Fight Club at 55: Generation X Advisors and the Midlife Sucker Punch

When we were trying to find inspiration, everybody, a sequence of events reminded both Suzanne and I that we are squarely in the middle of Generation X in the financial services industry. So today's title of our podcast, and hopefully you'll enjoy this, advisors out there is, Fight Club at 55: Generation X Advisors and the Midlife Sucker Punch. I'll share with you that I'll be turning 55 years old this year and part of where we wanted to jump off our conversation was a reflection on how advisors in the cohort of being born in between 1965 and 1980 are at a really interesting space, both in our careers and what's going on with the market and what's going on with the financial institutions that we serve in the ways that technology has impacted our careers so far. And the impact of technology in terms of the backend of our career. So we're excited to be able to talk a little bit about that. Suzanne, of course, without re revealing your real age, give me some reflections on your institutional background and thinking about your part of being this cohort of professionals that are trying to find our way, career-wise, market-wise, and being able to serve clients in this cohort that we serve. What comes to mind when you're reflecting on your own path?

[00:01:57] Suzanne Schmitt: Yeah, so you're a gentleman and a scholar. I'm just a few years behind you.

Thank you for not making me tell how many years.

Yeah, so it's interesting Tom, having grown up in bigger institutional home offices and service of advisors and of clients, Gen X is so much the forgotten generation, and as I think about a lot of what I have seen and lived through from a home office perspective.

I think advisors, would really be well served to remember a few key things that have really driven, material differences and the way Gen X advisors and their Gen X cohort of clients is moving through life. And I have certainly dealt with many of these personally. Thing one is think about the number of major financial shocks we as experts have been through.

And from a home office perspective, so much of the emphasis is on proactive planning. And yet things like the .com bust and COVID and a few of the other major financial shocks, like the great recession we moved through together as advisory community, as home office community and clients. Those were not things necessarily that we could proactively prepare for.

So I start there because there's a really interesting linkage, I think, in the way we, from the firm perspective have talked about the ways advisors should engage their clients during crisis. And I don't think anyone, frankly, has done a really good job of connecting the movement of Gen X advisors and clients through crisis to job loss. And the impact that has had, particularly on Gen X's ability to save, but particularly the exposure that they faced on the healthcare front.

So I came across some equally startling research that about half of Xers over the course of their lifetimes have skipped medical care because of cost. And that is not something I think most advisors are adept at engaging their clients around. And I think from a firm perspective, most major firms haven't done a lot until recently in the healthcare space, so I wanted to put that out there as an anchor point. The second thing that I've personally seen is the inability to really articulate the impact of Xers who have been on this kind of pointy edge of the spear of moving through life, where they've become effectively responsible for self-funding their retirement, self-funding their healthcare, and self-funding multiple generations moving through college.

So I was shocked to learn that actually Gen Xers are carrying the heaviest student loan debt burden, and it isn't just for themselves, it's for themselves and their kids. That is another thing that I think home office has started to get a little savvier around. But this notion of how do you help clients make trade-offs when it comes down to you can either help your kids go to college or you can fully fund your retirement, and that is something I have seen in my own household.

Put it this way, it's an ongoing and spirited debate. And then lastly, this idea of sandwich generation, and this is something I think we have both lived personally is felt so acutely. It's something I have lived experience with, you do, but think about for a second, the fact that Gen X is self-funding pretty much everything.

They're carrying a significant portion of debt for their parents. So much so that it's eroded their emergency savings. And they've got kids who now for a reason of factors or reason of factors that are not necessarily their fault, are failing to thrive. I've seen stats lately about 80% of people that are looking for a starter job in a white collar community can't find those jobs because AI is taking over. So I offer that backdrop just to say, from my home office perspective, these are trends that are long tailed, well known, and I don't think we've done a great job as an industry preparing ourselves to address them as an advisory community or for our clients who are navigating that.

So I feel like the Debbie Downer of this conversation. But what's your reaction to that as an advisor who is living this and also who's got clients who are navigating this?

