Why You Need to Talk to Your Aging Parents About Their Wills—and How to Do It Tactfully

Use this week's Money Confidential guest as a cautionary tale to help you start the conversation.

Photo: Sweety Wally Photography

Do you know if your parents have wills—and what their wishes are for who gets what? This week's Money Confidential guest, Drew (not his real name), a 26-year-old living in Texas, thought his mother, who had terminal cancer, had a will drawn up to let everyone know how to split up her estate. But when she died and no will was found, a battle began between his siblings and his stepfather over her estate. "She had a few little scribbles of paper of like, 'Oh, I leave my house to this child of mine,' but none of them were valid," Drew says. "So there ended up being no plan in place."

Drew and his siblings have already spent more than $15,000 on attorney fees in their battle over the estate, and they're still not close to getting resolution. "I fully expect it to probably be, like, over $50,000 whenever this is all said and done," he says. "I've drained a lot of my savings and I've had to pull from my 401k."

Money Confidential host Stefanie O'Connell Rodriguez tapped Cameron Huddleston, financial journalist and author of Mom and Dad, We Need to Talk: How to Have Essential Conversations With Your Parents About Their Finances, about the need to have these conversations as soon as possible.

Huddleston learned this lesson the hard way, when her own father died. "I have no idea what his wishes were because he never put them in writing," she says. "It wasn't until my stepmother passed away that I did get a few of my father's belongings and a desk that he used to work at that was really special to me."

Cameron Huddleston, author of Mom and Dad, We Need to Talk: How to Have Essential Conversations with Your Parents About Their Finances.

If you die without a will, your state essentially has one for you. And state law might determine that your money gets split up in a way that you don't want it to get split up.

— Cameron Huddleston, author of Mom and Dad, We Need to Talk: How to Have Essential Conversations with Your Parents About Their Finances.

Huddleston recommends making sure your parents not only have a will, but also a power of attorney that gives you or another responsible person the ability to step in if something happens. "If this document is not in place, then someone—possibly you—will have to go to court to prove your parent is no longer competent enough to manage his or her finances," she advises. "And this can be incredibly expensive. It can be emotionally challenging. It can take a lot of time. One person I interviewed for my book ended up spending nine months and $10,000 going through this process. And in the meantime, he was having to pay for his father's nursing home bills out of his own pocket until he could get access to his dad's bank account."

These can be uncomfortable conversations for families, so Huddleston recommends trying one of three approaches. Bring up your own plans that you've made (with perhaps a tie-in to how the pandemic has us all thinking about what could happen), mention stories you've heard, like Drew's, and how it has you thinking about their plans, or straight-up ask for advice, and use that as a segue into these important conversations.

"Keep the conversation going by asking more questions," Huddleston says. "But again, the key here is to make it look like you're looking for advice from your parents, because your parents are going to feel comfortable giving you, the child, advice. It avoids that role reversal that is what really trips up a lot of these conversations."

Check out this week's episode of Money Confidential, "My mother died without a will and I've spent over $15,000 (so far) trying to settle her estate," for more on how to broach these important topics with your parents. Money Confidential is available on Apple podcasts, Amazon, Spotify, Player FM, Stitcher, or wherever you listen to your favorite podcasts.



Drew: Whenever she first got the diagnosis to whenever she passed, I thought that we're all gonna work together. I never really imagined that I would have to face all these roadblocks.

Stefanie O'Connell Rodriguez: This is Money Confidential, a podcast from Real Simple about our money stories, struggles and secrets. I'm your host, Stefanie O'Connell Rodriguez. And today our guest is a 26-year-old living in Texas who we're calling Drew —not his real name.

Drew: I have six siblings. The oldest one is 45 years old and the youngest one is 19 years old. We grew up in this small town in Texas and money, similar to most people, it wasn't really ever talked about. It's considered rude. And my parents they were very lavish in their lifestyle choices. They bought this really big house. It was over 4,000 square feet. it had like seven bedrooms, and throughout my childhood, they just spent like tons and tons of money on renovations, and they bought jacuzzis, they bought new cars.

It didn't really like fully hit that they weren't really making as much money to afford all of these things until they actually got divorced. And I found out that both of them were in massive amounts of credit card debt, like tens of thousands of dollars.

