Death Is Taboo & Your Passwords Don't Care — with Niki Weiss of ENDevo

Hey there, happy Friday and welcome back to another episode of The Human Side of AI. Today I'm talking to Nikki Wise, founder of Endevo and a digital thanatologist. Yes, that's a real word, and yes, she'll explain it. Nikki spent years as a hospice clinician before becoming a project manager. Now she's combined both worlds to help people plan for dying, death, and incapacitation legally, financially, physically, and Digitally, we get into why most of us are walking around with zero plan for what happens to our digital lives when we're gone, how to set up legacy contacts on your phone in about 2 minutes, and you can do it on this while you're listening to today's podcast, and her philosophy, which I love: live fully, die ready. This is one of those conversations that sounds heavy but ends up being oddly comforting. Let's get into it. Hello, Nikki.

Hello, Flora.

How you doing this morning?

I am awesome. It's a Monday morning. You know, just got back from a weekend down the shore and sitting on the beach with my family. There was no AI. It was wild. It's like you could sit on the beach and look at the ocean and be like, artificial intelligence doesn't exist until I look at my phone and I've got like 4 pings from Claude asking me to approve, like, certain activities. So yeah, it's amazing.

How was that? Was it a nice little reset?

It was just a moment of reality. Like, in this age of AI, you know, what does it mean to be human? What does it mean to be like— we're, we're in it, you know, especially when we've got 3 or 4 screens in our, you know, phones and we're totally plugged in, but we have the ability to unplug. To go outside, to not be in front of a screen, to be attached to, you know, some sort of device and just take in a moment and a breath and be like, okay, I'm in front of the ocean, I'm outside with the trees. This is what it means to be human.

Does it feel harder for you to make that connection now?

Not for me because I've done a lot of personal work and a journey. So I have a pretty good ability to distinguish and differentiate between, Nikki the human and Nikki who is very engaged with the technology in this age. I mean, this, we're in a weird space. I just have to say it, Flora. We're in a super weird space.

Do you think it's just gonna get weirder?

You know, that's when I start leaning into what does it mean to be human? And you and I just met, you know, for the first time. And I asked you, have you ever met a thanatologist before? Do you even know what Thanatology is?

Are you gonna tell us? I'm like, I'm thinking my old Latin days and trying to come up with like the derivatives and the— okay, but tell us.

Yeah, so let's go Latin. So Thanos, Thanatos. Thanatos is the Greek god of death.

Yeah.

So, and, and then Thanatos is Greek god of death, and then Marvel Comics decided to take the Greek god of death and, and, and vilify it. Yeah, so The Greek god of death is actually very benign. Marvel Comics made it evil, but thanatology is the study of death and dying. So think of psychology, sociology, anthropology. So I am a thanatologist, but I am a digital thanatologist. So I focus on people's digital afterlife. What does it mean to be human? So when you ask me the question, how does that, how does it impact me? I always center myself of the human aspect of why am I here? What is the purpose of being here? And then understanding that there is a bridge between, um, this new technology that's only been around for a short period of time considering where man has been. And so sometimes I just need to be centered when things are going off the rails, when code isn't working, when the app isn't working, when, you know, my funnels aren't working. I just need to take a step back and be like, okay, What does it mean to be human?

You have a unique opportunity because you're reminded every single day how short life is.

Life can be, and this is as a thanatologist, running someone who's, who, who's, you know, leans into the conversation. Life can be short or it can be really, really long, right? So those caregivers that are, you know, have loved ones who have had Alzheimer's or dementia for, 10+ years.

Like, that's long. So, um, how did you get into this space?

So, as a thanatologist, something always motivates us to lean into our passion. It usually starts with a childhood experience. So I don't know, um, you, you can see it 'cause I'm sharing my video, but, um, for those that can't hear, I have a picture of my parents behind me. So my, both my parents, they passed away before they were 50. 10 years apart of cancer, both of cancer. So for me growing up as a child, it was just very much part of my childhood. And for some people, they run away. Say it again.

They suffered through cancer for a long time.

My father was 18 months. He was diagnosed at 40 and he was gone by the time he was 42. My mother was only 3 months.

Terrible. I'm sorry.

And you know, that's part of the experience, is part of my story. Yeah. For some people, they run away from the experience for whatever reason. I leaned into it. And, um, first part of my career, I actually worked in hospice as a bedside clinician supporting families as they transitioned to this end stage of life. So I've got the stories about what it means, you know, what it means what families go through, how hard it is to accept the most humanistic experience we're all gonna go through.

It's experience.

So what makes you comfortable? Like, you don't seem to shy away from this conversation. Some people will.

My daughter was diagnosed with leukemia 18 months ago and she's in remission. She's doing great, but it's definitely, you know, conversation.

I mean, it's a reality that we all face. Wow. So you are, you have been in it. You have seen the doctors. You, how do you get through each day?

