655 – Organizing Your Role as the Executor of an Estate

Anna, welcome back to the Organized 365 Connections podcast.

Hey, Lisa, I'm excited to be here.

I am really excited to have this conversation. It's not a happy conversation, but it is a needed conversation. We don't often talk about losing our parents or people close to us and the administration that we need to do after they pass. And we're going to talk today about you and your experience taking over your father's affairs after he passed. So just to start us off, would you mind sharing with us how you came to be in charge of your father's affairs after his passing, and also how old you were when this happened? Because I think that kind of comes into play as well.

Yeah, so, um, my dad passed away in the end of March 2019, and at the time I was a week— I was one week away from turning 31. I had a son who was almost 2 and a husband, and we lived in a home that we had built about a year before. And my house— my parents were divorced, and so I was halfway, like a half mile from my mom and a half mile from my dad. And so, yeah, so I had my own little family, and I think that's important to know what was going into it. I do have 2 younger brothers, one who's 2 years younger and one that's 5 years younger. And so we technically all became the custodians of my dad's estate, but I am the oldest and the only girl. So you know what that means.

Yeah, I totally know what that means.

I quickly became the go-to person for everything. Yeah.

So, and similar to my situation, my parents also were divorced. And your mom is alive. My mom was alive. And there's always that fun dynamic of like, you know, it's just a fun dynamic, isn't it?

Yes.

I think that's all we need to say there. Okay. But when I was talking to you about this further, I thought you were the executor of the estate, but actually you were not the executor of the estate, correct?

Correct. So technically my uncle was legally the executor because when my dad had made all of his documents, I was still in high school. So my uncle is the one who signed off on everything, but he let us be in charge of all of it. So like meeting with the lawyers and handling everything. My dad left behind a home that he had built himself, his vehicles, and a business. So there was a lot there.

Yeah, and I think like even myself, like my kids are 23 and 25, and they're not the executor of my estate if I pass. it's somebody else because, I mean, 23 and 25, that's kind of young to be handling all the complexities of this adult life that I have created. And at what point do you make your kids the executors versus a sibling or a parent? I mean, when my father passed away, literally every single person in the family had to go update their will because he was the executor of, of, he was the oldest of 6 kids. He was the executor on all of those kids. He, he was the executor on a lot of estates. And so, um, you go to your parents and then you go to your siblings and then you go to your kids. And so similar to you, I was 35, I think, when my father passed. And so my sister and I, she was 31, your age. I mean, your 30s, it, you're still young in your 30s. Like 40 is a different mindset and 50 is a different one after that. In hindsight, like in my 30s, I was very much in charge of my personal adult life. It's really hard to be in charge of another adult's life, uh, in your 30s, you're still kind of getting your sea legs of your own adult life. So it probably was nice to be able to say to his brother like, hey, okay, here's all the work. Double-check my work before we turn it into the court, like, or turn it into the accountant or turn it into whoever. Like, you have a little bit more lived experience than me. But also, uh, nice for him that you guys took on a lot of the work. It sounds like you had a good partnership.

Yes. And I do need to clarify too, there was a separate document apart from my dad's will That was for the business. And so the business was a transfer on death situation, and that transferred to me and my brothers, 30, 30, 30, like 33% to each of us. So technically, my uncle had no oversight of the business. It was just his personal affairs. But then it becomes complicated because everything's kind of intertwined. So it— oh my gosh, it was its own situation.

Is an understatement. So I think that, and this is what I wanted us to talk about, was the business. Because often when you talk about an estate, you think about, okay, there's a house, maybe there's a 401, vehicles, credit cards, physical assets that need to be dispersed, bank accounts. Any of those things will be of the person. But the United States is an extremely entrepreneurial country. Like so many people are entrepreneurs. And a lot of people have side hustles. So even if you have a 401, or I mean a W-2 job and you're an employee, you might also have a side hustle. And if it's a separate entity, then that needs a separate all of these things. I'm not even saying I have all of mine set up correctly, so I got to go check on that. And that's the thing, like the older you get and the more things you say yes to, the more things that you need to have contingencies for if you're not able to. Take over them. Okay. As you were involved with the— let's just stick with the non-business part first.

Mm-hmm.

So of the executor part, the house, the cars, the bank accounts, if there was a 401 or, or any of those things.

Mm-hmm.

Um, are there any things that you learned or you think would be helpful or you want to say to people for others that are going in a similar situation with you before we talk about the business?

Yeah, I mean, I guess that there are 2 things. Number one, like, Trying to have as best of a relationship with the people as possible who are also constituents. So, like, I just feel so fortunate that my brothers and I were raised with a certain set of values, and you can tell that we all feel those same things really strongly and had a strong desire to have things end as amicably and in our dad's wishes as possible. So like, that's number one, is just like trying to maintain good relationships with your family members is important. And then number 2 is having as much paperwork as possible for even that first time when you go in to talk with a lawyer. So I'm really lucky that my dad was extremely meticulous in everything that he did. And so his files actually were Good for me. I was able to use them and able to get as much information about like all his bank accounts and all that. And he had a manila folder that had nothing in it, but it was labeled passwords and it had every account username and password for every account that he had. And he would erase anything and like update the password.

Amazing.

So I highly suggest making sure that you have a physical document with all of that information so that if and when someone needs to access those Like, I mean, that is, it kept us out of probate for almost everything because we had access to everything.

