Not Your Average Death Blog
Why I Won't Leave My Kids Cash
If your children inherited a million dollars tomorrow, would you want them to receive a check—or a trusted guide?
In this episode, Jill pulls back the curtain on her own family's estate plan and walks you through exactly what would happen if she and Jeremy died while their children were still young. Using their own Wills, life insurance beneficiary designations, and testamentary trusts as real-life examples, she translates complicated legal language into plain English so you can understand how trusts actually work—and why they aren't just for wealthy families.
The Solution to Your Biggest Anxiety Might Be on a Trail with a Sausage Dog
The solution to your life's biggest anxieties might not be on a trail in the Adirondacks with a sausage dog. But you should probably check. The last time I was here was in December, the trails were covered in snow, and I was snowshoeing with one of our other dogs while trying to sort through a lot of uncertainty.
What You Need to Know Before Editing Your Will
What happens if you simply cross out part of your Will, write “VOID” above it, and initial the change?
The answer is more complicated, and riskier, than most people realize.
In this episode, estate planning attorney Jill Mastroianni explains why making handwritten changes to your estate planning documents can create confusion, trigger litigation, and ultimately change how your assets are distributed. Through two real Tennessee court cases, you'll learn why “just one little edit” can have consequences that last for years and why creating a fresh document is always the better solution.
My Summer Office Has Safari Wallpaper
This summer, my office is in a familiar place: my childhood bedroom in the Adirondacks. If you see photos or videos from me over the next couple of months, you might notice the safari wallpaper in the background. I picked it out when I was eleven years old, and somehow it has survived all these years.
Every time I sit down at this desk, I'm reminded that rooms can hold stories. This one certainly does. My mom helped me choose this wallpaper. Fourteen years ago, this is also the room where she died. On paper, it sounds like this room should be filled with sadness. But that's not what I experience when I'm here.
Thank You for Helping Make Estate Planning More Accessible
Recently, The Death Readiness Podcast became the #1 search result for "estate planning" on Apple Podcasts. While that's an exciting milestone, what means the most to me isn't the ranking itself. It's what it represents.
Every time you listen to an episode during your commute, share one with a friend, leave a review, or recommend the podcast to someone else, you're helping make conversations about estate planning and probate more accessible.
Why Your Power of Attorney Can't Do Everything
When someone you love names you as agent under a power of attorney, it can feel like you'll be able to step in and handle whatever needs to be done. But what happens when the law says otherwise?
In this episode, Jill shares the story of a Tennessee woman who discovered that even a broad financial power of attorney has limits. Through a real-life example involving a conservatorship, a probate estate, and a Florida real estate sale, she'll explore what powers of attorney can do, what they can't do, and how thoughtful estate planning can help ensure the right people have the right authority when it's needed most. Along the way, you'll learn why caring deeply about someone doesn't automatically give you the legal ability to act on their behalf, and how one woman's careful estate planning may continue helping others long after she's gone.
If the Dog Can Find Your Documents, Your Family Should Be Able To, Too
One of the first things I tell clients is that their important documents need to be accessible when their family needs them. Recently, our foster puppy Michael had his own interpretation of that advice. I walked into a room to discover him proudly carrying around a stack of legal papers in his mouth. Apparently, he had decided it was time to conduct his own document review.
While it wasn’t exactly what I had in mind, it did remind me of an important estate planning lesson. Too often, people spend time and money creating wills, trusts, powers of attorney, and other important documents, but they never tell anyone where those documents are located. As a result, when an emergency happens or someone dies, family members find themselves on a scavenger hunt.
What You Need to Know About Corporate Trustees
Michael thought he had done everything right. He created a revocable trust, avoided probate, and named a neutral third party to serve as trustee after his death. But when the corporate trustee declined to serve, his family spent fourteen years trying to untangle the consequences. In this episode, Jill explains what corporate trustees do, why they sometimes say no, and how to make sure your estate plan works not just on paper, but in real life.
Sometimes Love Looks Like a Bowl of Cold Water
Every morning on my run, my dog makes a stop at a house in the neighborhood where a very kind woman leaves out ice water for passing dogs. Every day, she fills a heavy bowl, places it in the shade under a tree, and freezes a huge block of ice so that the water stays cold even on hot days. It takes planning, effort and valuable freezer space.
And yet, she does it anyway.
She doesn't know which dogs will come by. But every day, she does this small thing to make life a little easier for these four-legged neighbors she'll likely never know.
It got me thinking about the ways we care for the people we love.
