Bri Conn, CFP®: [00:00:00] Welcome to Childfree Life by Design. Today, we’re talking about digital legacy and end-of-life planning and what it means for people who are building a Childfree life on their own terms. I’m Bri Conn, here with Niki Weiss, a digital thanatologist who help people navigate the emotional and logistical side of end-of-life planning in the digital age. She’s the founder of Endevo and creator of My Final Playbook app, and she brings us a background in healthcare, risk analysis, and data governance to a topic most of us would rather avoid. In this episode, we’re covering why digital legacy planning matters, how to move past the fear and overwhelm that keeps people stuck, and what an actionable end-of-life plan actually looks like in practice. If you’ve ever wondered what happens to your digital life, your accounts, your files, your wishes when you’re no longer here to manage them, this conversation will give you the clarity and tools to make intentional decisions that support the life you want.
Intro: From Childfree Insights, this is Childfree Life by Design, the go-to resource for building the Childfree life [00:01:00] you want. Every episode gives you practical guidance, clear direction, and meaningful conversations to help you live intentionally and design a future on your terms. This podcast is for educational and entertainment purposes only. Please consult your advisor before implementing any ideas heard on this podcast.
Bri Conn, CFP®: Niki, thank you so much for joining me today. I’m delighted to have you here and having you talk about all of the digital things. I first came across you on LinkedIn when I saw a post about death tech and sent you a message and said, you know, “What an interesting term. I hadn’t thought of it that way.” We often talk about age tech but your focus is really on the legacy after your one is gone and then the digital version of that. So I’d love for you to give a little any more about yourself that you’d like but also explain what it is that you do.
Niki Weiss: As a thanatologist. Well, Bri, you know, you and I had an initial conversation, and I felt like we could just talk for hours. We had so much to say about this topic, which is what both you and I do, which is just the [00:02:00] pre-planning important conversations. I mean, for your listeners, your clients, they choose to have a Childfree life. But if life didn’t happen, if we were no longer here, who’s gonna shut that down? And so for those that don’t know, a digital thanatology, thanatologist is what I call myself. So that’s a new word for you as well, right? I mean, you didn’t know. You never met a digital thanatologist before you met me.
Bri Conn, CFP®: I had not.
Niki Weiss: So the way I describe it is if you need a visual, think of Marvel Comics. It’s got the Thanos character, this big, evil kinda looking guy. But actually, Thanos or Thanatos is the name for the Greek god of death. Word of the day. So Thanatos, Greek god of death, is actually neither evil nor a hero. He’s benign. He’s neither benevolent or malevolent because death is neither. It just is part of the human [00:03:00] existence. So as a thanatologist, think of psychology, sociology, anthropology. So thanatology is the study of death and dying, and I specialize specifically in the digital piece because I’m fascinated by what happens to our digital afterlife.
Bri Conn, CFP®: Just even taking and thinking about all of that, how it comes together, the digital stuff, was that initial, like you knew you wanted to study this and go into the digital side of it? Or how did that work?
Niki Weiss: As a founder, we all have a story. There’s something that drives us to the work that we do. It’s a calling. My parents they both passed away before they were 50. 10 years apart of cancer because life happened. And so for me growing up, death was just part of my upbringing. For some people, they run away from the experience. For others, like myself, for whatever reason I’m just wired, I leaned into it. So the first part of my career, I actually worked in hospice as a bedside clinician where I supported families as they transitioned to this [00:04:00] end stage of life. Have you personally had anybody close to you and watched them pass?
Bri Conn, CFP®: Yeah, multiple times. I average one funeral a year for my life.
Niki Weiss: And are you always the person that they’ll call and say, “I just got the diagnosis,” or, “We just got the call”?
Bri Conn, CFP®: It definitely depends. Some of them, yes. Recently had some tough conversations with people too about similar things.