That's so great. And I know, I know you don't want to write down passwords because then what if they get compromised, whatever, like whatever. You need to know the passwords, write them down. Also more today, what I'm noticing in my own personal life is I have an iPhone and every time I log on to things, it will send a code to my iPhone and then I need to accept on the iPhone and then I'm back to the desktop. So another thing would be, number one, what is the passcode to get into your iPhone or whatever your phone is? Like, if you're going to be the executor of a will today, the first thing you need is that person's phone and then the passcode to get into that phone. And then if you're Google or Apple, what the heck is the password for the Apple thing? Because if you don't have the password for Apple, then you can't reset the device. You can't get in, you can't get into the accounts.

Right.

Those 2 things. I mean, once you're into an Apple phone, Your passwords are saved on there. Like, I have like 89 passwords on my Apple phone, so I, I can't get to everything, but that's a lot of passwords and they're updated every time that you log into things. So, um, having things like that is huge. Anything else?

The more documentation that you have for all of your accounts and all of that, like, it is going to cost you less with a lawyer because they're not having to go and find all of that. And then finally, like I had mentioned that the business had documentation for transfer on death, but you can actually put transfer on death on bank accounts, on vehicles, All of that stuff, and then it stays out of the courts. Then none of that has to go through probate because, I mean, I'm not a lawyer, so take this with a grain of salt. Just want to put that caveat out there. But like, it makes it so much easier to just—

Not only easier, but transfer on death means immediately that house transfers into whoever it transfers to, and there's no tax. So if it has to go through probate, then it goes through tax. But if it transfers on death, it would be like, so if your parents were still married and your father had passed, then the house would transfer automatically to your mom without any tax. But because they were divorced, now you put a different person in there as transfer on death. It goes to the children without any tax. So that transfer on death not only keeps it out of probate, it immediately transfers the ownership of that to the new entity without the tax, which is why it's so important. All 401s are set up that way. That's how beneficiary works. So like when my father passed, within a week we were the owners of the house, we were the owners of the cars, and we were the owners of all the 401. And as I mentioned in the Power of Attorney podcast, you can have multiple levels of power of attorney. Our power of attorney, my sister and I, was the highest level. So when our father was sick and we knew it was terminal, we actually went to the wherever. Wherever you register, the courthouse or whatever. And we transferred the vehicles and the house to transfer on death to my sister and I, because it wasn't set up that way. But we had the power of attorney to do that, and we did it a couple months before he passed. So then we also saved that. And those are— I mean, these are not happy conversations. No. But yet it's huge money. Like, there is a local farm here that had like all this land, and when you drive by now, it's just the house and the small little land because it wasn't set up Properly, and they had to sell all the land in order to satisfy all the taxes in order for that family just to keep the house. Like, it's a very visual every time we drive by that farm that that father of that estate didn't have his affairs in order correctly, and so his family lost all the land.

Yeah. And losing my dad so young, like, um, it made my mom go and set up all— I mean, like, everything for my mom is taken care of, and I appreciate that so much that, like, We know everything is in place so that someday, you know, it'll make it easier for that too.

Yeah. Once you settle an estate, you then get your affairs in order. But if there hasn't been anyone that's passed in a while, then you're like, oh yeah, la la la, we're all fine until someone does pass away. And then you're like, whoa, we're not fine.

Yeah. I mean, my husband and I are young, but we have a will and all of that in place because, yeah, we've been through it.

Okay, let's move on to talking about the business. So immediately upon passing, you were in charge of this business. Would you mind telling us a little bit about the business that your father had?

Yeah, so the business was called Haller Displays. It's my last name, my maiden name, Haller. And, uh, for over 30 years, my dad built custom cabinetry and trade show displays for businesses. So things like, um, the children's hospital in, uh, the city near us, like he built like the foyer in structure and the reception desk, like things like that, and then trade show displays. So when he passed, he'd had the business for about 30 years, and probably almost that entire 30 years he had an employee. His name was JR, and he worked for my dad forever. Like right after high school, he started working for my dad, and then my dad had other people who he hired here and there. Like he at sometimes, like he'd go years where he had 2 full-time employees, but mostly He was hiring contractors or like friends to come in and work on specific projects, things like that. And he owned— it was a warehouse building in Dayton, Ohio that had a ton of equipment and a small office. And so the business was also that.

Okay, so you told us how old you were and that you had a 2-year-old. What were you doing like when your father passed? Like, Your days weren't just like empty watching TV, playing with a 2-year-old. Like, what was your daily life like before your father passed? Like, how were you filling your time?

I worked full-time as a teacher, so I was a family and consumer science or home economic teacher at a local high school, and that's what I did all day, every day.

And your evenings and weekends?

Were mostly just being a mom at that point.

Yep.

I didn't have any extra other things really at that point.

And what time of year did you say that your father passed?

End of March.

Okay. So this is during the school year. You're in school and all of a sudden your father's passed, planning a funeral, and all of a sudden you're also in charge of this business.

Yes. And I took a really long time off of work. I probably took 3 weeks off.

I can't even— That doesn't seem like a long time to me. And you're like, a really long time.

But as a teacher, I mean, really, as a teacher, you get like no time. Like you're Given no bereavement days, at least in my district. So like, it was unpaid time. I think maybe sometimes they let me use sick time, but I took 3 weeks off just to figure things out. And one of my brothers lives in St. Louis, so pretty far from us. So he was there for about a week to help with what he could as well. So we had, we had that time to kind of figure it out. And My dad had always told me that, um, if anything happened to him and he still had his business, he really wanted me to keep his employee employed as long as possible. So make sure— making sure that JR could receive a paycheck for as long as he wanted and as long as I was able to.

