Jill Schlesinger (3:09)

I am delighted to be part of the dimensional world in this way. I'm excited.

Kathryn Williams (3:16)

Well, I would love before we dive in and there's a lot here, a lot here to talk about. And as you heard me say, you know, this is such a critical area when you think about the skills and the aptitude that advisors need to have these days. But also what are clients and what are investors thinking about what's maybe creating opportunity, creating stress. I know you get lots of phone calls and inquiries in your show from folks that are tackling this very thing. But I'd love to start at really what I would say is kind of the heart of where we operate on, across all of that in our work with advisors. And usually this idea of your early experiences growing up are what informs your relationship with money. So when you think about your own upbringing, and we're going to start just a few years back here, how did that inform your perspective on money? What comes to mind when I raise that question with you?

Jill Schlesinger (4:11)

Well, first of all, I'm lucky that I was born into a family that had. So let's be clear, I was kind of born on second base. I wish I were born on third base. There wasn't that much money. But I was born in a very fortunate place. I have a very strange upbringing because my dad was a trader on the floor of the American Stock Exchange. He was sort of one of the early math head guys in New York who was trading derivatives. And so when we talked about money in our household, my father would really come home and like say, I made this much, I lost this much. My dad was a bit of a risk taker in his care and that definitely informed me and my sister. I had just two of us. And we always like to say that we're such wimps because we saw my father blow out of his trading account three different times in our lives. And so it's not like the same thing as saying like, oh, my dad was a compulsive gambler and he lost all the family's money because there was always a nest egg that was set aside. But there was a real roller Coaster aspect to the way that we understood my father's career. I think that just for me and family of orig origin story was my parents were very conservative in the way they spent money. My father was sort of crazy early on in his career in terms of risk taking. Became scared enough to say, I can't do that anymore. Settled down and was kind of very lucky. We also had this very strange situation where my grandparents, my father's parents had a few bucks. They had set aside accounts for us for college. And my father. And I really say my father. Cause I don't think my mother really had a voice in this particular decision, which may have been the dumbest thing or the greatest thing ever. My father turned over the checkbooks to these accounts to me and my sister when we were 18 because they were just plain old custodial accounts. And we had to write our own tuition checks to our colleges. And so, you know, I mean, I guess I could have blown it, but we got very much involved in taking over our own financial lives early on and understood what it was to be reckless with that and understood what it was to be respectful of that. My mother, for her two cents on the whole matter, was really just somebody who came from workers. And she always worked. You know, I guess most of her friends didn't work or they had kind of the mommy jobs in our neighborhood, which was a travel agent and realtor. My mother was a teacher. She was a special ed teacher. But then she ended up taking one of those mommy jobs. And she's like, I don't love this school vacation thing. I'm going to try to figure out something else. So we always were told to work. We had to work every summer. We did not receive allowances. We at. It was just like a thumbs up or thumbs down on getting the ability to buy something. And so that was kind of us. So, you know, we were. My sister and I are both. I think that we would both agree that we are sort of conservative, wimpy people when it comes to money. I probably would be wealthier if I took more risk, but it just wasn't in our DNA or in our learned behavior to do that.

Kathryn Williams (7:09)

And I can. I can absolutely appreciate observing both the way your mom, you know, felt operated came from. From her side of the family and your father's side of the family. Both of those would be equally informative. It's kind of shaping your disposition around that. So that's interesting.

Jill Schlesinger (7:26)

I also have to say one thing about my father especially. Cause you know, we grew up around People who had a lot of wealth and people who didn't have as much wealth. And I think that my father, because he sort of grew up a rich boy, was very unimpressed by money. We used to joke, we used to say, like, oh, we're sort of WASPy Jews. Like we had family that came over a long time ago. We'd been in the United States very fully assimilated. But my parents and my grandparents and even their parents were very unimpressed by generalized wealth. It was not an important thing. So I think when I became a financial advisor, you know, after being a trader myself, I think the thing that was very helpful to me is that I wasn't. I wasn't blown away by someone who happened to choose a field where they made a lot of money. It just was like, you could be a teacher or you could be a trader. You could be great at both of those jobs. One is going to make you a lot more money than the other. And I had no judgment around it. So I think that was the other piece that we really grew up. Not to revere money and not to look down on someone who didn't have as much. That was a very clear message in my family.

Kathryn Williams (8:33)

So that's that value system that kicks in alongside with whatever might be sitting in your bank account. The intersection of the two of those. So you mentioned spending time on the commodities exchange and then ultimately co founding. Co running an investment advisory firm, which you did for 14 years. And we could probably have a whole conversation because M and A is such a big topic right now. Talking with you about what, that, you know, some of the decisions. I actually am going to ask you a couple questions about that. But what led you to establish a firm and want to step into that registered investment advisory space?

Jill Schlesinger (9:09)