[00:05:58] Tom West: Well, I'm going to take your beat where I'm going to start with my experience, coming into the industry in the 1990s.

And then with reflection, start thinking about what I'm noticing about the market and how my experience as a 55-year-old going through the industry is really shaped by a combination of personal journey and then what I'd like to think is prescient observations about what's going on around me.

So as a Gen X advisor, it's useful to remember, I was one of many that came on the advisor side of things. Whether it's through brokerage houses or insurance, through cold calling before the do not call list came around in 2003. So for everybody that's listening, if you're too young to know or you're just old enough to remember, the Gen X advisors that basically are continuing to work in the industry that came through this cold calling gauntlet. We had to have been vetted and shown our ability to sell, for lack of a better way to put it. And be established enough in our career before the do not call list came up, and then institutions had to make very, very different decisions about how they were going to recruit, how they were going to cull their talent, and to be able to advance them in their career.

Because we were the last generation of advisors that sort of came on, that got thrown into the deep end without a life preserver. And we'll see who floats and who sinks. I think it's also interesting that, generationally speaking, whether I'm a Gen Xer person or an advisor, we were the generation that saw, let's speak for myself in the industry, going from analog to digital. And that tracks with what we see in our personal life. But professionally, we did have the advantage of seeing what amounts to be our professional productivity, hopefully, really launch with sort of the application of better technologies and the internet and the, emails, let alone Zoom and everything else.

I can say though that, when we're starting, just like you did, Suzanne, to turn our attention on what's going on with the market. We're living right now, we're recording this in what summer of '25. We're living right now in this screaming cauldron of outrage where everybody's yelling about something or other. And what's interesting is I haven't found who our generational voice is that's picking up the microphone and whether describing reality in an uncomfortable way or truth to powering for this particular cohort. And I was reflecting a little bit in some writing that I was doing about.

It's so Gen X it to be like, yeah, this is really bad for us and we're going to just shrug, because that's kind of what we do. That's, we're really good at shrugging. But I do think for purposes of this podcast, I want to actually encourage both institutions and Gen X advisors to lean in to some personal experience, professional experience that I think is going to be increasingly important.

And I think maybe potentially undervalued in this back nine of my career. I think that the Boomers get so much of the attention, sucking all the oxygen out of the room about, not inappropriately by the way, about retirement crises, healthcare issues, millennial kids that can't get into the housing market, those sorts of pieces.

I think that we need to understand as Gen X advisors, we're like generation one and a half, like we're not quite old enough to be ready for retirement and rolling out of our spot in the industry. Those are the younger Boomers that are in that space generationally, and I'm obviously making generalizations here. But we're also the generation that speaks Boomer the best.

I think that the idea of millennials and Gen Zs and how AI's going to be coming up. We're the ones with the lived experience that's going to be able to connect emotionally, to be able to drive, cogent value propositions for Boomers that are going through life where their expectations about housing and their expectations about healthcare.

It's going to be a big swing and a miss for a lot of us. I think that's the way that I was thinking about it. I was taking your track of personal reflections and then. Observations about what's going on around me. Suzanne, I'll put back to you. If you were going to give Gen X advisors, some self-reflection on skills, on talents, on experiences that they maybe can lean into, maybe in ways that haven't been appreciated for the path that you see ahead, where would you, coach them?

[00:11:26] Suzanne Schmitt: I think as a generation and that's, I have so many follow up questions for you, my mind is racing, but I think as a generation we underestimate, particularly advisors I've worked with over the years, our ability to make trade offs. So much of our life has been around making trade-offs, that were not necessarily between great options.

And I think that's actually sharpened generationally critical thinking skills. And that is a unique way Gen X advisors can show up for their clients of all ages. I think particularly leaning into how we have collectively moved through a lot of those financial shocks and had to in real time adapt to financial impacts, like the self-funding of healthcare and like the self-funding of retirement.

Those required some hard internal conversations and some hard family conversations, and I think to your point earlier, that's honed our critical thinking, our trade-off capability, but also our way to help frame for clients and their families how do you think about making choices in real time? What is the logic that you apply and what is the language that you use?

