It’s Going to Be Okay
Episode 12 | The Death Readiness Podcast
I’ve said the words “It’s going to be okay” more times than I can count—after scraped knees, during tough days at work, and in moments when someone I love just needed to hear something steady.
But there’s one day I’ll never forget saying them. It was the day my mom died.
When I arrived at my parents’ house in the Adirondacks, my dad met me outside. He told me that my mom had died that morning. Inside, my brother Dan—who has Down syndrome—already knew. I hugged him and I told him, “It’s going to be okay.”
I said those words, not because I had all the answers—but because my dad, my brother, and I would find a way through it, together.
Twelve years later, I’m still trying to make good on that promise.
In this episode of The Death Readiness Podcast, I’m not speaking as an estate attorney or a podcast host. I’m showing up as a daughter, a sister, a mother. A woman in the thick of the sandwich generation—caring for a child, walking alongside a father, and quietly planning for the day I’ll be the one who has to tell Dan again: “It’s going to be okay.”
This episode is personal.
We cover:
🔸 The hidden mental load of “being the one who knows what to do”
🔸 Why the people we love most can be the hardest to plan for
🔸 What Aretha Franklin’s couch-cushion Will can teach the rest of us
🔸 Why the “harmless error rule” is not your backup plan
🔸 The three small steps I want you to take this week
Even when you’ve got all the training—when you’ve practiced as an estate planning attorney for more than a decade—when you host a podcast literally called The Death Readiness Podcast… these conversations are still difficult. But they’re also necessary.
The planning isn’t just about the paperwork. It’s about love. And courage. And action.
If you’ve been paralyzed by everything weighing on you, I get it. But if you’re ready to try a different way—to take one step at a time—I’ll walk with you.
👉 Start by downloading the free tools I mention in the episode:
And if you want help figuring out what’s next, schedule a free 15-minute consultation with me. No pressure. No sales pitch. Just a real conversation about where you are—and how I can help.
Because one day, someone you love is going to need to hear those words from you:
“It’s going to be okay.”
Let’s make sure they’re true.
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Intro: (00:03)
Welcome to The Death Readiness Podcast. I'm Jill Mastroianni, an attorney with more than a decade of practical experience in trusts and estates, here to demystify the complexities of planning for the inevitable. This podcast is your guide to navigating estate planning and end of life preparation with clarity, compassion, and empowerment. Let’s spark the conversation, shift perspectives, and explore how to embrace death readiness together, courageously and thoughtfully.
Jill Mastroianni: (00:34)
Welcome back to The Death Readiness Podcast. I’m your host, Jill Mastroianni.
Today, I’m inviting you behind the scenes—not as an expert, but as a daughter, a sister, and a mother. Because no amount of training or experience can fully prepare you for the realities of loving—and losing—the people closest to you.
I’ll share some of my own story with you today—the parts where I felt paralyzed, afraid, and unsure—and how I found a way to move forward anyway. I’ll also give you practical tools you can use to steady your own family’s future.
(1:18) You see, I’m part of the sandwich generation. I have kids who need me. I have a parent who, thankfully, is still very much himself—lucid, healthy, and both stubborn and supportive in all the ways that remind me he’s still my dad. And I have an older brother, Dan, who has Down syndrome.
Recently, my dad and my brother came to visit me here in Michigan. And while we packed the trip with really fun everyday moments—we had meals, we laughed, we went bowling, we watched Netflix movies—my dad and I also carved out time for something more difficult: Talking about his estate planning—what happens in the event of his death or incapacity.
We’ve had these conversations before. But estate planning is a continuing conversation. You get the foundational pieces in place, and then you keep revisiting them—because changed circumstances change your plan.
(2:30) You might think, because of what I do for a living—because I host this podcast, because I’ve practiced in estates and trust law for 12 years—that these conversations would be easy for me. They’re not. They’re actually really hard. Because no matter how much experience I have, at the end of the day, he’s still my dad.
There’s a specific concern I’ve had involving my brother’s future care. I brought it up with my dad a couple of months ago. We agreed it was a real concern. We agreed it needed a solution. And then…we got stuck. We didn’t know what the next step was.
