So many of us in the sandwich generation can see our parents’ challenges—mobility issues, memory lapses, financial disorganization—yet struggle to help our parents move beyond the problem to actually finding a solution. In this episode, I share my guest appearance on The Legacy of Love Podcast with Sara Ecklein, where we explore how to guide aging parents through estate and life planning in ways that are compassionate, collaborative, and empowering.
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The Death Readiness Podcast
Episode: 33
Title: Why Your Aging Parents Aren’t Planning and How to Change It
Guest Episode from Sara Ecklein’s Podcast “The Legacy of Love”
Published: September 19, 2025
Jill Mastroianni (00:00): Your parents may know they need assistance. They're problem aware. But they have no idea what to do next. Today, I'm sharing my guest appearance on the Legacy of Love podcast. In this episode, host Sarah Ecklein and I discuss how to guide your parents towards solution awareness in life care and estate planning with compassion, collaboration, and empowerment.
Welcome to the Death Readiness Podcast. This is not your dad’s estate planning podcast. I’m Jill Mastroianni, former estate attorney, current realist, and your guide to wills, trusts, probate and the conversations no one wants to have. If your Google search history includes, “Do I need a trust?” “What exactly is probate?” and “Am I supposed to do something with mom’s Will?” you’re in the right place.
(00:56) I loved to run, but for more than a year, I couldn't. Every attempt ended the same way: unbearable pain in my left hip and lower back that sometimes made it hard to even walk. I saw doctors, paid for x-rays, tried different fixes, and all I came away with was a sharper sense of the problem. Problem aware? Absolutely. Solution aware? Not even close.
In June, I left Michigan with my daughter and dogs to stay with my dad in the Adirondacks. The dogs and I hiked daily out to an old hunting lodge. I occasionally swam in the lake, which didn't hurt my body, but also didn't bring me the same joy that running always has. One morning after a hike, I met with a client and friend, Annette. She asked me whether I was still running. When I explained the pain, she suggested the real issue might not be my hip or my back but my IT band. What Annette didn't know is that even though I wasn't complaining out loud, I thought about running all the time. How much I missed it, how badly I wanted to feel that freedom again, especially surrounded by the beauty near my dad's house. To an outsider though, it might've looked like I didn't care. I wasn't going to PT, I wasn't doing exercises, I wasn't seeing another doctor.
(02:16) The truth was, I had lost trust in the solutions I'd been offered so far. And isn't that exactly what happens with our parents? We can see the problem so clearly from the outside. Mobility issues, memory lapses, cognitive changes. But when we just point out those concerns, all we do is agitate those problems. What would it look like instead to engage with our parents collaboratively? To move beyond problem awareness into solution awareness in a way that makes them feel seen and heard, and improves everyone's lives in the process.
Annette's perspective changed everything. I started foam rolling my IT band and slowly worked my way back to running. A half-mile jog became a mile, then two. We all get stuck in problem awareness. Sometimes it takes another voice, a professional, a friend, even a client, to open the path to solution awareness.
(03:18) For me, it meant experiencing the joy of running again. For your parents, it could mean finally creating an estate and life plan they understand and feel confident about. If there's more problem awareness around your parents' estate plan than solution awareness, my Parent Prep Plan makes estate planning manageable. I guide your parents through the process step by step, finding the right attorney, preparing for meetings, and even sitting in with them if they'd like.
At the end, they'll walk away with a personalized Death Readiness playbook, and you'll have the peace of mind of knowing that the work is finally done. You can learn more at deathreadiness.com/parentprepplan. That's deathreadiness.com/parentprepplan. The link is in the show notes.
Thank you so much to Sarah Ecklein, host of the Legacy of Love podcast, for allowing me to share this episode with you.
(04:16) Sara Ecklein: Today, I'm joined by Jill Mastroianni, a former estate planning attorney, host of The Death Readiness podcast. And Jill now serves families nationwide with estate planning and probate support. I think one of her many gifts is bridging the gap between legal planning and real life family dynamics. If you're navigating care for your aging parents while balancing kids and career, this conversation will help you breathe a little bit easier and also know that you're not alone.
