The 570 Hours of Hidden Work After a Loss with Tracy Flynn of Under Mountain Partners — Full Episode Transcript

Hello and welcome back to another episode of LT CareNav's Care Compass. I'm your host, Lindsay Friedman, and today we're here with Tracy Flynn from Under Mountain Partners. Welcome — thank you for joining us today.

I'm thrilled to be here and so excited about the work you're doing with LT CareNav.

Thank you so much, and I'm so thrilled about what you're doing. It's so interesting, and I hadn't heard of what you were doing before. So why don't you start by telling everyone who you are, what this amazing work is, and why you're doing it.

Sure. My name, as you said, is Tracy Flynn, and I am the founder of Under Mountain Partners. Essentially, I'm an after-loss advisory service. My background is in customer research and financial services, and in all of my years in financial services, the projects I liked the most were the ones that related to estate planning and estate administration. On the surface those are really dry legal and financial things, but under the surface, the people making these decisions are really grappling with what it is to be human and what life is about — it's really profound.

So I had some experience on the human side of the estate planning process, but the tipping point that really got me into the work was when I reached my mid-40s. There was a period of time when it seemed like I was getting a call maybe once a week or every other week from a close friend saying that they had lost a parent. There was all of a sudden this deluge of loss. And that was the point at which, for me, the personal and the professional came together.

What I was seeing on both sides of the house was that even people who have diligently done their estate planning end up leaving a whole lot of loose ends for people to tie up, and that work ends up falling on their loved ones. And secondly, we are a death-denying society, and we're not really set up to support those loved ones who are responsible for all this work. In the aftermath of that wave of deaths, my friends and I were looking at each other going, when do we get to cry? When do we get to grieve? And I thought, okay, there's an unmet need here. Somebody needs help taking some of that practical work off of people's plates so that they can focus on what really matters.

So besides your time with estate planning, what really made you more interested in what this actually looked like, and what it looked like as a whole?

I think it was seeing some of my friends who were the executors of their parents' estates — seeing how much work was required, the level of detail required to complete the work, and the fact that the work has to be done on top of all of our other daily responsibilities, whether that's raising kids or managing a demanding career. That was really what drew me to the work. I just went, wait a minute, there's gotta be a better way. You can't offload your grief — that's your journey, you gotta go through it, you can't go around it. But you can offload building spreadsheets and doing research and tying up some loose ends.

I think most people don't understand what that work is. They think, mom or dad has a will, I'm gonna go pick up the vase that I got left. What is that work, and what does it look like for most families?

It's a lot. The sheer amount of work is part of what's really shocking to people. First of all, in about half of cases, executors don't actually know that they've been named in the will until after their loved one has passed away — so not always a pleasant surprise. But even the people who know they're named probably don't realize how much work it is. Research shows that it takes on average 570 hours of effort for an executor to settle their loved one's affairs. 570 hours — and that's an average. That's the equivalent of 14 weeks of full-time work.

Fortunately, it doesn't all land at once. It's not a 14-week full-time project; it usually takes around 12 to 18 months, and it can take many more years. But the bottom line is that if you're an executor, you may be looking at taking on this emotionally loaded part-time job that you may or may not have aptitude for, for a significant and indefinite amount of time — and that's on top of everything else you have to do.

The work itself includes things like closing accounts, making sure any real estate is taken care of, doing Social Security reporting, going through the probate process — that's where you're probably going to be working very closely with an attorney. Tons of paperwork, tons of forms. You're responsible for notifying all the rest of the heirs every time something has changed in the estate. You've got to make sure the tax returns are filed — and that's the deceased's final tax return as well as the estate's tax return. It's a lot.

So it sounds like you need kind of a combination of legal, accounting — the things people don't have on a day to day. Do you come in and work with the executor to go through all the nitty-gritties and all these little pieces?

That's exactly right. I like to think of myself as a compassionate project manager. I have a background in financial services, but I don't do financial advice — I'm not a licensed advisor. I don't give legal advice — I'm not an attorney — and I don't file tax returns. But what I can do is work with all of those other professionals, as well as all the stuff that doesn't require a professional, and put it into a project plan. We treat it like an actual project, like you would at work, and make sure you understand what needs to be done, what needs to be done now, and what can wait.

We track progress over time to make sure nothing's falling through the cracks — that you're sending all of those notifications to the court and to the other heirs as much as you're supposed to — and making sure things aren't duplicated. Because when people are in a state of grief, there's a mountain of research demonstrating that part of grief is temporary cognitive impairment. You're typically in a state of brain fog, you're distracted. It's really not the right time to be taking on a complex, legally demanding and cognitively demanding project. So I take the project management off of their plate.

That's huge. Why do you think the average person has no idea this is coming for them?