I'm going to play back to you, and that is, Gen X advisors speak Boomer really well. So I'm going to put in a way that question back to you, talk if you would, about what that means in real time as you work with your Boomer clients and as a, part B of that question, how do you lean particularly into that space around framing trade offs for your clients?

[00:12:51] Tom West: That's a good question. I'd probably say, the first thing is I guess the skills that I try to employ, I don't know that they're specifically personalized to Boomers, but they can be very effective for Boomers and everybody else. I'll tell you specifically what I mean.

Before going into conversations about trade offs, I always like to remind myself, and we've had a podcast about this, about when folks are confronted with a bunch of unpreferred outcomes, choices that they don't want, we know that psychology is going to take us to a place of paralysis. I'm not going to do anything since I don't like any of the end points of the paths in front of me. Most of the time decision making locks up and folks basically wait until choices are taken away from them because they don't want to take ownership of making the choice that is going to be disappointing. They have to make a trade off. I think that the technique that I use a lot, and I think Gen X's ability to speak Boomer, I think it has a lot to do with trying to engage clients that are facing trade-offs with reflections on their own story that brought them to this particular point in their life.

Mr. Smith, you've clearly had to make trade offs in the past. Talk to me about an interesting thing, like when you were early married or when you had your own family issue, or there was an addiction or an unexpected death or something along those lines. Walk me through what you were hopeful for, what you were able to accept, what you were disappointed by, what you learned from that inflection point.

And then what I do, Suzanne, is I listen really carefully to see if I can pull out from them principles, themes, like no matter what family comes first or always pay for education or like whatever it ends up being. And when I get those principles that the client is using in the reflection of how they navigated a different point in time where they had trade-offs, I will play that back to them as guiding principles to help you through this set of unpreferred choices right now. I think because I speak Boomer, I can push the nostalgia button a little bit easier. Maybe I'll make a point of reference about the oil shock or inflation or housing problems in the 1970s or, there's a handful of other sort of historical points of reference that sometimes I can get my clients to connect with a little bit more quickly. But that's a good question and the technique I think applies to everybody. But coming back to a theme that I've got, I think Gen X advisors in our ability to speak boomer can engage them reflecting on different points of inflection in their own life, how they navigated in order to pull out principles that you can then apply to try to get them better to take action as compared to freeze when trying to make trade-offs right now.

[00:16:19] Suzanne Schmitt: Interesting. So I'm going to, if you don't mind, stay on that for a moment. As you think about the sheer number of major financial inflection points, world inflection points like COVID, how do you think some of the crises that Gen X advisors have lived through and coached clients through, how does that change the way you, as a Gen X advisor engage your clients? The language you use, for example.

[00:16:45] Tom West: If you're thinking about all of these different inflection points, let's just talk about the market, for example, or COVID or, depending on your political stripes, what's going on right now with difficulties that the country is facing.

I think that as a Gen Xer, I think I can speak with some conviction of how many times we're at a point of history where this time it's different and everything is changing. And whether it's the internet or a pandemic or the global bond market falling apart, I think that we can speak with conviction about looking back and appreciating in the moment everything looks like it's up in the air and we can't do everything because history never repeats itself. But, then it does, and there is life on the other side of these big transition points and the idea of coming back to, what are some, whether the financial principles, family decision making principles, those sorts of pieces. What are the things that have stood through all sorts of different periods of time. Like I do appreciate one thing that the Boomers and greatest generation will remind me, that for example, all of the things that I've encountered probably don't add up necessarily to all the things that was happening in the country in 1968.

Okay, so we're not the only ones that sometimes goes through hard things as a generation.

I can say though, that our, we seem to be living as professionals and as people through a period of history where the inflection points feel like you have society around the world all pivoting to a very different direction, all at the same time.

I don't think that story is going to end. So I guess I'd come back, Suzanne, is I think that we can speak with conviction as Gen X advisors about how this time everything's different, and then being able to pull back a little bit and say yeah, but some of these principles still can be pretty consistent.

