Bri Conn, CFP®: Welcome to Childfree Life by Design. I’m Bri, here with Dr. Jay Zigmont and Maddy Roche, and today we’re doing something we’ve never done on this show before. We have four real stories to share with you. The kind where someone was living their life doing everything more or less right, and then something happened that completely changed what they knew and the understood about their own situation.

A medical crisis, a fortune, nobody really knew existed. A tree, a piece of paper that turned out to be worth a lot more than anyone expected. If you ever thought you had your life pretty well figured out, this episode is for you.

Intro: From Child-Free Insights, this is Child-Free Life By Design, the go-to resource for building the child-free life you want. Every episode gives you practical guidance, clear direction, and meaningful conversations to help you live intentionally and design a future on your terms. This podcast is for educational and entertainment purposes only. Please consult your advisor before implementing any ideas heard on this podcast.

Bri Conn, CFP®: Alright, so here’s a setup for today, guys. I’ve got these four stories. All of them are real. Dr. J, you know them. Maddy, you don’t. So this is gonna be the first time for you hearing all of them.

Maddy Roche: Great.

Bri Conn, CFP®: Is there anything that Jay, you particularly want to share?

Dr. Jay Zigmont, CFP®: So I think the challenge is, you know, try to share as much as we can from our clients. We can’t share everything. It’s just privacy, so, so these stories are made anonymous, but the reality check is. Every time we all make a plan, life goes a different direction. Like it’s just that way. And I swear we’re here in 2026 and I was hoping 2026 would be different for everybody around me and life would go as planned and it never does. And I think that’s the reality check for all of us.

Bri Conn, CFP®: True. I wanna get into the first story here. So this first one, she had her life built around knowing what to do next. Years in healthcare, a deep working knowledge of the medical system, a career dedicated to helping other people’s families navigate the worst moments of their lives. She was good at it.

She had seen enough to know when things go sideways, the people who hold it together, are the ones who have a plan. She thought she was one of those people. Then her dad got sick. She found herself on the bathroom floor, cold tile, crying. She knew exactly what needed to happen. That was the worst part. The list was already forming in her head and it wouldn’t stop. Doctors, surgery, insurance, the anesthesiologist, always the anesthesiologist, the bill nobody warns you about. Did he have an estate plan?

She didn’t actually know. When does he come home and can he even come home? And who takes care of the person taking care of him? She had spent her whole career on the other side of the store. She knew exactly how this worked. She had walked other families through these exact questions hundreds of times. But when it’s your family, that knowledge doesn’t make it easier. It just means you understand every single thing that could go wrong. That is story one. Thoughts on hearing that?

Maddy Roche: Yeah, a lot comes up as you think about that, I immediately started thinking about what happens to me, even though I’m a planner, when all of a sudden life changes for the people I love the most. And I commend this woman on her aptitude and understanding of the different scenarios and requirements to make sure she’s taken care of.

But we can only support our loved ones in so far as they’re willing to support themselves and ensure that they have their plans in place. I do think that that’s probably one of the more painful things is that when you work in the medical environment and you see these things play out all the time you probably have a larger amount of stress on you just knowing the scenarios that can take place without the planning and protection of, say, an estate plan. So, I guess my first impression is just deep empathy for this woman. But I also recognize that, she can only do so much for herself, let alone those around her. Jay, what are your thoughts?

Dr. Jay Zigmont, CFP®: Yeah, I think the reality of this story is I could change the names, the places, the mom, dad to 10 different clients. And it’s all pretty much the same, which is we started working on a plan. And then something happened before we got the plan in place. In this particular example, we were working on how do we take care of your mom’s finances and what’s your plan for your parents?