Niki Weiss: So I think we just end up being that beacon, being the source that people will go to. So for me working in hospice, feeling very comfortable with this, and it was a calling, and I felt very blessed to have that opportunity. And the hospice agency that I worked for, we had a pediatric program all the way up to end-stage dementia and Alzheimer’s, so I got to see that full life cycle. But when I turned 40, I realized, oh, I actually wanna make some money. So I pivoted from hospice clinical work to project management, and that’s where I’ve been for the last 20 years, working in project management, specifically in healthcare. And it was about three years [00:05:00] ago when my husband and I realized, ooh, we had not updated our wills since our kids were in high school, and now they’re in their 30s. We’re grandparents, so we need to get to it. My husband and I started to work on our wills. Now granted, death is easy for me, and I’m a project manager, so doing the administrative step-by-step paperwork was not overwhelming. Oh, and by the way, my brother happens to be an estate attorney, so we got a really good deal. But when we started to do it, we realized, this is complicated. It’s a second marriage, adult children. Who gets to make decisions? The money, the assets, it’s really complicated. So I started just being obsessed and fascinated by, like, why is death so taboo? Why is it such a taboo topic? Why are we still having such a difficult time talking about it when it’s the most humanistic experience we’re all gonna go through? So I did a deep dive, went down the rabbit hole. I started doing some research, and then I realized what’s gonna change the conversation is our phone. It’s our data. That people [00:06:00] are like, “Oh, now I’m interested.” If you die tomorrow, and your phone died with you, think about multi-factor authentication. How much mayhem will there be for your loved ones to shut it down?
Bri Conn, CFP®: A lot.
Niki Weiss: I mean, for you and your clients, where do you see those pain points when it comes to the digital piece?
Bri Conn, CFP®: Many of them, it’s figuring out, oh, actually this is important things that I need to write down. And with the Childfree Trust system, we’ve really put in there descriptions of like, “Hey, where should these things go?” And I’m sure we can always add more descriptions, and as we go, we can always improve upon that. But it really was a conversation of, what is the information that somebody would need? I don’t know if you’ve seen the trend going around recently. It’s like, interview your spouse. Do they know how to pay the mortgage? And a lot of them say no. Those videos, while they’re meant to be lighthearted and funny, piss me off to no end, because as a financial planner, having to sit with that spouse who has lost their person and work through these things for [00:07:00] years, it is terrible sometimes.
Niki Weiss: As a thanatologist, most thanatologists that you’ll meet, they specialize in grief. A lot of them are grief counselors. For those that don’t know, thanatology is actually, like there’s a master’s program in thanatology. End-of-life doula is more like a weekend training program, but the thanatology really is the study of. There are master programs out there in thanatology. So for me personally, though, I made the choice that I really don’t wanna talk about grief. I wanna work on, take my project management skills and get people to be proactive way ahead of time, like so far upstream that when you have a plan, you have a final playbook, you know that when life happens, that you’ll have the instructions. And then so when you do get the phone call or mom does start to have memory care issues, or you get the diagnosis, you know what your decisions are already. You’ve already made them. [00:08:00] You can always change them. But as you’re going through the grieving process, you’re not burdened by the, all the administrative stuff. You know where the passwords are. You know your legacy contacts are set up on your phone. You’ve made those decisions of, do you want to be buried or cremated? Do you live in a state that offers medical aid in dying? That’s a hot topic that we aren’t talking about, but that’s a decision that needs to kind of be not made after you get the diagnosis. It’s kind of like, what do you believe today?
Bri Conn, CFP®: And that not made after you get the diagnosis is such an important part. We often will tell people of you’re going to make different decisions in crisis than you will when preparing for ahead of time. And so how do you work with people to get that point across to them?