You just do. You just do. So, okay, let's take it back. Nikki as a young girl, where were you?

Well, when my father got diagnosed.

Even younger.

Oh, younger.

Yeah.

Youngest of 4.

Okay.

Um, born in, uh, born in on the East Coast, born in Pennsylvania. I spent most of my childhood in New Jersey, bounced around a lot. Um, I had like, when I was 16, like fun fact, when I was 16, I was an international exchange student in France.

Cool.

Lived in France with a family for, um, from, for an entire year. Um, and that family, my French family, um, I always said that that's the family I was meant to be born into. They, um, 40-something years later, we still are close, and my children call them Papi and Mami, and it's just one big family.

So when is the first time that you remember even going back back, back, back, that you, you remember feeling some sort of connection to this, this idea of death?

Well, again, I mean, let's, let's go to my father. Um, when he was diagnosed, you know, I, again, youngest of 4. Um, so I was 9 when he was diagnosed, 11 by the time he passed. And, um, I used to spend my— at the time, I spent my weekends walking through Sloan Kettering hospital, which is in New York City, and just walking the halls. And it, to me, it was normal. So I guess that's what kind of prepped me for just being comfortable in that space. Some people are wired, some people are not wired for it. And I just acknowledge those that just are not comfortable. So as I keep mentioning, my four, there are four of us. So me and my eldest brother, he's an estate attorney. So he also is very comfortable with, you know, talking to people about end of life and planning for it and making sure their affairs in order. And then I have my two other siblings who like want nothing to do with it. They're not comfortable talking about it.

Like denial or?

Avoidance. Just a question of avoidance. So I, again, I think leaning into it. So if I get into the, and then leaning into why someone wants to work for hospice, what does it mean to support a family going through that journey? And then, but when I turned 40, I actually realized like as much as I appreciated the hospice experience, I wanted to actually make some money. So I transitioned from being a hospice clinician to being a project manager. And that's where I've been for the last 20 years doing project management. And I actually work for, healthcare organizations. I've been specializing in project management and healthcare.

And did you get your, like, your PPM or— I—

PMP, yep. So I act— yep. So I have my, um, there— I'm very involved with the Project Management Institute. I actually teach for them.

Awesome. What do you know about the first person I've met who has transitioned out of a medical role with their PMP? Is that pretty common? Have you seen that a good amount?

I think there's— yeah, I mean, there's— as project management, it's a framework, it's a format, just a framework that allows for business structure in managing projects. So it's like taking the CPA. It's highly— it's a challenging exam. It's accreditation. But the Project Management Institute has been a wonderful community and organization. And I also think that it's when it, as we're entering this age of AI, you know, that we're in the AI tsunami right now, we talk about agile. Agile came out of software development. AI is software. So, it's kind of like evolving and rolling into, so what does it mean to manage a project? And now that we're building, everyone's building, you know, AI projects, there's a format and a framework that we need to be following.

So you say it's evolving. So, so do you feel like it's still— do you feel like PMPs and Agile certifications, like, do you feel like those are still relevant?

More so now. And actually, the Project Management Institute just rolled out, I think tomorrow the content comes out on August 4th, for their new certification, which is Cognitive Project Management in Artificial Intelligence. So they have a new certification, professional designation. So any PMPs out there that are ready for the next level layer and acknowledgment. But I see now that companies and organizations are also starting to roll out their AI transformation. So people need to be or looking for some sort of acknowledgment and designation as well as like, you know, benchmark, like What is determining someone who has a skill set that can be identified and acknowledged? And I think the certifications help if someone's ready to sit down and take a standardized test.

Yeah, no, it's fascinating. So, so you lean into project management and talk to us kind of about this, you know, where's your head at this point? Are you, are you so excited about software? Like, talk to us about where Where, well, let's talk about the conversion, right?

Because I'm coming in as a thanatologist. So someone who's talking about death and dying, I have this project management background and now the AI piece, right? So it's like, floor's like, Nikki, how does all of this come together? So that's where the digital thanatology comes in. So I have basically taken the project management framework and wrapped it around this taboo topic of death. Death is taboo, right? I faced it. Your family has had moments of, oh no. And, but administratively it's very complicated. Death, dying, and incapacitation. The administrative piece, the legal, financial, physical, and now digital aspects of the life that we've built. So how do we take a taboo topic and administratively manage it as a roadmap That's where the project management piece comes in. So I've taken the concept of how, how to live a life well lived in an organized way when death, dying, or incapacitation happens— legal, financial, physical, digital— now wrap it in a project management framework. And now let's layer that with artificial intelligence technology, right? What—

and where did you— how did you land here?