And we have a step in our planning process for this. And this client was on board like, yeah, we should do that. And then by the way, something happened and that’s the way it happens. You’re trying to make a plan and life throws you for a loop. And for most of the Childfree folks that we’ve worked with, you get this, hey, well you don’t have kids, you can take care of mom or dad. And that just is hard. And how do you set boundaries? The part of the story that Bri’s not sharing is, we worked with this client for months afterwards and now we get into caregiver burnout and fatigue and how do we structure this and, how do we provide support for the people providing support? And how do we do that in real time? When it would’ve been better to do in advance, but you really can’t at times. We all try to plan for these things, but it just doesn’t happen. And I think anyone that’s ever cared for family members in this way knows that it just throws everything upside down. And I don’t know that knowing more about it helps you.

Maddy Roche: Yeah, I was struck by this balance between the administrative burden of someone being sick in your life, because we just know that, that requires a huge amount of orchestration from which doctors and how insurance works to when the appointments are to getting to the appointments. When someone has a diagnosis that requires active medical attention. It just becomes an administrative nightmare, quite frankly, of just trying to balance all of it while we’re all trying to just live our lives. So then they have on this layer of grief that I think we underestimate when as opposed to maybe just a death that has happened when there’s prolonged sickness. That grief contributes to that burnout. It contributes to the inability to manage all the affairs. So, plans are helpful and, having a plan in place can help mitigate some of this. But the reality is, as Jay has mentioned that, you’ve got an administrative process that you gotta work through while also balancing the grief, that’s a lot for one person.

Dr. Jay Zigmont, CFP®: And we often talk about setting boundaries in advance of these problems. It is different to respond to, oh, dad’s had an emergency, I need to go care for him. And then you get a couple weeks out or a month out or wherever else it is, and you’re like, I’ve stopped my whole life because of that. And that’s where it’s interesting, you wanna do the right thing for your family members, whether it’s your given family or chosen family, whatever it is. But at some point there is a limit. And if you’re trying to set a limit while you’re in the middle of it, that’s nearly impossible. It’s something you need to be thinking about before you’re in the middle of the mess, and that limit includes both time, money, effort, everything.

Maddy Roche: I think back to the podcast that we had recently with the advisor, Chris Dale, and he just said so beautifully and eloquently that the last time you wanna be planning for an emergency is during the emergency. It’s just not the right time to start setting up the people and processes to make sure that life can continue for you and the person that you’re caring for.

Bri Conn, CFP®: You’re exactly right. Is there any other last thoughts you guys have on this particular story before I move on to the next one?

Dr. Jay Zigmont, CFP®: I think the one thing to take away from it is take the time to do your plan for parents as soon as possible. It’s just a step you have to get done in your own planning. Even though it may or may not be your responsibility, you need to have a plan around.

Bri Conn, CFP®: Well said. Alright, the next one, this is a little happier. She had done everything right, school, marriage, a good job, savings. She was building towards something steady and deliberate. She knew her mother had built a company and that she owned a small piece of it. She had never looked too hard at the details because the details, as far as she could tell, didn’t matter much. A helpful footnote to a life she was building on her own terms.

Years went by, she stopped thinking about it. Then in a routine financial planning meeting, she mentioned the sale of her mother’s company. Almost as an aside, something about documents she had been sent, her financial planner stopped, not a pause, a full stop. The kind of stop that means I need you to say that again. What followed was months of paperwork, a deep dive into numbers she had never looked at. A growing understanding that the small amount was not in any meaningful sense of the phrase, a small amount. She was a millionaire. She just hadn’t known. She had paid off her house. She quit her job. She started traveling. Eventually, she took on new work, a different kind of work purely to keep busy and enjoy life. The money changed what was possible. The version of her that had been building a careful deliberate life before she knew that version had already been doing just fine.

Maddy Roche: First impression is, I wouldn’t want this woman not to take credit for the hard work that she had before this. We don’t wanna forget that she was really intentional and built a life that would’ve had her be comfortable and successful in her own right. And I say that because I’ve had a lot of conversations with friends who have had inheritances. And the difference among their opinions and perspectives around it is fascinating. I think we could spend hours and hours and hours talking about how people process inheritance and whether they’re good or bad, and whether they’ve been helpful or destructive, whether there’s been guilt or happiness delivered through them.