Stefanie O'Connell Rodriguez: Did you have a conception of what tens of thousands of dollars of credit card debt actually meant at the time?

Drew: No. No. So I was 14 years old whenever they got a divorce and you know whenever you're a teenager, you think that like even a hundred dollars is considered like a lot of money.

So when I was 18, I went off to college and I just remember thinking how can anybody afford anything? Is everybody in credit card debt?

Stefanie O'Connell Rodriguez: After going away for college and graduating, Drew moved back home to live with his mother while he started look for a job.

Drew: We saw each other every day we were like really close because I would always go out to eat with her all the time and always help her with stuff. But then I got like another job where I actually moved out of the U S and to Thailand. And so I wasn't as close to her, being in different countries, different time zones. but one of the things that I guess brought us back closer together was she was diagnosed with colon cancer. And so I was like, okay I'm just going to like finish out my teaching contract here in Thailand.

And then I'm going to come back to the U S. But when she found out, they said it's stage four, it's terminal and they didn't give an exact like, estimate, like, oh you know, this is when you're going to pass. But they said like it'd probably be about like two to five years like that you have left.

Stefanie O'Connell Rodriguez: So given that this was a terminal disease, was there any kind of open discussion about the financial planning and estate planning associated with that?

Drew: Yeah, there was a little bit, but she was very secretive about money. She said like oh, hey these are like some of my plans of what I want you to do after I pass. But I tried to delve deeper into it, like, hey, we need to like plan this out exactly. We need to say like, hey, this, this thing is going here. This thing is going there. And she was like, yeah I understand. And I tried to get her to do that several times, but she was very secretive again about her money, her assets, and she didn't really want to talk about it whenever I tried to press her about it.

So she just always said oh, well, you know, it's fine. I have everything planned out. She had a few, like little scribbles of paper of like, like, oh, I leave my house to this child of mine but none of them were like valid. So there ended up being like no plan in place.

Stefanie O'Connell Rodriguez: Drew learned all of this just after his mother passed away, while making funeral arrangements and sorting through her things.

Drew: There was just mountains upon mountains, upon mountains of paperwork and it took us several days to go through all of the different papers. And we were just trying to find this plan that she was talking about because originally she was like, I'll put it in my dresser in my bedroom.

And then I look there and this moment of panic set in, because I looked in the dresser and nothing was there.

Stefanie O'Connell Rodriguez:Are there other things you're finding as you're going through the paperwork that you didn't expect?

Drew: Yeah, there was like a lot of surprising stuff that I found I found out that she had been married like a total of five times.

I found out that she had her first marriage when she was still in high school. So that was shocking. And then I found out about these assets that I never realized that she had.

It was also like a lot of confusion too. Just sitting there, going through all of this stuff, like why couldn't she be more forthcoming?

And not just like all the secrets that I uncovered, but just creating a will and making sure that everything was organized because something that people don't really tell you whenever like a loved one dies is that you're having to deal with all of this stuff.

You have your regular life responsibilities, you have your full-time job, your relationships and all of your miscellaneous, everyday errands. And then now this new big thing gets thrown into the mix and whenever she passed, I didn't cry at first.

It didn't happen until several months later because you have so much to do. I have to prep the funeral arrangements. I have to make sure this gets done. You almost have to schedule in a time to grieve. Like okay, well I have to do all of this paperwork first and then maybe I can like cry after 8:00 PM tonight, once I'm all done.

After several days of looking through the assortment of paperwork and realizing that there was no plan, people's true intentions started to come out.

My stepdad, her husband, who none of my siblings had ever had like a super close relationship with him, he started to get more reserved and he wanted to take control of everything. He didn't want to go through the process of probate.

He said that the two cars that my mom had, those were completely his, that we shouldn't get anything from them. He said that like any money that was left in my mom's retirement account, that that was all his, that we shouldn't get any of it. And he also said that the house that they lived in that we, like us seven kids, that we didn't own any of it, that the house was completely his and that he intended to take it fully.

Stefanie O'Connell Rodriguez: Did you wind up having to hire an attorney?

Drew: Yeah. Which that's another thing people don't realize, how crazy expensive it is whenever a person passes away without a will. He was like it's going to be $4,000 for the retainer. And I thought, 'Oh my gosh, this is so much money.' And that was just the initial retainer. So after about five months of him doing legal work, he said, 'Hey, here's another bill.'