So It happened 3 years ago when my husband and I realized like, ooh, we had not updated our will since our kids were in high school and now they're in their 30s, we're grandparents. So 3 years ago, he and I started to like realize like, oh, we had to update them. So I called up my brother who happens to be an estate attorney. Now understand that death is easy for me. Project management is, you know, I know how to do the step by step and when, my husband and I started to refresh our wills. Like, we'd already done them, we were just refreshing them. Second marriage, adult grown children. It was hard, Flora. It was really like, there's a lot of decisions that need to be made. Who makes those decisions? How is it equitable? You know, when are, you know, certain decisions made? When do you pay for them? So I'm like, why is this conversation still so difficult? So then I started to do deeper research. I reached out to my hospice peeps. Hospice people are still coming in 6 days, 6 weeks instead of 6 months, which is like, you can go into hospice 6 months, um, when you have a terminal diagnosis, people don't wanna talk about death and dying. So I'm like, why is this the most humanistic experience we will all go through? Which, and death is indiscriminate, as you know. I mean, it doesn't care how old you are, what your socioeconomic health status is. It doesn't care. You get, it just doesn't care.

So do you— so you look at this, and I imagine you're trying to figure this out as a project manager. It's like, what are the next steps? What is the—

De-emotionalize it, though.

Yeah. Correct.

And in that, it was still challenging until I realized what's going to open up the conversation is our phone. It's our data.

Right? Because our phones have everything.

So instead of me saying, ah, you know, what if you died? What do you wanna do? Do you have a will or trust? Like, people don't wanna have that conversation. There's this, you know, 10 reasons why people avoid this conversation. Procrastination, lack of urgency, overwhelm, complexity, cost. Like, I can go through all 10, but what engages people in this conversation with me is their data on their phone. So if I said to you, hey Flora, If life happened and you died tomorrow and your phone died with you, think about multifactor authentication. How much mayhem would there be for your loved ones?

Yeah, I mean, it'd be a nightmare. My husband doesn't even know how to get into some of our credit cards and bank statements. Like, really inconvenient.

Yeah, well, it would— I call it the shit show. I mean, you know, or the mayhem, right? I mean, wherever you want to— I speak French fluently, don't forget. So, Do you have an iPhone or Android?

iPhone.

Can we do an exercise super quickly and then—

I'm ready. You'll sign me in? I have my phone right next to me. Cool.

All right. So this is the question I ask people and this will land for them. So if you died tomorrow, your phone died with you, think about multifactor authentication. Do you have your legacy contacts set up on your iPhone?

I know sometimes when I accidentally put emergency, it calls my mother-in-law. So I think so, yes.

Let's test it. So open up your iPhone. Hit on Settings.

Settings, yeah.

Yeah, so everyone can do this while we're doing this. Hit your Settings.

OK, I'm here.

Top left-hand corner, hit your face or your initials.

Yeah.

See where it says Sign In Security?

Yes.

Hit that. It'll spin.

This is not your first time doing this.

OK. Scroll to the bottom. OK. See where it says Legacy Contacts?

No, I have to set it up.

Hit— now hit Legacy. Okay, so you don't have it set up, so hit Legacy Contacts.

Oh wait, wait, I accidentally— I didn't listen and I pushed something and then it gave me the option to—

don't set it up yet. Don't— this is where the fanatology comes in. So let's go back. So I went— there's 3 paragraphs there. Read out loud what those 3 paragraphs say.

Wait, okay, I got ahead of myself. So do I do Add Legacy Contact?

Don't add. Um, okay, so You're at your legacy contacts. Does it have like 3 paragraphs that it tells you what to read out loud?

Yeah.

Awesome.

Add a legacy contact. Choose someone you trust to add as a legacy contact. This person will be able to access the data stored in your account after your death. Oh, share. Even, yeah, even hearing that, I'm like, don't, iPhone, don't talk about my death like that.

Nah, keep going.

Share your access key. Send an access key now or print and save a copy for later. Your legacy contact will need this key and a copy of your death certificate to access your account. Pass down your digital legacy. Share your legacy with people you care about through photos, videos, notes, documents, and personal information that you've stored in the iCloud. So I add him now.

So before you start adding them, so who— so you can— here's the legacy context. Ready? Know, love, and trust. Who are the people in your life that you know, love, and trust?

Oh, I have a wonderful list.

Okay, so you— 1 to 5 people that you know, love, and trust. Do you have a will or trust? Do you have a will or trust?

No.

So then it— this is like the— this is like the next level of adulting. Next level of adulting.

Wait, can I add my husband?

So before you start adding people, I always say have a conversation with them because as soon as you add them, they'll get an SMS and then they'll be, you know, what's up? So I always say, hey, I just found this really cool feature on my iPhone. You know, I'm going to set it up. You can add 1 to 5 people. Once you add them, you're going to— they're going to get an SMS. Then you'll see. And I tell anyone who's in your trust, if you have— do you— are your parents still around?

Yes.