I shared my concern with Paul Hood, an estates and trusts scholar who lives just a couple miles from me. Every week or so we meet for breakfast at a local diner; we talk about work, life, and everything in between. I told Paul that I felt paralyzed. I couldn’t figure out how to move forward for my brother.
Paul listened, and then said something that stayed with me: "Jill, this is about Dan and what’s best for him. Being paralyzed is not an option." It was hard to hear. But it was exactly right. The mental load I was carrying—the worry, the indecision, the fear—it wasn’t going to get any lighter by ignoring it. If anything, it was only going to grow heavier.
(04:18) Because that’s what happens in the sandwich generation: No matter how full your plate already is, there’s always another thing that needs to be added. And we keep balancing it, because we have to.
Talking to my dad about his estate planning—it forces me to confront a memory I’ll never forget.
I lived with my parents at their home in the Adirondack Mountains during the summer of 2012, while I studied for the Tennessee bar exam. My mother was ill, and I wanted to be present. When July came, I drove back to Nashville to take the bar exam. I planned to visit my parents again in August. But I caught a stomach virus, and I couldn’t make the trip.
Then, on September 21, 2012, my dad called me at work. I was sitting in a small basement office. He told me he didn’t think my mom had much longer to live. I cried right there at my desk. I asked my dad to put me on speaker so I could talk to my mom. I told her that I loved her. And then I booked the earliest flight I could get. But the earliest flight wasn’t until the next morning.
(05:43) That night, my friend Bethany stayed with me at the house I shared with a stranger I’d found on Craigslist. We tried to distract ourselves. We walked my foster dog, Oliver, along Charlotte Avenue in Nashville. We even tried to walk through a McDonald’s drive-through—which, by the way, they don’t let you do that without a car (chuckles). We bought a lottery ticket at the gas station instead. I didn’t win anything.
Bethany stayed with me until morning, and then she took me to the airport. I landed in Albany, rented a car, and called my parents’ house to say that I’d arrived. My dad answered the phone. And in that instant, I knew… But I pretended I didn’t. I played the part of the unsuspecting daughter because that’s what I thought my dad needed.
I drove the two and a half hours to my parents' house. I pulled into the spot where I usually parked—under the tree, facing the lake. My dad opened the screened-in porch. His dog, Hans, raced out to greet me. My dad and my sister followed Hans. Their faces told me what I already knew. My dad told me, simply, that my mom had died that morning.
I hugged my dad. I hugged my sister. I walked into the house and found Dan. I hugged him, and I told him, "It’s going to be okay." I hugged my mom’s two surviving sisters. My mom had been the youngest of five girls.
(07:31) My mom’s body was still there, in her bed. Or—in what used to be my bed growing up. I laid next to her for a long time. I don’t know why I did that. Maybe I just needed to be close to her one more time.
When my mom died, my dad hadn’t wanted her body removed until I arrived. When the time finally came, I sat across the hall with my Aunt Eileen while these people—I don’t know even what they’re called; what their job title is—but came to take my mom away—to remove her body.
So, no—talking with my dad about his death—it is not easy. It never will be. But it’s necessary. Because I know what happens when we don’t plan: The mental load that feels unbearable today—it will explode tomorrow—at the exact moment when I am least able to carry it.
I don’t want to be left guessing what my dad wanted. I don’t want to be stuck playing detective. I don’t want to argue, or to wonder. I want to know. I want him to tell me. I want him to do this—for me, and for Dan. Because when the time comes, I’ll be the one who tells Dan. And just like I did the day we lost our mom, I want to be able to hug him and say, "It’s going to be okay."
It will be okay because my dad and I had the hard conversations in advance. Because we chose action over paralysis. Because we loved each other enough to plan.
(09:40) And, what if I predecease my dad? Well, his carefully thought-out plan will still be there. The successor executor and trustee will carry it out. By forcing these conversations and taking action now, I’m not just protecting today. I’m leaving a gift for my family, for the future.
I’m telling you all of this because even though I do this for a living, even though I have the training and the experience— At the end of the day, I’m still a daughter. A sister. A mother. A wife. And love doesn’t cancel out fear. It doesn’t cancel out grief. But love, paired with action, can ease the burden we leave behind.
