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126: Understanding Multigenerational Estate Planning with Tess Brigham Part 1

The battle between the generations is real and seems to be everywhere. Yes, generational divides even play a role in estate planning. In fact, estate plans nowadays are built around more diverse and multigenerational families than ever before. In this new episode of Absolute Trust Talk, we are joined by psychotherapist and certified coach Tess Brigham, MFT, BCC. Tess specializes in helping young adults discover their unique life path to enter the world and make an impact. Join us as we discuss how the generations are defined, what makes each one unique, and how these factors influence estate planning.

Time-stamped Show Notes:

0:00 Introduction

1:18 Please join us in welcoming expert psychotherapist, certified coach, author, and public speaker Tess Brigham!

3:26 To begin our discussion, Tess lays a foundation by defining the various generations, starting with the Silent Generation.

4:58 Next, we discuss the Baby Boomers, who currently make up about 20-25% of our population.

5:53 Gen X: Raised on hose water and neglect, those born between 1965 and 1980.

6:57 Millennials have gotten a lot of negative attention, so we’re digging in to get a deeper understanding.

10:51 Finally, listen in to find out what makes Gen Z so different from the rest.

12:28 Here, we discuss some of the main things that determine generational differences. These include world events, parenting styles, research, and the environment.

19:25 Did you know that generational differences have a fairly large impact on estate planning? Listen in to learn more, especially regarding living situations.

28:14 In this episode, we delve into important details about the impact of different generations’ upbringings and how they influence certain estate planning decisions. We’re just getting started! Thank you, Tess. We can’t wait to continue our discussion with you in Understanding Multigenerational Estate Planning Part 2!


Madison, you wanted to start this episode with a joke along the lines of “A boomer, a Gen X, and a millennial walk into a podcast,” but we didn’t have a punchline or a story. Did you think of anything in the meantime? No, I’m sure the punchline will be the episode, probably. The episode, yeah. I did kind of look around. There are a lot of things that I wanted to talk about. Of those jokes, a boomer, a blah, blah, blah, blah, blah, walk into a bar – there are a lot of those jokes on Reddit. But they all seem to point toward the millennial has a PhD, but is the bartender. And the Gen X is already in the bar and they’re passed out drunk. So just putting that out there. We’re not finishing that joke.

Hello, everyone. I’m Kirsten Howe. This is Absolute Trust Talk. And here with me is Madison Gunn, my co-host. And we are going to be talking today about a state planning with multiple generations and trying to understand how those different generations behave and think.

With us today is my guest, Tess Brigham. She is dubbed the Millennial Therapist by CNBC. She’s an expert psychotherapist, a certified coach, an author, and a public speaker. Wow, she’s very, very well qualified for this conversation. She specializes in helping young adults discover their unique life path in order to go out in the world and make an impact. Her acclaimed one-on-one coaching empowers young adults to gain the confidence they need to create their dream life through concrete and actionable steps. She is a vital resource for those who are feeling stuck, uninspired, or uncertain about where they are in life. She’s got lots of keynote speeches and workshops under her belt on topics like creating a culture of empathy, even while working remotely, which is something that we strive to do, virtual leadership, emotional intelligence, and filling generational gaps in the workplace. She has helped literally thousands of people find their purpose and develop their confidence. She is a regular contributor at CNBC and Forbes. She’s been featured on the TV show The Doctors to talk about millennial mental health. She also has been featured in Oprah Magazine, New York Times, San Francisco Chronicle, NBC News, HuffPost, Insider, Yahoo News, Marie Claire, BuzzFeed, Newsweek, Real Simple… I could probably go on for most of the afternoon, but we don’t have time for that. Yeah. Yes, we are so honored and, and odd to have you here, so thank you. Thank you. Don’t worry, she’s not here to psychoanalyze us. We don’t have time for that. Little did you know! She’s doing that all the time, I’m sure. That’s the thing, you know, you can’t turn it off, as we know, being lawyers.

So let’s just start, Tess, with just a brief conversation about what the various generations are by name, by ages, and kind of what that all means. Yeah, so usually people are always very confused about “What generation am I in?”And “What am I?” And so I just want to go through, I’m going to give you the years and the name, and these are all the generations that are currently in the workforce right now.

