The Great Money Reset with Jill Schlesinger (EP.108)

0:28We all need to make smart decisions with our money. award-winning business analyst for CBS News. She is also host of the wildly popular podcast and nationally syndicated radio show, Jill on Money, and author of the new book, The Great Money Reset, which gives readers 10 timely financial steps to build the life they really want. As always, you can find all the notes and resources mentioned during the conversation at thelongterminvestor.com. And with that, here is my conversation with Jill Schlesinger. Jill Schlesinger, welcome to The Long-Term Investor. Well, thanks for having me. Great to be with you.

1:08I am so excited to have you here today to talk about your latest book, The Great Money Reset, which I find was exploring a lot of those key areas of your financial life that has to be addressed when making a personal transition. And I think you'd agree with me that big personal transitions are something a lot of people fantasize about and rarely take action on. And yet your background, you left a successful financial advisory practice to join the media. I would love to just start off the conversation by hearing your story in that transition before diving into some of the content of your book. I think that I come to the concept of a reset because not only of the conversations I've had with clients when I was a financial advisor, people on the radio show and the podcast, but because of my own story.

1:57And I actually have had two big resets, not including the personal ones about divorces and marriages and things like that, but career resets. The first one was when I was really young in my 20s, I was a trader and I thought my whole life I was going to follow my dad's footsteps. And he was a trader on the floor of the American Stock Exchange. I started my career as an options trader on the floor of the Commodities Exchange in New York. And I really thought that's where I was going to end my career, which, you know, put in the time, make the money, get out. And, you know, three, four, five years later, I was like, oh, I don't really like this.

2:31And it was kind of tough. And dad kind of pulled me aside and said, you know, honey, if you don't like making money and you don't like the short hours, this is not the greatest job for you. You're not saving lives. You're not changing lives. So you're looking for meaning, trading, not exactly the right career. And that's what kind of led me to financial advising. And I thought that was a really good match for my skill set because I could solve problems and use my little nerdy math head. But, you know, I'm an extrovert and I like talking to people. And so it was like an interesting combination of skills.

3:07And I really did like that combination quite a bit. So I was a financial advisor for 14 years. And one of the ways that I was tasked with growing the business was, you know, figure out how to get tushies in the door, right? Butts in the seats. I had a client who was a radio show general manager. and I said, hey, you've got some dude on your radio station who sounds like he's doing what I'm doing. Like, how do I get a radio show? And so he's like, well, you know, it doesn't work like that. And then the guy, he and the guy on the radio had a fight and he called me up. He's like, you want a radio show?

3:42Come in and audition. I had done a little bit of radio and TV stuff in my collegiate career. And so we kind of used a radio show to grow our business. And I was in a small New England city. And when you're on the radio, you're sort of a mini celeb and that turned into television. And so that was like a great way to grow the business. And, you know, as I was approaching a transition where I was dating someone who was living in New York City, and I was really kind of like, well, we sold the business. It's a different business going forward. I had a contract I was working out and I was saying, maybe I can actually make a go of this.

4:20Maybe I could actually try to do media stuff full time. And that was kind of the moment where I was like, how do I do this? What do I really need to think about? I had a very dear friend of mine who was the queen of planning. And she goes, you need a pink notebook. What's a pink notebook? She goes, you know, like a three ring binder and you have different sections. And she said, you know, you have one section where it's the money stuff. How long are you going to last until you get a real job? And The other sections are maybe people you've met in radio or TV and just conversations you have, and you're going to complete the binder and it will guide you.

4:57And this is really the ultimate framework that I came up with when I was thinking about the Great Money Reset in that these were sort of the sections of my pink binder became different questions that I would ask people who came on the radio show and the podcast and were asking me questions. And it's kind of like a mini financial plan, but much more expansive in terms of, well, tell me what you really want and what's your sort of best case, worst case and middle case scenario. And that's kind of what led me to where I am. I talked to a lot of different people. I had been doing media in New York and traveling between New England and New York quite a bit.