Jill Mastroianni, welcome to the Legacy of Love podcast.
Jill Mastroianni: Thanks, Sarah. Thanks so much for having me today.
Sara Ecklein: I knew you had to come on. I feel like we're, you know, after a similar message and supporting similar woman, the similar mother. And I love how your brain works, which is very different than mine. And you have a gift for breaking things down and teaching really complex topics. I think probably part of that is the fact that you're an attorney that helps.
(05:21) Jill Mastroianni: I love technical. I love technical language, I love the law. I was Russian language and literature major. I loved learning that language. So if it's complicated, I want to get into it and break it down in a way that I can understand it and hopefully help others understand it too.
Sara Ecklein: It's so good. This actually is like a big point of contention in my marriage. My husband's an engineer and he like always needs to know the breakdowns and why things happen. And I'm like, I don't need to know the why.
Jill Mastroianni: Yeah, I'm like your husband. I need to know. I need to understand that.
Sara Ecklein: So just really starting out, let's talk big picture. For our listeners that maybe their parents just had a sudden health decline and they're seeing the writing on the wall of, boy, my parents have never planned and we need to start planning for supporting our aging parents. That's a big question, but I want to hear kind of your response of what to recommend to this woman.
(06:26) Jill Mastroianni: So I agree, it's a big question, but it is a big question that so many of us face because our parents are aging and they do need more help. That's just the state of our lives right now. And I think that a lot of us, when we think about how we need to help our parents, it feels really overwhelming because we have so much on our plates.
We are taking care of young children. We are working our jobs. It feels like this is another thing to do. And we want to go in there like a project manager and say, you need to give me this information, that information. Here's what we need to do. I'm going to talk to so and so. And I don't think that's the best way to go about it. And I don't blame anyone who thinks of going about it that way or has gone about it that way because we are at our tipping point.
(07:24) But I think you have to think of it from the perspective of the problem, right? If your parent is declining physically, if your parent has a partner who's declining mentally, they are aware of the problem. They are very problem aware. But problem aware is not the same thing as solution aware. If we have a problem, we might like to do nothing about it because we don't know how to solve the problem.
But that's where I think a professional can come in and maybe help you navigate the solution. But before you get there, I would say go to your parents with a feeling of collaboration, a feeling of empowerment. Maybe you've not done your estate plan. Maybe you think you've done it, but maybe Sara and I would disagree that you've done your estate plan. There is always something that you can do in collaboration with your parent about how you start planning your estate. And maybe if you have done yours, if you have those documents in place, maybe you talk to your parent about what you've done. See what they think about what you've done.
(08:47) Maybe you both fill out a medical information sheet together so that not only do you know what your parents' medical situation is, but they know what yours is. And it's not coming at it from a sense of, OK, now mom and dad, you're the problem. We need to take care of this, and this is how we're going to do it. It's, OK, we both have a problem. We're both going to die someday. We're both going to get old. Let's figure out how we can make this better for both of us from a sense of collaborating, empowering, and modeling the behavior that we want to see in our parents.
Sara Ecklein: I think that's one of the biggest pieces that I see. Usually once I get involved, I'm taking over from a family member who usually just no longer wants to do the job in those kind of resignation situations. And just because I'm not the daughter, right, telling the parent what to do, it's different. It's received differently.
(09:48) Jill Mastroianni: It is received differently. And when I work with aging parents to get their estate plan in place, whether it's finding the attorney to work with, working with the attorney, attending the meetings, it's not just the estate plan that I'm working with. I am hearing the client.
So for example, when's your mom's next doctor's appointment? Are you sick of hearing that? Are you sick of hearing the story about the banana cake that everyone loved when you were in college? It's the first time I'm hearing it. I enjoy a good story about banana cake. And you know, if your mom tells me when her doctor's appointment is, I'm going to put it on my calendar and I'm going to ask her about it. And it takes me but two minutes to listen to this story. Your mom wants to be heard.