So, yeah, like it was another bill for $3,600. So literally, anytime I'm working with him, even if I'm just giving like a phone call to him for like 15 minutes, that's like $88 right there. In total I had to pay the retainer up front $4,000. And then so far I've spent like $15,700.

And then I fully expect it to probably be like, over $50,000 whenever this is all said and done.

Stefanie O'Connell Rodriguez: And are you shouldering that cost alone? Are your siblings helping you?

Drew: That's another exhausting thing everybody seems to be broke whenever expenses come up. Most of my siblings, so like five out of the seven of us paid, like we each divided up that initial $4,000 retainer but all of the rest of the expenses I've paid for out of my own pocket, which is obviously really hard. I just I hate it so much. I've drained a lot of my savings and I've had to like pull from my 401k. I hate having to do that, but I basically have been shouldering most of the costs, like for all of it I never imagined that number one, that it would be so expensive. And then number two, that I would be like shouldering most of the costs.

I try not to think about it because it just makes me sad whenever I think about like how much money I'm spending on this.

But at the same time I can't just not think about it, so maybe like once all of the assets are distributed, like once the houses are sold and like any other money is distributed, that it'll all come back to me.

So I'll be on like level footing again. And I can put the money that I withdrew from my 401k back into it. So I'm optimistic, but I don't know. It's just everything in this process has been really unpredictable so far.

But I don't really have any, anyone to lean on, like anyone to ask questions like what should I do here? What should I do there?

Especially because I don't want to live in Texas. Like I want to move away from Texas, I want to do other things with my life. But I just feel like this probate process—it's just like keeping me like chained to where I am and it's hard for me to even plan anything out. Like I can't say oh, you know, I can save up this amount of money for moving and then I can move next summer or, or anything because like, I have no idea yet.

I expect it to take two years more, but I truly have no idea how long it could take. So I can't really fully plan my life because there's this massive thing that's causing me to spend a bunch of money. I can't fully plan out my financial goals. I can't fully just plan out my personal goals. I just really can't plan out anything at all. Like I just have to stay put and just keep signing the checks

Stefanie O'Connell Rodriguez: Roughly 2 in 3 Americans still do not have essential estate planning documents like a will according to a 2021 survey —which can lead to painful and costly consequences, like those Drew has been dealing with for the last few years.

So after the break, we'll speak to personal finance journalist and author Cameron Huddleston, about how we can talk to our loved ones about these essential documents and revisit our own financial plans, to avoid leaving our loved ones in a similar position.

Cameron Huddleston is a veteran personal finance journalist and the author of Mom and Dad, We Need to Talk: How to Have Essential Conversations with Your Parents About Their Finances.

Cameron Huddleston: There are actually two reasons why I wrote my book. One, my father died at the age of 61 without a will. And he was an attorney. He was in a second marriage. He should have known better. I have no idea what his wishes were because he never put them in writing. It wasn't until my stepmother passed away that I did get a few of my father's belongings and a desk that he used to work at that was really special to me. But we never had those conversations, never saw a reason to ask my dad if he had a will. I think in large part, because I just assumed that he did.

Then when I was 35 and my mom was 65, she was diagnosed with Alzheimer's disease. Again, I had not had any detailed conversations with her about her finances. So I suddenly had to scramble to get her in to meet with an attorney, to update all of her legal documents. And then I had to have conversations with her about her finances because I knew I was going to be the one to have to manage them for her as her memory declined. And I eventually took over managing all of her money as her Alzheimer's progressed.

And when I made that first step of asking her to meet with an attorney to update her legal documents, she said, "Sure." And this was really a great place to start, because meeting with that third party, that professional, that person who wasn't involved with our personal lives but who was approaching her as this unbiased professional saying, "Okay, now you've got these documents in place. You have named a power of attorney, that is your daughter, and she can make financial decisions for you. You need to go to the bank. That's the next step you need to take. And you need to take that power of attorney document and let the bank know."

So that attorney played sort of a guide for us. And my mother was willing to listen to the attorney because it wasn't coming from her daughter necessarily. So having someone else say, "You need to take these next steps," was super helpful. And then I did have to play detective a lot of the times because she was forgetting things. So it's a conversation that needs to happen, but I realize a lot of people don't have these conversations until it's too late.