You should be in their legacy contacts.

Yeah. Yeah, I definitely should.

Right. Anyone who has children who have phones, you should be in their legacy contacts.

So, so what you offer though is so much more than this. Talk to us about what people come to you for.

We, we build out what we call a final playbook. We walk people through the legal, financial, physical, and digital aspects of the life that they've built. So you're coming to us to workshop all of the decisions, all of the conversations, to de-emotionalize what it means if there is a death, dying, or incapacitation, whether for yourself or a loved one, right? Because sometimes I'm working with, um, people who have, um, parents and that you're the primary caregiver of the parents, or, hey, parent of mine, you know, what happens if, um, life happens. Are you going to be, are you going to be the caregiver for that? What is their plan? So we build out that final playbook, project manage, and empower people because it's complicated. Yeah. So you come to us before you go to an estate attorney, a wealth manager. We work, we actually work with estate attorneys and wealth managers because they are very niche in their, the work they do, but they don't necessarily pull all of the pieces together and ask those deep sensitive questions. So you said, this is creepy, why, why am I having this conversation with iPhone? Because why didn't the salesperson, um, why didn't they tell you about this feature? Yeah, because death is taboo and you just spent $1,500, you know, on a new phone. It's a bit of a buzzkill.

But speaking of sales pitch, you have a My Final Playbook. Yes.. And as a 35-year-old, in my head I'm like, this isn't my final playbook. So how do you overcome that concept that your final playbook can be done at 35? It can be done at 85. It can be done, you know, what, what is that? Talk to us a little bit about that.

Because we said that death is indiscriminate, right? It's death is indiscriminate. So you need, it's that next level of adulting. Did you know that an 18-year-old needs to start because at 18, they, they need all of their documentation in order. They need a HIPAA form. They might not need a will, but they need a HIPAA form. The parents need to make sure that they have their legacy contacts set up on their bank accounts. Do they have beneficiaries? What we call— there's a term in banking called payable on death. I mean, it's heartbreaking, but I've had clients who have had 26-year-old children who've died in motorcycle accidents, freak accidents.

Like, yeah, no, it's not—

it's indiscriminate.

So, so you're— when we jumped on this call initially, you have this beautiful poster behind you, and honestly, it reminded me of an older poster for like the Denver Botanical Gardens. And, and, and on it, and now I could read it a little closer, it says, um, it says, live fully, die ready. And before we close out this call, I want you to share two things. How you got that tagline and how people can find out more about what you offer.

Well, thank you, because I, I want people live fully. Like, life is for the living, right? I always be— I came up with the concept when we were talking, um, I think of the Vikings, right? Vikings in the old days, they went, they lived their life knowing that they were going to die in war. Like, that's what their lives was. So because of that, they lived fully, they lived without fear. And I honestly believe that what stops people from living fully is that fear of the unknown. And death is probably the most unknown experience people will go through. We don't know what is on the other side. So because of that, people are just like fearful. So the fact that you're 35 and you don't have a plan, it's like, if you and I were having a session to be like, why don't you have a plan? And then if we had more time, I would start pressure testing, like, where are your parents? Where's their plan? Do you have copies of it? Where are the copies held? The communication?

Because I'm too busy to die. I don't have time for that.

But when, when Life happens. I listen, and when I talk to people as a thanatologist, I'm like, the fact that we're having this conversation, it's like you're carrying an umbrella. It's not gonna happen. It's when you don't have the conversation, when you sit in denial, when you don't have a plan in place. You know, the one piece, you know, I wanna share is what's changed. You know, Flora, you and I, we're the first generation to die with more digital assets than physical ones.

Totally.

Our physical body has an expiration date. Our digital footprint, our digital afterlife does not. So we need to embrace this concept of living fully, but knowing that there's gonna come a time, whether for ourselves or our loved ones. So to have a comprehensive plan, one that, you know, it's iterative, you can change it, you can update it. It's a playbook. The playbook is constantly, it's a live document.. But if you don't have a playbook and life does happen, that's where the grief hits. Why would you want to be dealing with the administrative stuff?

Go ahead. And where do they find out more about you?

I am so easy to find on LinkedIn.

You know, we just look up Nikki Weiss, digital thanatologist, and then, um, A-I-W-E-I-S-S, and I'll link it obviously in the resources, right?

Endevo.life. What do we do? We go into companies and organizations and we are offering end-of-life planning, a final playbook as a wellness program. We are changing the conversation. Let's just live fully, die ready, as a wellness opportunity.

Well, Nikki, thank you so much. I feel like I could sit here and pick your brain for several more hours, and I really appreciate— I appreciate this perspective, and I appreciate the conversation. And I'll go add some legacy contacts.

What an opportunity. This was great, Flora. Thank you so much for the, the coffee chat.

Talk soon. Cheers. Cheers. Bye.