So the oldest generation, which is what they call the silent generation or traditionalists – they’re currently about, the studies have shown about 2% of the workforce, I feel like that might be even a little bit lower. My father’s part of this group. He’s like one of these cuspers of that generation and Baby Boomer and at 80, he’s finally like, okay, maybe I’ll retire. Well, maybe. You know, he’s thinking about, “Okay, maybe I’ll retire.” So I’m not going to spend a lot of time on them because they’re not really in the workforce so much at the tippy tippy top. But, you know, this, the silent generation, they were born between 1928 and 1945. And their wedged between the greatest generation and the baby boomers. And so it’s just what you have to understand about them is this is a very small generation, because between the Great Depression and World War Two, it caused people to have fewer children. So these, you know, they are heavily influenced by parents that were in the Great Depression. So they’re going to see things very differently.

And they were coming of age with the big boomers, which is next, which is currently about 20-25% of the current population. These are people that are born between 1946 and 1964. So this, as we all know, is a huge generation, over 80 million. And these, these were the kids of the greatest generation and the silent generation. So it’s a little bit you’ve got a mix of, of parents in there. But you know, the baby boomers are heavily influenced by the Vietnam War, the Cold War, the Civil Rights Movement, the Women’s Movement. You know, there were the – and I know my parents talk about this, because they were in Washington, DC at the time – the Kennedy and King assassinations, like heavily influenced by what was going on in the world at that time.

And then the next generation is my generation, Generation X. And we always laugh because my generation always gets forgotten for everything. I saw this T-shirt the other day. It was great. It was like “Generation X: Raised on hose water and neglect.” That’s pretty much it. So born between 1965 and 1980. And so we’re about 40 million, a little less than 40 million. And a lot of us are children of baby boomers influenced by the Cold War, the Persian Gulf War, AIDS, the tripling of the divorce rates, and, you know, the start of MTV. And, you know, we were the first to have personal computers. That’s what was happening. But I think for my generation, we were heavily influenced, I think, by this combination of the Women’s Movement and more women going back to work, and a lot more divorces and being the kind of first generation of latchkey kids. And we’re sort of known to be very independent and that’s what motivates us. We want, you know, we don’t want anyone telling us what to do.

And then there’s millennials who have been talked about so much and they are currently about 35% of the current workforce, but this is just gonna get bigger. You know, they are becoming now the managers and they’re leading more. And these are people that are born between 1981 and 1996, another huge population of 80 million. And so what it is about millennials is that 40, almost 40% of millennials have college degrees and that’s the highest of the most educated group ever. But the flip side has been is that they’ve been really saddled by student debt. So they’re highly influenced by you know, by 9/11, by terrorist attacks, school shootings. But with parenting at that time, parenting became more child center focused. So what we have seen is that millennials have gotten a lot of flack for being, kind of lazy or entitled or needy. And some of this has got to do with the fact that their parents, there were just less kids and parents were more focused on their kids.

But it was also because millennials came of age when we had a lot of misinformation about why kids struggle. There was a lot of – in the early 80s – teen pregnancy and drug and alcohol use. And so researchers were trying to figure out, “How do we help kids,” and they falsely thought that Improving their self-esteem was the answer and so they thought well self-esteem is “Well let’s give everyone a trophy! Let’s give everyone a medal or an award, let’s get rid of red pens because red pens are too aggressive,” and this is sort of what led to a lot of what got millennials in a lot of trouble by the media is some of these things that they grew up with, because the problem was once they got into, “Well, not only was that wrong, the information was wrong, that’s not how you improve someone’s self-esteem by giving them a trophy.” But what millennials found, and maybe Madison can speak to this, is right, like once you enter the workforce, you’re like, this is very different. Like not everyone gets a trophy. They’re not giving out trophies here. So they’re really not helping you as much as it seems. Like it was a  – quote-unquote – “nice thing to do,” they weren’t really setting you up for success in that moment.

The interesting part too is I didn’t experience that. I experienced more of the Gen X side of things. ‘Cause I’m a Jerry millennial. You’re an older millennial. Yeah, I was left to my own devices a lot of the times. So I don’t, but my brother is seven years younger than me and he probably experienced the other part. So I didn’t, yeah, I definitely got the red pen. Yeah, I got the red pen. I got the notes home. I got the, you know, there was no, there was no sugar coating anything. Yeah. I was a child. And that’s the interesting thing.

And I’ll talk about Gen Z in a second, but that’s the interesting thing about the generations is, is a couple different things, right? One thing I always tell people that, you know, these are generality, this is general information about people. This is not who – I’m not saying this is exactly who you are, but when you’re born in that, it does make a difference. Whether you’re on a cusp somewhere, you know, I know with my own parents, they very much feel like Baby Boomers, even though technically they weren’t born during that time. So the cusp part, and then also with millennials, what I’ve seen in my own practice is just the differences between my millennial clients that graduated in 2008, 2009, 2010, and my millennial clients that were graduated in 2015, 2016, 2017. And while they’re part of the same generation, these are sort of two different ones.

