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Jean Chatzky
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Heather Winston
Clarity is kindness, right?
If you can clearly outline your wishes, you're preventing confusion. You're preventing conflict among your loved ones.
Jean Chatzky
You're prepared.
Heather Winston
That doesn't matter how much money you have. It's just, you know, making sure that everyone understands. This was your set of beliefs, your values, and your intention.
Jean Chatzky
Hey everyone, I'm Jean Chatzky. Thank you so much for joining me today on HerMoney. Let me ask you a question. What happens to everything that you have worked so hard for? Your home, your savings, your memories, even your values after you're gone? For many of us, this is just not something that we think about every day. And when we do, words like estate planning and legacy building can sound intimidating, maybe even like something reserved for billionaires with sprawling properties and family foundations. But the truth is, this kind of planning is for all of us. Whether you're single, part of a blended family, a young parent just starting out, or a retiree thinking about the next chapter, you already have a legacy, and the steps you take now can make life easier, clearer, and less stressful for the people that you love. So today we're digging into the essentials. What documents should you have in place and when do you need them? How do you make sure that your wishes are honored while minimizing confusion, taxes, and tough decisions for your loved ones? And what does it really mean to leave a legacy, not just financially, but emotionally and ethically? To help us break it all down, I'm joined by Heather Winston, certified Financial planner and Assistant Vice President, Head of Product Strategy for Individuals within Retirement and Income Solutions at Principal Financial Group. She spent her career helping people think about how to plan for the future in a way that feels empowering and not overwhelming. We're going to take a very quick break.
Podcast Host/Producer Haley Pascalides
Back in a sec.
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Jean Chatzky
We are backed with certified financial planner at Principal Financial Group. Heather, welcome.
Heather Winston
Thanks so much, Jean, for having me.
Jean Chatzky
I'd love to just start here. So many people hear the word estate, quote unquote, and immediately think, that is not me. I do not have enough. Can you talk about why everyone, no matter their income or asset level, should.
Podcast Host/Producer Haley Pascalides
Think about planning for the future, whether they want to use that word or not?
Heather Winston
I agree wholeheartedly. It seems to be kind of a misconception that exists and has existed for a really long time, right? That somehow a state estate planning is.
This nebulous thing and that's what rich people do. That's what people who have lots of property and things really need. Estate planning.
But the reality is that planning happens.
For a multitude of reasons throughout our lives. And being able to make sure you're able to think about what happens when to your things, to the money you've accumulated, to your property, and quite frankly to your family, all of those things, they're still equally important, no matter what's in the bank account that you have versus what's not. And so when I start thinking about this kind of planning, it really comes down to three concepts.
And I think about them in the way that they shape truly what matters.
For the decisions that you're making. Right? So it's about your values, what really matters to you, it's about your intentions in terms of what do you really hope to accomplish and then your beliefs and how you see the world.
All three of these things, they work.
Together to help guide how you want your loved ones to remember you.
And at the same time, they help you make decisions about your future.
Jean Chatzky
Right?
Heather Winston
So thinking about these ideas can help.
You feel more confident and less overwhelmed when you're making a plan for what comes next.
Jean Chatzky
You know, when you talk about the fact that people don't have to have a ton of assets, a ton of money, a ton of property, I always come back to the fact that a will is the only document that allows you to name guardians for minor children. So as soon as you're a parent.
Podcast Host/Producer Haley Pascalides
That becomes an absolute necessity. And I continue, 30 years into doing.
Jean Chatzky
This sort of reporting to be blown.
Podcast Host/Producer Haley Pascalides
Away by the number of parents that don't have wills. So let's talk about the basic documents, let's talk about the key documents and.
Jean Chatzky
Every adult should have, no matter what. And then let's talk about the ones.
Podcast Host/Producer Haley Pascalides
That you need as you acquire certain things like a will, a health Care proxy, a power of attorney, why do they matter? When should you get them?
Heather Winston
It's a fantastic question, Jean, because I actually think there are at least four key documents and you just mentioned three of them. So first, wholeheartedly, I agree with you. A will is a must have a healthcare proxy, sometimes it's called a power of attorney for healthcare and a financial.
Power of attorney are all certainly important.
And then I'd probably also include a living will. Or sometimes, depending on where you live, it could be called an advance directive, right? So all of these are essential for ensuring that your wishes are respected and.
Your loved ones are protected in the.
Event you can't care for yourself or you pass away.
And so I always suggest truly, when someone is considered legally an adult, so.
They'Re 18 in most places across the.
U.S. although some states differ in that.
Definition, but they should really be thinking.