Okay. So you take these 3 weeks off. Obviously we're doing a funeral. We're finding out all of this information. Did you know anything about, like, estates and transfer on death and any of this before this happened?

No. I knew that my dad had made a will when I was in graduate school, and that's when we first had this conversation about the business. But that was—

That was a while ago?

Yes. That had probably been at least 5 or 6 years. No, more than that. Yeah. Okay.

So this is like out of the blue. So you take these 3 weeks off of work. Other than the funeral and the family and stuff, like, what were you thinking? Like, what did you get done? Can you even remember what you got done in those 3 weeks before you went back to teaching?

Yeah. You can?

Oh.

Um, of course you can. So it was complicated. So my relationship with JR is super interesting. So he was one of my dad's really good friends. My dad was also good friends with JR's dad. So it was like our families were intertwined. I was the flower girl in JR's wedding. And I was also the one who had to call and tell him that my dad had passed away. So like, it was just a weird place to be in. And then I ended up having to call him and say like, we need a meeting. So he comes to my house and it's me and him and my 2 brothers, and we're all just kind of looking at each other. And that's when I stepped into the leadership role for the business because no one really knew what was going on. And so I basically had to say, What do you want? What are you willing to take over the day-to-day operations? I don't know how to operate a saw. I don't know how to look at plans for a job and know how to get it done. Like, if I do everything else, I do all the behind-the-scenes stuff. Like, what are you comfortable with? What would you need from me? And we were able to figure it out. So essentially what happened is He said he wanted to keep seeing what he could do. And my brothers and I had to go to the bank and fill out information for like the, the business checking account. And it's funny because my one brother was the CFO because he's in finance. So he wanted to be the CFO. My other brother wanted to be a laborer and I was a project manager. But really, I was the CEO of the business at the time. I just think it's so funny to like look back at that paperwork and see our job titles. But I became the CEO of the business, and that meant I did all of the behind-the-scenes work. So I was checking email, I was communicating with clients. So was JR, because it just— there was a lot of communication that needed to happen because everyone needed to know. I did like all the accounts payable and receivable, all of— paid all the bills. Yeah. And so I just—

When did you do that? Evenings and weekends?

Took on the role. Yep. Evenings.

And then in the summer, did you like go into your dad's office or?

Not really. Nope. I just did it all from home. Yeah. Okay.

And your other brothers, did they keep doing the— how long did they keep doing the business?

They didn't.

They didn't.

Okay.

So you're the hashtag all the things, but on paper it was a 3-way partnership.

Yeah. Yes, exactly. Which, and that's fine. Like, it also could have gotten complicated. Like, for a while I would send them reports about, like, what was happening, and then I realized none of them were opening them, and I was like, I'm— if you need information, let me know.

Yeah. How many hours a week would you say, like, could you guess that you were working on the business?

Probably 5 to 10.

Oh, that's not a lot. No.

Okay.

Well, I mean, a business with 1 employee where that 1 employee is mostly building things, which takes a long time. Yeah, that makes sense.

I mean, there were times like when I was preparing quarterly taxes or annual taxes where I obviously was spending a lot more time. But, and at the beginning, it was a lot more time just trying to sort through the information that we had and come up with a system for how to keep everything managed. But on the majority of the weeks, it'd be 5 to 10 hours.

So how long did you do this?

I did this for a little over— for 4 and a half years.

Wow, that's a long time.

Yes.

Okay. Thoughts that you have about that?

So I did this for 4 and a half years. At one point I had told everyone, all the constituents, like, I think I'm ready to be done. This was probably about 3 and a half years in. I said, I'm trying to have a baby. I don't really wanna do anything. I need this off my plate. Oh, and in that time I started my doctorate. And I said, I really wanna be done, but no one picked it up. So I just continued just doing it, doing it. Then I got pregnant and I was like, okay, I think I'm ready to be done. But then the logistics, I started to think through the logistics and I was like, I cannot close a business that has a physical location. And is stuffed to the brim with everything from the last 30 years. Like, I physically can't do that while I'm pregnant. So we just waited. And fate would have it that my father-in-law's friend owns a similar business and started to plant a seed with him that we might be wanting to sell if they were interested. So fast forward to like 4 years, we started that process to sell the business to this new company called CaseCrafters, and they really needed another full-time person who knew what they were doing. So they were interested in hiring JR. So, and he was interested in going to work there. So we really got so lucky that, and at that point, like, he wasn't working 40 hours a week for us really, like.

Right. It—

we did. We were slower on business, and he was okay with that and whatever. But, um, this gave an opportunity for him to stay employed. I got to maintain my promise to my dad that I would make sure that he was employed. And yeah, we were able to sell the business. So it kind of got complicated too, because they bought the business, but not— and the customers, but not the building. So I decided we would put the building up for sale when I was in the spring so that I would have time when I was not in school to clean out the physical space. So we ended up that year, I had like whenever I ended school, like May, the end of May through the end of June to get everything cleared out and that whole process. Yeah.

So did you just like sell the tools and like, what did you do?