Clarification is the firm was already established. It was like a year or two old. And I came in right after that. FYI, I am not one of these people. I love these people who are so directed. I'm like the accidental owner. I never meant to own a company. I really didn't. I was a trader on the floor of the commodities exchange. I traded gold, silver and copper options for like four or five years. And as it turns out, like, I thought I was going to be a lifelong career. I thought I was going to join my father's specialist book or my uncle's specialist book on the New York Stock Exchange. I didn't. I left and I didn't have a job that was like. I didn't have a transferable skill. So I went up to where I went to college, which is in Providence, Rhode island, and was potchking around there doing stupid jobs here and there, and then met this guy who was. Came from the insurance industry, who was like, I just started a financial planning firm. I'm like, what really does that mean? Like, I. I literally, you know, and I come from an institutional bias against the retail business. My father's like, ugh, you're going to be a customer woman. Like, that' sounds horrible. Like, why would you ever do that? And I sat with this guy. He says, just come to my office and hang out with me. For I'm in my 20s. And he was too. And he said, well, get permission and you'll see what I do. I talk to people about their money. So I sat with him for a day, and I was like, this is pretty cool. This man is kind of half therapist and half planner, and that's kind of cool. I like what he's doing. And so that is how I joined that firm. And I learned how to become a financial planner. A year into the mission, he's said to me, you act like an owner, you should buy part of this firm. So I did. I was the person who was essentially learning how to be a financial planner. I knew the money side of it. I knew. I even. I didn't even really. I knew how to trade. I didn't know how to invest, but I learned it and I understood the concepts and I understood the macro. What I really found fascinating was just how emotional that work is. I just thought that that was like, to me, a highly therapized New York Jew. That, to me was like, that is something I can get into, like, people opening up not just about their money, but their hopes and their dreams and their fears. And I thought that was really compelling. Yeah. As I went along in my career, I think what happens when you're young is that you want, like, oh, you become a cfp, which I did, and you get all your designations, and you want to prove to people that you're not just a young kid, you're really smart. So you do these very long involved plans, which we did. And then you're like, nobody cares. What I realized was just how much this work was about helping people, as you said, through their transitions, helping people overcome some of their family of origin stories, helping people to just unclutter their paths, not to massively change things, but to point out to them there are a lot of ways to get where you want to go. And I thought that was really compelling. Work. And I really, really liked it. I had a great time doing it. And it was fun. It was fun and it felt important.

Kathryn Williams (12:38)

I was speaking recently actually with an Australian advisor and he said our goal every day is to simply help clients to remove the intimidation factor, whether it's on the investment side, the planning side. And I thought, you know, that's, that was, that was an interesting way to think about that because it can be intimidating even for, you know, for someone such as yourself, that you had more than a working knowledge of elements of the business, of the industry, but certainly engaging with clients. And yes, we've seen some Olympic level financial plans. And when I ask them which parts of these did your clients read, it's very hard to answer. So taking much like a dimensional here, taking the complex and how do you simplify it, how do you make it actionable as well too, I think is another important way to think about that. So I love that. So having spent time as an advisor, as someone who has your fingers on the pulse of the industry and are engaging with clients and professionals in the industry, what makes a good advisor? What makes a great advisor, maybe, I think is a better question.

Jill Schlesinger (13:45)

You know, it depends. In your introduction, you talked about meeting people where they are. I think what, what great advisors do is they meet their clients and their prospects where they are. I think they listen and I think they have empathy and I think they don't judge if you can do those things. Notice I had tied nothing about math in here. I had nothing about calculating retirement numbers. I think if you can do those things and then you can provide people with the steps they can choose to take to get where they say they'd like to go, I think that's great. But every client needs something slightly different, right? I mean, I had to get over the fact. I think one of the reasons I sort of flamed out in the advisory world, just like exhausted and somewhat cooked, is that I got overly involved with whether or not the client would choose the outcome that I thought was best for them. And I think that that was a very emotionally draining thing. I was like the over involved doctor. And you know, I had happened to have a few friends from college who were physicians and they would point out to me, you are like classically so over involved. You cannot maintain this pace. You cannot do this for every single person because you're gonna just be done. So I think that there's a lot of boundaries that you need to keep. And I think that many advisors, like, they're great cause they overstep the boundary, and they go beyond. But you also have to take care of yourself to make sure that you're not so involved that you are personally tied to that person's outcome, because people are people. You know, I remember early in my career, a friend of mine is a surgeon, and she would say, jill, do you know how many times I have to tell people, stop smoking. Like, they know they should stop smoking. I cannot get so connected to their outcome that, like, they're not smoking. And that's gonna be made. That surgery is gonna be a lot harder. If they're smokers, she's like, they know that. So you give people the best advice you can, but you cannot, like, get sucked down that rabbit hole with them. But, you know, listen, I think that one of the things that also became clear to me is that I didn't love owning a firm. As I said to you earlier, I didn't mean to be an owner. I am not a great employee, and I am not a great owner. What I'm really great at is delivering service to clients and delivering the goods. So right now, if my client is Katherine, I'm going to be great on this podcast. And if you are my boss, I don't know if I'd feel quite as passionate about that as a boss. I was not a great boss because, as someone pointed out to me, you're a great boss of people who excel. But that's not what a boss is. A boss has to be a great boss to everybody. And I didn't love that feeling. I didn't like. Again, sort of that same. Now you're going to see my own personal emotional flaws, which is I would get very worried about my employees in a way that was not healthy for me and that was not good for me. So now you're. Now you already can see, like, go get. Here's my shrink Bill to you guys all listening, which is that I'm so empathic that it can drag me down, and that's not good. So I had to recognize that, and that was really what led to me getting out of this business, because I think I would have kept doing it under the right circumstances. But I think that and learning that communicating with the masses is something I'm really good at, and that I could make a leap from giving advice to individuals in an office to giving advice and telling stories to people on television, radio, and in podcasting.

Kathryn Williams (17:33)

I really appreciate your comments and perspective on that. I'm thinking about how often, even at our Deals in Succession conference, which is all about M and A and even the succession planning piece. Of course, I sometimes joke. We have a room full of, you know, at least half of reluctant CEOs. You, you know, you got into the industry to, to take care of clients and now you've got bricks and mortar and people and tech and all kinds of stuff. And as you said, you have to be leader to all of it. So. And for sure, it's, it's a factor that's driving a lot of the M and A activity that we're seeing in our industry. And you know, I think in a really wonderful way, if you can get back to the things that you love the most, then my belief is that's where you then will be delivering the greatest value to your business, whatever that business looks like.