That’s what Death Readiness really is. It’s not about the paperwork. It’s about love. And courage. And being willing to say and do the hard things now, while we still can.
The good news—the thing I keep reminding myself of—is that when it comes to Death Readiness, every step you take—it matters. Every single thing you do to prepare, no matter how small, it makes a difference. And today, I want to talk about why that matters. Because when we don’t take these steps—when we put it off or hope it’ll all work out—things can go sideways in ways you can’t predict.
(11:29) I’m going to share a few real-life examples of estate planning gone wrong, or—estate planning that never really got to the finish line, and how to avoid some very preventable heartache, and preventable financial loss.
I should probably tell you that I’m new to the Metro Detroit area. And contrary to all my expectations, I’m loving it here. There’s a lot of pride in Detroit. People here wear Detroit t-shirts, Detroit hats—everything Detroit. We don't need to go anywhere else when we have Detroit. And one of Detroit’s heroes—the Queen herself—is Aretha Franklin. In fact, she’s entombed at Woodlawn Cemetery, just down the road from where I live. My husband and daughter recently went to pay their respects.
Aretha Franklin died on August 16, 2018, at the age of 76. At the time of her death, she wasn’t married, she had four adult children, and one of those children had special needs.
At first, it seems that Aretha had died without a Will at all. And that means that her probate assets—they would have passed according to the laws of intestate succession. When somebody dies without a Will, it’s how the state determines your probate assets will pass.
Then on May 20, 2019, Aretha Franklin’s niece, Sabrina Owens, who had been appointed as the estate’s personal representative, filed a petition in Oakland County probate court. While cleaning out Aretha’s home, Ms. Owens found a key to a locked cabinet that she hadn’t previously been able to open. So, she opened that cabinet. And inside were two handwritten documents, referred to in Ms. Owen’s petition as purported holographic Wills. They were dated June 21, 2010, and October 20, 2010.
(13:55) Now, whether a handwritten Will is valid depends on your state’s law. Here in Michigan, a holographic Will can be valid—as long as the document was intended to be a Will, is dated, signed by the person making it, and the material portions are in that person’s handwriting.
But then, after finding those two documents from 2010, things got even messier. Later that day, while searching under the living room couch cushions, Ms. Owens found another handwritten document. This one was dated March 31, 2014.
So, fast forward from that May 20, 2019 petition, and in August 2023—that’s more than four years later—a Michigan jury concluded that the 2014 document—the one that was found under the living room couch cushion—was Aretha Franklin’s valid holographic Will.
But here’s the problem—or here are a few problems—Even now, years later, no one agrees on exactly what that 2014 holographic Will means. And I’m going to provide links to the actual documents in the show notes from the Detroit Free Press article, if you want to look at those documents for yourself. They are not easy to read and even if you can decipher the words, the meaning is unclear.
So, this is a really powerful reminder that even when a Will technically exists—if it’s confusing, if it’s incomplete, or if it’s (chuckles) hidden away under the couch cushions, it can create years of litigation and uncertainty, and irreversible emotional toll.
(16:07) Aretha Franklin’s case is a big public example with a sizable estate. But her situation is not unusual. A lot of families, maybe yours or mine included, might think, "I have time." "I’ll get to it eventually." "Look, everybody knows what I want." And, that last one, it’s irrelevant if everyone knows what you want if those “wants” are not legally enforceable.
And life doesn’t always give us the time we expect. Even really good intentions left unsigned or unclear—they leave chaos. And that brings me to another case—a more everyday example.
In Michigan, a man named David Frankford died of cancer in 2022. Now David had taken a really good first step. He had met with an estate planning attorney years before—in 2015, actually. And that attorney drafted a complete estate plan for him. The problem was that David never signed it.
For seven years, those documents, they sat unsigned in a box. And next to those unsigned documents, were David’s handwritten notes. Notes about who should get the house, the cabin, the guns, the bank accounts. Even notes about funeral plans and terms for a trust, and who should pay for the memorial service, and exactly how much they should pay.