(10:39) And I'm not judging any adult child for kind of rolling their eyes at, you know, the 10th time they heard the banana cake story, because it's the 10th time you heard it. But bringing somebody from the outside in who can really give your parent the treatment that they deserve and that you're not capable of giving right now because you have too much on your plate, that makes things better for both sides.
And I see the problem in myself too with my own father who's going to be 79 in September. And I was fortunate enough to spend the summer with him. He lives on a lake. And so my daughter and I went out there for the summer. And even though he lives on a lake in the mountains, I am fast moving. I am a taskmaster. I know what I have to do. I'm getting up at the same time every day, and I'm doing it. And then one evening, I went and sat on the deck with him. And we were chatting. And he said, you know, Jill, there's something I've been worried about. And I've been worrying about it every day, all day long, for so many days. And I said, what is it? And he told me an estate planning issue that I am uniquely qualified to help him with.
(11:57) But he didn't want to bother me. He saw how fast I was moving. He saw what I was doing. And he would rather hold that, be very problem aware. He was very problem aware. And he couldn't stop thinking about it, but he didn't know how to solve it. And it made me think, okay, I am this person for so many other people's parents, but my dad didn't think that he could come to me because I myself didn't slow down enough for it. And I'm not necessarily faulting myself for that because this is how we live our lives now. Estate planning is hard, right?
So I think we've got a lot of problems if we're thinking about we need more people to complete their estate plans. Number one, people don't want to have the conversation because it's uncomfortable. And I don't think that we need to make the uncomfortable comfortable. It's uncomfortable. When I'm talking to my dad about his estate plan, I'm talking about the day when he will not be here anymore. That is uncomfortable for me and I'm not going to get over it, but I'm going to have the conversation anyway.
(13:16) And so we have that discomfort, the discomfort of the conversation, and then the discomfort of not really understanding what estate planning is and what goes into it. I think a lot of people have had bad experiences with attorneys, where maybe they come in, the attorney talks down to them, they don't understand what the attorney is saying.
It ends up costing a lot of money and they're confused and they're not empowered. They don't know what they signed. They don't know what they did, but they felt like they had to do it because everyone told them they had to. So then we go from not having an estate plan to having an estate plan that we don't understand and we don't know what it does and an attorney that we're not comfortable talking to about it. And so I'm not really sure that we accomplished anything in that situation.
(14:10) It's really about taking the time to make sure that people are comfortable and that they understand because it is not rocket science, but it is not intuitive. And so to take the time with people to understand the plan that they're creating and to advocate for them when they're with the estate planning attorney in their specific state to make sure that that estate plan actually gets done the way they want it to be done and not just the way that's easiest for the attorney to get it done and cross it off their list.
Sara Ecklein: In the age of information and AI. If attorneys aren't changing their approach, there's so many attorneys I find that are really approaching this with more care, more heart, more like let's sit down and really educate the client the old school way where it was exactly that scenario where you pointed out where people are in essence disempowered, outsourcing their power to their attorney, not really understanding their documents and letting the chips fall where they may.
(15:18) Jill Mastroianni: When we're talking about estate planning, it is a place for somebody to use their voice and have agency. So aren't we really doing a disservice if what we end up with is an estate plan that doesn't work, because often that's the case, and doesn't meet the goals of the person doing the planning.
Both of our podcasts and both of our businesses, we are trying to give women back their voice or any segment of society that is maybe disserved. So anyone that isn't traditionally listened to, and that happens a lot with aging parents or seniors, we need to listen to what people say and what they want and make sure that they understand what they're getting. Because at the end of the day, that's the goal. This is your life and this is your death. So you better understand what you're saying you want to happen during your lifetime if you're incapacitated and what you want to happen with your things after you die.
(16:24) Sara Ecklein: Can you give an example of a success case of you supporting what that looks like from beginning to end?
Jill Mastroianni: I guess a recent example is with a set of parents. They're in their 70s. They have one child who has three minor children, working mom, very highly educated, went to Stanford University. She has a whole lot on her plate, but she also knows that she's going to be the sole person responsible for taking care of her parents as they get older.