And then this is, I think, what we’re gonna see again with Gen Zers. So Gen Zers are born between 1997 and 2012. They are around 67 million. And so these are true digital natives. They have no memory of life before the internet. They have very few memories of life before the smartphone if any. You know, they tend to be very well behaved, risk averse, high, high rates of anxiety. So some of the issues that we had before in terms of teen pregnancy and some of these things that were up have lowered, but the flip side of it is that less Gen Zers aren’t out dating and meeting people. Yeah, they’re not doing the things that got the millennials in trouble. Yeah.

Yeah. And while I think drug use is still high, we see what happens with kids all the time with fentanyl and what’s happening, right? But I do notice that, like, a lot of the kind of party drugs are gone and it’s a lot more people smoking weed all day, every day. Like it’s more even like the way in which kids rebel is it’s different. It’s more, yeah, like lonely and depressing. Yeah.

And so I – It’s that party time. Yeah, yeah. Retreat into your bedroom and – Well, and you can order it for delivery. Yeah. that’s true. It’s too convenient for it. It’s a lot different now. Yeah. You don’t have to go out in the streets to do things. You don’t have to leave your house to do anything anymore. Yeah, right. You can hang out with your friends at home alone. Yeah, with your friends. Yeah.

So, Tess, I mean, one of the things that I’m hearing you saying is that these are different. Generations differentiate themselves by the things that influenced them, maybe during certain primary or formative years, like the Silent Generation, where they grew up with parents who lived through the Depression and World War Two and all of that hardship. And I’m sure that influenced them a lot. But also I’m hearing you say, not just the things that happened in the wide world, but parenting styles and what was understood at the time about child development and how that influenced parenting styles. ‘Cause you know, we will always talk about, you said it for yourself – you were a Gen Xer raised on hose water and neglect. And the Baby Boomers, speaking as a Baby Boomer – so just in case nobody put these together, I’m a Boomer, Madison is a Millennial, and Tess is a Gen Xer. We also had what we would call free-range childhoods, you know, that there wasn’t anybody paying attention to – if we came home for dinner – that was expected, but that’s about it. So… But I know my kids. Oh my god, no, my Millennial children – I knew where they were every second of every day and that’s kind of a – would you say that’s a backlash or a swinging of the pendulum as a result of my childhood?  Some of it has been, right? So some of it is, a lot of Baby Boomers did feel like they weren’t, you know, parented or were a bit neglected by their parents and they wanted to have fewer children, right? Because they felt like “I’m part of a family, four, five, six, seven, like I feel lost in this.” So people were having less children and that just means that you have more time and energy to really focus on them. And so that part’s really important.

And also the other part was what was going on and what we understood about parenting and research. I mean, and parenting, it’s changed, it continues to evolve the more research we do and the more we understand, the more we can study our brains. Like, when they came up with all the self-esteem, stuff in the 80s, like we didn’t have a way of really studying this. It was taken from someone’s, “Oh, this is my theory. And so here we go. Let’s go with it.” So we have a lot more science to back it up.

And then there’s also the, there’s the technology and the piece of it is, is that yeah, if there were phones around when we were younger, then it would be different. I think our parents would be paying attention to us. I certainly do not feel like I – you know, my parents are great – I was not neglected at all. But because there was no way of them reaching me, there was no discussion around it. So there was a little bit of, “Okay, well, I can’t track her whereabouts anyway, so I’m not going to worry about it.” And it’s not, it’s not all, “Oh, remember what we were doing when we were that age? So we’re going to pay attention to what they’re doing now.” It’s not all that. It’s a combination of “I can also see exactly where she is and what she’s doing.” It’s a combination of the two.

Yeah. And I think that parents now, right, they’re trying to figure out how to find this balance between understanding and recognizing them. My kids are going to do things that I did and that maybe I’m a little nervous about, “but how do I not ignore it?” I think that was sort of the way it was, was like, “Oh, all kids are going to do this.”Let’s just ignore it and they’ll get through it.” And that’s really what changed. It started with Baby Boomers. They really wanted to have a different kind of relationship with their children. And it’s interesting to see that each generation has gotten a bit more comfortable, a bit more relaxed about what you talk about. And at the same time, we just live in this really weird world where everybody has a platform to talk about everybody else and comment on things and all of that. So that is, that’s really, that influences – I’ve seen a lot of it in Millennials, and I see it with Gen Z. And I, you know, you have to laugh because I think it was two years, maybe last year or the year before where the Surgeon General came out and said, “Oh, you know, oh, a lot of smartphone use for kids isn’t good.” And it’s like, “No kidding.” We all know that. Yeah, it took 10 years for you to figure that out. Finally, yeah, somebody official said it.