Jill Schlesinger (18:19)

Yeah, it's fascinating because, you know, I was at your women's group out in California, in Santa Monica. It was a phenomenal group of women. Just really a shot in the arm for me. Just a reminder of how many people are doing incredibly great work. And it was fascinating to me that some of the people who were there, people who had sold and then gotten back to their roots, like, here's what I like to do. I'm going to go do that. And that's so cool to be able to like monetize the thing you built and then go back to your roots and that is your next chapter. I think that is an amazing story

Kathryn Williams (18:49)

to tell and I think that's also an opportunity there if you are currently head of a business, CEO, Founder, G1, as we often sometimes refer to, to recognize that not just because of the size and complexity of the business, that you're going to need maybe two or three G2. It's not going to be a one to one transition relative to selling the business or transitioning the business, but also recognizing that all of the skills that are needed for a business that's of any size or complexity, you know, you may have them in one person, but do they want to hang out in each of those spaces on a regular basis that, you know what, what allows for your leadership team to ultimately show up and bring their very individually to whatever the business needs? I think there's a nice opportunity there if you're willing to think about it in that way as well.

Jill Schlesinger (19:41)

Yeah, absolutely. And it's funny, like, I'm an aging athlete, so I always like the idea of building your team and saying, like, what does this team need? Right. Like, I am great offensive player. I'm great on my first three steps playing defense, but I need a Real amazing defense woman. I need a great goalie. I need this, I need that. And to think about that critically and also to be honest with yourself about what you. Not just what you're good at, but what do you like. And there are other people who are probably going to be able to do these things as well as you. They may not be you. Because I think the thing that is often missed in the founder is like look, it's. It takes a lot of work to build these firms. And people who go through it, like I went through it myself, which is like, you know, you take it from three people and yes, you're cleaning the toilets, you're making sure that you're going to the stores and you're stocking this and you're doing this and you're holding the hand and you're.

Kathryn Williams (20:37)

And were you the one that took the backup tapes and put em in your purse or bag and took them home every night?

Jill Schlesinger (20:43)

I mean practically. I mean what I do remember is being there on Saturday afternoons after the. And we would have Saturday hours. No one had Saturday hours. We're like get them in the door. If they can come on Saturday, we'll have Saturday. And then meeting on Sundays going over cases with my business partner. And so it was a seven day a week job building something. And you know, G2 has a different perspective. They are not gonna be as gritty as you are building that and you. So for me I think that that was. I understood that. I think that we had a couple of people who were younger folks in the firm that I knew could take over. I just knew it. What they could not do was they could not make rain like me and my co and my partner. They could not. They were not built for that. And so in the next iteration, when I left the firm, cause I was moving back to New York, I was done with New England, sorry, Red Sox fans. That was enough. And I knew when I left, I said you need to hire very highly skilled salespeople. You don't need anybody. Like I was the chief investment officer, big deal. That's. Anybody can do that. And you can hire someone for marketing. You don't need to have that person who has all those skills. But you need salespeople. And I say salespeople not in a pejorative. I know some people think that's a terrible thing. But this is what we do, right? Like we gather assets. You're gonna have to sell your service and yourself. And so I think what's interesting about the difference between G1, G2 G3 is you learn what you need in each successive generation and you don't have to hire many yous can hire a few different people who can get you there. Yeah.

Kathryn Williams (22:28)

I've talked in a prior podcast with John Jones who's co founder of Brighton Jones and of the Seattle area and we talk about this need for that you need a technician, manager, entrepreneur and I can for sure tell you we're working with a lot of businesses that have transitioned. In some cases it's G2 going to G3 at this point, but definitely G1 and G2 and that entrepreneur piece, aka business builder is the one piece that's missing for sure.

Jill Schlesinger (22:53)

It's hard.

Kathryn Williams (22:54)

Yeah. And it's, it's also why we we just finished our Global Advisor study, our advisor benchmark study this year and we look at channels of growth and for the first time in my time, which I've, I've been a part of the study for about seven years now, it's the first time that advisors as a channel of growth has actually surpassed centers of influence, which is always number two after client referrals. Most advisors go through growth through client referrals. Not really shocking there and it's just a slight uptick. But we are super excited by that because it indicates to us that firms and businesses are absolutely figuring out how to build the muscle, create the capacity, really drive growth across the advisor's ability to get out there, to build their own network, to find their prospective clients beyond the client referrals or custodial networks or whatever it might be. And so we were actually, you know, we sort of geek out on the data anyway. But we were super excited about that move this year. I mean hopefully that that speaks to a lot of the organizations that are beginning to really tackle what you just described. It's really important.

Jill Schlesinger (23:55)

Yeah, it's fascinating to really understand that the growth of this industry and like what has happened and I think a firm like Dimensional has recognized that in maybe well before a lot of others. I really do. And I think that, you know, when you talk about M and A, I mean look, I, I had a strange exit from my firm in that I kind of had like a business divorce in some respects. So it was like an M and A. But it was driven by the fact I knew that I could not survive with this person as a partner as we. And like in, in any relationship people grow in different ways. And I think that there's also a recognition of hey, just because I started this company, that is not me. I have a Life. He loved the idea of being the CEO. I was like again, the accidental person who owned and I didn't. I was not connected to that. But I think that when you're looking at partnerships and who you were when you were 25 starting something, you're very different when you're 55 or 45 and you know your goals and your objectives might change yourself. And so that might lead you down a different path. I think the cool thing for me is when I like talk to some of the advisors who work with Dimensional is that there's like a like mindedness that's kind of beautiful to me and that's really appealing to someone who observes something from the outside.

Kathryn Williams (25:21)

Well, I appreciate you saying that. And for sure, from a practice management perspective, it's, you know, I could sort of joke and say that's why we have a job. But to your point, you know, we spend so much of our time, you know, helping advisors in particular, but also business owners. Think about what is your personal why it can be very easy to refer to mission, vision and values as sort of this kumbaya kind of a thing, but it actually like, it's just good business. When you get that figured out also, that'll test it. You know, when your value system gets a little tested because you've done some sort of M and A or some sort of, some sort of meaningful transition has happened in the business. Hopefully it's nothing but like that great feeling on the other side of it to know we know why we show up every day and it's been tested and it also shows up in how we care for our clients. So it's kind of what gets practice management out of their pajamas every day. Anyway, so you wrote the great money reset during the pandemic. You talk about it as a guide to getting real and building your best life. I feel like we've talked some, you know, we've just finished, you know, talking so much about what drove you for some pretty significant transitions in your own life. But what were you seeing at the time that, you know, when, when it, when you made the decision, I need to sit down and put pen to paper and really start kind of talking about this. What did that look like for you?