And she's been trying to get her parents to do their estate plan for a really long time. And they tried. They tried once 15 years ago. And the attorney made them uncomfortable. So they never went back. So I met with them. And we don't live in the same state. They're actually in your state. They're in California.
(17:21) So we've met over Zoom. We've figured out what assets they have, who the beneficiaries are, what the values are, all their different log in information and I found them an attorney in their state of California who did the estate planning, but I attended the meeting. I provided all of the documentation that the attorney needed. After that initial meeting with the attorney, my clients had no idea what happened. Not because they're not smart and not because the attorney did a bad job. It was like drinking from a fire hose.
Sara Ecklein: It's drinking from a fire hose. Yeah, exactly.
Jill Mastroianni: So we went through that and I explained what had happened, what the remaining questions were, what we were doing that it was exactly consistent with what we had always talked about. And maybe the attorney said it a different way and the attorney drafted the estate planning documents. Those documents are signed. Then we went through and funded the trust. So I actually worked with them to fund the trust.
(18:23) And now we have everything that they need in one place and their daughter has access to it. And it's not just the legal information. It's their medical information, it's their personal information about the key people in their life, their accountant, their attorney, their real estate agent, all those things, their insurance agent and all their insurance policies.
It's the complete picture that their daughter is going to need to take care of them someday if they're no longer able to take care of themselves, and then ultimately at their death. And she didn't have to lift a finger, and it still got done. And her parents understood what they were doing the entire time, and now they have that done and they've crossed it off their list. So nobody had to get into an argument. Nobody had to stage an intervention to get this done. We just did it.
(19:23) Sara Ecklein: Did the parents find you or did the daughter make an introduction?
Jill Mastroianni: The daughter made an introduction, but I don't tell the daughter what I did with her parents. I asked her parents at the end what they wanted me to share with her. They said they wanted to share everything. So I did, and I shared that with her securely. But the information that I get from the parents is 100 % confidential unless they ask me to share.
Sara Ecklein: I like that you're distinguishing that. Let's actually hone in on this because I've seen situations where the adult child is basically doing all the talking and it's really putting the cart before the horse, but setting that boundary from the beginning of who's the client. The client isn't the adult child that's making the introduction. It's really the parents.
Jill Mastroianni: Yeah. And I had another client who was administering a probate estate.
Sara Ecklein: Okay.
(20:20) Jill Mastroianni: And often the introduction to my clients comes through their adult children. This client is a woman in her mid seventies and her son thought that he was going to be involved. And I specifically asked my client, do you want me to share information with him? And she said, no. So I didn't.
Even though he reached out to me and said, my mom's comfortable with you sharing information with me. And I said, well, I'm not going to. I didn't say, “she said, no, you can't have this information”. I'm not going to, right? She could always share that information if she wanted to, but that's a very clear boundary that I'm going to draw. It's not going to be, “Oh, she told you it was okay. Okay, I will share it”.
No, that's not how it works. And even when I was practicing, the big red flag to me would be when an adult child called and requested one document, a power of attorney, because they needed to be able to make decisions for their parent. I wouldn't go any further because that says to me that there's already a loss of capacity. If you're calling requesting this one document that is going to give you control.
(21:42) And also, to be honest, from an estate planning attorney perspective, it is not worth the potential liability to have someone come in and try and vet them for whether they have the capacity to sign something. So that's just a really good indication that maybe planning started too late, and maybe the appropriate route at that point is perhaps a guardianship. Or if there is an attorney who knew this person for their entire life and could kind of gauge the capacity, then that's a better route. You don't start with an attorney who never met this person when there's potentially already some decline happening.
Sara Ecklein: I think for the listener, let's assume they are well-meaning. They're wanting to do right and support their parent and they're putting out a crisis, a fire. Their parent never planned. What would be your recommendation and next step?