Niki Weiss: Well, that’s where the thanatology comes in. And I work with therapists who have traditional practices. I’ve also experienced when a therapist has a patient who gets a diagnosis or the patient is actually going through end of life and [00:09:00] they’ve worked with this patient for years, they’re so unprepared to have those end of life conversations. It’s a different skill set. Because probably they themselves are dealing with their own, there’s a Yiddish word that’s popping in my head. It’s called mushagas. They’re dealing with their own like, conflicts and inner emotions that they don’t know how to handle. It’s hard for them to support their patients in front of them because they themselves have not faced the thought of their own mortality or what they would do. First thing we do is we just come to the fact, “Hey, Bri, part of living is dying. We’re all gonna die. We’ll die one of three ways. We’ll die either sudden, unexpected, or we’ll get a terminal diagnosis, or we’ll need a long-term care plan.” Those are the three ways. But we need to plan for each of those, what we call scenarios. And what are we planning for? We’re planning for what I call the domains, the four domains. So you’re gonna plan for your legal, which is where your company comes in. You’re really gonna do that legal [00:10:00] piece, right? The legal, the estate planning, power of attorney, medical advance directive, fiduciary responsibilities. That’s the legal piece. But then we’re also gonna step into and start talking about the financial. Do you have your correct beneficiaries? Are your life insurance policies that you’ve had spread out over the last multiple decades? Do you have all of your accounts consolidated onto one location that if something happened to you, that your go-to person, it’s not a treasure hunt, that they have a roadmap. So legal, financial. Now we go to the physical piece, your physical questions. You die tomorrow, do you wanna be buried or cremated? Oh, you wanna be cremated. What do you want done with your ashes? Do you want them sitting on a shelf for twenty years, or do you want them turned into a piece of artwork? Or, maybe you want a green burial. Hospice, that’s a big question. I talk to hospice professionals all the time. A lot of them, people are just coming into hospice late. They’re coming in six days, six weeks, not six months, which [00:11:00] people don’t understand. The hospice is fully paid for. It’s the only benefit in the United States that is fully paid for, is six months of hospice care. People don’t go into hospice care early. Or what about long-term care? Like, “Hey, Mom, you’re seventy-plus years old. I know you’re in good shape now, but I’m your eldest daughter and I’ve got a life of my own, and if you need help, I hope you’re not depending on me to take care of you full-time.” People aren’t having those conversations. So that’s the physical domain. Legal, financial, physical. And now, Bri, let’s talk digital. You and I, we’re the first generation to have more digital assets than physical ones.
Bri Conn, CFP®: Oh, absolutely. I we’ve just,
Niki Weiss: Your phone?
Bri Conn, CFP®: Before this past weekend, 17,000 something. And it’s not even all of them, ’cause I switched from Samsung to Apple. So that on my iCloud.
Niki Weiss: And your [00:12:00] grandparents, are they still around?
Bri Conn, CFP®: I’ve got one left.
Niki Weiss: I mean, when my grandparents, my uncle, they died with a box of photos. Few photo albums. And then how many passwords and logins do you have?
Bri Conn, CFP®: I think like 500 something.
Niki Weiss: I bet that quadrupled between now 2026 and 2019 before the pandemic.
Bri Conn, CFP®: Probably.
Niki Weiss: And then not to go down the rabbit hole too quickly, too deep, but I mean, with Web3 and blockchain it’s the AI tsunami is upon us. So administratively planning for end of life, legal, financial, physical, digital. You die tomorrow, terminal diagnosis, long-term care. It takes time. It’s not just a weekend checklist.
Bri Conn, CFP®: No, not at all. Because I look at it and I go, “Oh my God, just ignore the accounts. Some of these, it’s not even worth the conversation.” And I can see your eyebrows raising already I know you’ve got something to share. Please.
Niki Weiss: Well, just because I think it’s by design. Okay, here’s [00:13:00] a oh no moment. Our wills, our trusts, they do not supersede the contractual privacy agreements with the platforms.
Niki Weiss: So just because you say in your will or trust, “I want so and so to memorialize or to own my Spotify account—”
Niki Weiss: Just because you say it in your will, Spotify owns it. Spotify owns your data, Meta owns your data. Just ’cause you say you wanna own your data in your will. The platforms in some aspects, I think, they make it complicated, or we just haven’t figured out how to have more sovereignty. So because of that, we have to be more vigilant, mindful.
Bri Conn, CFP®: And going through and sitting down. I have some friends who have passed and their accounts have been memorialized. And so you’ll go to their account on like Facebook, it’ll say, “In memory of…” But even then, my thought [00:14:00] is like, I don’t care at that point. I know there’s all the privacy, like I just, really don’t care what happens to my Facebook account after I’m gone. It’s not like anybody can find it anyway, so—
Niki Weiss: But so are you familiar with Meta receiving a patent back in December of 2025?
Bri Conn, CFP®: I just was on a thing recently about their new stuff, but I can’t remember what it’s called now.
Niki Weiss: They have a few things being released, but they received a patent back in December 2025, it’s an AI enablement that will allow them legally to go in and to create content on ghost accounts. So people who have died, they can go in and generate content with their likeness ’cause they own the data and they’re saying that by 2035, 2037, that will be a ghost platform. There’ll be more users that are dead on the account than alive.
