Smart Money Podcast: Making Your Big Money Reset, With Jill Schlesinger

Sara Rathner
Sean Pyles
By Sean Pyles and  Sara Rathner 
Edited by Kathy Hinson

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Welcome to NerdWallet’s Smart Money podcast, where we answer your real-world money questions.

This week’s episode is dedicated to a conversation with Jill Schlesinger, CBS business analyst, host of the “Jill on Money” podcast and author of “The Great Money Reset.”

Check out this episode on either of these platforms:

Our take

To do a “great money reset” the right way, Jill Schlesinger suggests you start by taking stock of where you are now. That means listing out some numbers — like what assets you have and what debts you’re on the hook for. But you should also consider obligations to loved ones, like whether you promised to pay for your children’s education or are caring for a parent. You can change your life while still following through on commitments you’ve already made.

Documenting your current financial situation and where you want to be can be complicated and packed with details, so think about using a fun colored binder or dedicated notebook to track your journey.

Transforming your financial life might mean that you are earning less money or spending more at certain times in the process, so now is a good time to get deep into your spending habits. Think about what you’re spending money on, whether your spending aligns with your values and where you can cut back. If you find yourself making impulse purchases, take a moment to analyze the circumstances and feelings you experience. You might find that the purchase is just a coping mechanism. Realizing that can help you rework how you respond to certain situations.

And if your great money reset involves earning more money, be strategic about how you ask for a raise or shop around for a job that pays more. If you’re looking for a raise, know exactly what you want and understand whether now is a good time to ask, given the state of your company and broader macroeconomic conditions. Then, during the conversation, avoid getting too hotheaded if you meet resistance. Maintaining good relationships with your bosses and colleagues can help you later in your career if you find yourself working with them at a different organization.

More about managing finances on NerdWallet:

Have a money question? Text or call us at 901-730-6373. Or you can email us at [email protected]. To hear previous episodes, go to the podcast homepage.

Episode transcript

Sean Pyles: Welcome to the NerdWallet Smart Money podcast, where we typically answer your personal finance questions and help you feel a little smarter about what you do with your money. I'm Sean Pyles.

Sara Rathner: And I'm Sara Rathner. We have a special episode in store for you today. Jill Schlesinger is here with us. You may have seen her on the "CBS Evening News" or morning show where she serves as a regular analyst of business and the economy and, as she says, anything else with a dollar sign.

Nate Burleson: Joining us now to discuss the fallout is CBS News business analyst Jill Schlesinger. Good morning, Jill. How you doing?

Jill Schlesinger: I'm well.

Nate Burleson: Now, we broke it down a little bit, but I want your thoughts on it. What's going on here and could this happen to other banks?

Jill Schlesinger: Well, you know, as Errol just described, there was this very strange event that occurred last week and it was a slow-moving crisis because if you look back, say, 18 months ago —

Nate Burleson: Yes.

Sara Rathner: She's a certified financial planner who also has her own podcast called "Jill on Money." Just like us, she takes calls and questions from listeners on her show.

Sean Pyles: Jill is also the author most recently of “The Great Money Reset: Change Your Work, Change Your Wealth, Change Your Life.” The book is an outgrowth of the questions Jill got on her podcast throughout the pandemic. People are trying to figure out how to make and bankroll significant changes to their lives coming out of a global crisis. So, we're going to talk about all that and more. Jill, we are delighted to have you on Smart Money. Welcome.

Jill Schlesinger: This is amazing. So, thank you for having me and let's rock and roll. I'm excited.

Sean Pyles: Well, let's start with the genesis of your new book, which was about what you describe as a real shift in the kinds of questions you were getting on your show during the pandemic. And, I would say the same thing happened here at NerdWallet. Can you describe that shift? What did it sound like?

Jill Schlesinger: Well, first of all, I used to have a twice-a-week podcast, which was somewhat personal finance but also had financial guests. And all of the sudden the pandemic hits and we just got slammed with questions. Actually, as I am talking to you today, it is the exact anniversary because on March 14th of 2020, we went from having a two-day-a-week podcast to a seven-day-a-week podcast, where we answered questions and just got people on the line.

And, you know, in the beginning, it was just, "Well, what is PPP?" Or, "How do I access this loan?" Or, "How do I file for unemployment?" And, there were those general fear-based questions.

As we got a few months into the pandemic, the questions became much more existential. There were people who were questioning, is this really the way I want to live? I mean, I am now home. I am collectively experiencing this with my family. I am collectively experiencing this thing called a once-in-a-century pandemic with my co-workers and it is making me reassess everything going on in my life.

And so, someone asked me recently and they said, "Well, you know, what's the difference between the kinds of questions you were fielding out of the financial crisis and the Great Recession to the pandemic?" And, I would say that at that time, people would really say to me in those kind of like stressor situations, they would say, "What should I do?" And, I would say that the pandemic really asked, people would ask me the questions, "Who am I and how do I get to be the person I want to be?" And, I love that because I've always believed that the whole reason that you actually have money is to live a life that you want to live.

And so, to me, I was understanding in real time that people needed a framework to make some of these big decisions that these existential questions caused them to answer.