Don't Hide the Baklava From Your Estate Planning Attorney
Yesterday, I went to my annual physical. My doctor asked what I had eaten the day before. I dutifully recited the healthy highlights: eggs, watermelon, yogurt, and sweet potatoes.
What I somehow neglected to mention was the baklava I had eaten after dinner.
I really like my doctor. She was kind, thoughtful, and only doing her job. But when she gently suggested that the four slices of bread I'd eaten that day might have been a little carb-heavy, I decided introducing the baklava into the conversation would probably overwhelm everyone involved.
The encounter got me thinking about something I see all the time in estate planning. People leave things out. And it’s not because they're dishonest. Usually, it's because they're embarrassed or because the situation is complicated or because they assume a detail isn't important enough to mention.
How Creditors Can Delay a Probate Estate
Can you open a probate estate, distribute the assets, close the file, and move on without worrying about creditors?
Not quite.
In this episode of The Death Readiness Podcast, Jill answers a listener's question about why probate sometimes feels painfully slow. Using Tennessee law as an example, she explains how the creditor claims process works, why executors can't simply skip legal formalities, and what can happen if beneficiaries receive their inheritances before all of the creditor deadlines have expired.
What You Need to Know About Estate Planning at 30
What estate planning documents does a healthy 30-year-old actually need?
In this episode of The Death Readiness Podcast, Jill answers a question from a young listener who wondered what someone her age should be doing about estate planning. Using stories from her own life, including the loss of several young friends, Jill explains why estate planning isn't just for retirees.
You'll learn why powers of attorney and healthcare advance directives may be more important than a Will when you're young, how the famous Nancy Cruzan case changed the conversation around end-of-life decision-making, and what a recent Michigan court decision means for pregnant individuals and advance directives. Most importantly, you'll learn why estate planning doesn't have to be perfect; it just has to start.
What My Blank Diploma Taught Me About Estate Planning
In 2005, I graduated from Dartmouth College with a degree in Russian language and literature. I worked hard and got good grades. I was the kind of student who took academics seriously.
And yet, on graduation day, I was holding a blank piece of paper.
Why?
How to Prepare for Retirement Without Panic
Jill Mastroianni is joined by her close friend and financial advisor, Blair Coffman Martin, to discuss how to approach retirement planning, long-term care, and helping adult children without feeling overwhelmed. Blair emphasizes that financial planning isn’t about having all the answers upfront; it’s about starting with what you know, organizing your spending, and creating a flexible plan for the future. They also cover required minimum distributions (RMDs), consolidating accounts, and strategies to involve adult children responsibly in financial decisions.
How Do You Know If Mom Can Still Sign
What happens when someone with memory changes needs to sign a will, trust, or power of attorney? Who actually decides whether they’re “competent” enough to sign, and what happens if people disagree?
In this episode, Jill Mastroianni shares personal stories involving her own mom, a deathbed signing that never happened, and what the law actually says about mental capacity and estate planning. We talk about why competency is not an all-or-nothing question, who acts as the initial gatekeepers during a signing, and why families often begin asking “Can Mom still sign?” when they’re already standing in the middle of a crisis. Most importantly, we talk about why estate planning works best when decisions are made from a place of choice, not urgency.
Why Your Weighted Vest Might Be Better Than Your Perfect Plan
I know I’m supposed to lift weights. I also don’t own weights or belong to a gym. For the past few years, my strength-training strategy has consisted mostly of thinking about strength training.
So yesterday I dug a weighted vest and wrist weights out of the garage and went for a walk. Is it the same as a carefully designed strength program? Nope. Is it perfect? Definitely not. But it was something. And isn’t estate planning exactly the same?
How to Update Estate Planning After a Dementia Diagnosis
What happens when a parent develops dementia and an attorney tells your family it’s “too late” to update estate planning? In this week’s Tuesday Triage episode, Jill walks through a real-life scenario involving outdated trusts, powers of attorney, probate versus non-probate property, and the estate planning opportunities that may still exist even after incapacity enters the picture. This episode explores how understanding asset titling, existing estate planning documents, and revocable trusts can help families creatively adapt an older estate plan to current realities.
The Bark Management Strategy Behind My Podcast
Monday is podcast recording day in our house, and Artie absolutely knows the routine. The second I head toward the basement to record the next episode of The Death Readiness Podcast, he follows right behind me like it’s his full-time job.
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.
Boots Got Adopted (And Yes, It’s Bittersweet)
Boots got adopted. She was curious, scrappy, and somehow always exactly where she shouldn’t be. The house feels quieter without her… and little less chaotic too. But mostly, it just feels different.
I got this message from Detroit Dog Rescue today about her new home:“She is fitting in incredibly well and they are obsessed with her!”