Jill Schlesinger (26:44)

You know, first of all, writing a book is such a dreadful process. I really, I'm not one of these people who I naturally can bang out 600 to 800 word articles all the time and blog posts. It's not a problem. But sitting down and writing a book is actually very difficult. I wrote a Book. My first book was called the Dumb Things Smart People do with Their Money. And that was basically like your first financial planning 101 kind of book. It was like a good entry point. It was a way for me to maybe distinguish myself in my background, you know, cfp, but now in the media, but a way to really level the field. Like, it's not actually about whether you're smart or dumb. It's just that we're emotional and really bringing that to the fore. So, you know, I started working at cbs. My transition was essentially that when I sold my firm, I had been doing, we had a radio show that we hosted, and it was a great way to drive business. And then I started doing television. And I have the really wonderful people who kind of coach me along and say, you should try to do this professionally. And so I was able to do it professionally. By the way, if it didn't work out, I was going to try to be a financial planner for somebody else who was a dimensional firm. By the way, I had been a guest during the financial crisis 2008, beginning of 2008, I was on some national television and someone at CBS saw me and they had me come on and do some on the set analysis and holding hands of people when the blank hit the fan in 2008. And so in 2009, I got a call and said, okay, come to CBS essay. So I, I joined CBS in 2009, which was a time of such great turmoil and so scary and sad, and people were losing houses. And what I can tell you is that during that time, I'm a woman born of crises. I was on a trading floor during the 1987 crash. I remember recessions very well. Again, I saw my father flame out and blow out of his trading account doing something stupid. But 2008, 2009 was a remarkable period. And it really was like people were freaking out. What should I do? What should I do? What should I do? What should I do? So fast forward to Covid and as the crisis unfolded, what happened for me personally was I was on the air a lot at CBS doing TV and radio, and I was hosting this podcast, the podcast I own separately, and the podcast is called Jill on Money. And that podcast at that time was twice a week. We, but my producer, Mark and I, he called me up one day and he's like, oh, my God, we have so many emails. People are freaking out during COVID It is insane. And at the very same time, Goldman Sachs was the sponsor of the podcast. They called me up and they Said, we're not renewing. We're done. We're done at the end of March of 2020. And so I was like, okay, well, you don't get to tell me what to do. So that's fine, you're out. And we went from that point. We were like doing interviews and interesting people. Aren't we smart? And then we were like, forget it. All I'm doing is seven days a week, we are answering people's questions about what is going on right now amid this calamitous period that people were scared about whether they're going to die and then they were going to scared about their money. So that's like two big factors. And so we went to answering questions every single day. Okay, now what are the nature of those questions? Like, in the moment, there is some what should I do? But what emerged about nine months into Covid was the questions started to shift very dramatically. And this is what I noticed. It wasn't what should I do? It was who am I and where can I go next? And that was a very different kind of question. And what we noticed was people were coming onto our podcast seeking permission to do something with their financial lives that they maybe had were bubbling in the back. But maybe with the pandemic, the reality, the fear, the time being away from your normal routine, it just came up, bubbling up. So now I'm gonna say something that sounds obnoxious, but it was true. I have a book agent, which sounds snobby, but it's not. Anyway, so my friend Brian, who helps me with write books, he calls me because you gotta write a book. I said, what do you mean? Like, the world's on fire. I'm not writing a book right now. I can't do that. So I told him, he's like, what's interesting? And I said this exact thing. I said, you know, it's like, not what should I do? It's like, who am I? It's like people are really rethinking their lives. In a moment, he goes, that's the book. And so that is the great money reset, which is people were seeking ways to make big changes in their lives, and they wanted guardrails. And so I just wrote a book which was about their stories. And some of those stories are pre Covid stories because, you know, when people get sick, when they get divorced, when they get married, like when there are these life cycle events, they are resetting in some way.

Kathryn Williams (31:36)

Yeah. Of which you. You had in your own family. We'll talk in a moment too yeah.

Jill Schlesinger (31:40)

And. And so what I was really interested in was saying to people, when you come on the podcast, I spend 15 minutes with you, and I do a mini financial plan. That's essentially what I'm doing. I'm not getting paid for it. So no one come down hard on me from any organizations. Right. So it's just. It's just guidance. And I just put that into a book. And I said, here are the questions you ask yourself. This is how you put yourself through the process and give yourself permission and figure out different ways to get where you think you'd like to go. Maybe you run. I mean, one of the beautiful things about working with an advisor is obviously having that scenario planning. I can't tell you how often someone would walk into my office when I was a financial advisor, ostensibly, by the way, I was like, we did a lot of work in the 90s. There was a ton of money being made, and people would start talking about, can you make more money for me? And I would say, probably not. Probably not. But I might give you some great advice that'll move you in a different direction. And so this is kind of like, to me, a bit of my. When you say, what's your why? My why is to give people permission to do what they want to do and not worry about what's going on next door to them, but to say, what are the different ways I can try to get where I want to go? I'll figure it out. Jill. Just map out three different scenarios for me and take me through what each one would mean, and that's kind of what the book does.

Kathryn Williams (33:06)

I love one of the. I think he was a caller. Mike, I think, is the name he has in your book. And he talks about. It's kind of a riff on that Financial independence, retire early, fire. And he referred to it as fine, which is financial independence, new endeavor. What does that mean to you? Or when you hear that, because it sounds like Mike was definitely looking for permission for. To make a transition of some kind. I think that's an interesting way to sort of package the thought process on it, if you will.

Jill Schlesinger (33:38)

Oh, gosh. Yeah. I mean, because remember, like, the fire movement was so big. I remember, like, interviewing these knucklehead young people, and they're like, I have a million dollars, and I'm 35, and I'm never gonna work again. I mean, let's see how that worked out. Maybe it's great. Whatever. That's not mostly which.