David told his step-granddaughter exactly where to find those documents. He talked about his wishes with multiple people in his life. But still he never signed anything. He never signed those documents that his attorney had prepared in 2015.
So, when David died, his brother, Michael, stood to inherit the entire probate estate. Because if David died without a Will, Michael, his brother, was his sole intestate heir.
(18:36) So, the case went to trial. The court ultimately admitted David’s handwritten notes as his valid Will under Michigan’s “harmless error” rule—MCL 700.2503. This is a rule that allows documents that don’t meet the strict formalities of a Will to be admitted if there’s clear and convincing evidence of the decedent’s intent.
In this case, the court weighed:
Testimony from friends and family.
A consistent story about who David saw as his family—which was actually his deceased wife’s family, and not his biological family—his surviving brother.
And his detailed handwritten instructions.
The appellate court later upheld the decision that these handwritten notes were David’s valid Will under the harmless error rule. The courts even acknowledged that parts of the notes looked more like a "to-do list" than a Will. But the overall picture showed what the court felt was clear testamentary intent.
So, yes—it worked out—technically. But think about the cost—imagine the time, the legal fees, the emotional stress and the strain on relationships. And imagine if the court had ruled the other way—if Michael had ended up inheriting everything, despite David’s real intentions.
(20:28) Seven years of delay almost rewrote David’s entire legacy. And yet, I do understand why David didn’t follow through with his plan. For those of you who have never worked with an estate planning attorney, I’m going to explain what you might expect when you make an appointment.
Most likely, you’ll receive a very long questionnaire—either before the initial appointment or consultation, or during that first appointment. You probably won’t understand all the questions or even some of the terms used in the questions, because you’re not an estate planning attorney.
The attorney will ask you for information about your family, your beneficiaries, what you own, how you own it, your trusted advisors. You’ll be asked to choose an executor, a trustee, determine how long assets should be held in trust. You’ll be asked whether you have concerns about any of your beneficiaries. Are there any minors or beneficiaries with special needs?
You’ll be asked who should manage your finances if you can’t manage your own. Who should be the guardian for your minor children? Have you named any beneficiaries on your retirement accounts? Who? What about contingent beneficiaries—have you named those? Who should make healthcare decisions for you? Do you have life insurance? Do you have long-term care insurance?
It’ll likely be overwhelming. You’re not quite sure how to answer, but you don’t want to ask questions because the hourly rate is so high. Over the course of the next few weeks, or months, you’ll give answers to questions that you don’t totally understand, just to move things forward. You’ll have all sorts of really long documents filled with legalese and boilerplate prepared, and you’ll sign them, most likely. Maybe you asked questions, maybe you didn’t. Maybe you got answers, maybe you didn’t.
(22:40) After you sign the documents, the attorney might give you a list of all the things you need to do to actually make the estate plan work, but you’ll just add it to the mental load you already have. You’ll figure it out later. Because you’re overwhelmed, you’re exhausted. And you think you just crossed something off your list, but you’re not sure. Is it possible that you actually added a whole lot more? But if you at least signed the documents, you did one better than David.
Here’s the hard truth about the harmless error doctrine, which ultimately worked in David’s stepfamily’s favor: It is not a safety net. It’s a courtroom gamble. We shouldn’t normalize stories like David’s as proof that "it’ll all work out." Instead, let’s let these cases serve as a warning: Don’t leave your loved ones to piece together your wishes from scraps of paper, voicemail messages, or memories of conversations. Don’t make them spend thousands—or even hundreds of thousands of dollars—just trying to prove what you meant to do but never finalized.
Put yourself in a box. Now I’m not talking about a literal box (not yet anyway), but don’t be creative. You want to put yourself in the kind of box where your wishes are clear, they’re signed, they’re legally enforceable, and they are easy to find.
(24:20) Even heartfelt attempts to document your wishes in a nontraditional way, which you might think are incredibly clear—like recording a video on your cell phone—it’s not enough. And sometimes, when tragedy strikes unexpectedly, families are left holding a video, and no formal legal documents at all.
