Not Your Average Death Blog
How to Take Your Estate Plan Off Script
You can follow all the estate planning rules and still end up with the wrong plan. In this episode, Jill walks through a question from a young attorney who’s been handed traditional estate planning forms and is wondering whether they actually serve her clients. Jill break down how a standard trust structure can limit flexibility for families who don’t need estate tax planning, and how small adjustments can make a big difference. Estate planning isn’t about checking boxes. It’s about building something that works.
Why your life insurance trust might not work
New clients came in with two life insurance trusts—professionally drafted, signed, notarized, and organized in beautiful binders. There was just one problem: the trusts didn’t do anything.
In this episode, Jill breaks down what an irrevocable life insurance trust (ILIT) is, when it actually makes sense, and how it fails when no one follows through. This is a real-life look at the gap between having documents and having an estate plan that actually works.
Michigan Just Changed How Advance Directives Work
Until a few days ago, there was a significant limitation built into Michigan law that most people didn’t know about.
If a patient was pregnant, their end-of-life decisions could be overridden, even if those decisions were clearly stated and even if they had chosen someone they trusted to speak for them.
Michigan law required advance directives to include this language:
“The patient advocate designation cannot be used to make a medical treatment decision to withhold or withdraw treatment from a patient who is pregnant that would result in the pregnant patient’s death.”
In other words, there were circumstances where your voice didn’t control, even when you had done everything “right.” That restriction has now been struck down as a violation of the Michigan Constitution.
How assets get lost after death and what to do
When someone dies, there’s no master list of what they owned and no automatic system that pulls it all together. In this episode, Jill walks through what actually happens when families try to track down assets, why unclaimed property isn’t the safety net people think it is, and how a lack of organization can turn estate administration into a frustrating, years-long scavenger hunt. This is where estate planning meets real life and where most plans break down.
Why saying yes to serving as agent under a POA can backfire
Agreeing to serve as an executor, trustee, or agent under a power of attorney often feels like the right thing to do but it’s also one of the most overlooked risks in estate planning. In this episode, Jill flips the perspective and walks through what you need to evaluate before you say yes to a fiduciary role in someone else’s estate plan. From compensation and liability to knowing when to step in and how to step out, this episode highlights the gap between estate planning documents and real-life execution. Because a well-drafted estate plan only works if the people named in it are set up to succeed.
What You Can and Can’t Do with the Trust You Inherited
Can you stop your child from inheriting money, even if the trust says they should? In this estate planning episode, we walk through a real-life scenario where a mother is trying to protect her son from receiving a large inheritance at the wrong time. Along the way, we break down how estate planning tools like trusts actually work in real life, what trustees can and can’t do, and why you can’t simply “use up” a trust to avoid passing money on. We also introduce a powerful (and often overlooked) tool, a power of appointment, that might allow you to adjust what happens next, even when a trust is irrevocable. Because sometimes the plan is set… but not completely locked.
Death Readiness Doesn’t Happen in a Vacuum
My best friend came to Michigan this week, and we did what best friends do. We ran, we biked, we wandered, and we talked about everything. And somewhere in the middle of all of that, we also got her ready for her first meeting with a financial advisor.
Why That Retirement Account May Not Go Where You Think
What happens if you don’t name a beneficiary on your retirement account? Most people assume it goes to the estate. But that assumption can be dangerously wrong. In this episode, Jill walks through a real case where getting this wrong would have cost a surviving spouse more than $300,000, and explains what actually controls the outcome in your estate planning.
Why Estate Plans Fail Adult Children
Your parents paid thousands of dollars for a revocable trust but none of the assets were ever transferred into it. Did their estate planning attorney make a mistake?
In this episode of The Death Readiness Podcast, Jill Mastroianni explains what it actually means to fund a trust, why this step is essential for the plan to work, and who is typically responsible for doing it. She also walks through a real-world example showing how failing to fund a trust can cost families hundreds of thousands of dollars in probate fees and create a huge administrative burden for adult children.
More importantly, Jill highlights the hidden emotional cost when estate planning work falls on family members instead of being handled during the parent’s lifetime.
Why Good Powers of Attorney Still Fail
Most people think signing a power of attorney is the hard part but the real challenge is making sure it actually works when someone you love needs to use it.
In this episode, Jill shares a real-life story of a daughter trying to help her mother and running into unexpected roadblocks with a bank, even though the legal documents were properly signed years earlier. You’ll learn why “good” estate planning can still fail in the real world and the five practical steps you can take now to reduce friction later.