Kathryn Williams (33:51)

When my son said that, I mean, my sons are in their late 20s. I'm like, that would be fine as long as you account for mom retiring as well too. So.

Jill Schlesinger (33:57)

Yeah, exactly. And you know, I think what's always funny is that like that's the folly of youth. It's great. Like literally they're in my studio and I'm like, but where do you put your stuff? You're traveling the world right now. And they're like, they point to a corner, there's like two little duffel bags up. They're like, that's your stuff. And I remember my producer being like, there's no way I could do that. I'm like, there's really no way I would do that. But what I do think is fascinating is that we have different chapters in our lives. And listen, my own experience is that, you know, in spades. But what I think many people would like is to know when can I make a new choice in my life where I am not going to blow up my retirement, where I'm not going to blow up my kids education. And we sort of went out to the audience and said, what should we call that? Because we all sort of decided, I mean, obviously, listen, there's a filter, right? I don't have Marc Maron's podcast numbers. I'm reaching millions and millions of people, but my people are kind of like, who, like your clients probably. Which is like, I want to do what I want to do and like when can I get there? And I'm not looking to be so flashy. Okay. So we said it was financial independence was one key to this. And then having something else to do, what is that next thing? So is it new or next endeavor? And I think that I've like now just even this year in 2025, I have a whole new crop of people who are coming in, coming on the show, who are federal government employees who were offered a buyout or a retirement or they're getting their pink slips and it is happening before they had intended that to happen. And then we are once again in this cycle of what is that new endeavor? What is that next thing that you can do and what's so great if you're an advisor, it is like granting someone's greatest wish to say you've got the base, you've done the hard work, give yourself permission to walk into something else that is interesting, exciting, it doesn't have to be as lucrative, but it's something else. What is that next thing? You know, I just like a hat tip to my brother in law. Okay, so I have two brother in Laws. One my sister married, and one is through my spouse. And both of them are, like, incredible examples of this. And my sister's husband was the biggest silver trader on the floor of the commodities exchange. Yes. I fixed them up on a blind date. So let me just be clear about that.

Kathryn Williams (36:29)

I mean, sounds like a good sister to me.

Jill Schlesinger (36:31)

Fabulous. And one, you know, I'm doing my financial planning thing. He's doing his trading thing in New York. And he calls me up one day and he goes, I hate myself right now. I cannot be on this floor one more day. And so he ended up really doing some soul searching. I want to be a teacher. I want to be a teacher. I love kids. So he went back to school and he got his master's in education, and then he became a teacher. And then they put him through this cycle of, like, maybe you could be an administrator because he's so entrepreneurial. And he opened up a charter school, which he has done. So he's opened up a charter school, and he loves it. It is his. Why? It is incredible. And it's interesting because, you know, he walked away from an incredibly lucrative life with enough money to make this choice. And I remember running the numbers. I'm like, there's no way you can screw this up, Evan. You guys are gonna be fine. Like, you cannot screw this up. I guess if you started spending three times as much money. So that's one idea of like, wow, that's a passion project. But then I think of my other brother in law, John, who was a corporate attorney on Wall street who really was kind of fried by the time he was like, 62. He thought he was gonna work till he was 65, had an opportunity to take a buyout and ran the numbers, worked with an advisor. And I came to a really fascinating place, which is, I have enough money for us in retirement for me and my wife. I got everything set. What do I want to do to make meaning of my life? And it just so happens he's really terrific with old people. Like, he just kind of loves talking to older people. And so he started. He started to volunteer in a local hospital. And they were like, you should be in our chaplain program. You're a man of faith. You should be in our chaplain program. And so he entered this program, and when you're with him now, it's like a million miles away from being a compliance lawyer on Wall Street. He's like, I feel like I am the luckiest man in the world. I get to be with people at this moment of weakness. And I can provide comfort to them. And so what I think about these two stories and about what Fine means to people, it depends what it is to you. And for my brother in law, John, it was. I know that I had a different plan. This thing came up. Now what is my next chapter looking like? What is that next or new endeavor? And for my brother in law, Evan, it was really about, you know what? I am stopping at a point in my life I never thought I would. I thought I would have a much different life and a trajectory. But I do not like who I am in this job right now. I turned into something that is not particularly someone I want to be. And what can I do? Where can I go? This is a. Okay, so of course these two stories are like people who have means, right? So they're very lucky. But a lot of your clients are going to be very lucky people like that. If you open the door and have conversations like this, you would be shocked to find out what people really want in their lives and your job as the advisor, try to help them make it happen.

Kathryn Williams (39:46)

Yeah, well, and you're right, I think that there is a common belief, and it's not incorrect per se, that if you have a financial advisor, then you must have some sort of wealth accumulated. And in fact, there's actually a category of clients that are specifically called wealth accumulators because they're, because they're actually building that wealth right now. Some, some people refer to them as Henry's high earners. Not rich yet that's one group of clients. Certainly as an advisor, you're likely to be poised with a similar question or opportunity with all kinds of clients. But I am, as you were talking, I was thinking about, you know, if I'm an advisor listening today. And maybe I want to begin to unearth this just a little bit and really and maybe foster some conversation with my clients just to see where are they at. And by the way, as you know, you can probably relate or have seen this where it's. You have spouses sitting in the room, they may not be on the same page. And so how do you do that? You know, if someone's listening today thinking like, yeah, maybe what's of a couple, what's one or two kind of good questions I might ask to start to unpack this with my clients. What comes to mind?

Jill Schlesinger (40:57)

Let's pretend you're not Katherine of dimensional. Let's make up a different job for you and then we can role play and that's fun. That's one of my Fun things to do. Okay, so it's about time it got

Kathryn Williams (41:06)

inflicted on me because we inflicted on our clients all the time.

Jill Schlesinger (41:10)

So let's pretend you're Katherine and you know, let's just make it like, you know, you're an accountant or your lawyer or whatever, some professional, and you're mid career. Okay. You're in your 40s. And so I might say I like this even better. I knew you might. So you might, you might say something like, how are you doing at work? How's work? And you answer. Give me an answer.