Well, the majority of the tools, like everything that was like really in pretty good condition, moved to the new facility. Okay. So they bought all of that and then some of it we put out. We were in a city, so we put it out for scrappers. I had found a younger guy who was interested in starting to do some woodworking that lived in my town. And so he was so excited to come and just like take some stuff. Have at it. And it was really cool because a lot of my dad's friends from throughout his life, or who had worked with him at any point, would come by and they would take something, or they would come and help us clean things out. And that was really cool too.

That is cool. So during this time, this 4 and a half years that you're doing all this, okay, so when this started, you were— you had a 2-year-old and you were Working at a high school.

Mm-hmm.

And you were on your off hours doing your other job of parenting.

Yes.

Then you decided to start getting your doctorate.

Yes.

And you got pregnant and had a baby.

Yes. So that accidentally all ended up at the same time. So I gave birth at the, the first week of my second semester of grad school. So Well, I guess I started classes in the summer, so I found out I was pregnant like a week into my first semester, and then my third semester I had my baby the first week of class.

The first week. Inconvenient. And you didn't take that, that session off?

No, I overloaded my courses that semester because my professor told me that I couldn't, and I was like, challenge accepted.

So you were running a business where you weren't also teaching. So you're on maternity leave.

Yes.

You overloaded your dissertation classes, PhD classes.

Yes.

How did it go? Great.

It was fine.

Okay. I look at you and I'm like, you're crazy. But then I know also I am crazy. And then I also know whoever's listening to this podcast, you're also crazy too.

And I think it's just Women, we're just like, yeah, well, I mean, it works out because I just had a baby strapped to me while I was working here, you know. Like, my daughter Myra loves to look at pictures of her as a baby, and so many of them, like, I'm holding her and I'm typing. Or I had one professor who was actually pregnant with twins that semester when I had my baby, and so she had told me that I could— you're gonna be so jealous— voice memo my papers. Oh my gosh.

Oh, that would be— I would be done already.

I just talked to her. I just talked to her and told her all the information, and then she gave me a grade.

I'd be done already. And also, like, having been a mom, like, even looking back at my own PhD journey, I started when Grayson, our grandson, was 1 and a half. Anyway, I knew I'd be done by the time he got to kindergarten. And it is getting harder and harder because he knows who I am and wants to play with me. And now I have to not be at home in order to get my PhD work done. Like, it is, it is harder when they're newborns because you don't have that middle of the night sleep, but you can just put them in a bouncer or put them here, or somebody else will hold the baby or whatever. Like, it's much harder with a 2-year-old, a 3-year-old, a 4-year-old. Yeah.

And I knew I wanted my doctorate, and I knew that I didn't want to miss my kids' basketball games or, you know, field trips or whatever. And Yeah, it was, you just, it really was strategic in the end. It was fine.

Yeah. Okay. Um, so you had a lot of things to manage. So there was the business and the business was 3 things. It was an actual revenue generating business. It had employees. So there was employee management. It had physical assets within the building and also ownership of the building. So that's, that's a lot of things to manage. Like in my business, we don't own the building. So the building lease, you know, you just get out of the lease. But we do have physical, like, you're gonna have to keep the lease because we got a whole 4,000 square feet of product. So, and we have employees. Like if you're a solopreneur without a lease, without physical products, you know, you could sell the intellectual property or whatever, but you had like a lot of different things. When you think back to being the executor of the will, I know you weren't officially the executor of a will, but also you had in there. Your father had a house, he had cars, he had bank accounts, he had all of those. Um, can we talk about the house?

Sure.

Okay. Share with us about the house situation. You had mentioned that, um, you custom built your house to be halfway between your mother and your father's house.

Yes, I did. Um, but my dad being a builder, he'd always dreamed of building his own house, like doing the work himself. And so he had spent Years. He bought this lot, um, and he spent years designing what he wanted his house to be like, and then did all— most of the physical work himself. His brother helped, JR helped, some friends helped, but like, he nailed every nail into his house. Um, and when he died, my brothers and I were all like, we can't sell this house. Um, and I got really lucky because I was the one that lived here and I was the one with a family and could afford the house. So I get to live there now. So I was able to purchase my dad's house. So it transferred to all 3 of our names. That transfer on death is really nice. And then we were able to just— my brothers each did a quitclaim deed to the house where they essentially withdrew their rights to it and it became mine.

That's so awesome. And that's where you live today.

It is. And I am not moving. And I'm 1 mile from my mom, so still not far.

Still fine. I mean, I'm sure your 7-year-old could probably ride the bike. How far were you from your dad's old building? Like his—

Yeah, I was about 25 minutes away.

Oh, not close. I mean, close, right?

It wasn't like right down the street. Yeah. Okay. So I used to go and stop in 3 or 4 times a month. So I would like stop down there. I would pick up all the mail from that week. I would check on the employee. I would just, you know.

Yeah.

Yeah. But I wasn't there all the time. In the summer, we'd go more often. Like, my son thought it was so fun to hang out there because it was like, yeah. Yeah.

So by the time you sold the business, uh, you were 35? Yes. 36. Okay. And what's the process of selling a business like? Well, depends on who the buyer is, I'm sure.

But I was gonna say it depends on the buyer. So the buyer's lawyer really wrote up all of our paperwork for us, and then I just had someone look over everything. But it really was a couple of different pieces. So included like the client list, the materials in the building. The name, things like that. Yeah.