(22:40) Jill Mastroianni: So if they don't have a plan and we have diminished capacity, it's a spectrum, right? Whether you can have diminished capacity but still have capacity to do an estate plan. So generally you have to understand what you own, who you want to give it to, what you want to happen and who would generally be entitled to your property if you didn't plan. So you could still plan with diminished capacity, but it's not a situation that an attorney who's never met your parent is likely going to feel comfortable taking on because you don't know what the person used to understand or sort of the level of diminished capacity that there is.
Sara Ecklein: Yeah, that baseline.
Jill Mastroianni: At that point, I think it's really about figuring out what assets your parent owns and if you're able to get a power of attorney in place to help manage those assets. And then unfortunately, if there is no capacity, you're really left with what we call intestate succession. So the assets passing according to the laws of intestate succession meaning without a will. So for example, if I'm married in Michigan and I don't have a husband and I don't have parents, but I do have kids, it would pass to my kids. And that varies by state what the laws of intestate succession are. But really you're kind of doing your best case scenario of controlling the situation, even though it's not ideal. There's some damage control that you can do at that point.
(24:35) Sara Ecklein: I get these calls of my parent had a medical crisis, they're in the hospital, what can I do? Also, I've had adult children contact me and their parents struggle with alcohol and drug abuse and they lack capacity now later in life. And also looking for resources of how to support their parent now that they're aging and no longer can have capacities. We want to, of course, be supportive and collaborative, but if we’re unclear about capacity. I mean, in that scenario, is it the adult child hiring an attorney to figure out what needs to be done?
Jill Mastroianni: So I'll give you links to a couple of episodes that I did on my podcast that might be helpful for this situation just to learn exactly about what powers of attorney are and how powers of attorney differ from a guardianship or a conservatorship. So I think the first step is educating yourself on how that works. And I do want to point out that with medical powers, each state will generally have a statute that gives authority to act to certain individuals in the family based on their relational closeness to you. So generally, if you are married, that first person in the statute is your spouse, and that's for making medical decisions only. There is not that sort of preference where someone could start making financial decisions for you without any kind of court proceeding. That would have to go before a probate court judge.
(26:14) But I do think that in terms of determining whether someone has capacity, there are professionals who do that for a living who determine capacity. With an attorney, they're not going to make a formal evaluation of capacity, but they're going to figure out whether they personally feel that the person they're talking to has capacity to sign the document and do the planning that they're talking about and that 100 % has to be done without the adult child in the room. Even if the adult child is needed to bring the parent to the attorney for the appointment, the only individuals in that appointment should be the attorney and the parent just to make sure that there is no undue duress or any kind of influence coming from the adult child.
And then of course, if there is a guardianship proceeding, meaning you're trying to get control over your parents' finances through the court because you don't think that they have capacity to sign a power of attorney. If your parent is not willing to otherwise submit to a medical evaluation from a doctor, the judge will order that medical evaluation be done.
(27:33) Sara Ecklein: Yeah, I've gone through that. It's very hard. And it's even hard to find doctors willing to do these evaluations. This is where once we go down these rabbit holes and seeing the complexity of these scenarios, this is where, and I think why we're both two women on a mission to reach people upstream. If you start planning well before there's a crisis, I mean, it just really changes the whole ballgame. These scenarios are like worst case scenarios where it's like, you you've got a court involved as you're having a medical crisis.
Jill Mastroianni: And I think just sort of getting back to the whole problem awareness, if you are listening to this podcast and you are aware of a problem, especially if the problem is something that you're thinking about all the time, let's find your solution. I think about the fact my parents, my older brother has Down syndrome. And when he was born, they really had to try hard to seek resources to help with his development.
(28:36) Now, if they had ignored that, if they had not tried to find a solution to help him develop and have a better life, would they have forgotten that he had Down syndrome? Would their failure to seek a solution cause that problem to go away? No, they would always be keenly aware that he had Down syndrome and that he needed assistance. So ignoring it isn't an option that helps, right?
That problem and the problem awareness is always going to be there. If you get to a solution, if you're able to find a solution for in their circumstance, find the programs, find the people, find the school system where he could thrive, that's when you stop thinking about it all the time because you have that solution in place.