Bri Conn, CFP®: That makes [00:15:00] sense. I mean, just even think about the demographic of who is on that platform typically. We’re not seeing a lot of Gen Z on there, Gen Alpha, anything like that. Maybe Instagram they’re on, but that feels very gross and disgusting to me. How can we take and make sure that if somebody’s hearing this and goes, “I really don’t want that to happen,” how can we make sure that doesn’t
Niki Weiss: Be proactive. So part of your end-of-life planning, and again, I wanna differentiate between estate planning. Estate planning is just one component of your end-of-life planning. Estate planning is like you’re dead. Or these are the people. But end-of-life planning really is those three scenarios and looking holistically, comprehensively at all of these aspects of life that we’ve built today. It honestly is just writing stuff down. I mean, that’s what it is. It’s creating what I call a physical system, like pen and paper or typing, but I mean a hard copy and a digital to create a physigital system. Why? Because floods and fires [00:16:00] happen and cybers hack happens. And we’re just in a really weird time right now. I mean, life is weird right now. So we’re kind of in a chasm of, if the electricity goes out, we’re not gonna have the digital. To stay super high, and what I do with Endevo, which is let’s just have the meaningful conversations. Let’s talk. Let’s put a plan in place. And I just wanna emphasize I have three children, and all of them are in like different stages of life. They’re all married. One has children. One is unsure whether she wants to have kids or not. And the other one always knew when they got married that they didn’t want to have children. But my eldest daughter, her 34-year-old husband as of yesterday, just decided that he was going on hospice because he has a brain tumor, it’s his third round with a brain tumor. He had it twice when he was in his 20s. He was cancer-free for seven years, and then 10 [00:17:00] days after he proposed to my daughter he had a headache and it came back. So they’ve been fighting this brain tumor for the last 16 months. The point I’m bringing up is that just because you have children doesn’t mean that making a plan is gonna be either less complicated or more complicated. It’s not about your situation, it’s about the people you surround yourself with.
Niki Weiss: And that’s what I want to emphasize to your audience, that it doesn’t matter if you have kids or don’t have kids. Sometimes people have a ton of kids, and the kids don’t get along, they’re not functional, they’re not honest. You don’t want them managing your end of life plan. Versus I think people who don’t have children end up being more creative, more mindful of who they invite into their lives. Especially if they have assets, they might be more resourceful to professional services. I really want to empower and encourage people who don’t have children that this really needs to be like button it up. [00:18:00] Just build your final playbook, comprehensive, three scenarios. You can always change it, who’s in your life today might not be there tomorrow. That life is dynamic. Tell me more about how you talk to your clients about this topic, pre-planning.
Bri Conn, CFP®: A lot of it is getting that initial conversation started, and it usually starts with parents. That is when a lot of I see clients are ready to go ahead and have a conversation of like, “We saw something happen with our parents, now we need to do something.” I think it’s good that that sparks the drive, but I also don’t want traumatic incidents to be the reason that those drives in people are sparked to get going on some of these things and working through of it. It’s really a conversation of, first of all, let’s start with do you have your legal documents done? Because just because you’re married to somebody or just because you want somebody to make decisions for you, doesn’t necessarily mean that they actually can. I mean, the Terri Schiavo case that lasted for years, what a horrible [00:19:00] situation to have. But making sure things are written down legally, documented, saying this is what—
Niki Weiss: Updated. Updated.
Bri Conn, CFP®: Yes.
Niki Weiss: Oh my God, I have to tell you a story.
Bri Conn, CFP®: Please do. I love your stories.
Niki Weiss: Okay, so I have a dear friend. Back in the ’90s, we traveled to Europe together. Like, love her to death. A week before her 30th birthday, she had a head-on collision car accident. So this was, like, 33 years ago, and she has been a quadriplegic ever since. And her husband for the last 33 years, they have been rocking it. She’s a quadriplegic, right? She doesn’t have use of her hands. I mean, she has use of her arms, but not her hands. Anyway, this woman, living life fully, but now she’s 61, 62, and her body is breaking down, and it’s just been like she’s circling the drain now. It’s like she’s been hospitalized I think three times in the last four months, and I was on the phone with her a couple nights ago. It’s her and her husband, no children. They’ve [00:20:00] been managing somehow in the last 30-something years, but now they’re at the point at 61 that she and I had that conversation. Like, “Chris, where’s your paperwork?” She tells me, and she knows the work I’m doing. She told me two days ago, “Bri, oh, we have a trust, but it was written 15 years ago, and we haven’t looked at it since.”