5:35And I just talked to lots and lots of people, some of whom said, you know, you're terrible, you'll never make it in this business. And a couple who were very encouraging and, you know, long story short or long story, which a little bit longer, is that in the beginning of 2009, I got a call from some folks at CBS News. I had been on their air to kind of explain what was going on in the financial crisis. And they said, we'd like to talk to you about maybe coming aboard here in a more permanent way. I said, that's fine. I just sold my company. I'm moving back to New York and just like in transition.

6:13I'm happy to talk to you, but I don't want a job. And three weeks later, I signed a contract and I have been with CBS News ever since. So there's the origin story of Jill on money. I love it. And it's interesting that you went through that transition, like you said, back closer to the financial crisis. And yet the common theme of the book is of the great money reset is the pandemic and how that allowed so many people to question what they were doing day to day. Obviously, people think about, you know, getting up and uprooting their life and making a transition. But do you think you would have written this book if it hadn't been for the pandemic?

6:48I don't know. First of all, I have a very nudgy book agent and I love him to death. But Brian had said to me in the pandemic, we were talking and I had written a book that was like your traditional financial 101 kind of book. It was called The Dumb Things Smart People Do With Their Money. And that was a book that was essentially my entree and said, I got to write a book. You know, I've been in this business a long time. And why do people do really bad things to themselves? And it was an exploration of sort of how financial decisions and psychology behind them meet and how to avoid making a bad decision in that moment.

7:24But this was a moment really when my agent, Brian DeFiori, called me up one day and he's like, what are you doing? I'm like, you know, I'm really busy. I'm crazy. On the air a ton. It's a pandemic. He goes, what about another book? and this was probably in the summer of 2020. And I was like, I don't know. And I put together a few different treatments, nothing quite worked. You know, I sort of did the two ends of the spectrum. Wow, should I do like a roaring 20s book? Like, are we about to have a roaring 20s? And should I do a doomsday book? You know, like I didn't even know what I wanted. And one day late in 2020, I'm having a conversation with him.

8:00He goes, well, what jazzes you right now? Because I said, I just, I'm not coming up with anything. Go away. And I said, well, it's interesting. You know, we had a podcast that was twice a week and a weekend radio show. And in March of 2020, my lead sponsor of the podcast was Goldman Sachs. They basically said to me, you know, the world's falling apart. Our contract's up March of 2020. We're not going to renew. We don't know what's happening. And I was like, oh, God, great. So I was not going to make any money on the podcast. And so what my producer, Mark, and I had decided was we were getting inundated with so many questions in the pandemic.

8:36And we went to a daily podcast and we would record it after the market closed. And I would kind of hold people's hands. And every day it seemed like there was a new some sort of PPP announcement, the loan, people who couldn't get unemployment benefits. And we were just getting inundated with questions, floods and floods of questions. And then, you know, what I will tell you is that, you know, sort of the middle of 2020, maybe the end of the summer, the questions shifted pretty dramatically away from we are in this panic stricken mode to, wow, I don't know if I want to go back to the way things were.

9:09And those are the questions, I think, collectively that many of us started to really ask ourselves amid the pandemic. So I think that what happened in the pandemic is that I've always had people who asked me questions at inflection points in their lives, a birth, a death, a divorce, a job loss. You know, when people are just forced to think about these things. I cannot recall in my life, you know, and I've been doing this for more than three decades, where there was an event that caused all of us or many of us to have the time and the space to really sit down and say, is this how I want to live my life?

9:50What is different? How can I make different choices? It was like this collective moment of great existential questioning. And that's the book. That's the product of the questioning and the conversations I had really did come about. And I think it was pandemic related because it just seemed like every single day our inbox was flooded with people who were really trying to understand, well, if I do want to do something different, then what does that mean? And how can I make a smart decision without blowing up my financial life in the process? And obviously there are people feeling this way across the age spectrum.