(19:27) Sara Ecklein: I really want to thank you for just sharing that and also just separating the problem awareness versus solution awareness. I hadn't quite heard things said in that way before. I talk a lot about people choosing to live in denial and having the denial of death, and that's where I believe so many people don't plan. But this is a different angle and different way of looking at things. And it also puts me into a place of having radical empathy and compassion for people.
I think at the end of the day when we do this work, this is a very caring profession. I do always have that, but even just not putting the stamp of someone's living in denial, maybe it's their problem aware, but not really solution aware yet. So, I want to thank you for saying that because I hadn't heard anyone say it that way. And I definitely know for the listener right now, right? Like the overwhelmed mom that needs to do something, whether it's for herself or her parents or both, and is just spread so thin. I think it's also having that like self-compassion, right? We might also just be in that space of problem aware and not yet to solution aware.
(30:44) Jill Mastroianni: If you don't know how to get to the solution or if the solution isn't within your grasp, and I think that's what a lot of our aging parents have trouble with, yeah, they know that it's hard for them to get up the stairs. They know that because they try to go up the stairs every single day. They're not pretending they can go up the stairs. OK, maybe they pretend in front of you. And that's what you see. And that's why it looks like denial. But this is the house they have and they don't know what they might be able to do to fix it. So they're just stuck in that problem awareness without the solution.
Sara Ecklein: Jill, thank you. I've taken a lot from the conversation. I know our listeners will too. You've shared a lot of resources. We'll definitely include links to The Death Readiness podcast and also the specific episodes you referenced. Anything you want to leave listeners with?
(31:39) Jill Mastroianni: I guess I would just leave listeners with the acknowledgement that you and I, Sarah, we are the same as them. We are going through life. We are overwhelmed and we are uniquely situated to help people in this area of life. Just like there are people uniquely situated to help with nutrition, for example. So if this is an area of life where people have a problem, reach out, find your expert, get to the solution.
Because when you experience the transformation of what going from not having a plan, being so worried about your parents or even yourselves or even what will happen to your kids, if you go from that problem and that sort of lack of understanding of what it all entails and not even knowing where to begin to the transformation of having it all in place, the improvement to your life is going to be significant. And it's okay if you need to ask for help to get from problem to solution because we all need help in these different areas of life.
(32:53) Sara Ecklein: Yeah, absolutely. All right, Jill, I want to say thank you.
Jill Mastroianni: Thank you, Sarah.
Sara Ecklein: Today's conversation with Jill Mastroianni was such a reminder that supporting our aging parents isn't about just swooping in with all the answers. It's about slowing down, listening, and approaching things with collaboration.
Jill Mastroianni: If there's more problem awareness around your parent's estate plan than solution awareness, my Parent Prep Plan makes estate planning manageable. I guide your parents through the process step by step, finding the right attorney, preparing for meetings, and even sitting in with them if they'd like. At the end, they'll walk away with a personalized Death Readiness playbook, and you'll have the peace of mind of knowing that the work is finally done. You can learn more at www.deathreadiness.com/parentprepplan. That's www.deathreadiness.com/parentprepplan. The link is in the show notes.
(33:55) Thanks for joining me today. On next week's Tuesday Triage, I'm tackling this question from my daughter, April. If you forget to list something in your will, where does it end up? And if two people are named for the same thing, like a piece of jewelry, who actually gets it?
Join me as we dig into how the law sorts these situations out and what you can do to keep your family out of conflict.
This is Death Readiness, real, messy, and yours to own. I'm Jill Mastroianni, and I'm here to help you sort through it, especially when you don't know where to start.
Hi, I'm April, Jill's daughter. Thanks for listening to The Death Readiness Podcast. While my mom is an attorney, she’s not your attorney. The Death Readiness Podcast is for educational and entertainment purposes only. It does not provide legal advice. For legal guidance tailored to your unique situation, consult with a licensed attorney in your state. To learn more about the services my mom offers, visit DeathReadiness.com.