Yeah. And I've mentioned before on the podcast, you know, the way I have my business structured is it's actually 2 businesses. So there's the C corporation, which is Organized 365, which is what you all see that has the license to manufacture, sell, and distribute products and to— has employees and leases the building. And I'm an employee of that company. And then I have a separate entity. It's now an S corp. It was an LLC, and that company owns all the intellectual property of Organized 365. And that's actually the company that you license with if you are a certified organizer. So we have now, I think, 12 trademarks, a patent, over 100 copyrights. The ownership of my books, my podcast, me is all within that secondary company. And the reason why I set this up attorney set it up in 2017 for me. He said when I moved from that LLC to creating this C corp, he said, keep the LLC and retain all of your intellectual property in it so that one day when you do sell your company, there will be the forward-facing brand, the physical entity, and all of the employees. And then there'll be this secondary intellectual property company. So the company is set up that if anything happens to me, Organized 365 can be sold separate from the intellectual property of Lisa Woodruff so that there can be a royalty for my family for the intellectual property. And Organized 365 would keep paying that royalty. Whoever buys that company would have to pay that royalty for a predetermined period of time. Like, I've tried to establish a way in which, like, one of the benefits of being a business owner, like you could— Dad, is that there are multiple streams of income. There's obviously the regular income that was coming in from the company. But then there's the physical assets that have been acquired that could be sold. And then there is the building that he purchased that also can be sold. And then there is the goodwill that he had of the client list and all of that and the name that he could sell. So they had 4 different things to sell. And while they were deciding what to sell, they had the ongoing revenue coming in from the business, which I'm sure declined over time because I'm sure your dad was the salesperson and you didn't have somebody actively selling. You didn't step into that role. But as a business owner, we start from a side hustle and you move towards these businesses. You know, last summer I was looking at buying a building because it's another asset that my family would have to sell once I, you know, if I were to pass, because right now I'm kind of a lot of the money coming into our family. And so there are all these different ways that our family gets paid from the business. And there are ways in which if I am not generating income as the CEO, there are other revenue streams that'll still come into the family after I pass. And the more you get into business, the more you start to see, you know, companies that have been in business 10, 20 years, they all start to acquire these additional revenue streams. And so then it is, you can unwind them slower over time, and it also gives you a longer runway to unwind them because like you weren't in a lease situation where you had to renegotiate that and you didn't like All your dad's equipment wasn't in a lease where you had to bring in a certain amount of money in order to pay the lease. And like, he didn't have 20 people on staff. He had one person on staff who obviously was okay with their hours not being a full 40 hours by the time you were at the end. So those are just all, you know, gives you more time in order to unwind a company. A company is like, it's a whole other entity.

Yeah, that's very true. Like, I do feel so fortunate that since my dad had 30 years in business, like he owned a lot of those assets. We also had a box truck and a forklift and things like that, that, yes, that we didn't have to worry about. Whereas if, you know, if you're inheriting a business that's only 3 years in, it's probably still bottom up. So things are gonna have to move faster and you're gonna have to make really tough decisions pretty quickly. Yeah.

At this point in Organized 365, we own all of our inventory outright. We do own our forklift. We're about to own our copier. And so, you know, as I was growing the business, these were all huge things that I was pouring all the profits of the company into establish. But at this point, I mean, other than the lease, I can't even think of anything that we have on the books that would be a, oh my goodness, how are we going to cover that? And even the lease we have, you know, we've had it for a long time. So it's not small, but it's not terrible, especially based on the revenue of the company. So as you're growing a company, you don't imagine that you won't be around. But we do need to think about, you know, in addition to the house and all of those things inside of a company, you have to make all those decisions as well. Actually, if you have a reference for this, let me know because I don't— just like there wasn't a workbook to go through to settle my dad's estate, I have not found a workbook to go through for all of these things for our business either. And we haven't created it on our own. So if it's already been created, let me know. Otherwise, we'll just keep it in our queue to create on our own eventually. I know Anna's like chomping at the bit.

I told you we need it.

I'm ready.

I'm ready.

Because a lot of our businesses are solopreneurs, or you have one employee, and it's like a lot of what is out there is for like the Fortune 50 company or the $10 million company, which is not our companies. You know, like it's more, it's more complication than we need.

Especially if you have multiple owners and multiple like executive team members, things are going to continue to run smoothly if one person's missing, whereas—

Correct, correct. I'm a solo—

Because more people are going to have that institutional knowledge.

Yeah, I'm the solo owner of all of my companies, but the leadership of Organize 365 at this point could run the company without me. And we do tests while I go on vacation. It's so fun. Um, anything else you want to say about the business part?

I don't really think so. I mean, it is so cool to get to be a second-generation business owner. Like, I don't think we really Talk about that a lot. Like, it is a huge responsibility, but it also feels really cool. And Lisa and I were talking yesterday about like how things really shift 5 years in-ish. And I, I was thinking it was 5 years. It's been 6 years since my dad died. But for me, that really started happening at that 4 years. And I started to think like, okay, I, I will be okay without this. But like, there was some— it felt like I continued to have that connection with my dad when I got to own this thing that was his, and, um, that feels really cool. Um, I don't think— like, if you've ever seen the, the show Hamilton, the play, the last song in that show is, um, basically all about like, you can do whatever you want when you're alive, but you don't control what happens when you die. You don't control who's going to tell your story and what that narrative is going to be. going to be. And it is so cool to be that person and to be entrusted by your loved one to put those final touches on your life and your legacy and your business. And like, that is really cool. And it did feel— while it was a lot of responsibility, it was very healing. And like, I got to continue to have those connections that my dad had after his passing. And that's really neat. Like, I feel I feel very grateful for that experience.