Bri Conn, CFP®: That’s so common I mean, the amount of conversations that I have with people of, “Yeah, you have these documents,” and they go, “Oh, I wrote it when? Great, but that is three houses ago for your address. Those phone numbers don’t exist anymore. Those people have passed. The names aren’t even right anymore, ’cause you’ve changed your names too.”
Niki Weiss: And when she said 15 years ago, I’m like, 15 years ago, that trust is out of, like, you’ll go through probate, and it will be probate hell. And it was hard for me because I love her to death, and at the same time as a thanatologist, I am like, red flags all over. I’m like, what if Kevin dies [00:21:00] first? What if he just doesn’t wake up one day, and you’re lying there, and he doesn’t wake up, Chris? What are you gonna do? And I hate to be like the alarmist, but as a risk manager, but it’s like you’ll have to go into a facility, and then what happens to the house, who’s gonna financially take care of it? Or he can’t physically take care of you anymore, and you have to go into a facility. Like, so guess what I’m doing on Memorial Weekend?
Bri Conn, CFP®: Going and—
Niki Weiss: We’re gonna go sit down. But these are hard conversations. But if we don’t have the conversations, when the event actually does happen, you’re not equipped. I think it’s a crime that people have to go pick out caskets and make funeral arrangements after someone tragically dies. Oh, by the way, sign here on the dotted line when you can’t even spell your name. Some of the funeral industry is a bit unfair. I mean, unethical. My point is, like now I’m working with Chris she’s under a bit distress. [00:22:00] Like this is not an ideal situation because there’s a level of urgency.
Niki Weiss: The urgency is, yes, having her take action, but it would certainly be better for people to be able to make these decisions, to reflect, to decide, to document, to execute, which is where your team comes in, communicate who needs to know where these documents are? Who needs to have a copy of the documents, and then you need to iterate them. Hey, every two to three years, you should probably look at this paperwork. And oh, by the way, if they need updating, ’cause, I mean, you could talk more about the trust piece, where’s the biggest pain point for you when people don’t update their trust and you’re trying to help them?
Bri Conn, CFP®: Hey, we wanna look at these whenever there’s a big life event, but also we wanna at minimum make sure you’re looking at it once a year and updating, like your taxes. I had so many conversations like this recently, but somebody said every Thanksgiving they had a family member who’d pull out their documents and [00:23:00] say, “All right, we’re going through it this Thanksgiving.” And I think that’s a good point of like having a check-in throughout the year of having those conversations. If nothing bad happens to anybody, fantastic. I prefer that to happen for you. But then if you don’t have that to trigger the let’s review this, having a dedicated time every year to go through and think about it.
Niki Weiss: We do it between Christmas and New Year’s, and then after New Year’s between January into February, that’s when we start doing our taxes. And then I’m always trying to get my taxes done like the second week in February. So then we’re good to go. Because you need to have it between Christmas and New Year’s ’cause then it’s like you’ve just seen all the family. You kinda know where everybody is, who you like, who you don’t like, who’s in good health, who’s not in good health. You kinda do that family check-in, and then you look at your documents and also if you’re doing family stuff, if you need signatures, right? You need to share documentation. I think that we just need to stop making death such a taboo topic.
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Bri Conn, CFP®: I think too it’s so far removed from so many people that that’s probably part of why it’s a taboo topic is ’cause people aren’t necessarily seeing it. My wife, for example, she’s been to two funerals, both of them for my grandparents. She’s only ever seen one person’s remains lying in a casket. I had one grandparent who was cremated before the funeral, and the other one who was buried in a casket. And for her, talking about it is difficult because she’s [00:25:00] just hasn’t seen that. And I’ve had people ask me too of, “Well, how do I plan this? Is there like a Pinterest board that I can look at?” There is maybe a Pinterest board, I guess, to plan some of this, but it’s difficult. I’d love to know from your perspective, if we’re thinking about, now that you asked me how many passwords I have, it’s just been swirling in my mind this whole time,
Niki Weiss: I’m sure, Bri, if I pressure test you, I’m sure there’s gonna be lots of opportunity for it. As we say in project management, continuous improvement, continuous delivery. It’s