Kathryn Williams (41:36)

I'm fine.

Jill Schlesinger (41:37)

That's exactly it. That is exactly the answer you're gonna get.

Kathryn Williams (41:40)

Yeah, that's a little bit of anxiety. But you know, it's, it's, it's really, it's really busy and you know, I'm working a lot.

Jill Schlesinger (41:49)

How do you feel about like just in general, how do you feel you're balancing that amount of work with just other things you would like to do in your life, whether it's your family or other things. How do you, how do you think about that?

Kathryn Williams (42:04)

I definitely don't feel like I'm balanced. I feel like I, if, if something has to give week to week, it almost is always on the personal side. So either my kids or my family, the dog or you or me, and it's not really ever pullback on the other side.

Jill Schlesinger (42:26)

Do you ever think, Katherine, that it might be helpful if we could look at your future in a different way? You know, we've always talked about how to do your retirement and you said you're gonna work till you're 62 or 65, whatever. But maybe we, what you think would be helpful if we looked at this is, you know, what you might be able to do, like from age 50 to 60, and do something different in that 10 year chunk, even if you don't even know what it is. But like, do you think that would be helpful to just look at that as a planning option?

Kathryn Williams (43:01)

I think it would because this I don't feel myself. I feel like it was my parents that marked to this. I'm going to work a certain number of years, even probably at a certain company and retire at a certain age. And that's ultimately, that's the only thing we're marking to. But I'm definitely feeling like I need to consider what could I do ultimately to serve that long term goal, but maybe make, if you can help me make some decisions in more of a three to five year increment, I think that's really compelling.

Jill Schlesinger (43:32)

Yeah, I Mean, look, the. And so now we're back to us. I think that the hard thing for the advisor is to sit still and don't fill the gap. Right. How do you feel about that? And you can talk to friends of yours. You gotta find someone who's a shrink and you'll find out how to like, sit there in silence and let the client fill the void. And you bet they'll surprise themselves. Most of them are gonna be like, are you out of your mind? Of course, I'm just gonna keep working till I'm 62. But I think you again, this is a permission structure. You're in this very special place in their hearts and minds. They are going to come to you. You're going to give them the permission to explore this for themselves. You're never going to make the decision for them. You're going to say, hey, if you are making $200,000 a year right now and you keep doing that till you're 62 and we'd like to blah, blah, blah, blah, blah, okay, everything's fine. Now. Did it ever occur to you that you may not make it to 62 because this balance being out of whack might prevent that. Also life might prevent that. So maybe we should try to figure out something you would like to do that you could do longer but make less money. What would that look like for you?

Kathryn Williams (44:56)

And I like the idea of advisors. I mean, look, certainly in all areas of my life, if I'm seeking permission, if I'm seeking advice, I usually go to people I trust. Right. And so, so to your point, you know, advisors and somebody listening today have built an incredible amount of trust. And we see that in the, in the global investor study, but we just, we just see it, you know, it's the, the one thing that could be removed so quickly if something, if you do something or don't show up in a certain way for clients, but when it's there, and it's there, by and large for, you know, most of your clients, it's a really powerful, that's why they're coming to talk with you. And so I think that there's a gift in that even if, even if you as an advisor don't necessarily know exactly. You know, maybe the fear is, well, what if they ask me a follow up question? You know, what do I, what do I do? But it's not about necessarily having the answers per se, it's about helping them think about it a little differently. Which I love that, I love that.

Jill Schlesinger (45:54)

Yeah. And you may not have all the answers, they may lay out a path that they can't achieve based on that. So this is like the, the. The spouse being there, right? And the spouse is like, okay, what is that going to do to my life? First of all, I don't know if I want that or I don't like there. So there are different conversations that can happen. You don't have to have all the answers, but you do have to be honest enough. If you don't. If you say, like, I don't know if you could do that. Like, sometimes we joke. Mark, my producer, will say to me, like, today you're Jill the dream maker. Tomorrow you could be Jill the dream crusher. Because there are times when people will say to me, what do you think? Should I. I really want to call it quits. I'm 57. My first thing is I'm like, you're too young. Because, you know, I'm older than 57 and I'm still working. But then also to sometimes say, I don't think you can do what you want to do. Here's how I think you might be able to get there. And that's okay, right?

Kathryn Williams (46:52)

Well, I think two skills that require just an incredible amount of fortitude, in my opinion, as an advisor, as a manager of people, even if you're running a business. One, being willing to, as you just talked about, sit in silence and not just fill the space. And number two, having the fortitude to do what we actually know from our data, actually even that clients want, which is a willingness to have a candid conversation and to speak truthful. Now, there's obviously in most cases, a right and a wrong way to go about that. But again, you know, just having the fortitude to lean into those difficult conversations is something that, you know, when, especially when we're talking to young advisors or established advisors that are responsible for young advisors, you know, they talk about, how do I build these skill sets? And, and that's an important one for sure, because we know clients value it. I, I certainly value candid feedback in my life. Most people do, especially if it's coming from someone we trust. But you've gotta be willing to, as you said, you could not be the dream maker one day and the dream crusher the next. But, you know, you've gotta be willing. You've gotta build that fortitude over time. When people ask me about skill sets for advisors, that's certainly one that I think about as well.