10:34How do you feel like it's different for people earlier in their careers? And I don't know what ages to assign to that, maybe 30s and 40s versus later in their careers, say 50s and 60s. I have a great benefit because I have a life partner who is part of a large Italian American family. So I have nieces and nephews on her side that are ranging on age from the 20s to the 40s. So I had this like mini Petri dish of information and I have three nieces, two nieces and a nephew from my sister who were in their 20s. And so there was a lot of interesting and deep conversations. And we were starting to get many more questions from people who were early in their careers who really were asking questions like this.

11:19I know that I chose to go into a field where I was going to make a lot of money. and maybe that's investment banking and maybe that's consulting. But as it turns out, now that I really see what this is like and now that maybe I see what it is like to not have to be in an office every single day and maybe to have a different lifestyle, maybe I don't want that. Maybe that's not so important to me. And maybe even someone in their 30s who might say, I remember getting a lot of questions from people who were thinking like, hey, you know, I've been at home and I have a partner and I have kids and some of the choices I made when I was single and trying to forge my life, they've shifted.

12:01And I don't want to actually be married to a job. I really like my partner or spouse and I really like my kids. And I'd really like to try to figure out a way to live a life with them that is more consistent with kind of a lifestyle that I want. I think that for people in their 40s and their 50s, I think that the questions were much more about, I'm not going to make it to 65. There's no way I'm going to do what I do until I'm 65. What choices can I make today to pivot, to make maybe less money, but be able to work longer? How can I take my love of something that was a side hustle and turn it into a real hustle?

12:44Or, hey, I have a business that I've been growing. It's been great, but you know what? This is so hard, or maybe my business was really impacted either positively or negatively by the pandemic. And it gives me different choices to make in the future. So at each point in your career, you might have the opportunity to ask these questions to yourself. I hope it doesn't take a once in a century pandemic to pose those questions, but the book is there as a guideline to be able to help you understand if you're going to make a different choice, you have the opportunity to create a pathway for yourself forward.

13:21And there's not just one path. I mean, one thing I have learned since being a little puppy financial advisor is that I think that life is really filled with nuance. And I can remember, you know, being a 30-year-old CFP and like sort of being pissy with a client and being like, no, this is the way to do it. You know what? There isn't one way. There are many ways. And I think that I have learned as I've gotten older that people want to have agency over their lives. They want to be able to make different choices. They don't want to feel trapped and they make better choices when they don't feel trapped.

13:55So if you lay out different opportunities and different options and you don't wag your finger and you don't say the world is black or white, that they are much more satisfied with the outcome that they come to. You know, it's interesting that you say that, and you do often throughout the book refer to, you know, some type of scenario analysis. And actually earlier on in the conversation, you mentioned worst case, middle case, best case. And those aren't always black and white for everybody, but at least you're defining them for yourself. It's not that hard of a framework to tackle, but I do find it to be very effective.

14:27And it's part of my regular role as chief investment officer. I have to do that sort of stuff with investments. But when you think about planning for a transition like this, how did that come to be such a common framework? It sounds like you used it yourself in your own transition. Is that a big reason why? Well, you know, I think that we share this like I was the chief investment officer of my little teeny tiny firm. Of course, because I was trained as a trader, worst case was my favorite case. It may not surprise you, but it may surprise some of your listeners that when you really talk to people who are investment professionals, they're sort of like professional golfers.

15:03They'll tell you about their worst round of golf, not their best round of golf. I used to have a tack board in my office and I remember I would have the symbols of the worst trades of my career and I had them sitting there in front of me. And I had a client who was a shrink who said to me, why would you have that up there? I said, it's a reminder that things can go south. And he's like, well, why don't you put your best trades up there also? I was like, oh, that's a great idea. I never thought of that. But I think for me and maybe again, it's like nice Jewish girl from New York in my DNA is often to look at worst case first.