I love that. I love that. I want to talk about the responsibility and then the 5-year part. So the responsibility. You are a person who has a lot of capacity.

Yes.

I think you have more capacity than me, which is saying a lot, actually. I think part of it is because I'm just a little bit older now. But even when I think back to my 30s, I'm like, I couldn't do what you— you have an abundance of capacity. And you thrive on being busy.

You love it. You love it. I do.

So was there, was there any point in this where you felt overwhelmed? And if so, what did you do with that?

I mean, frequently I felt overwhelmed. I, I was also, was like over my head. Like, I had no—

Yeah.

I would think. I had no place to be running a construction business. I had no idea what I was doing. So, I mean, just figuring it out and, and leaning on trusted people. So I'm really— I feel very lucky that, like, our— the attorney that we used for the estate was my dad's childhood best friend. So I felt like I could just trust him 100% with helping to advise me on decisions to make. And my dad had used the same accountant for a very long time. And so that accountant was so wonderful and met with me frequently to answer all of my questions and help me figure out what my role was as the person in charge of all of the books, because that for me, I mean, I had no idea what I was doing. So really finding people that I could trust to help with that. And sometimes it took my husband being like, you are really stressed out. You need to change something, or you need to ask for help. But sometimes I would, and no one would respond to the help, which is fine. At least, at least I felt like I was doing something.

Which is fine, which I know, which is fine. Um, I think that sometimes the messages that I hear— books, podcasts, experts, wherever— like, get help, offload to other people, hire help. Like, okay, that all sounds well and good. Sometimes you can't afford to hire the help. More likely than that, you can't find the help to hire.

Yeah. I mean, that's kind of— At all, period.

And also, who else is going to do it? Because even if there are other family members, I mean, we're going to do it. So my husband said to me the other day, I don't remember what we were doing. And I was like, you know, I do all the things around here. And he's like, to be fair, you want to do all the things around here. I was like, you're right. I do. Now get out of my way. Like, I do want to be the one in charge. I do want to be the one that has the say. Um, I, I like being busy. I'm not really overwhelmed. I do like having my hands in all of the different things going on. I don't need to go take a bubble bath. Like, I would much rather be doing the work than going to a spa thing. Now, if my shoulders get to the point where they won't go back down again, I must go get a massage. It is not even optional. A lot of times in my 30s and 40s, I would get stressed to the point where I could not breathe and I had to go get a massage. By the way, that has gone away with menopause. I don't get to the point where I have to have that massage anymore. I'm not really sure if that's a hormonal thing or anyway. Anyways, sometimes I do have to just stop and care for myself, but for the most part, I could take a lot and you could keep adding more and more on and it's like you're just making the jigsaw puzzle harder. And so I just reorient all of the things and I keep going. I think we should acknowledge how amazingly dynamic women are that they can keep doing that.

Yeah.

They really can. They really can wear a lot of hats at the same time really, really well. And we do get to points where it gets overwhelming. But if you just give us like even half a day, we usually can figure it out by the end of the day. We just might not be able to figure it out within the minute. Usually I could get really overwhelmed, but within 1 or 2 days I'm like, okay, I've got another— I, I just have to go from I was pushing too hard in this plan If I just change it to this plan, 80% of it's gonna work. So let's just run that way. And I, I like that. I don't ever hear us talking about how, about that. Have you ever heard that talked about anywhere?

Like, no. But I think it's true.

I think it's how we are. I think it's how women are wired. Like we can do caregiving and monetary, you know, be a monetary contributor and also run our household and run another household and still volunteer and still know what the weather is and what's going on. Like, We just really have a lot of capacity to be able to do that.

Yep. And I guess I do wanna say, like, the other thing that I did to help manage all of this was I did not take on the sales role in the business.

Right. True.

Like, I didn't have the capacity to do that. So I basically told the employee, like, either you do what you can with sales or, like, the company will have to end up closing sooner rather than later because, like, I don't have the capacity for that. And I could have left teaching and pursued that, and I didn't want to. I wasn't willing to, to do that. So also making decisions.

I will say, just a side note, um, I, I love hearing your story, and the more I learn about it, I love it so much because I feel like now I'm a fairly good example of someone who is putting her own wants and desires At least on par with my family and sometimes ahead of my family, like getting a PhD that nobody wanted me to do and I'm doing it anyway. Or I'm starting to just take trips and I'm like, yeah, that's great, Greg, you went to the Keys fishing and I'm going to go do this. And he's like, why? I'm like, just because I want to and I'm just going to do it. I did not do that in my 20s and 30s and even in my early 40s. Partly we didn't have money for me to do things like that. Like, I was primarily the Stay-at-home mom, wife, and mother, and I earned some money on the side. And that was my primary role, which I definitely, definitely wanted to do. But also, I couldn't figure it out. I, I couldn't figure out how to do that. And like, I wasn't really good at that. And I see you as being a really good example of someone much younger than me being able to say like, okay, well, that's good for you and this is good for me. And so the family's gonna figure out how to make this work for what is good for me. I also don't hear us I don't necessarily hear us talking about that. I hear that message more than the other one, but I still don't hear about that a lot.

Yeah, I don't. Well, thank you for saying that. That's really nice. And you know what?

I'm having children. Yeah.