That’s what happened in Montana, in the Estate of Jesse Beck. On July 15, 2022, Jesse Beck was riding his motorcycle on Highway 212 in Carbon County, Montana. He got into an accident, but it was not fatal, not at first. Another driver stopped to help him. But while Jesse and that other driver were waiting on the side of the road, a Sheriff’s deputy, who was actually responding to the scene, he accidentally struck and killed both men.
Jesse was survived by his only child, and then things got even more complicated.
Four days before Jesse’s death, he had recorded a short video on his cellphone. In that video, he said: "I, Jesse Beck, give all my possessions, if anything happens to me whatsoever, I give all my possessions, everything, to Jason Beck, my brother.”
And then Jesse sent that video to Jason’s cellphone. Unfortunately, Jesse’s words were not written down or signed. There wasn’t even clear information about exactly why Jesse recorded the video or under what circumstances he made that recording.
(26:22) The case made it all the way up to the Montana Supreme Court, which eventually ruled that Jesse’s video could not be admitted as a valid Will. And the reason was that it did not meet Montana’s requirements for a Will—that must be in writing, signed, and witnessed.
And Montana does have a harmless error rule, like Michigan, but it only helps when there’s clear and convincing evidence that a document was meant to serve as a Will. And this video alone, it simply wasn’t enough.
So the result here is that Jesse’s probate assets passed according to Montana’s intestacy laws to Jesse’s child, not to his brother, according to the wishes in that video. And Jason Beck, he had no legal claim, but he likely did have a sizable legal bill trying to fulfill his brother’s intent.
The reality is that intentions are not enough. Videos are not enough. Good conversations are not enough. The law requires us to follow formalities—to put our wishes in writing, to sign them properly, to make sure they’re legally enforceable. And if we don't? We risk leaving our loved ones to fight battles they should never have had to fight.
You already know that estate planning is important. Otherwise, you wouldn’t be listening to this podcast. And if you haven’t started planning yet, maybe it's because—like me—you’ve felt paralyzed. Overwhelmed. Too busy trying to survive today to plan for tomorrow.
If that's where you are, I get it. And if you need help getting started—if you don’t know where to begin—I can help. Just go to my website and schedule a free 15-minute consultation. I’ll also include a link in the show notes.
(28:36) But for right now, I want you to keep listening. Because I’m going to talk to you about an area of estate planning that you can do yourself. An area that can make a huge impact for your family, with small steps you can start today. I'm also going to give you some free tools you can use—and I’ll walk you through some simple goals to help you break this down into something manageable.
So today, I’m going to talk to you about digital assets. In future podcasts, we will take deeper dives into estate planning documents like Wills, trusts, and powers of attorney. But for today, I want to start with digital assets.
The term "digital assets"—it covers a wide range of online and electronic items—some of these have financial value, some sentimental value, and others are just plain practical.
So when you’re thinking of digital assets, you’re thinking about social media accounts (Facebook, Instagram, LinkedIn), email accounts (Gmail, yahoo—and I know some of you are still rocking your AOL email accounts). You’ve also got online banking and investment accounts, maybe some of you have cryptocurrency holdings (like Bitcoin). Many of you have digital photos, videos, documents (stored in places like Google Drive, your iCloud, or Dropbox), and you’ve likely got subscriptions to streaming services, whether it’s Netflix, Spotify, Hulu, Disney+. And don’t forget about the loyalty programs and your reward accounts (whether it’s through airlines, hotels, credit cards).
(30:34) And here’s the tricky part: Unlike physical assets, digital assets often come with terms of service agreements that restrict what can be done with them after you’re gone. Those agreements—the ones you agree to by checking the box without reading—often trump even the laws in your state regarding access to and distribution of digital assets. Today, that state law is likely some version of the Fiduciary Access to Digital Assets Act, which is a law that was created by the Uniform Law Commission.
One strong piece of advice I often hear is that you should have a password manager. And that’s excellent advice. But—I don’t have one. I used to, but it didn’t stay updated—and that was probably user error.
Instead, I have a system:
I have a Word document with my passwords organized in a table.
I keep a printed copy in our home bin, alongside our legal documents.
I store a copy digitally only in Everplans, and this requires two-factor authentication to access.
I keep a hard copy with me at work.