I just really respect that this woman didn’t carry it as her plan the whole time and continued to work really hard and to build a life that would’ve been successful in its own right. Because we can never and should never rely on inheritance as a plan. Dr. J may disagree with me, and you may too, Bri, but I just know from so many people’s experiences that, an inheritance is not something that we should take for granted and that we should actually prepare for emotionally if and when they ever come through.

Dr. Jay Zigmont, CFP®: Yeah, I think the hard part is, I mean, I can list a pile of clients that said, yeah, I’m gonna get something in the future, but I don’t wanna plan around it. And I’m like, help me understand what something means. And most of the time when they say that just off the cuff, I’m gonna get something, it means five or $10 million. We’re not talking like, I’m getting a car. Life changing money. And then what they’ll say to me is, well, but I don’t wanna plan around that. I’m like, okay, cool. We don’t assume you’re gonna get the money. ’cause there’s a whole bunch of things that can happen. But to tell me we’re gonna ignore five or $10 million, that’s gonna take your net worth from a million dollars to 10, that is just not realistic.

So how do we find that middle ground of being appreciative for whatever’s coming? And I think in this current and political cultural environment, inheriting money, the nepo babies, all that. Like there’s a lot of baggage that comes with that. And if you haven’t actually faced it before the money drops in your lap, it’s hard. I’ve also had the same type of thing happen where people are in a tech world, their company does really well, what they thought were stock options not worth anything, all of a sudden are worth a boatload of money. It’s the same problem of like, how is that gonna change your identity? And how do you look at it? And if you haven’t actually done any of that reflection when it happens, it can be almost as hard as like losing money, which sounds wrong, but like sudden wealth and sudden loss are flip sides of the same coin.

Maddy Roche: Fascinating. Bri, what are your first impressions of this story?

Bri Conn, CFP®: I mean, I have seen this story throughout and so to me it is interesting how people perceive it and the different things and just conversing with the people who were like, oh yeah, I didn’t pay attention to it. ’cause it’s a small amount, but, oh, it’s not a small amount. It is a thing to take and process deeply and understand, and I am very much of the don’t count on it, but you need to be ready for that emotionally as well, because otherwise it can take and really jar your life as you go through.

Maddy Roche: And it’s interesting also that without a planner, without someone that can really provide you the numbers and the examples and the scenarios and prove to you that this amount of inheritance is a life changing amount. Some people might just be stuck with a huge amount of money and then never change their lifestyle about it. Still carry stress. Scarcity with them. And I’ve seen it play out over and over and over again where people have a level of wealth that could and should change their lives. They could leave their jobs, they could buy, as you guys joke, the organic blueberries. And they don’t, because there’s still so much fear around the money going away or them just not really having a deep understanding of how investments work and how, you’re able to withdraw a certain amount every year and it not really touch the principle.

This is where I just encourage our audience members to have a professional in your corner because inheritance and windfalls are some of the biggest planning opportunities there are, but there’s also this huge opportunity for behavioral coaching and behavioral support on how do we actually look at this and help you understand, that this is in fact a life changing amount of money. Because the worst case scenario is that you get an inheritance and you continue to lose sleep and you live with a nervous system that’s just dysregulated and you’re uncomfortable with the level of confidence you can have in your own financial picture. So I just encourage folks to find a group that can support you and Childfree Wealth®, of course, can work on that.

Dr. Jay Zigmont, CFP®: And you’re on the right page. I met with a client last night who, for whatever a reason, has a boatload of money coming in, like big numbers. And their first reaction was, well, I don’t like rich people. And I’m like, well, you are now. That is you. And by the way, I’ve had this with inheritances, with tech, this is a common thing. And they’re like that your identity just switched. Now what do you do with the money? But the other part of this is if it isn’t an inheritance, the thing I watch out for a lot is true generational wealth often comes with generation skipping trusts. Where the money’s supposed to go to your kids. Grandma’s giving you money and it’s a generation skipping trust and you are not having kids. It breaks the estate system big time. In California, they actually have a decent system of how to go to court and prove you’re not gonna have kids. But I’m deep in the south. I’m not sure what the court would say if I went to them and said, Hey, I wanna undo grandma’s trust because I’m never having kids. I don’t think that would fly.