I'm using some of the money that I got from the business to help subsidize my Disney addiction. I went to Disney World once, and now I wanna go back all the time. So, yeah. My daughter, myself, and my mom are going to Disney in September. And I'm going to use some of the money from the family business to help pay for that. Because I— that's also something that kind of kept me going was knowing, like, when we do sell the business, like, I will have some money that I can use to help my kids buy their first car or travel, you know, like these things that are then gifts from me and my dad to my children. And that's pretty cool.

Yes.

Oh, I love that. And I'm just prioritizing that. My husband really is not interested. But I'm prioritizing that because it's something that brings me joy, right? Making those decisions. Yeah.

Okay. Let's talk about the 5 years. So when I was doing in-home professional organizing, I would find that clients would call me in about 5 years after a parent or a spouse's passing, and they were all of a sudden ready to just declutter, declutter whatever space it was that had been that person's space. And over and over and over again, I figured out it was 5 years. And I— that's so odd that it's 5 years. And I started my in-home professional organizing business. I don't know how long it was, like 3 to 5 years after my father had passed. And I found I had done the same thing. So when my father passed, we, my sister and I, became the owners of the house and all of the contents inside of the house. And I mean, we lived in that house for 30 years. There were a lot of contents. And the contents in that house were very much nicer than the contents in my own house. So I got like a moving— the largest U-Haul you can buy, you can drive on your own. And I filled it. I filled it with art and lamps and furniture and whatever. And I brought it all home to my house in Cincinnati, and I put it all in the basement. And about 5 years later, I'd gotten rid of almost everything. But in that moment, I couldn't really decide what I want and what I didn't want. And you got pennies on the dollar for selling it, or people didn't want it. I was like, well, We're just going to donate it to Goodwill. I might as well take it. I might as well take it. And I kept doing that. And I found for myself and the people that I organized that somewhere around 5 years, all of a sudden, the— not the spirit of the person, but like when you looked at that item, like you saw your family member, it just became a chair. It just became a lamp. It just became a whatever. And it became much easier to declutter the item. What has been your experience?

I'd say that's probably about on par.

So we—

I officially was like, okay, I'm ready. I can— I feel like I can let go of the business. at about 4 years. But same, same. Like, um, I think I kept most of my dad's belongings because when we moved into the house, it was fully furnished. So we had everything. And, um, my brothers did take some things, or since then have taken some things. But, um, at the point, like, my dad's clothes, I just bought a ton of big Tupperware bins and just like put everything into bins, and they are in our— Oh, that's great. Metal barn in our— on our property. But I do feel like I can get rid of that. And I would say about a year ago, at the 5-year mark, I started to say like, okay, my dad had a big record collection and lots of speakers and turntables and all of that. And about a year ago, I started like, when people come over, I'd say, would you like any records? Please take some records. Like, it It became— it started to be the thing where I was like, I would rather other people be using these things than them just be here as an artifact. And I think that some of that, I'm sure, like a psychiatrist or something could help us better understand it. But, um, I really do think that, you know, when someone first passes, you just think like, oh my gosh, I cannot go on without this person. So you like cling to all of the stuff that you possibly can.

Yeah.

And then as time goes on, you realize like, They're still part of my memory. They're still part of my, you know, I think about them daily or weekly or whatever. And I don't need that lamp or those records or whatever in order to remember them. And so I think as you, as time goes on, you realize, you know, that your memory of them isn't actually tied to those things in the same way. And it's good to keep some of the things like you've talked about how you have, you know, some golf balls or, you know, things in a display cabinet. I love that. Like, keep the things that are really important and then the furniture or whatever can be less.