15:35So that's the easiest one for me always. It's almost like the best case and the worst case kind of work are easy to define. I think it's that middle lane that's often the challenging one. So, you know, in my own case, it was, okay, if I'm going to make a transition from being a financial advisor, an investment advisor, a financial planner, and I'm going to go into the media, the best case is some media company hires me. And, you know, I had been on the air at CBS. I had been on the air at CNN. I had been on the air on Fox and Fox Business. I had written for publications. So I kind of knew a little bit about that world.

16:13The worst case was that like nobody would want me at all. And, you know, I could go sell something like the world was falling apart. Don't forget it's 2008, 2009. You know, maybe the stock market will go to zero. I remember coming home from the high holiday services in the fall of 2008 and looking at my brother-in-law, the former commodities trader, and him saying to me, well, if it goes down by this much every day where we'll be done in 12 days. This is great. Then we'll figure out what happens next. And we really did feel that way. It's kind of like that black humor, you know, the gallows humor.

16:44And I was like, I can sell. I'm really good at selling. I can sell software. I can sell a car. Everyone always likes a salesperson. So best case, worst case, easy. The middle case was a more interesting one. The middle case was that I had friends in the industry who were saying to me, hey, do you want to come work here? Do you want to come hang your hat? We'll hold your license, your registration. Don't give anything up. Come work here. And I think that my middle case was some combination of I could do some work for the financial planning industry, do a little writing on the side, maybe try to do a little speaking and make it work there.

17:19That was a real gray area for me. And in some respects, it didn't scare me. I just knew it wouldn't be like the most thrilling thing. But it was the most likely scenario because I know how to gather assets. I know how to manage assets and I know how to manage clients. So I knew that I was marketable. It wasn't what I wanted to do, but I could totally do that. So I gave myself a year to figure out which of those three scenarios would pan out. I'm going to dig into this a little bit. I love that you mentioned the background of trading because a lot of times when I'm going through client conversations, I don't have any clients of my own.

17:54I mostly go and talk to our clients who are worried about something. And we talked just about that, where it's, hey, what would be the best outcome here? What would be the absolute worst outcome? What do you think is most likely to happen? And honestly, that's how people are setting prices every day. I thought it was really interesting, though. So I appreciate you mentioning that. But I think in the book, what I found so interesting was the tactic that you explained for transitions within those different scenarios, where you go to groups of people who are in a position similar to what your best case scenario looks like, or what your worst case scenario looks like or what your most likely or middle outcome looks like just to get a better sense of what does that look like?

18:33That probably helps you calibrate your expectations a bit better, right? Absolutely. I mean, when I think about my pink binder and I think about the different tabs that I had, I kind of had a tab for each of those scenarios. So I did have funny conversations. Like I can go back and look at that now. It's so hysterical. Like I remember talking to a friend of mine who was basically selling a software solution for financial service companies. And I'm like, tell me, what do you do all day long? How does that work? And who are your clients? And why did that? And like just different scenarios of things that were happening.

19:09I talked to somebody who's like in the pharmaceutical sales business, which by the way, makes financial services look really crisp and perfect. Not to piss any of you guys off, but that's a different business. And I really wanted to talk to them. And then I talked to a number of financial advisors in the New York metropolitan area. I talked to people at large companies like big investment banks who had sales and marketing divisions who thought that, you know, they wanted to get into the sort of the small medium client business, which I knew pretty well. And then I talked to every single producer, anchor, booker that ever contacted me about being on their air.

19:48And I talked about that. But, you know, like I said, you have to you have to understand that everybody's got a bias, right? It doesn't mean that, you know, any one person is right or wrong. Although in the case of one individual, you know, I remember going in and talking and it's, well, you know, I've been on your air and this, that, and the other thing. And the guy said to me, well, you know what? I think you're fine as a guest, but I think the timber of your voice is such that you'll never make it in radio. So I wouldn't pursue that if I were you. And when I went to talk to people at CBS in their radio division, they thought that was the funniest thing they ever heard.