About, okay, who do I designate, right, to make medical decisions on my behalf, because medical emergencies, they can happen at any time, right? And so when you have this adulthood moment, right, you have that magical 18th.
Birthday, truly figuring out who is someone.
That they not only trust, but they.
Respect, that will advocate for their best interest, even if it's not life threatening.
Something could happen and you might not be able to actually speak or you.
Might not be able to do things like that. And so having that person in place.
Place can be super helpful.
Jean Chatzky
This is something a lot of parents should think about when their kids go off to college and often just don't. It slides by undone, but it should be among those forms that you have to sign when your kids go off to school.
Heather Winston
Absolutely. I think too when you, you've mentioned it a couple times so far.
But when you have dependents, it can.
Also be just as important to set.
Up a financial power of attorney, especially once you have any financial responsibilities, any.
Assets, things like that. So if you own a house or you're in the process of paying a.
Mortgage, things like that, right, you institute a financial power of attorney so that.
Someone can manage your financial life if you're unable to do so. Where a will really establishes how your.
Assets are given to others to match your wishes, that financial power of attorney.
Can become equally important. I always suggest that comes in especially at that first job and that time in someone's life when they start saying, maybe I'm going to save for a house. Okay, great. These are financial decisions and financial property you also need to be thinking about at that stage.
Podcast Host/Producer Haley Pascalides
How does a living, how does a living will differ from a health care power of Attorney.
Heather Winston
So it's a fantastic question, one that comes up a lot.
So when you start thinking about end.
Of life care, medical treatment plans, things like that, having a living will in place or an advanced directive.
Right.
Can help ensure that your wishes are followed and remove the burden of those decisions from friends and family, rather than forcing them in a very difficult moment to choose or to make a decision on your behalf. Right. That ability to just sort of say, nope, I put this in writing. More often than not, those documents have to be approved and filed. I know here, where I live, not.
Only does my primary care doctor require me to provide them an advanced directive.
But also most hospitals, things like that.
They want to know the minute that.
You'Re at that moment in your life.
They want to know truly what were your wishes? Not necessarily what someone who's advocating for you is saying, hey, I think Heather.
Would have liked to do X or Jean would have wanted to do.
Jean Chatzky
Yeah, it's so important. And if you move between states, you may need different documents in different states.
Podcast Host/Producer Haley Pascalides
And if you've got older parents and you're dealing with these issues all the.
Jean Chatzky
Time, and we've got a lot of.
Podcast Host/Producer Haley Pascalides
Listeners I know who are caregivers for their older parents, the living will I found in my experience with my mom was not sufficient that when she no longer wanted intubation, you need a dnr, you need a do not resuscitate order, you need to have that piece of paper. Not to go down a dark road, but it's important, and it's important to talk about these things and they don't get talked about. So I appreciate the chance to do it with you. We know that life is not one size fits all. So how do things shift for families that are blended or single parent households or. Or people who want to leave a portion of their money to charity. Can you walk us through how those conversations might happen?
Heather Winston
Sure.
So first, when I think about blended families, one of the things to consider for sure is how you're going to.
Clearly speak about your assets, your property, and who gets what. And it becomes even more critical to update any will you had before the blended family was created. Right. So being able to think through, okay, I know how much and what needs to go to my spouse, or maybe you have children from a previous marriage or stepchildren, all of those types of elements. The more clearly you can articulate that through one of these documents, the better you can avoid potential conflict among family members. And quite frankly, at a point in time where often and sadly it can really Destroy who remains when you're no longer here. I think at the same time, when.
You think about people with significant assets.
Or there may be a lot of people to account for, each partner might.
Bring children into the relationship. And this blended family think about things like a qualified terminal interest property trust. Now, it sounds really overwhelming. I get it.
Right.
But a Q tip gives you the ability to determine assets for your current spouse and preserving other assets for children.
From a previous marriage, for example. And so it's one of a myriad of solutions that are available to help in these blended family circumstances.
Podcast Host/Producer Haley Pascalides
Right.
Jean Chatzky
And of course, these are not things you would ever do alone, but these are the kind of questions that when you go see the estate planning attorney, you can say, I heard about a QTEP trust.
Podcast Host/Producer Haley Pascalides
Do I need that?
Jean Chatzky
Right.
Podcast Host/Producer Haley Pascalides
And you may find that they say yes, you may find that they say no, but at least you've put these options on the table.
Heather Winston
Exactly.
I would also add one of the things that we see most often, especially for, say, second marriages or households that.
Have stickier situations, if you will.
Right.
Is that sometimes the one thing that is overlooked or forgotten is updating beneficiaries.