We just don't talk about it. And that actually ends up being part of the problem for executors — they don't know it's coming because we don't talk about it. And then when you are the executor, you feel like there's nobody to talk to about it. The rest of the heirs might be thinking, when am I gonna get the watch? Where's the vase I was supposed to get? It's been a year, what's going on? It ends up being a really lonely job because, as a society, we don't really talk about the end and what's gonna happen in the end.

That's kind of the reason why only about one-third of American adults has a will — two-thirds of people don't even have the will to get the process started. That's how death-denying we are. So all of these practical elements don't really end up in the conversation, and then you're in the middle of it and you go, my God, nobody told me this is what I was on the hook for.

So two-thirds of our population doesn't have a will or documents in place. Can you still help them, and what does that process look like? That has to be even more convoluted and argumentative.

It is, and it varies significantly by state. When a person passes without a will, that's called dying intestate. In that case the court makes all the decisions for you. They're going to assign the executor — that may or may not be the executor you would have wanted managing your affairs. And they're going to basically tell the executor, well, we think the fair thing to do here is to split things this way and that way and the other way. It does end up being a longer and more convoluted process. And of course, the larger and more complex the estate without a will, the longer it can take to really sort that out.

If a family is dealing with this, is it too early to come to you? Say somebody is even in their own planning process — can they come to you prior to their passing and say, hey, this is what it's gonna look like, I want you to help my executor because I know they're gonna struggle?

Absolutely. I love it when people come to me and say, my parents aren't willing to talk to us about their money, but we're really scared because we think it's probably pretty complicated — can you please sit and help them figure it out? The legal estate planning documents are incredibly important. But the legal plan is not the same thing as an executable plan. There's a usability layer that's missing.

A will might say, Mary's my oldest daughter, I want Mary to be my executor, and I want Mary to divide all of my possessions equally between herself and her brother Bobby. Great — we've got a great starting point. We know who is doing what, and we know at a high level what they're doing. But we don't really have any details on the what or the where or the how. The best thing to do, in addition to creating your estate planning documents with an attorney, is to put together more detailed instructions: okay, we know the money's gonna get divided between two, but where is all that money? What does one do to get access to that money and distribute it? How's that process going to work?

So I can absolutely sit with people and help them work through what they want those plans to be. I have a special box with many files — everything's coordinated, and there are instructions for the executors. So when that person passes away, there's a box waiting for the executor, and they can go, I've got the passwords, I know where all the bank accounts are, I know where all the life insurance policies are, I've got the deed to the house — I've got everything I need to get started on this process.

And you mentioned 'I want it split equally.' Sometimes equally looks very different in people's minds when it's not just, here's a hundred dollars, split it equally. There's all this jewelry — my mom and my aunt got into the equal thing, and what did equal mean? Because this is what I remember her wearing. Equal was not the best way to word it.

Absolutely. Estate plans rarely go into detail on things like tangible personal property. We collect a lot of stuff — we are Americans, we accumulate over the course of our lives. And particularly for baby boomers, the China sets and the record collection and that high-quality stereo from 1994 — those are the markers of a successful life, your status symbols. So it's really hard for them to get rid of these things.

When the will just says split it equally, most people don't think about what that's really gonna look like for Mary to walk into my 3,000-square-foot house with tens of thousands of items — where great-grandpa's Purple Heart is buried in a box in the attic, and mom's diamond tennis bracelet is sitting in among 200 pieces of costume jewelry. For all they know, there could be a Fabergé egg buried somewhere in that home. How is the executor supposed to go in and say, okay, most of this stuff is junk? Most of our stuff loses all of its financial value the minute we take it home. But some of it is family heirlooms, some of it has sentimental value, and some of it does have financial value. How am I supposed to figure out what's what?

Personally, I think the kindest thing you can do for your loved ones is, first of all, downsize as much as you can bring yourself to. It's difficult emotionally, but downsize if you can. Provide specific instructions for the personal items that matter — that doesn't mean a full inventory of every single thing in your house, but if there are five family heirlooms, make sure that's documented somewhere your executor can find it. And then give your executor and your loved ones explicit permission to get rid of everything else — donate it or throw it away. Because without that explicit permission, your loved ones could be tying themselves into pretzels and getting into fights about what to do with every single item in the house.

My grandma actually went through her entire house — and there were seven granddaughters — and on the bottom of every item in her house she put a name with a Sharpie. So when we finally sat down with all the stuff, it was like, you get this, you get this. And then it was up to you — once it was assigned to me, I could say, I'm not gonna take this, does anyone else want it? She started asking like ten years before she passed away. She was ready.

Grandma, that is inspiring. That is estate planning goals right there. Go, Grandma.

There are actually now some really great modern tools to help with this. There's a tool called Artifcts — A-R-T-I-F-C-T-S — where you take a photo of the item and indicate in the app what should be done with that thing. You can write a story about the item if there's a backstory to why it's important to you. It will enable you to print out a QR code you can tape on the back of the item, so family members can grab their phones, scan it, and go, I didn't know this was great-great-grandma's christening gown. I had no idea the story behind this. Then the meaning of the thing comes to the fore. It's great.