Yeah, and so now you’re seeing a lot of things come into place, right, that they’re trying to address that. So again, you’re going to see all these generations of, I guess the next generation after this is what, Generation Alpha, that’s how they’re calling them, like the little kids. So maybe their cell phone use and their smartphone use will look very different. Maybe we’ll react to that one. Yeah, we’ll have learned something. Yeah.

But just to go back to, you know, what influences you, I think that there is, when you’re young, everyone goes through – this is universal – we all go through a period of figuring out who we are what we want what life’s all about what, you know, “Who am I going to be,” you know, who to be in this world. How long that is for people is different. We do know that that period of time is getting longer and longer and longer for people. For various reasons, it’s getting longer and longer. But so that’s that core piece of like, we universally, together, we all go through that. Like we’re all human, we’re all part of that. What shifts us and what makes us different within the generation is just what was happening in the world and what were our attitudes about certain things during that time where you were coming of age.

And that’s hard to get away from because that defines who you are. And that’s what I try to teach people is that so much of this isn’t about “We all have to agree,” or “We all have to get on the same page.” A lot of it is we just have to understand each other. We just have to understand what’s motivating people what their situation was so that when you have this Baby Boomer who seems to be scared or worried about doing something It’s a little bit like, “Why?” You know, is it because their parents were more fear-based and that’s what they grew up with or did they, you know, or maybe they swing in the opposite direction because their parents were so fear-based. And so they were going to rebel against that or you graduated during the recession, you know, all of those things, right? Yeah, okay.

So let’s focus on estate planning for a minute. ‘Cause that was a good, really great background and sets up this conversation. And what you just said – so important. The thing that we have to strive toward is understanding each other because we cannot change the fact that we grew up during the period that we grew up during. And that’s our history and that influenced us – each of us. And some of us are still being influenced. But understanding each other and understanding where everybody’s coming from.

I’m going to put out there a common combination of parent and child because we do estate planning. So we’re talking oftentimes to the parent, planning for their children is what it really comes down to. And if we kind of pull this apart and focus on a common pairing, the Baby Boomer parent doing estate planning and they have Millennial children. Let’s talk just a bit about how their different attributes, the different influences that those two generations have experienced might impact this kind of planning. Okay so we’ve got, I, I see this – Baby Boomers with Millennial children – a lot of times we’re still seeing that the parents aren’t seeing the children as completely fully formed adults, even though they’re, you know, in their 30s. What do you think about that?

Um, yeah, I mean, it’s interesting because is it, do you get this, because I’m assuming you’ve been doing this for a while – So 10, 15 years ago, did you find that your clients normally saw their 30-year-olds as fully formed adults? Well, it varies. I mean, every family is different. But it does seem that when I’m talking to parents of millennials specifically, you know, they’ll often say, I’ll ask them, you know, “Are they live at home? Where do they live?” And if the child’s living at home, there’s some eye-rolling. If the child’s not living at home it’s like, “Yeah, hey,” you know, “We did it,” and we’re talking about kids in their 30s. Yeah, there’s definitely a lot more commentary from the parents. I guess that’s what I’m saying. We didn’t have conversations like that maybe 10 or 15 years ago. Yeah.

Well, and I think that one thing that’s changed, and this has changed, this has been like this for 100 years now plus, right? Which is the way in which we see children has changed, the way in which we, right? Once upon a time, you were about have a bunch of kids that were gonna do all the farming and, yeah, right? So I think as we become more of a technological society, that what we’re seeing is it does allow for young people to have this much longer time of finding themselves. So I think it’s a couple different things. I think the parents’ attitude about their kid is very different. They see their kid in a different way. They see them as a child and that “My role is to be your parent. And my role is to protect you and care for you.” And yeah, if they watch their kid being a kid for so long, it does influence you versus the person who has a kid who was an “adult” by the time they were 12. So I think that that’s a big piece of it.

I also think, because I talked to a lot of these parents, there’s a lot of shame and there’s a lot of judgment about this. And recently, I did a TED Talk and I spoke really to parents. And the first two things I said was, “This is not your fault and you’re not alone.” And this is the biggest thing that parents have to hear because there’s so much shame in terms of it’s only my kid living at home, even though maybe they might read the stats and realize that that’s not true. But as a parent, right, what is your job? Your job is to raise your child to be happy, healthy, and then eventually leave the house, right? So there’s a lot of parents that feel like they’ve failed already. They’ve failed. And so then there’s that feeling of, “is my kid ready for this? I’ve failed. I’m a bad parent. You know, maybe I shouldn’t give them all this responsibility.” I think, I think you’re getting a lot of that shame, you know, the shame that people feel. That’s really interesting that you call it shame because that would color how you feel about things and not maybe appreciating that the boomeranging is very common. You’re not alone. It’s very common.