And when I think about that, as a parent, of having two parents essentially in my family who were married for a very long period of time, then.
Divorced and one remarried, ensuring that the current spouse is named as the beneficiary.
Versus your, say, former spouse, pretty important.
Don't make those changes. Right. You're maybe going to be legally bound or whomever is remaining right to do that on your behalf. And it can create huge drama and challenges for people.
Jean Chatzky
It can get really ugly really fast. Because I think what people don't understand.
Podcast Host/Producer Haley Pascalides
Is the basic notion that the beneficiaries that you name on your life insurance policies, on your retirement accounts, beneficiaries trump wills.
Jean Chatzky
So you can say something in your will, but if you say it in a beneficiary designation, whoever you said in that beneficiary designation is going to get that money or get that property. So you have to get that. Right.
Heather Winston
Exactly. Now, you asked about single parent households.
And that goes back to that topic about why a will is so critical. So when you think about single parent households, right.
In your will, designating a guardian for.
Minor children to ensure that they are cared for by someone you trust, if.
Something should happen to you, absolutely has to be one of the very first things you do.
If you have money involved, if there are serious health issues that one of your minor children may have, things like that. There are varying Trusts that can be established to truly manage for the assets of your children or all the way up until they reach adulthood. Some can be used for even education or living expenses.
And so things like that are always going to be really critical. The other piece that comes to mind.
Right, is that healthcare proxies, financial power of attorney documents, they're still very essential so that you're naming someone you trust to make medical and financial decisions.
If you become incapacitated because there's not.
A spouse involved, there can be limitations otherwise where they may truly, in a scenario where you can't speak for yourself, they may just look to your spouse.
Or your former spouse even, right, to.
Be the one to provide your voice. So making sure those documents are up to date and written the way that.
Like, it fits your life, right. That's one of the most critical components.
Jean Chatzky
I get this question a lot from single people. I write a column for ARP magazine where I help people with real questions, real things that are going on in their life. And I get this question from a lot of older single people who don't have kids and are really struggling with this question of who do I name to make decisions for me? Because their siblings are getting older just as they are. Some of them have younger nieces and nephews or younger friends that they're comfortable with. But often it gets to the point where they wonder, should I name a professional as a trustee, is that something that is okay to do? What do you say to that?
Heather Winston
I think for sure you have to make the choice of who, whether that's an independent person, whether that's someone you really know and trust, regardless, Right. How you choose to do that and when you choose to do that I think matters immensely.
At the same time, it's really critical.
If you're choosing, say it's a third party that you don't even know, but you're counting on, say, an outside firm to designate that it's still just as critical to name that person or company or provider who may they are than it is to just leave that line blank, right? So you want to be able to ensure that people are truly aware of. There are lots of different options if you're setting up a trust, you can set up trusts to do all sorts of things, including, especially you mentioned earlier, this idea about charitable inclinations. And so when I think about that, that's also another option that people can consider, right? If they want to designate, say, a certain dollar amount or even a percentage of their financial assets to a specific.
Charity, all of those types of options are available.
And I don't know that everyone certainly of not only your listeners, but if we expanded it beyond this podcast.
Right.
I don't know that everyone realizes there are this huge myriad of options. And so some of it is just creating better awareness of. You can name charities as a beneficiary of your retirement account or a life insurance policy, and those types of things are common. It doesn't matter if you have millions.
Or if you have thousands. You can do all of those same things.
Jean Chatzky
It's such a good point. And for families that don't have a ton of financial assets, what is this future planning tend to look like? Can you just talk a little bit about how important it is to leave instructions and important documents that it's not really all about the stuff?
Heather Winston
Yep. I like to think about leaving instruction is quite possibly one of the most crucial things that any of us can do. Because one, it starts with something I like to think of as clarity is kindness.
Jean Chatzky
Right.
Heather Winston
So if you can clearly outline your wishes, you're preventing confusion, you're preventing conflict among your loved ones. That doesn't matter how much money you have.
It's just, you know, making sure that everyone understands.
This was your set of beliefs, your values, and your intention.
Right. And then even down to instructions for your funeral.
Do you want to be cremated?
You know, as morbid as it sounds, right. There are a lot of people that don't do that.
Jean Chatzky
Yeah. It's so kind. I mean, the word you used was kind. And you're so right. My stepfather left a manual. It was literally a manual that he said was a letter of instruction and suggestion. And it was so detailed. It told us so. We're Jewish, which means we. We have shiva after people die, which is a period where people come and they. They tell you that they're sorry, but they spend a little time and they eat something and they tell stories about the person who was lost. And he told us what food to order for the shiba. Right. He said, order the good trays for the shiva. And that was. It was just. It was so appreciated at a time when none of us could think straight. And so I think it's a gift when you leave instructions. Heather, we're going to take a very quick break. When we come back, we're going to just get into how we get into.