Maddy Roche: Can you explain that a little bit more, Dr. Jay, for those of us who are not super familiar with generational skipping trust. What’s actually the mechanism and what’s the scenario that it would be set up for?

Dr. Jay Zigmont, CFP®: . So very common. If you go to set up a trust, they’re really trying to set up, they call it dynasty trust. They last forever. Here in Tennessee, you can set up a trust that lasts for 360 years, and what you’re doing is the first person to get the money might get a small amount, and then the second person gets a amount and then the third and keeps going. It’s very common. The kids will get the interest from it. The grandkids will get the principal, something like that. There’s some type of structure where you’re splitting the money, but what happens is that has built into it an assumption you have kids. And now we get into the structure where it’s like, how do we change that? And I’ve had folks where, my client is not having kids, but their sister is, or their brother is or whatever. Does the brother’s kids get everything now? It starts making a lot of issues and you can fix that documentation, fix the trust structure while they’re alive. But once that passed and that trust is set in stone, it’s really hard because they’re not designed for Childfree people.

Maddy Roche: Fascinating. Any tips for folks that are listening in that maybe are thinking they’re gonna get an inheritance around how to check for that? Because that would feel like worst case scenario is you think you’re gonna get it and then you’re skipped.

Dr. Jay Zigmont, CFP®: Yeah, Bri and I have two episodes and we’ll link to ’em. We have a plan for parents that are broke and plan for parents that are rich. And it’s a complete divergence, but the best I’ve ever had was I went into a meeting as the financial planner for my clients and their parents came into the meeting with their financial planner. And we could all talk about, here’s the structure, here’s what we expect, here’s where it’s going. And by the time we were done, we were actually able to update their estate planning paperwork. Now mind you, the parents had to be willing to do that. But we’re talking about something that takes years to have that conversation, because your parents have been assuming you’re gonna have kids. And part of the discussion is like, mom, dad, it’s really not happening. And now you need to change your state paperwork. And sometimes that’s better with a professional in the room.

Maddy Roche: Yeah, really helpful.

Bri Conn, CFP®: Important conversations to have sooner rather than later if you can.

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Bri Conn, CFP®: Alright, we’ll go into the next story. She was running late. Not late in a meaningful way. Just the ordinary, irritating kind of late that happens when traffic decides to punish you for having somewhere to be. She was on her way home from work for a nap, something she did regularly. A routine, so ingrained, she barely thought about it.

She would pull in the driveway, walk to the bedroom, and sleep for exactly as long as she needed, except that day traffic held her up. She was annoyed about it the way you are annoyed about small things that don’t matter. When she finally pulled into the driveway, something was wrong. She couldn’t name it immediately, just that things looked different. The yard felt off, and then she understood why. The large pine tree that had stood in her front yard, the one that had just been there the way permanent things are, just there, was no longer standing. It had come down across the roof, through the bedroom, across her bed, the exact place where she would’ve been sleeping.

Maddy Roche: I’m speechless. What a horrible thing to have happen. One, I thought it was just that the tree had fallen and what a heartbreak that can be, just seeing a tree that you’ve loved all these years not be there. I grieve anytime I see an old tree have to be removed. I mean this, reminds me of a lot of the scenarios I’ve seen in life where these unexpected things happen. And there is no plan for that. You can’t plan for that. You have no idea your tree is gonna fall on your roof. You have no idea if you’re gonna have an electrical fire in your house or something like that happen. These are those, shocks from the universe that remind us that we’re mortal and alive, and that this is just part of the living experience. It helps connect us to others. I don’t know if I have any advice other than just, I give my condolences to this woman of just how hard that is to process, and I’m so grateful that she wasn’t there. Is there advice in this scenario, Jay? I mean, how do you plan for that?