When I create new passwords, I add them by hand to my hard copy that I have at work first, then update the digital version in Everplans later. When I update the digital version, I replace the copy in my home bin and with my work documents with this updated hard copy. I shred the old copies.
If you're listening to this and thinking, "That sounds terrible, and way more complicated than using a password manager,” you are probably right. But for me, done is better than perfect. I tried the password manager route—it didn’t work for me. This does.
(32:38) My husband knows where the information is. My friend Erin, who would step in if anything happened to both of us, also has access. It is not perfect. But for me it's reliable, and it’s better than leaving my family scrambling.
You might be wondering if I have any real-life examples of what can go wrong if you don't address your digital assets. Well—yes. Yes, I do.
James Howells accidentally discarded a hard drive containing 8,000 bitcoins in a garbage bag in 2013. And as of January 2025, those 8,000 bitcoins were worth about $757 million. And since 2013, James has been trying to get permission to search the landfill where he believes the hard drive ended up. Earlier this year, a judge rejected his latest request.
One mistake—one overlooked piece of technology—and 12 years of time, money and fighting, and he’s no closer to even being able to look for his hard drive, let alone actually finding it.
And one other thing to think about with regards to digital assets: Your homeowner’s insurance probably covers your tangible personal property, only. Most policies were written long before ownership of digital assets was common. Many insurance policies require “physical loss” or “physical damage” to trigger coverage. This doesn’t necessarily apply to digital assets like cryptocurrency, digital photo collections, or loyalty points. Which means if something happens—and your digital assets are lost—they might not be covered as part of your homeowner’s insurance.
(34:44) Here’s what I’d like you to do as a starting point for documenting digital assets. I’d like you to try “body doubling.” Body doubling is when you perform a task, something you’d otherwise procrastinate doing, in the presence of another person. The goal is to increase motivation, to increase your focus and to increase efficiency. This can be done in person, or it can also be done over Zoom. And Zoom works well because you can share your screen and walk through questions together.
I’m going to ask you to make three appointments—virtual or in-person—with your body double. After each appointment, save the document in a secure place. Make sure the person responsible for you if something should happen knows where it is and has access to it.
First, on Day 1: Schedule a time—send a calendar invitation to sit down with your partner, your sibling, your best friend, your parent—Download the Personal Important Information Sheet from the Resources page on my website. I’ll also include the link in the show notes.
First, I recommend setting up online "legacy contacts" for your major accounts—Google, Apple, Facebook. I’ll include instructional links in the show notes.
Document on that information sheet whom you've chosen and fill out the rest of the information as best you can. If you don’t know something, see if your body double can help you figure it out. If you get stuck with a particular question, skip it. It’s better to skip a question than let that question derail you from moving forward with the rest of the document.
Here’s the type of information you’ll include in here: your full name, your maiden name if that applies, your parents’ full names, your phone password, your computer password, your iPad password, email addresses and passwords, Apple IDs, social media passwords. I updated my Personal Important Information Sheet before I recorded this podcast so that I could speak authentically.
(37:11) Once you’re done, save it in a secure place. Give it to your person. And email me. Tell me how it went. Did you run into any problems? Could the process be easier? My email is jill@deathreadiness.com, and I’ll also include that in the show notes for you.
On a different day, I’d like you to schedule a time with your body double to fill out your Key People Information Sheet. Again, you can find it on the Resources page at deathreadiness.com, but I’ll also include links in the show notes.
Here, you’ll include information for the people who should be notified if something happens to you—not just if you die, but if you get sick, or are in an accident. For example, friends, your employer, family members, financial advisor. When you’ve completed that, I want to know how it went. Send me your comments and your suggestions.
And lastly, on a different day, document your passwords. If you have a password manager and it works for you, I commend you. In fact, I’m both impressed by you and I’m envious of you. But if you’re like me, or, even if you’re a password manager guru but you’re responsible for a person who is like me, keep listening.
I’ll include a link in the show notes for instructions as to how to find all of your saved Google passwords on your computer. This is a good exercise to do with a body double. I’ll also include a template for you.