Podcast Host/Producer Haley Pascalides
Estate planning conversations with people who don't really want to have them. Back in a sec.
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Jean Chatzky
We are backed with certified financial planner at Principal Financial Group, Heather Winston. All right, Heather, let's get real for a sec. Talking to your kids or your parents about end of life, anything that can be really hard. So what's your best advice for getting these conversations going? Whether you're talking to somebody who is willing or really not.
Heather Winston
Yeah.
So it is a very not only necessary step, but to your point, you know, when you're doing this and you're communicating about, hey, I put together this.
Very thoughtful plan, not only does it demonstrate the love and care and concern that you have for others, not so much for yourself at that juncture.
Right. But, but I always advocate starting with empathy. It might be that you start by saying something like, I want to make.
Things easier for you someday, and so I want to talk to you about this. And then you can really be framing that conversation in truly a loving and supportive way. Try always to normalize that conversation.
Remind them that talking about these sort.
Of end of life plans.
Right.
It's responsible. And I've been in conversations where people.
It almost feels like they're telling you.
More about themselves than they are about what to do.
And I remember when, now granted, my father chose to have this conversation with me on a significant birthday that I.
Had in public in a restaurant with lots of people around.
I will encourage others.
Perhaps you don't want to do that.
But I think what he was trying to do was make it like a normal thing thing. And to be honest, in that moment, I didn't really want to hear it. It was like we're having lunch and there are like people roaming around in this space. And I just kept thinking I wanted a private conversation to me that felt more genuine. And in his mind, he thought, I'm.
Just doing this, like I'm checking a thing off the list and I'm going to have this conversation with you.
And it works for me, so it'll work for you. I think when you're the person communicating.
It to your children, to whomever you.
Consider part of your family, try to do it privately. Try to recognize signs of if someone's emotionally reacting to what you're walking into.
It'S okay to break apart the conversation.
And to keep it short and snippets and revisit it regularly.
It doesn't all have to happen all.
At one time because it can be really overwhelming, probably quite frankly, for both.
Parties or multiple people within the family.
And so if you're truly delivering this message, doing so in a way that genuinely honors that relationship is incredibly helpful.
And thoughtful at the same time.
Jean Chatzky
Thank you so much for sharing that story.
Podcast Host/Producer Haley Pascalides
I think it's really, really helpful and important. And I just want to say, from.
Jean Chatzky
My perspective, the first time I talked to one of my parents about this, it was just so hard. But the next time it was a little easier. And the time after that, it was.
Podcast Host/Producer Haley Pascalides
A little easier still because the ice had been broken and it just, you know, I sort of had some information. I didn't have all the information. And talking to my parents has helped me think about talking to my kids, which I have also started to do. Which brings me to my next question. When we choose the people to carry out our wishes, the executor, the health care proxy, somebody to handle your digital life, those are really big decisions. Why is it so important to make the choices? What happens if you don't make them? And do they all need to be the same person?
Heather Winston
So they don't all need to be the same person?
First and foremost, part of why this is so critical and they are big decisions is because, for example, if you don't name an executor for your estate, the courts are going to appoint someone to do that. If you don't name a health care proxy, typically the medical professionals do that.
Are treating you or helping you in.
That moment, or your next of kin are left to decide on your end of life medical needs, right? Well, they may or may not know.
You really well in order to be.
Able to do that. If you don't have a financial power of attorney, then a court may appoint.
A guardian, a conservator to handle your.
Affairs, which unfortunately for a lot of Americans ends up being both Time consuming and really expensive.
Jean Chatzky
Right. We do not want to be Britney Spears.
Heather Winston
No, no, not at all.
At the same time.
And you brought it up.
Which is such an important thing to.
Keep in mind when you think about your digital life.
Jean Chatzky
Right.
Heather Winston
Ensuring that someone knows how to access those accounts, how to get and download, say, pictures that are on social media.
Or access to online banking.
Things like that are always going to.
Be really important to be considering because.
Otherwise, without any clear instruction, the people.
Left behind may not be able to actually access anything.
Jean Chatzky
I'm going through this right now, Heather. This is my mother's. This is. And there are tabs.
Podcast Host/Producer Haley Pascalides
There's tabs for financials and newspapers because, you know, you gotta cancel the newspaper and medical. And like all the things with all the passwords.
Jean Chatzky
This has been my.
Podcast Host/Producer Haley Pascalides
This little notebook with all the things and all the passwords has just been my bible. I'm just so grateful for it.