[00:19:02] Suzanne Schmitt: Yeah. Yeah. Well said. You touched on this earlier, but as you look at Boomer advisors that are rolling off into their own retirement, and you think about your cohort of Gen X. What are some things that are top of mind for you when you think about onboarding a younger advisor who might be coming out of school, and how do you think Gen X advisors can and should show up in really schooling up, especially in the art of client engagement, younger advisors who don't have those same life experiences and who frankly are going to have a very different professional life, with the advent of tools that are coming up through AI and that increased specialization, that makes them almost less knowledge workers and more relationship managers?

[00:19:46] Tom West: Yeah. Yeah. So there's two things when you're thinking about technology. Because this is basically my kids' age in terms of people coming into the industry. My daughter just graduated from college and will be joining me in the industry, which is really exciting and terrifying at the same time. So this is a question that sort of hits home for me.

There was a conference that I presented at, what was it, the Global Wealth Tech Summit or something like that in New York in the spring. There was a guy that said something that was really interesting. He was talking about if I was going to be giving advice for what skills and talents for new financial advisors to develop in the age of AI.

It was something along the lines ago of 10, 20 years ago, it was always EQ and good communication skills. And then, 5-7 years ago, it was like, listen, you're going to need to code. That's really what you need to focus on. And then 2-3 years ago is you're going to need to speak English really, really well to tell the code or the coders what the code needs to do.

And now with the idea that you don't even really need to speak English really well, to tell the code, to tell what do, what the codes, he made the reflection of it's back to emotional intelligence and communication skills and being supportive and whatnot. And I thought that was, I thought that was an interesting way to look at it.

I'll share with you that what I've done with my team right now. I did this earlier in the week. I found a handful of different prompts to put into, I figured initially at ChatGPT, and no, no client information or any of that sort of stuff is going in there, but what I wanted everybody to do was I wanted everybody to put their job description in ChatGPT to tell the AI how to start coaching.

I wanted them to put in company manuals. I wanted to put in their training guides, all of the CFP type of stuff, like jam it all in there. And then start asking it what are the things that you need to do your job better? And we're starting this experiment, Suzanne, and this is what I told my team and some of the younger people too.

Whatever's coming out of the other side of this very introductory exercise, I think people coming into the financial services industry need to know that's what you're competing with right from the jump. You are not competing with millennial advisors. You're not competing with CFAs and CFPs the same way that you were before.

This is an entirely new thing. And like we do know, and I'm a student of this, not an expert, but we do know about artificial intelligence that we, as humankind, haven't decided whether we're going to, we want to let it take control or whether we want to have it enhance the human experience.

And we haven't made the decision. In my mind, I think that we've got to have people coming into the industry bet hard on enhancing the advisor experience. And knowing exactly how those tools are going to be used are important. But this just comes back to the Gen X advisor. Think of how our roles and responsibilities are going to change in the next, so I'm like, Gen X is what, age 45 to 60 at this moment, somewhere in there. So what that means is we're going to be the generation that will be more or less the experienced leadership class as artificial intelligence really starts sinking into all of our institutions. So we're going to be the ones, and in a way, this is a really encouraging thing for our generation.

We might be the best generation to be in that spot because we will have been the ones that went from analog to digital. We will have been the ones that got squeezed from two generations in our personal lives and in our professional lives. And would probably, maybe some closing thoughts. I'd probably get our Gen X advisors that are listening to this to start thinking forward.

Why don't you just start asking your artificial intelligence what are the trends and where are the where, what skills, talents, and experiences are going to be most critical for the back half, the back third of your career. Of course a lot of it is going to be tied to retirement security and Boomers and healthcare and everything, Suzanne, that you and I have been talking about.

But that's how I was thinking about it. You had me start with what would you do with new advisors, but I wanted to put it back to those of us in the Gen X advisor seat and thinking about the years ahead that we've gotten the rest of our careers.