Dr. Jay Zigmont, CFP®: Well, the natural disaster stuff, unfortunately happens all the time at this point. The weather stuff is weird. It’s also part of the reason why I like that I rent because seriously, if something happened to my apartment complex, we had a ice storm here, trees were exploding and things were breaking. Not my problem. But it’s different when you own the house. And the question there becomes do you have enough homeowner’s insurance to cover it and who’s it with? So I remember talking to this client and I said, all right, I’m listening to what happened and, you empathize, you work through the whole process and I’m like, you’re gonna be outta the house for 12 to 18 months. And they’re like, no way. And I’m like, Hmm, yeah, it’s gonna take that long. Because now the insurance company has to come and do the adjusting and then they have to come and they figure out how much it is. Then you have to get a builder, all these things. And it’s one of those things where you assume your insurance is gonna magically take care of it, and you’re gonna be settled again in a month. It’s not gonna happen. Where it becomes one of those opportunities of like, am I even gonna move back in this house? Am I gonna sell it? Am I gonna fix it up? What’s the cost? Does it cost more to fix it than the house value? All of these things. This is why when we do checkups, we look at your homeowner’s insurance and say, Hey, do you have enough coverage? And it’s amazing to me, and Bri, I’m sure you can weigh in on this, of how many times we look at people’s homeowners insurance and figure out they don’t have enough coverage.

Bri Conn, CFP®: It’s definitely more than you would think, although I have noticed that as we talk about it more on the podcast, more people are having the correct amount, so we must be doing something right there.

Dr. Jay Zigmont, CFP®: Yeah, and the answer by the way is you want 80% coverage of the home value. So if your house has gone up considerably and you haven’t updated your insurance, there’s a good chance that tree coming through could wipe out the entire house. And you might not even have enough money to pay off the mortgage. That’s the problem as kind of work through this. I think the other thing, when something like this happens, a lot of folks try to search for meaning or what did I miss? What happened? Should I cut that tree down in advance? It’s like, there’s no way to know. These freak weather things happen all the time, but how can you use that as an opportunity to kinda reset? Do I still wanna stay in this house? Do I want to move? Where am I going? What happens? And then the other thing you’re gonna find out real quickly is did the insurance company actually deliver what they promised? Unfortunately, there’s a lot of insurance companies that their prices are great, but I also can tell you that they’re big to fight with and they’re gonna be a pain in the butt to get the money out of. And that’s, something people don’t think about. We get house insurance, we get car insurance. We don’t think about actually having to put a claim in. And all of a sudden you’re like, oh, now I understand the difference between good coverage and good companies and not so good coverage.

Bri Conn, CFP®: Sometimes it’s worth it to pay a little bit more for the insurance if the company is better. All right, and now our final story. He had never been in it for the money. That was his thing about him. He chased titles and promotions for the challenge, for the satisfaction of being the person who could figure it out. Along the way, the company handed him stock options, little documents he had signed and filed and mostly forgotten about. He had been told they might be worth something someday. He had taken that to mean probably not much, but then the chatter started. Rumors in the office, something about an acquisition. The kind of whispers that are either going to be nothing. Or are going to completely change your life and you have no way of knowing which while they’re happening. He brought the documents to his financial planner. Routine check, probably nothing. It was not nothing. If he timed his exercises correctly, navigated the tax windows, worked through the meetings with his CPA and his planner, he would have more than enough to retire. He did the meetings, he did the waiting. He navigated the hurry up and wait grind of acquisition paperwork with the patients, that probably even surprise. He navigated the hurry up and wait grind of the acquisition paperwork with a patients that probably surprised even him. It worked out. It did not always work out. The difference in stories like this, is almost always the same. Someone who knew to ask the right question before it was too late, and someone else who actually had the answer. That is the end of our final story.