Stefanie O'Connell Rodriguez: So given that this is a conversation that needs to happen Do you have any specific language or scripts that you recommend people use to get started?

Cameron Huddleston: You could say to your parents, "This pandemic has made me really think about the need to plan for emergencies." And maybe you could use yourself as an example, as some of the things you've done. "I've made sure I've started setting aside money in an emergency fund. I've made sure that I have life insurance. I've made sure that I now have a will. Mom and Dad, I'd love to hear what sort of emergency planning you've done just in case there is an emergency and I need to step in and help you." So that's one way to do it. You could use a story. Talk about someone you know.

Say, "Hey, I was listening to this podcast. And there was this woman who was talking about how her dad died at the age of 61 without a will. And it made things really difficult for their family." If you're really young yourself and just starting out, go to your parents for advice. And the key is by asking these questions about what sort of things you need to do at your stage of life, you're going to get insight into what sort of planning your parents have done.

So for example, you might say, "Hey, I just started a new job. Do I need to be contributing to my retirement plan at work?" And your parents might say, "Oh yes, you should definitely do that because we didn't save enough for retirement. And now we're trying to figure out how we're going to live comfortably in retirement." Well, that should lead to some other conversations. "Well, are you counting on social security? Are you planning on working longer then?" Keep the conversation going by asking more questions. But again, the key here is to make it look like you're looking for advice for your parents. Because your parents are going to feel comfortable giving you the child advice. It avoids that role reversal that is what really trips up a lot of these conversations.

Stefanie O'Connell Rodriguez: So let's say I get the conversation started. What are the things I need to make sure I cover in that conversation?

Cameron Huddleston: So you want to make sure you do take this slowly. You don't want to start grilling your parents for every detail about their finances. And they might not be ready to give you all those details, especially dollars and cents.

The key things you really need to find out are, do your parents have essential estate planning documents? A will or a trust, something that spells out who gets what when they die. Because if you die without a will, your state essentially has one for you. And state law might determine that your money gets split up in a way that you don't want it to get split up. So your parents need to realize this. And a lot of people think, "Well, I don't need a will. My family members get along great. They're going to sort it out." I can tell you that once money gets involved, family members don't always get along great. In fact, fights erupt, and people can end up in court. So it's important to let your parents know you need to put your wishes in writing. Please don't make us guess. Please don't make us figure it out, figure out what you want. You tell us so that we can honor those wishes, and so that a court will honor those wishes more importantly, so that it's not a judge making the decision who gets what. It's your will that's going to spell out who gets what or the trust that spells out who gets what and when they get it.

Power of attorney, this document I think is even more important than a will because a power of attorney lets you name someone to make financial decisions and make financial transactions for you if you're no longer able to. And the key here is to make sure your parents have a durable power of attorney. It goes into effect essentially right away. And it remains in effect if they become mentally incompetent.

If this document is not in place, then someone, possibly you will have to go to court to prove your parent is no longer competent enough to manage his or her finances. And this can be incredibly expensive. It can be emotionally challenging. It can take a lot of time. One person I interviewed for my book ended up spending nine months and $10,000 going through this process. And in the meantime, he was having to pay for his father's nursing home bills out of his own pocket until he could get access to his dad's bank account.

So this document is so important. If your parents think, "Well, why do I want to give you so much power now?" You just simply say to your parents, "Look, I don't have any true power until I have that document in my hand. The bank's not going to take my word for it. Get the document, put it someplace safe. And tell me under what circumstances I'm allowed to access it and start acting as your power of attorney."

The final document is an advanced directive. Spells out what sort of end of life medical treatment your parents do or do not want. You can also name a healthcare proxy, someone to make medical decisions for you if you can't. Parents need to have this in place too while they are still mentally competent. Because if mom has a stroke and you're the one who's going to have to make decisions about her care, you can't do this without being named her healthcare proxy. And if there's not a healthcare proxy, then you run into those situations where families are fighting over what mom's care should be. Do we keep her hooked up to life support? And we know from paying attention to the media that these types of things end up in really long, drawn out court cases and court battles that can last for years. So let your parents know these documents are essential. And if they don't have them, encourage them to meet with an attorney.

