee may be able to manage the account if you become incapacitated, depending on the trust's terms. A payable-on-death designation, on the other hand, doesn't transfer ownership or management authority until death. Your estate planning decisions should account for what happens during your lifetime as well as after your death.
What makes an asset subject to probate. An asset owned solely in your individual name at death, without a surviving joint owner, effective beneficiary designation, or another method of transferring ownership outside probate, may need to go through the probate process before it can pass to its next owner. Understanding which assets are probate assets is an important part of reviewing your estate plan.
Why probate is like a bridge. Think of probate as the bridge that gets an asset from its deceased owner to its next owner. A pour-over Will can tell us where the asset should go after it crosses that bridge, but it doesn't eliminate the bridge itself. A properly funded revocable trust can allow certain assets to reach their intended beneficiaries without crossing that bridge.
Why one forgotten asset doesn't necessarily mean your estate plan failed. Financial lives change. You might open a new bank account, change financial institutions, purchase property, or overlook an asset when funding your revocable trust. A pour-over Will provides a backup for assets that remain outside the trust, although probate is still necessary to transfer them.
What happens if you die without a pour-over Will. If an asset is subject to probate and you don't have a valid Will directing where it should go, state intestacy laws generally determine who inherits it. That could produce a different result from the distribution plan you've established in your revocable trust.
The estate planning question to ask about every asset you own. Rather than focusing exclusively on whether you have a Will or trust, consider how each asset is titled, whether it has a beneficiary designation, and what happens to it when you die. A well-coordinated estate plan considers the documents, the assets, and how ownership transfers at death.
One Question to Ask When Reviewing Your Estate Plan
What happens to each of my assets when I die?
If you have a revocable trust, review your bank accounts, investment accounts, real estate, and other property to determine which assets are owned by your trust, which will pass through beneficiary designations, and which may still be subject to probate.
A revocable trust can be an effective estate planning tool, but it only works as intended when the trust documents and the way you own your assets work together.
Take the Next Step with The Death Readiness Playbook
Estate planning can feel overwhelming, especially when you don't know what you don't know.
The Death Readiness Playbook is an educational guide and hands-on workbook that helps you understand the legal, financial, and practical considerations involved in preparing for incapacity and death.
Through plain-English explanations, real-life examples, and practical worksheets, you'll learn what questions to ask, what decisions to consider, and how to organize the information your loved ones may someday need.
Whether you're just beginning to think about estate planning or already have documents in place, the Playbook helps you take the next step.
Estate planning, without the legal jargon or the lectures. Join attorney Jill Mastroianni for honest conversations about Wills, trusts, probate, aging parents, family dynamics, and all the things we'd rather put off until tomorrow. More at DeathReadiness.com.
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.