It’s definitely dependent upon market conditions. Yes. I mean, it’s not in a vacuum. Yes. And you know, I mean, one of the things is we’ve all moved away from each other. This is why we feel so isolated. Once upon a time, people, right – they fell in love with someone that lived within a couple blocks of yourself, like you would marry that person. And that was when we had these communities and we had people living together. I actually, I was very lucky. I lived in – my mom owns her home in Berkeley – and my husband and I, we were supposed to live in my mom’s rental unit that’s attached to our house for a year. We were there 12 years. And I had my son during that time. And, but that was really, even though I felt a little bit like “Well yeah I pay rent don’t worry, I’m not a loser, I’m a grown-up,” at the same time I wouldn’t trade that for anything and I think that’s really, you know, my son got to get up every day and walk over to his Nana’s house with the very multigenerational living. Yeah.

So yeah, so what is this judgment that we have about our kids living with us or you know, building an ADU and having them live there with my mom getting older? I can see the importance. Like now I’m like, “Oh God, I wish I still lived there,” ’cause I’m constantly going back and forth all the time. It’s interesting that it’s – look, it’s almost, like you said – shameful if your kids are still living with you. But now we’re going back to that. Oh, but if I build an ADU and put my parents in there, it’s “Look, I get a tax credit and I look great because I’m not sticking them in a home.” Oh, yeah, yeah. But it’s not okay If I move back in with them to help me get a leg up. Yeah something like that. Well, and that’s interesting. People in my generation are looking at it not so much for  “I’m gonna bring my parents to live near me,” but “I’m gonna build an ADU so I can live in it and be near my kids.” Yeah, that whole multigenerational thing is becoming very attractive, but at the same time, as you said, there’s something in us that makes us feel like we’ve got to get the kids out of the house at some point, or we’ve failed. Despite even what maybe people want, do you know what I mean? I think people would like for their family to be closer. They would like these situations, but they don’t feel like they can.

But I think what we’re seeing now is, is that because people are living a lot longer, that’s one big problem, right? The thing is, people are living a lot longer and the care that they have in the amount of time. And I can also understand for people where you don’t, you know, your parents’ estate, do you want that eaten up with them? 10 years, 15 years of them being somewhere else versus, yeah, versus, you know. And we’re here in California. So housing is so expensive. I mean, it’s so, it’s unreal. So that’s the other part of it, too, is that I think a lot of times what I see a lot of is people are – especially in Berkeley, right? – people are passing their homes down to their kids. So there is that desire. to want to like give. You know, “I know you can’t afford a home. So let’s, here you go.” And, and again, that’s our own stuff, right? About what does it mean to be a successful person in this world and all these standards we have. Yeah. Right. Yeah. That’s interesting.

Our guest has been psychotherapist, coach and author, Tess Brigham. Thank you very much, Tess Brigham, for being with us. Thank you. Thank you for having me. So that’s all the time for this episode, but we are going to continue this conversation in our next episode. So be sure to join us. And we at Absolute Trust Council look forward to connecting with you next time.

Thank you for joining us today for another episode of Absolute Trust Talk Live. If you enjoyed listening in, then don’t forget to subscribe. You can find us on Apple podcasts or wherever you may listen. Thank you so much for joining us today.

Resources Related to This Episode:

  • A Will is Not Enough – Securing Your Legacy with Estate Planning Life can change in an instant. A will is not enough to be prepared. Get free access to our actionable E-book Guidebook #1 and start protecting your legacy today. https://absolutetrustcounsel.com/guidebooks/
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  • Get our free introductory guide to the most used estate planning tool, family trusts, and understand how we plan to help protect your family. Guidebook #3: https://absolutetrustcounsel.com/guidebooks/
  • Absolute Trust Counsel would love to offer access to our Incapacity Planning resource page: https://AbsoluteTrustCounsel.com/Incapacity-Planning/. We’ve collected our top planning information all in one place so listeners can find videos, guidebooks, blog posts, and a host of information with tips and strategies on implementing, planning, and protecting themselves and their loved ones.
  • We’re pleased to provide a library of e-books to address common estate planning questions and concerns in practical, easy-to-understand language. https://AbsoluteTrustCounsel.com/Resources/.
  • ​ASK KIRSTEN: If you’d like Kirsten to answer your question on the air, please email her at Info@AbsoluteTrustCounsel.com.

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