Jill Schlesinger (48:11)

It's interesting. I mean, I think that empathy and listening and, and you have to like caring. You know, it's very interesting. I was joking when Cain was interviewing me out in Santa Monica, your colleague Kane, and we were talking about how sometimes it's very hard when you have a client going through something very difficult. And I know that there are a lot of people who have discomfort with this idea of an aging client, a client who's been given a bad diagnosis. And I think another part of being an advisor is being present for all those pieces, all those parts that even the ones you don't wanna go through and you wanna make them go away. And somebody in the audience said, like, if you can't deal with death, get over it. And it's kind of true. It's like, you have to be there for people. You have to be willing to be on this journey with them. And it is an intimate relationship. So I think that you're right. It's like there's a sacredness to that. And I think when we. Going back to your question, like, what makes a great advisor is someone who understands that this is not a transactional relationship. Otherwise you'd be brokers in a wirehouse or selling a bunch of product. But if you're somebody who wants to be in these relationships where people trust you, and there's a great psychic payback for it, that you have to show up and be present in the good and the bad times. And I think that's another part of this, to be on the journey. And, you know, sometimes you have to remind people, like, it ain't all unicorns and rainbows. And sometimes there's some really crappy things that happen in life, and we're going to help you get through those, too.

Kathryn Williams (49:58)

One of my favorite quotes from your book, you say, people who succeed in making big, weighty changes in their lives manage to think their way past sources of resistance. They bring change about from within, often thanks to conscious effort on their part, spending potentially months or years even envisioning it, thinking it through in terms of any sacrifices or losses involved. And evolving as people in ways that support the change over time. They ask and answer tough questions about their life goals to arrive at a place of clarity. That probably was kind of weird for me to be reading your words back to you. That was great.

Jill Schlesinger (50:34)

I was like, that sounds pretty good. I like that.

Kathryn Williams (50:37)

Yeah. Who wrote that? That was really good. But. And so, you know, as we've been speaking and I'm thinking again, you know, if you're an advisor that has a client that, you know is thinking about a big, weighty Change of some kind. What do you see as maybe from a kind of a tactical, practical standpoint that sometimes gets a little bit overlooked, even if on the investor side or on that, on that client side when they're thinking about it, that they maybe need to give themselves permission to take into consideration.

Jill Schlesinger (51:06)

Well, first of all, I had remember very distinctly having a, a client issue, like with someone going through this big change around retiring. I mean, this is very late 90s story from a place called Texas Instruments, which is outside Boston. So we're in like the technology boom. And the husband was reluctant to do this, and the wife was like, I can't live with you right now, like, I don't like you. And like literally she's like not saying it out loud, but just like, you are so wrapped up in work that this is causing us great distress as a family. And I could see in his face she is actually thinking that she's gonna walk away from me. It was like a crazy moment. And I think that the weightiness of that and the noise in his head, which was about be there, we're making money. I finally have a million dollars in my 401. What are you talking about? Like all those other things, but to have a moment and to literally for me to say to him, do you hear what she's saying? Do you hear that? We can figure this out together. And I think that that's the other part, that we're, as an advisor, look, you're not the shrink, and maybe you have to refer them to a shrink, but you can say to them, we can figure this out. The three of us in this room and my back office staff, we can figure this out. This is not something you don't have to fight. These messages in your head, as you said, like your parents idea of what this was, your idea of what this was. And you don't have to extract every last dollar from this organization. We can figure this out. And I think that the tactical issue that's always missed is people need to hear that you can help them through this and that, like, don't worry about the math. This dude was an engineer, so much smarter than I am, okay? He could have figured it out, but he was stuck. And so we're gonna figure this out. We're gonna get you a few different ways to get where you wanna go. And I think that you have to listen to what this woman who's been with you for 40 something years is saying to you. And so the tactical part is to don't be afraid when the Spouse raises something to like, step in and be like, hey, that sounds like actually a pretty real deal. Like, she's pissed. And we have to figure out a way around this. So I think that's one tactical solution. I always think that the math is the easiest part of the job. Honest to God. They just don't. And it's easy and it's like you can carve it up. And the other thing that's kind of cool about the planning part and relying on your models is that you don't have to say that everything's gonna be great. You can say, like, if you're really freaked out about this, we're gonna use really terrible assumptions. We're gonna look at like, what's like the worst case, and we're gonna play that out for you. And so I think that a lot of people also need permission to say, it is enough. It's enough. It's okay. By the way, this guy left Texas Instruments and his friend didn't and the stock collapsed after the dot com boom and bust. And they were both clients of mine. And the guy who stayed said to me, oh, I should have done what he did. And the thing is that he was not emotionally ready to do that. He just wasn't.

Kathryn Williams (54:36)

Yep, yep.

Jill Schlesinger (54:38)

So I think that you have this really distinct, again, point of like the reality check. So that's sort of the math, but also the emotional check, like, hey, let's open the door. Let's see what is possible. That's the coolest part. Like, hey, we figured this out and there are different ways to get there.

Kathryn Williams (55:00)

So here we are in 2025, and it's certainly been an interesting year so far. That could be. Well, we could sit here for a whole nother hour or two and talk about that. But even in our work and in our data, we do continue to still see some of, I will call it sort of the impact of, of the pandemic. For example, we continue to see talent moving around in the industry. And one of the reasons cited can be a lack of alignment with in office work expectations as businesses, as some businesses attempt anyway to return to maybe five days or, you know, whatever, whatever that change might be. And certainly potential employees, candidates are asking about these kinds of things. So that to me is something that's an indicator that while we're five years out, there are some things that linger. What still is in play in your mind, particularly as you think about some of the topics that you tackle in the great money reset.

Jill Schlesinger (56:04)

So, I mean, it's very funny that you mentioned this. So yesterday I interviewed the CEO of a huge hedge fund called Man Group. And we were laughing because we were at another investment bank, huge event. And we were talking about this, about talent and about what that means, and we were talking about diversity. And we were talking about how she thinks it's, you know, she works for a 240-year-old company, she became the CEO, okay? She comes from a legal background, she becomes a CEO. It's very weird, right? She's a gay woman out forever, never in the closet. And I asked her, like, talk about diversity. She's like, well, we think De and I are very important. We are not watering that down because we think talent cannot come from one place. And I think that one of the fundamental issues from the pandemic was this concept that some people felt very shut out of organizations and the office. Not even politics, but like the rhythm of the office. And specifically, what I will tell you is that I heard from a lot of working moms who are like, hey, my life is so much better when I don't have to be in the office five days a week. And actually I'm a better and more productive employee. So this woman said the exact same thing. She goes, you know, we found out she has a bunch of quants who work for her. And I would like to just implant this because I know we have a lot of numbers people who are listening. She says, we have a lot of like engineer quants, math heads who work for us. And she goes, we did a fascinating thing that during the pandemic, we noticed they were logging on at all different times of the day and night. And she said, I do not want to be an organization that is shoehorning people into what we thought was the idea of a workplace when they're doing their best work or work day or work day, when we know that they did their best work from say, maybe 11 o' clock at night to 3 o' clock in the morning, and then they didn't log on again till 10 o' clock in the morning. She goes, what do I care? Now we. If you're thinking about your client business, I think it is fair to say that there are some clients who still want an in person meeting. Not so many anymore. Not so many.