Yeah. I haven't done a deep literature search, but so far I, I've searched some things now that I'm getting my PhD that I always wonder has been studied in academia. I have not found support for middle-aged women being studied as a phase of life at all. I have not found support for this 3-year cycle of learning, which I know is true in Montessori and in my experience. I can't find support for that at all. This 5-year mark of being able to let go of physical items, I have not found support for that. I haven't searched that one as much, but I haven't found support for that at all. But I know it to be true. And so when I was doing in-home professional organizing, and once I figured out it's this 5-year mark, whenever someone was moving or having a really hard time because the items were associated with somebody who was very close to them and it had not been 5 years yet. I actually counseled them to just go ahead and buy an external storage unit and move everything there, which I know has a fee. And people are like, you know, don't pay for this external storage. You should just declutter it. There's just something about you have to give your brain and your body this 5 years to decouple the person from the stuff. And, you know, I'm not a licensed counselor, but I think that it is better to have this stuff and even be paying to store the stuff to give yourself the opportunity to go visit the stuff. than to just say, well, that's going to be a financial cost and we can't afford the cost, so we're just going to get rid of it and make that more abrupt change. It's just been my observation. It's not always possible, but when it's possible, I usually say, you know, in my, in my observation, this is what I've seen, and I'd rather you hold on to it than declutter it out of— I don't know, because you think you should just live a minimalist lifestyle. Live a minimalist lifestyle 5 years from now. And it's not every single person that passes. It's when it's a significant person that passes, like a parent. Spouse, something like that, sibling, that you tend to want to hang on to things. The other thing I would say just along this vein, as I'm thinking about it, is when my— my family is very large. And so when I was younger, I'm the oldest of the grandchildren on both sides. So I had a lot of great-grandchildren or great-grandparents alive when I was born. As they would pass, I was allowed to, you know, have things because I was not, you know, a baby. I was a child. And so, like, I took the button box from my grandmother, my great-grandmother. And as people have continued to pass, I've, I noticed that like my son always asks for the wedding ring. So my son has his great-grandfather's and my father's. And I think there's another— oh, and now my husband and I got new wedding rings for each other for our 30th anniversary a year early. And so my father and my husband's original wedding ring, like we have all these, I'm holding on to them, by the way. I don't want them lost in the condo with the video games or whatever, but they are Joey's. And so he has all of these wedding— men's wedding rings, not the diamond ones, just the male wedding bands. And someday I could see him doing something with all these male wedding bands. Like, you know, if there is something that is— Another thing that we have taken from anyone who has passed when we were given the opportunity to choose Is one of their Bibles. Like, my dad had multiple Bibles. So we have my father's Bible, we have my grandfather's Bible, we have Greg's grandfather's Bible. We have just this stack of family Bibles. It's another thing, like, if we're offered the opportunity to take something when someone passes, we ask if they have a Bible and if we can have the Bible. That's something Greg started. So thinking through, you know, you don't have to have everything, but if there's something you're like, oh, you know, I would like to have, I would like to start collecting this from my family as they pass. Because you are going to be asked. They're going to say, do you want anything? That's such a broad, like, anything. And you're like, yes, I would like the diamond ring. You know, there's going to be conversations over that. But if you're like, I want the, you know, Bible, I want to have a lamp from every person or a piece of art from every person or whatever is your uniqueness. And you're like, this is my uniqueness and I want this uniqueness from everyone else. I mean, maybe it's morbid to think about this. I think it is. productive to think about it when everybody is healthy and well. When my grandmother, you know, my grandmother was very proactive about this kind of stuff. Like when you flipped over anything, it had like people's names on it. Like from the time you could talk, she was walking you around the house. What year do you want? When she passed, you just opened up the list. It was like, okay, pack up what you guys want and let's go. 'Cause I mean, it was all already decided. You don't have to go to that extreme, but. Yeah, that's a lot of what I did when my father passed was walking through the house. It is all my sister's and mine. What do I want? What don't I want? And ultimately at the end of the day, what will I keep, you know, 50 years from now?

So that was actually something that I did. Uh, well, I wa— my brothers and my aunt and uncle, like I took them all around the house saying like, please take anything you want, my cousins. But then at the shop, like I went around and I just took pictures of things that were cool. Like anything I thought was neat, like an old-fashioned phone or like all these different things. And I made a Google Slides. presentation. And then I had little spots where people could put their name by anything that they wanted. And I said, okay, like, please add your name anywhere that you want, and I will make sure that that item gets to you when we're ready to get rid of it. Because I wanted to make sure that everyone had at least something that they wanted. And like, I took—

love that.

I took all the tape measures, like the metal tape measures, and gave them to my cousin's children. Um, so that, because they knew my dad and I just, yeah, I wanted to make sure that everybody had something.

Yeah. So cool. Is there anything else you want to share, Anna?

Nope. I mean, I guess, yes, actually I do. It's just to be proactive that it's not fun to have these conversations, especially with your aging family members, but start thinking about it for yourself. Start thinking about it for your parents. Um, I feel really blessed that my mom has taken care of all of her affairs, you know, for us. And we've tried to have this conversation with my in-laws, and it's harder with them. Um, but it really— it sets people up for success in the future. Yeah.

And what I would say is this is a season of your life. For Anna, it was 4 and a half years. Sometimes it's not that long, but it's usually not 2 weeks. So the season of your life when someone significant passes, that you are the executor of the estate or an immediate family member that is supporting the executor of the estate. Like, there's a lot of work to be done. There's a lot of legal work to be done. There's a lot of physical work to be done. There's a lot of cognitive and emotional work to be done. Um, and it's never planned. Like, it is never planned, and it's on top of everything else you're already doing. And so the more you can support yourself and how I've said, you know, like having a go bag and a suitcase ready to go so that you are meeting your own needs. But also, I would just lean into it. Like, I hate to say enjoy it, but it, it is, it is a season with your family that there can be enjoyment there of like reliving that person's life and integrating it into yours and creating the next iteration of the family. While there's a lot of pain, there is, there can be a lot of joy as well.

Exactly. You're putting the final touches on their legacy. It's pretty cool.

Yeah.

It's an honor.

Well, Anna, thank you for having this conversation. I know it's like, can be awkward. Um, but I think that if I were listening to this, I'd be like, oh my gosh, I didn't even think of half of the things that we've talked about, especially if you are the business owner. But also you may be looking and going, oh geez, my parents have businesses, my grandparents have businesses. Like they talk about the, um, amount of businesses that will be sold in the next 10 years is so significant as the baby boomers start selling the businesses that they have. Um, you know, my father-in-law is in his 80s and he's still running his business. Like, people aren't— entrepreneurs don't retire at 65. Let me just tell you that. They work like right up to the end. They're like, I'm going to keep going because they like it. They like the game. They like what they built. They like what they created. It's part of who they're uniquely gifted and created to be. Like, they're not really retiring to go play golf because this is their golf. Like, this is, this is the thing that they love to do. So, um, yeah, that work's coming your way if you're the family members that are inheriting that.

So maybe do take your kid to work day even as an adult and see what your parent does if they own a business and ask them lots of questions.

Yeah. Hey, I just listened to a podcast. I'd like to camp at your office for a week and check out a couple of things for myself. Anna, thank you so much.

You're welcome. Thanks, Lisa. Bye.