The next thing that you want to find out is how do they pay their bills? Are they paying them by check, or are they paying them by direct deposit, automatic bill payment? And the reason this is important is for emergency planning. If that stroke were to happen, if your parents were to contract the coronavirus, if there was a car accident, you want to be able to step in and make sure their bills continue to get paid if they are for example, in the hospital and can't pay those bills themselves, These are the key things that you want to start with. Do they have a life insurance policy? Do they have long-term care insurance? You want to find out about their retirement planning and what their retirement plans are. You want to find out all of the details if you can and ask them to write it down, if they don't feel comfortable telling you. Ask them to make a list, put it with those estate planning documents. And then again, tell you when and how you can access it.

If you don't have these conversations you can end up in court and you can end up spending thousands and tens of thousands of dollars trying to settle an estate.

Your listener it already sounds like he's really deep into it. I feel like if he were in the early stages, the best advice might be, "Well, maybe you just want to cut your losses here. I guess in a way, it depends on how much money he could potentially receive from the estate of his mother. I mean if we're talking millions of dollars, then perhaps the fight is worth it. If we're talking maybe all that's left is a family home and he wants to have access to that house that he grew up in, but the stepfather is reluctant to hand that over, it might be better to cut his losses rather than to go pull more money out of his own retirement account, to end up going into debt.

Stefanie O'Connell Rodriguez: Is there kind of an overview process of what happens and what you should do when somebody does die without a will?

Cameron Huddleston: Even if you have a will, in most states, you will still have to go through what is called the probate process. It is the legal process for dividing up someone's assets and settling their debts. So if your parent had a trust, a trust will allow you to avoid the probate process. But if you simply have a will, in most places, you do have to go through the probate process. It's just that at that point, rather than dying without a will and having the state law determine who gets what, the judge is going to look at the will. And in most cases, will divide up those assets according to the will.

If there is no will, then you have no choice but to go through that probate process. You can't touch any money, any of your parents' money. You can't sell the house, you can't touch anything in the bank until the probate process is settled.

So let's say mom died and she didn't have any sort of life insurance that you would receive as a beneficiary to help pay for funeral costs. You can't access the bank account until everything goes through probate. You don't have 5,000, 10,000, $15,000 sitting around to pay those funeral costs. So now, you're going to have to start a GoFundMe account, or you're going to have to reach out to family members and ask everyone to chip in.

So it makes everything take longer. And you've got family members who are going to come out of the woodwork. And really, it just leads to more arguments, more attorneys possibly getting involved. Cousin Fred gets an attorney, and sister Sally, and Aunt Sue. And everyone now is hiring an attorney so they can get what they think they deserve.

So having a will does make things easier. it's really best to meet with an attorney and figure out what option is best for you, best for your parent, whether it's the will, the trust, depending on the probate laws in your state.

But another reason to have these conversations is even if your parent does die with the will, you have to take inventory of all those assets. The court wants to know what your parent has. And especially because creditors are going to want to be paid back. And if you don't know what your parents have, it makes the process a lot more difficult.

And that's just not something you want to have to deal with when you are grieving. So the more information you have, the more things are in place, the easier it will be when you lose a parent.

Now I know that does not mean that you should ask your parents, "How much am I getting? How much are my siblings getting?" They don't have to tell you that. Like I said, the key is to know whether they had these documents.

People will still fight over things. I mean, people will fight over the smallest thing. And I think in some families, there's not going to be a way to resolve your differences. And you're going to have to get a third party to help. A counselor. If it's really bad, reach out to a social worker. Reach out to a family counselor who can help you.

Maybe reach out to the leader of the place where you worship, whether it's your pastor, your rabbi, a clergy member who can help.

But you know, unfortunately in some families, you can try all of these things, and it's not going to solve all of the issues. And at that point sometimes you might have to say, "Well gee, I really would have loved to have gotten the family home. But it's not worth it to continue fighting with my sister, my brother, my aunt, my uncle." You got to figure out what matters most to you at that point.

Stefanie O'Connell Rodriguez: Now speaking of trying to hire professionals, whether it is a mediator or an attorney is there something that we should be looking out for, something we should be asking when we are trying to hire these professionals?

Cameron Huddleston: Well, definitely if this has to do with estate planning, you do want to hire an estate planning attorney. Someone who specializes in this area of the law. That's the first place you want to start. When you meet with the estate planning attorney, you want to ask them what sort of experience they have in situations that are similar to yours.