(38:55) Let me remind you that this is not perfect. If you can set up a password manager and stay with it, please do. Until then, do it messy, but do it safely. Whether you’re saving your information digitally or in hard copy, make sure you’re doing so in a safe and secure manner and in a safe and secure location.
If you have already put together an asset list, that’s an excellent place to start. Document online usernames and passwords for accounts related to those assets.
And here are some tips:
List all the email addresses you use.
Write down your key banking, retirement, and investment accounts.
Write down your streaming services
Your social media, your utility accounts – I’m also going to link to a Home Information Sheet in the show notes as another option for documenting this utility information.
Document your accounts that earn income: Etsy, Patreon, Substack
And domain names – If you own your own business, you might have quite a few of these.
When you’ve completed your Day 3 task, email me again. Send some feedback. And congratulate yourself.
This morning, I read an article in The New York Times about how the flu leads to an estimated 36,000 deaths each year in the United States—many of them are sudden and unexpected. The article highlighted the stories of three people who died this past winter:
(40:35) Lauren Caggiano was a 49-year-old paralegal, a new grandmother, and she had two dogs that she adored. Ca’Myiah Simmons was just 16 years old—a high school junior who sang in the choir and dreamed of becoming a nurse. Mark Walsh was a detective for the Boston Police Department. He was married and the father of two little boys, ages 1 and 4. He had been planning to coach his son’s T-ball team in the spring.
I came across another headline this morning, too—about some of the specific difficulties that may have contributed to the deadly collision between an Army Black Hawk helicopter and American Airlines Flight 5342 over the Potomac River back in January. Sixty passengers and four crew members on the jet died, along with the three soldiers aboard the helicopter.
People die tragically every single day.
I’m not sharing these stories to scare you. I’m sharing them to remind you: Life is fragile. Being ready—for yourself and for the people you love—it isn’t about fear. It’s about making sure that when life takes an unexpected turn, you have what you need to find your footing again.
This work is not easy. It’s heavy. But doing it now, even imperfectly, is the difference between chaos and clarity later. Between heartbreak that breaks you—and heartbreak you can survive. So that someday, when the worst moment comes and someone you love looks to you for steadiness, you can say, with honesty and strength: "It’s going to be okay." And you’ll be right.
I know this, because I’ve lived it.
(42:35) Do you remember the foster dog I mentioned? Oliver? When my friend Bethany picked me up at the airport, returning to Nashville after my mom’s death, Oliver was with her—a gangly brown beast with enormous floppy ears.
Not long after, Oliver stopped being a foster dog. He became my dog. Oliver was there when I bought my ugly little house in 2013. And he was there as we built a whole new life inside those walls—a husband, two children, three dogs, and a future. When Oliver died, we were all with him—my husband, our two kids and I.
Oliver entered my life because someone tied him to a fence outside an animal shelter one night. I was his steadiness. And he was mine.
Oliver taught me something: Healing doesn’t always look like fixing everything. Sometimes it just looks like having someone by your side when it feels like everything’s been broken.
That’s what planning can offer, too: A hand to steady you, even in the worst moments.
Thanks for spending this time with me. I’m Jill Mastroianni, and this is The Death Readiness Podcast.
Disclaimer: (44:00)
Before we wrap up, I want to remind you that while I am an attorney, I'm not your attorney. The Death Readiness Podcast is for educational and entertainment purposes only. It does not provide legal advice. Use of the information from this podcast without careful analysis and review by your attorney, CPA, and/or financial advisor may cause serious adverse consequences. I provide no warranty or representation concerning the appropriateness or legal sufficiency of this information as to any individual's tax, estate or related planning. For legal guidance tailored to your unique situation, consult with a licensed attorney in your state. To learn more about the services I offer, visit DeathReadiness.com.
April: (44:52)
Hi, I'm April, Jill's daughter. Thanks for listening to The Death Readiness Podcast. My mom always says that death readiness isn't just about planning. It's about the people you leave behind and the legacy you create for them. We hope today's episode helps you think about how to take care of yourself and your loved ones, now and in the future. If you liked what you heard today, share this episode with someone you care about. Follow our show for free on Apple Podcasts, Spotify, YouTube, or wherever you're listening right now.