I love that. My grandma missed that part — there were no QR codes when she passed. But that would have been amazing. She would have loved to take the story with us. So for families who are listening, what is the first thing you do? Say you had no idea — you're the executor, but there is a will in place. What's the first thing a family should do upon the passing?

First of all, the most important thing to do before you do anything else is to start a list. There are a bunch of generic checklists available online — a quick Google search, or you might get one from your attorney or financial advisor. But those lists are generic, and your person was not generic. There's no such thing as a generic life. As the family and the executor, you are responsible for tying up all the loose ends of this unique, dynamic, nuanced life. That generic checklist from a standard website is a great place to start — don't get me wrong — but it's gonna lose its utility pretty quickly as the actual details get filled in.

There's a lot to keep track of. You're gonna remember things at odd times; you're gonna forget what you didn't do. Whatever format works best for you — I'm a spreadsheet girl, so an Excel doc or a Google Sheets doc is perfect. But a Word document, Post-it notes on your wall, or a dedicated notebook to capture all of your messy scribbles — that's the first thing to do. Recognize this is gonna be messy and I'm gonna have a lot to keep track of, so have a list.

The second thing, of course, everybody knows, is funeral planning. There are two sides to this: there's the disposition of the body, and then there's the services — the actual funeral or memorial service. Those two things do not typically need to be figured out at the same time. You may have a religious tradition that dictates timing on the disposition of the body, but a lot of times the funeral part can wait. If you're not up for making those arrangements right off the bat, just wait — it can wait a few months, and then everybody goes to the service with a few months of perspective after their person has passed.

If you're not sure what that person would have wanted for their funeral or their body, their advance directive document might include some preferences, so it's worth checking if you have access to it. You wouldn't want to cremate and then find out later they really didn't want to be cremated — there's no back button on cremation. And about 20% of American adults over 40 have pre-planned or done some prepayment for a portion of their funeral services. A lot of times families don't know those arrangements have been made. It's worth calling around to local funeral homes to see if your loved one has already made and paid for arrangements, because you could save a whole bunch of money.

The third thing — I could go on and on; I'll stop after three — and this might not be what people think of right away: if the deceased's home is now vacant, secure the home. There are a couple of reasons. The first is that eventually the home and all of its contents are going to be transferred to heirs — but until that happens as part of the legal estate administration process, it's all the property of the estate. Nobody has it right away. Executors are typically warned against distributing any property until the estate has paid off all of its debts, the legal fees, the realtors if you're selling the house. There are a lot of expenses that go into dying — dying's very expensive. People may think it's okay to just go in and grab the watch Dad promised you while he was alive, but that probably shouldn't happen.

The second reason to secure the home quickly is that, sadly, when word gets out that a homeowner has died, the home can become a target for burglars — particularly during the hours of the funeral, when they know nobody's going to be home. It's not unheard of for a house to get robbed during the funeral. It's insane. So lock up, check if there are any spare keys sitting outside in case anybody ever got locked out, and get rid of those. And if you think there's some risk — in your neighborhood or even with family members — yes, as the executor, you're allowed to change the locks.

Wow — that is definitely one I wouldn't have thought about. I feel like we should do another episode where we just do the twenty things, because I'm sure there are another seventeen that most people aren't thinking about. For somebody who has had a recent passing, or knows it's kind of imminent — can anyone anywhere in the country work with you? Can anyone reach out right now?

Yes, absolutely. I can work remotely with anybody. I'm based in Connecticut, so if I'm working with clients who are not local to me, I can't go into the home and help them sort through items — if they're local, I'm happy to do that. But yes, I can work remotely with anybody because it's a spreadsheet, it's a project plan, it's a weekly meeting, it's making sure things are staying on track — and it's an accountability partner.

I actually don't see how anyone can do this without you. That is where you've left me — I don't see how anyone can do this alone. For anyone out there who's struggling, where can they find you?

You can find me at undermountainpartners.com — that is all one word — or you can email me at tracy@undermountainpartners.com anytime.

And what would be a final word you have for people who are listening and trying to go through this right now?

After somebody passes, families are tasked with becoming project managers at exactly the worst possible time, when they are experiencing profound grief and loss. The will or the trust can answer the really important legal questions, but a legal plan is not an executable plan — it doesn't necessarily tell you who to call, what to do first, or how to avoid costly mistakes. The work of Under Mountain Partners is all about adding practical structure to that experience, so that families aren't left on a scavenger hunt — lonely, stressed, and grieving.

Anyone who's going through this, you shouldn't have to go through it alone. Thank you so much — and we'll have you back, because there's so much more to touch on that people need to be aware of. And to everyone listening, we will be back next time. Stay tuned, because Tracy will be back at some point too. Thank you.

I would love to come back any time. This has been great.