Same sort of financial situation, same sort of family dynamic. "Who are your clients? What are your clients like? Do you have any clients who might be willing to provide references, share their experience with you?"

So certainly asking for recommendations from friends and family. Reach out to people who are older, maybe older family members who have worked with an attorney. That's a way to start.

I mean, it can be hard to find a good attorney if you can have some conversations with that person though before you actually start writing checks to them so you can get a feel for that person. And are you comfortable with this person? And can they speak to you on your level? Can they speak to you in terms you understand? If they're just going to speak to you with a lot of legalese, then maybe that's not the right person for you. Because you're not going to be able to speak openly with that person, because you're not going to understand what they're saying.

I really feel for your listener. He's in a really tough situation. But I do think it's the perfect example of why these conversations are important. And I understand you said that he tried to talk with his mom. And some people are just so reluctant. But let's revert to, "Okay. You don't want to tell me, put it in writing."

Stefanie O'Connell Rodriguez: So another thing is, it's not just about dividing potential assets among siblings. But it's also shouldering the cost of all of these attorney's fees among the siblings. So any thoughts about how do you get people on board to kind of pull their weight in the effort?

Cameron Huddleston: When you're talking to your siblings and family members, "I know you care about the outcome. If you truly do care, I would hope that you would be willing to help shoulder some of the cost. If perhaps it doesn't fit within your budget now, maybe we can set up some sort of payment plan. This is how much I would hope that you could contribute in total. And maybe you contribute $50 a month until we reach that total amount."

I've just heard so many of these stories about family members who are torn apart because someone really digs their heels in, and they're not willing to give an inch. And they are fighting tooth and nail so that they can hang on to the family home, or whatever it might be. And I hate that. I just hate hearing about families who are torn apart over money.

Stefanie O'Connell Rodriguez: I think there's also this idea that estate planning is something that's reserved for the ultrawealthy. What do you think of that?

Cameron Huddleston: No, it is not reserved for the ultrawealthy. I think it's just as important for people who don't have a lot of money to do this. Because again, it's going to lead to fighting. And it's especially important to have that power of attorney set up. Because if you don't have a lot of money, you are going to be more likely to have to rely on family members for that caregiving support. And you need to name someone you trust to be making your financial and healthcare decisions for you, because if you don't, someone might step up and try to become your conservator or guardian. And that might not be the person you want making those decisions for you.

Everyone needs these estate planning documents. It is not just for the rich. It's not just for the famous. It just makes life so much easier for everyone involved.

Stefanie O'Connell Rodriguez: Whether you're talking to a grandparent, a parent or a spouse about estate planning—or even working to get it done for yourself —you can start with Cameron's essential estate planning documents —a will or trust, a durable power of attorney and an advanced healthcare directive. From there, consider other potential needs like life and long-term care insurance, and how financial details – like how bills are paid and where and how essential documents can be accessed – will be communicated should loved ones need to step in on your behalf or should you need to step in on theirs.

Of course, these conversations aren't easy— so remember Cameron's conversation starters, like using a current event, a story like the one you heard today, or a question about your own financial planning to start digging into the details. An outside professional like an attorney or a financial planner can also serve as a neutral guide throughout this process. And if all else fails, remember Cameron's key phrase, "If you don't want to tell me, just put it in writing."

This has been Money Confidential from Real Simple. If, like "Drew" you have a money story or question to share, you can send me an email at money dot confidential at real simple dot com. You can also leave us a voicemail at ‪(929) 352-4106.

Come back next week when we'll be talking to a California based listener, who asks a familiar question – Is renting really throwing away money?

Be sure to follow Money Confidential on Apple Podcasts, Spotify or wherever you listen so you don't miss an episode. And we'd love your feedback. If you're enjoying the show leave us a review, we'd really appreciate it. You can also find us online at realsimple.com

Money Confidential is produced by Mickey O'Connor, Heather Morgan Shott and me, Stefanie O'Connell Rodriguez: O'Connell Rodriguez. Thanks to our production team at Pod People: Rachael King, Matt Sav, Danielle Roth, Chris Browning and Trae [rhymes with ray] Budde [boo*dee].

Was this page helpful?
Related Articles