[00:24:48] Suzanne Schmitt: Yes, my "yes and" there is, I also think it's really important for advisors, those Xers especially, to make sure that they have a seat at the table as those institutional AI driven experiences are dropped into, or I should say, dropped onto their desktop because what I've seen time and time again is the best solutions are heavily informed by the folks that are actually using them.

And I think to your point, sounds obvious, often gets overlooked. I think to your point, Gen X advisors are in a really interesting position to translate that combination of their lived experience, they're extensive career serving boomer clients, and now triangulating into the AI that they are starting to cultivate familiarity and awareness.

All that to say, I think that is a really unique perspective to bring to institutional AI solutions and the way that different solutions get stitched together. So advisors get time back and actually get to focus on what brings them joy in their practice and delegate more of the administrative work and the low value work to well-informed AI solutions.

Really interesting.

[00:25:56] Tom West: Sure. Well, I'll bring the audience back to our title where we referenced Fight Club.

So I was trying to think about fun ways to think about Gen X. So Fight Club, one of my personal favorite movies, Office Space, and The Matrix all came out in 1999.

So 1999 means that those of us in Gen X were out of high school and were going into college or the early chapters of our career.

So I thought it was prescient it that those three, those are like our cultural moment, right? Which, just the brief period of time. I always got a kick at about the idea that Tyler Durden in Fight Club, he completely outsourced his rage to an imaginary person before he blew everything up.

But there's something. About each of those different movies about institutions or environments that were changing and people didn't have a whole lot of control over, which I thought was interesting foreshadowing to I think the pressure that sometimes we as advisors or we as plain old Gen Xers is feeling.

But, I think that it's a good jumping off point to maybe say thank you to our audience, for how long that you've and, the support that you've given this podcast so far. We've got two things basically in store for you, everybody. One is we've got one or two more podcasts, which are basically going to be the highlights and the greatest hits of The Family Financial Conversation, which we've been lucky enough to be on this Advisorpedia platform. But we also want to foreshadow what our next project is going to be. And Suzanne and I didn't choose this idea of the Gen X Fight Club thing lightly. I'd like to invite everybody to tune into the next one or two podcasts before we wrap up to hear a little bit more about our new project of Longevity Strategists, which is going to be focusing a little bit more on practical tools that all advisors, but maybe Gen X advisors more than usual would really be able to use to make the most impact in their careers.

And impact on their clients' lives in ways that we haven't really explored, I think as an industry so far. So with that said, let me put back to Suzanne. Any final thoughts or wrap up on our discussion today?

[00:28:36] Suzanne Schmitt: I would add simply that I am excited, for a change, to be in this generation because I think that we are really in a prime position to make a really material difference to our clients' lives, to our family, and loved ones' lives, through the lens of our new project, which is coming up, heavily oriented around how do you make lives better and help more people age well with dignity, live independently longer.

And I think that no generation beyond Gen X knows better what clients and families are facing. So I am excited to be able to, in partnership with you and the team, drive that vision forward and offer practical solutions that we think will be particularly resonant with Gen X advisors. So more on that to follow.

[00:29:18] Tom West: So.

to my Gen Z, millennial, Gen X, and Boomer friends in the audience, appreciate again your attention. Tune in next time on Advisorpedia for some of the wrap ups of our Family Financial Conversation podcast and look forward to our next project. We will be talking with you again soon. Bye-bye.

​

[00:29:44] Disclosure: Thank you for listening to The Family Financial Conversation podcast. Click the subscribe button below to be notified when new episodes become available. The information covered in the podcast represents the views and opinions of the guests and do not necessarily represent the views or opinions of Signature Estate and Investment Advisors.

Disclosure: Signature Estate and Investment Advisors, LLC is an SEC Registered Investment Advisor. However, such registration does not imply a certain level of skill or training and no inference to the contrary should be made. Securities offered through Signature Estate Securities, LLC. Member FINRA, SIPC. Investment advisory services offered through SEIA LLC.

2121 Avenue of the Stars, Suite 1600, Los Angeles, California, 90016. Telephone number (310) 712-2323.