Heather Winston
Well, and as well, when you're.
If you're in the position of being.
Chosen as an executor for someone, it's.
Entirely possible that executor is going to uncover things that family may not have even known about. We learned when my grandmother passed away and she. She had numerous trusts and different things in place. She was always a planner by nature, and so she thought ahead about a lot, a whole lot. But what she didn't consider is how many accounts she had opened like 40 years prior to her passing on behalf.
Of all of us.
And none of us knew that they existed as her grandchildren until the executor was like, hey, by the way, here's this account and it's now transferring to you and you have these pieces in place. So truly making these types of choices, right is one of those loving things that we're able to do to make sure our opinions are still heard and that we retain some control in a process when we can't necessarily speak for ourselves. Right. We want to make sure that everyone understands truly what we're looking to accomplish and how it's going to. Going to work in the best way possible. And I love the notebook. The notebook is fantastic because truly, like when my mother passed away more recently.
Sorry, it. Thank you. It was truly difficult to find passwords.
And all of these things and she.
Even had a list.
But because we hadn't discussed it among myself and my sisters, we just kept finding new credit reports with accounts and different things. And I thought, great, now I don't know how to get access to that. And she didn't have it in her secret little spot with all the details. So it's probably one of the most truly and genuine thoughtful things as human beings we can do for another person.
Jean Chatzky
Yeah, absolutely. We only have a couple of minutes left, Heather, but I just before we leave and we've talked about so many of the important pieces, talk to me about legacy letters and ethical wills and the idea that you need to not just pass along your again, your stuff and your belongings, but you have to figure out a way to pass along these family stories and your values.
Heather Winston
Absolutely.
So I love that a you asked about this because I don't know that people understand. It could be something that you craft throughout your life just as easily as it could be content. You're pulling together and sharing with your family while you're with us.
Right. But it's really about what do you want to pass down, what do you want them to know about your life and your history and what you were thinking in varying moments? And it can be simple, it can be clean and easy. You can just jot down little thoughts. Many moons ago, I had a client who did that very thing. They took little sheets of paper and.
It was like, here's my latest thought for the day. And they just kind of dropped it in this big bucket that they had in their home.
And it was so helpful and quite frankly, comforting to the people around them, their family, myself as a professional that.
Was working with them to be able to know, oh, when their great grandchild was born.
It was such an amazing moment in their life to know they were a great grandparent. You don't get those thoughts unless someone.
Actually puts it in place.
And you know, as somebody who does a lot of genealogical research, quite frankly.
On my own family, I wish there were more of that. I wish that we knew truly what generations that came before us were thinking.
Doing what mattered to them, what did they value?
And we don't often get that chance. And so being able to, to leave some type of legacy documentation, if you.
Will, really does open up having that very clear intention present in the moment when you're no longer here to tell us all those great stories and all those great memories, we will leave it there.
Jean Chatzky
Heather Winston from Principal Financial, thank you so much for this amazing conversation. I think we've got a lot of listeners who are going to learn a lot of really important things.
Heather Winston
Yeah, absolutely. My pleasure.
It's always great to talk with Eugene.
And thank you for asking.
Jean Chatzky
If you love today's episode, please take a moment to leave us a five star review on Apple Podcast. Your theme back means the world to Me and if you're ready to keep the Money conversation going, HerMoney has three amazing programs designed to help you feel more confident and in control of your money. There's Finance Fix. It's our four week coaching program that helps you rethink your spending, find hidden savings and make smarter choices for the future. Our Pre Retirement program runs for six weeks and walks you through building a retirement strategy that's personalized for your next chapter. Finally, there's Investing Fix, our investing club for women. It meets every other week on Zoom. It is a supportive space to learn, ask questions, grow your investing confidence and build your profile portfolio. And your first month is absolutely free. These programs are truly helping level the playing field for women financially. I'd love for you to join us. Her money is produced by Haley Pascalides and our music is provided by Video Helper. Thanks so much for listening and we'll talk soon.
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EP 499: Estate Planning Is an Act of Love: Here’s How to Start
Date: October 29, 2025
Guest: Heather Winston, Certified Financial Planner, Assistant Vice President, Principal Financial Group
In this episode, Jean Chatzky and guest Heather Winston break down the essentials of estate planning. They aim to dispel the myth that estate planning is only for the wealthy and make a compelling case for why every adult—regardless of net worth—should have a plan in place. Through compassionate discussion, practical advice, and personal anecdotes, they demystify key documents, highlight common pitfalls, and underline that planning your legacy is an act of love.
For full resources and more episodes, visit HerMoney.