This episode is about moving from legal theory to real-life implementation because Death Readiness isn’t just paperwork; it’s making sure your plan works when life gets messy.
How to Give Without Jeopardizing Government Benefits
A grandmother wants to divide her wealth equally among her grandchildren — but one grandchild has Down syndrome, and a simple gift could unintentionally jeopardize eligibility for important government benefits. In this Tuesday Triage episode, Jill walks through required minimum distributions (RMDs), why “equal” doesn’t always mean “fair,” and how thoughtful planning protects both generosity and long-term support. You’ll learn how special needs planning tools like ABLE accounts and third-party special needs trusts help families give with love without causing unintended consequences.
Why You Should Beware of Tax Advice Via Social Media
A viral Instagram reel claims California’s Proposition 19 “hijacks your kids’ inheritance.” In this Tuesday Triage episode, Jill walks through the facts behind the fear. Using a real-world example, she explains how California property taxes actually work, what changed under Proposition 19, and why federal tax rules like step-up in tax basis still protect many beneficiaries. This episode is about slowing down, adding context, and replacing social-media sound bites with real understanding.
Why Selling the Lake House Can Rewrite Your Will
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.
How Business Interests Create Estate Planning Blind Spots
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.
How Poor Estate Planning Cost a First Lady Her Home
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.
Why You Should Question the Estate Planning Expert
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.
Why Disinheritance Can Be the Riskiest Estate Plan
As much as we’re sold the idea of “holiday magic,” the reality is that holidays are often where long-standing family tensions come into sharp focus. Especially once you’re the one hosting, coordinating, cooking, cleaning, and trying to keep everyone emotionally regulated. When you’re tired and stretched thin, it’s not uncommon for an unsettling thought to creep in: There’s someone in this family I might need to disinherit.
Disinheritance is usually framed as a decisive solution, a way to protect assets, stop enabling bad behavior, and finally draw a boundary. But in practice, disinheritance is often one of the riskiest estate-planning decisions people make—legally and relationally.
Why Housing Security Gets Overlooked in Blended Families
Many families look stable from the outside—until one illness, one death, or one move changes everything. I see this especially in blended families and long-term relationships where people share a life but not legal ownership of the home they live in.
Today’s Tuesday Triage episode is about this quietly risky situation when someone lives in a home they don’t own. Things go sideways not because anyone has bad intentions, but because the legal protections people assume are there often aren’t.
Today’s question is from a listener named Sarah. Sarah’s dad lives in a condo owned by his long-term partner. They’re committed and they’ve made a life together. But legally, Sarah’s dad has no guaranteed right to stay in that home. If her dad’s partner became ill and needed to move out, or if she died, her father could suddenly find himself without housing. This situation is common in blended families, second relationships, and couples who choose not to marry.
How to Write Your Own Will (and Why It’s Not as Simple as You Think)
I spend a lot of time thinking about how people avoid estate planning, not because they don’t care, but because they genuinely don’t know where to start. And nothing captures that better than a question I got recently while checking out at Trader Joe’s in Michigan.
A cashier named Ron noticed my Death Readiness sweatshirt and asked the question almost everyone has wondered at some point: “If I want to leave everything to my brother, can I just write it down and sign it?”
The short legal answer, at least in Michigan, is yes. A handwritten Will (called a holographic Will) is valid if it’s dated, signed, and the material portions are in your handwriting. But when it comes to planning for real-life families, real-life assets, and real-life drama, the better answer is: this gets messy fast.
How to Keep Your Ex Out of Your Estate Plan
When you go through a major life change, you think the moment of “finalizing” something will bring a sense of closure. But usually, it doesn’t. When my husband and I bought our house this fall, I was convinced I’d feel relieved the minute we signed the paperwork. Instead, we immediately plunged into the real work—packing, moving, cleaning out the old place, dealing with inspection repairs, and pretending we’d get around to changing the keypad code “tomorrow.” Weeks later, most of that list is still waiting for us. That weird gap between being “done” on paper and nowhere near done in reality is exactly where one of my listeners, Amy from Nashville, finds herself right now.
Amy is newly divorced after ten years of marriage. The court has signed off. The marital dissolution agreement is official. She is, in theory, “legally done.” But like so many people who reach this point, she quickly realized there’s a long list of loose ends that don’t magically handle themselves. One of the questions at the top of her list was: does she need to update her Will to remove her ex-spouse?