Kathryn Williams (58:25)

A lot of people like, but not as many as you might think.

Jill Schlesinger (58:27)

Yeah, exactly. And so rethinking what the office of your office is and what that is providing to people and how you can really bring in the most interesting, productive, diverse workplace is important. If I hear. Cause I'm going to say this now. Get on my soapbox. If I hear another man say to me, I really want to hire a woman. Do you know any women? You know any good women? Yeah, I know like a billion good women. Okay. I got binders full of women, right? And you have to make a workplace that is amenable to the group of people that you are seeking to bring in. And just because I, and probably you, Katherine, grew up in a world where we were in the office five days a week, tough luck, that was the way we did it, doesn't mean that's the way it has to be going forward. And so one of the things that I think is a great outcome of the terrible pandemic is that we can rethink how we work and what we do and how we bring technology to the fore and how we are going to now bring AI to basically eliminate a lot of the hard number crunching work that we thought was necessary. Like that they're all different things that are happening in the world right now that give you the opportunity to rethink your workspace, your workday, your interactions, how you manage that. I think that it is something that is like one of those weird gifts of the pandemic. The other thing is that I do believe that people are. Listen, anyone who's like kind of over 50 at this point who went through the pandemic is now had this very acute period of time where they were left with their own thoughts. And I think that it may be five years later, but some of those people are like, now those thoughts are back. I was just getting through and now they're coming. So I think that there's opportunities to learn more about your clients, learn more about yourself. Thinking about this. Look, I wrote the great Money Reset thinking I would be at CBS News for as long as I ever wanted to be. Now I'm like, eh, this media environment kind of stinks. I'm drinking from the fire hose. I'm exhausted. It's a crazy schedule. Maybe I'd rather be doing different. Like, it's the first time this year is the first time. Me, Jill, who is turning 60 this year, thinking like, what is my next chapter? And I'm not sure I want it to be on a 247 news cycle. You know, thank God I cover the economy because it's like, it is mostly shut down on the weekends. But it is a. It's weird to be in a shrinking business when I know like, what that means. Right. A lot of my journalist friends didn't see what was coming, which was sort of obvious, which is, you know, it's. It's kind of like a very significantly evolving business and not in the direction for a lot of people that's going to work. So, you know, I think that some of those lessons that I learned in the pandemic. You know what I really love? I freaking love my podcast. I love talking to people 15 or 20 minutes a day. That will always be the thing I can do for as long as the listeners want me on the air.

Kathryn Williams (61:48)

Well, you. You say change your work, change your wealth, change your life, and I suppose it's technically a catchphrase, but that's not how it bears out for you. And I. And I. I love that. And, and, and for everyone that reaches out to you for permission or advice in either one of those.

Jill Schlesinger (62:10)

And sometimes it's like you don't have to make big changes. It maybe it's like change your notion of your work. Right. Use that wealth to help you get where you want to go and that maybe you're going to have a different kind of life as a result. And by the way, Brian, the book agent, came up with that tag. It was his line, not even mine.

Kathryn Williams (62:34)

That's a win for Brian, though. We'll give it to him.

Jill Schlesinger (62:36)

Listen, he got his commission. He's fine.

Kathryn Williams (62:39)

I love it. I love it. Well, I will say this month we release our. And I shouldn't say this month because we're not exactly sure when folks will actually be listening to this podcast, but once again, this year, in the early summer of 2025, we will be releasing our. I think it's our third or fourth annual summer reading list. One of the things we get asked a lot is, what are y' all reading? And it's not just business. We have voracious readers around Dimensional here, so every year we cast a survey out across the entire organization. The Great money Reset made the summer reading list. I'm really proud to say. You should be very proud of you.

Jill Schlesinger (63:18)

Amazing.

Kathryn Williams (63:18)

Thank you so much. But I think that it's also, it reflects, you know, so much of what we absolutely are hearing and, and wanting and spending time talking to advisors who are spending so much time and, and to your comments earlier, they're so invested in their clients, and we want to help them just double down on that as much as. As possible in a very healthy way. Right. That's what he talked about earlier. Jill, thank you so much for your time today. It's been such a pleasure to speak with you, and I feel like we I think we gave some really good ideas to advisors to think about with their clients and maybe even the end clients who are listening to the podcast. Maybe some questions that they themselves can also put forth in their next discussion with their advisor. So thank you for that.

Jill Schlesinger (64:01)

Well, thank you so much for having me. It's always a delight and I really do appreciate all of the hard work that you guys do at Dimensional. Your advisors do, and you have a lot to show for it and it's really a joy to be connected to this type of advisor in this way. So anyone who's got a question, shoot me a note. I'm happy to hear from them.

Kathryn Williams (64:25)

I love that. I was just gonna say you can find Jill on jillonmoney.com, find her on X. You can watch her on CBS for sure, which I always enjoy doing. And thank you again.

Jill Schlesinger (64:37)

Thanks for having me. Appreciate it Katherine.

Kathryn Williams (64:40)

So for those of you that are listening today, if you also want to know a little bit more about how Dimensional works with financial advisors, you can check us out on dimensional.com and with that we will catch you next time. Thanks everyone.

Podcast Host/Announcer (64:53)

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