Maddy Roche: My first response is that I’ve met so many people over the years who just throw their hands up and are like, I don’t wanna look at it. I don’t know what it means. It’s just an administrative nightmare. I don’t wanna figure it out. And how that mental approach to your finances can really keep you in the dark. One, it keeps women traditionally out of control of their finances, which I’m passionate about having women have control of their finances. So you do need to, actually participate in what’s happening around you from negotiating the right salary to understanding what your stock options are. I think there’s a lot of overwhelm to some of these acronyms and offers and people just don’t wanna take the time to do it. And it’s amazing. I’m thinking back to a recommendation from my high school mentor. He said, apply for as many scholarships and grants as you can because it’s the fastest way to make money. You’ll never get a $10,000 something for an hour worth of work. And I thought, oh, that’s so great. And I think this is a really perfect example of that. If you spend a couple hours starting to learn about what your company has offered you here, you could end up with several millions of dollars and have caught the opportunities for the appropriate tax allocations and things like that. So I just encourage people really to despite the discomfort with it and how scary it can be, work with a professional and ask someone to help you navigate some of this, because you wouldn’t wanna miss out on these opportunities.

Dr. Jay Zigmont, CFP®: Yeah and I could talk about this one from both sides. So I made my first million, buy an IPO, I was working with a company, got stock options, got an IPO, made money. I also paid a giant tax bill ’cause I didn’t know planning, which is how it works. And I think when we work with clients on this, what they say is, that’s monopoly money. It’s not real. And I’m like, yeah but, it can be real. And the difference in good planning around stock options. We’re talking about millions of dollars of tax saved. And I don’t know about you, but anytime I can save taxes legally, I wanna do that. And the challenge there is, it’s a long decision making process where you have to figure out, all right, where do I think the company’s going and what’s my role? How am I gonna do this? What do I wanna invest? There’s a whole bunch of moving parts. And if you don’t do the planning when the company says, oh, by the way, we’re IPOing or getting bought or sold, or whatever it is all of a sudden, you have no choices. They’re all gone for you. And in this example of the client, what’s interesting is some of their peers are like, they didn’t do any planning. They just like, okay, I get a check and I’m like, great, you paid 20% more taxes ’cause you didn’t plan. And 20% on a couple million dollars is a lot of taxes. And we’re not talking about being shady around your taxes. I was having another client, and after you get your initial stock options, in some cases you could file one form with the IRS and that form, as long as it’s filed within 30 days, gets you $10 million tax free. Now mind you, the stocks have to go up to that, but it’s one form, but it needs to be filed at 30 days and it’s not a big issue. But did you file that form or not? By the way, if you ask me six months later should I file the form, I’m like too late. Sorry. And that’s the type of things that you need to plan around, especially if you’re in that tech world option, stock options, you might not have a large net worth now, but you have that potential. You need to have a plan around.

Maddy Roche: And this is another good example where, don’t be hard on yourself if you don’t understand all of this. This is just a perfect outsourcing opportunity, and Bri and I had a great podcast about how to build a team around you. I’m not a physical therapist, I’m not a massage therapist. I’m not a perimenopause doctor. But I get all those people around me so I can have their expert opinions about how to proceed through my life. This is a perfect example of, Hey, I don’t get it, so I’m gonna go find someone that does, and I’m gonna pay them to take care of me. And if you’re finding an advisor who’s a fiduciary, you’re finding an advisor who has a legal and ethical obligation to act in your best interest. And those are the teammates you want around you as you have opportunities like this. So don’t lose sleepover because you don’t get it. You don’t have to get it. A lot of this stuff is objectively, really complicated and you are not a tax expert, so don’t try to be, just hire one.

Bri Conn, CFP®: Exactly. I think you nailed it there, Maddy. So in this episode, it is really do the planning early, make sure you’re having conversations, and don’t be afraid to have a question and explanation from somebody if you don’t understand everything. Any other key points you guys might think of to leave people with on this episode?

Dr. Jay Zigmont, CFP®: I think the one I’m actually gonna ask the audience, send us messages. Do you want stories like this? Do you want to hear the good, bad, and ugly? Because we’ve got a lot of them. At some point it also feels like, do we really wanna share those and how do we find a balance? But we want your feedback.

Bri Conn, CFP®: Wonderful. Well, that’s all for this episode of Childfree Life by Design. Remember, intentionally choosing to invest in moments of joy is just as important as investing in your future. Until next time, happy designing.

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