20:19They're like, that makes no sense. That is weird. I don't know what you did to that guy, but we think you're great on the radio and you should keep doing it. So, you know, sometimes you have to take the hard news, but you can also say, well, it's not the only news, especially if you're talking about such a subjective business, like being on-air talent. You know, with someone who's in sales or someone who is in the business you're in, there is a bottom line. What am I being measured against? You know, what are the expectations? What is success? And that is something that's really important. But, you know, with some of these other, like if you're in the arts, I want to be a writer, it's kind of tough, but there are many ways to get to a different outcome.

21:01And what I really knew was that I felt in my bones that I was sort of in transition and that I was really open to anything that came next. I really appreciate that extra background. So much of the book has amazing financially tactical moves, but it seemed like to me when I was reading that this probably was one of the more impactful exercises that you went through. And so I really appreciate you sharing that. And there's also points in the book where you give some tough love, which I also like, where people might go through some of the financial steps that you recommend throughout the book, as well as some of the scenario analysis.

21:37And hopefully they arrive at the conclusion or the realization that maybe they shouldn't do a great money reset. Are there some ways that you feel like people can reach that conclusion or specific steps that might help them recognize it and gain that bit of self-awareness? Well, I think that when I lay out how to kind of go about structuring the money and the questions to ask yourself and to try, especially in those early chapters, to say like, you know, what's the money you have? What are your resources? What are your debts? What do you think about your house? What do you think about your family?

22:11You know, and I think that something that's quite profound about the pandemic specifically is that it also shifted some of those priorities around. I think there are plenty of people who were really psyched about like, I moved 3 ,000 miles away from my parents. See ya. And then the pandemic hit and your parents are getting older and you're saying to yourself, well, I don't know if I want that. That's actually, I'm reprioritizing. And I think that sometimes when you're considering a reset, those priorities start to really shake out in a way that may surprise you. And I have felt like even as I talk to people today, you know, I was on the phone with somebody and he called in and asked me an asset allocation question, which turned into a very different conversation when I was like, well, tell me what you want to do.

23:02Like, where do you see this going? And the little micro thing that he was thinking about was like insignificant compared to the bigger thing. And I think that when people are saying like, I hate my job, I'm like, do you? Do you hate what you do? Or do you hate the person you do it for? Do you hate the place where you do it? I think that there are a lot of really interesting questions that you can ask yourself. And, you know, also when you're going through this process, it may be that you, you arrive at a conclusion that is so far out from what you ever thought you would be doing, it's okay, but it can be daunting.

23:38One of my favorite stories of the book is about this couple from Pittsburgh who were, you know, she was a nurse and in an operating room. So she works for an anesthesiologist and she's in the operating room. Her name is Pam. And it's like 2020, early 2021. And they're in the operating room. This is what doctors talk about in the operating room, I guess, by the way, because the doctor says to her, hey, you know, like the real estate market's going crazy in our neighborhood. She's like, really? I didn't even know that because all I've been doing is working. So they were talking and he says, you should like, you know, do you have a friend who's a realtor, have that person come over and like check out your house.

24:17Now, what's interesting about this story is here's a woman, she was in her 50s, late 50s, you know, sort of mid to late 50s. Her husband is a physical therapist. She's a nurse. They were very frontline folks who were working their butts off during the pandemic. But prior to the pandemic, if you kind of thought, you said, hey, Pam, Tom, what do you think is the likely outcome of like where you're, like, what's your game plan? It would be like, okay, we work for 10 more years. We pay off all the debt. We had assumed the debts of our kids for their college. We have a mortgage. We're just going to like gut it out.

24:49I'm going to work a little extra overtime to pay off the debt that we have out there. We'll limp to the finish line and we'll hang out and life will be good. That's kind of what they thought. The pandemic happens. This question arises about like the real estate in the area. Friend comes over, does a little walkthrough and says, you know, I think I can sell this house for five, six, maybe even$700 ,000. They are shocked and delighted. And they quickly start talking about selling the house. And they quickly realize that they never want to own a house for a long time because they don't want that burden.