Sara Rathner: So, this book, “The Great Money Reset,” it's not about finding out the answers to who you are and figuring out your values, especially as they might have shifted. Such a dramatic time in our history. But, once you've already figured out how your values have changed and how your priorities have changed, this is the book to turn to to handle the logistics of that and start taking action.

Jill Schlesinger: Yeah. That's exactly right. I mean, when I think about the conversations that I would have with people, I'm not the person who says, "Hey, you know what? What you really need to do is go get a shrink and let's walk through those questions."

I presume that most people get in touch with us and start to say, "I have now determined that I hate my job and I need to take a different track. I have now determined that I want to actually move across the country to be closer to my parents because that is actually something really important to me." And, then what I would find is that I would listen to them tell their stories about what they wanted to do and I was helping them figure out what are the guardrails we need to put up to get you there without blowing your entire financial life up.

So, what I hope this book is used for is really to put your dream into action mode, whatever that dream is. I'm going to rely on you guys to know what your own dreams are.

Sean Pyles: Right. And, as people are working through that process, you recommend they strike up a partnership with a pink binder. Can you tell us about that and what purpose it serves? And, also, does it have to be pink or could I use an aubergine or a lime green binder?

Jill Schlesinger: I would encourage you to use any color binder that you would like. And, I'll tell you a little story about the pink binder because it does kind of weave in a number of themes of the book.

So, the pink binder is a concept that my friend Maureen Guthman basically presented to me. Because I was a certified financial planner, an investment advisor, I was running a company for 14 years. I sold the company. I didn't really know what I wanted to do. And, I would talk to her and I said, "Well, you know, I really like the idea of doing something in media." That's how I was really finding myself and my excitement would grow when I would be on TV and radio, talking to people about financial stuff. But, I was really using the media to get new business in the door. Right?

And so, could I do this really in my life? And, she said to me, "You know you need a pink binder." I said, "What?" And, she said, "Basically, it is a three-ring binder." Gang, I know it doesn't feel like very current, but it worked for me. Very old school. I'm a tactile person.

And, she says, she pulls out this pink binder and has little tabs in it and there's looseleaf in there and she says, "You know, each one of these tabs is something you need to do. These are your tasks to figure out whether you can do media full time." And, you know, she said, looked at me, and she goes, "You're the financial person. You'll be able to figure out the money. This next section is you need to talk to every single person you ever dealt with when it came to television and then to radio and then writing and then consulting."

And so, we kind of laid it out, really tab by tab, about the things I needed to consider. That was the framework that Maureen gave me.

Sara Rathner: So, if you are a person who wants to make a big life change because of the pandemic, because of any other reason, really, let's get down to the brass tacks of how you go about assessing your financial ability to do that, because big changes sometimes cost money.

Jill Schlesinger: Yeah.

Sara Rathner: So, walk us through what you call your fabulous five first steps.

Jill Schlesinger: OK. So, every single time I would have somebody that would come on to the show, I would ask these questions and then I just had to make up a funny name because I come from network television and that's what we do. We do silly things like this.

So, step one is calculate the resources that you have. Now, what are resources? You know, I'm not just talking about your assets, which are important. You know, what you own. And, that can be your bank accounts, it can be your investment accounts, it can be your retirement account, it could be equity in a house. It could be a lot of different things. But, also resources I consider in this process, also your income and all the benefits that you receive through your workplace. Because I do believe that people tend to look past those benefits when they have them but when they don't have them, it becomes quite glaring how much they're worth. So, that number one step is pretty easy. It's sort of the left side of your balance sheet.

The second step is to look at the right side of your balance sheet, your debt and your other liabilities. Again, we're not asking you to do anything with this information except list it. That's really important, that a lot of people get freaked out. They're like, I'm not good at math. So, I'm like, how are you at lists? Can you do a list? A list is what I'm asking.

Sean Pyles: This list just happens to have numbers in it.

Jill Schlesinger: Yeah. Don't freak out, really.

Sara Rathner: And, really, it's like four-function math. It's like adding stuff together. We're not doing calculus.

Jill Schlesinger: Yeah. Exactly right. And, even calculus isn't that hard. You know? You just have to have a good teacher.

Sara Rathner: Ugh. I got a C on it in high school, so I'm not the person to ask.

Jill Schlesinger: So, the third step is to think about your housing situation. I think this is kind of fascinating to me because I know that people know the value of their home. But I do find that during the pandemic, our whole relationship to where we dwell shifted. Right? Because, all of a sudden, it's like, well, wait a minute. It's not just where I live and sleep. It's actually where I work two days a week. And, all I want you to consider is that there could be something in that equation of, like, the equity in your home that might help you get to your next place, that might help your great money reset.

The fourth step, which I just list in this early chapter but then spend an entire chapter talking about consumption, which is to kind of consider how you spend your money. It's so weird when we think about this because I remember during the pandemic, people were like, "I'm saving money hand over fist because I realize I don't need anything." Which is great, except then we came out of the pandemic and then people were like, "I want to spend more than I ever spent before in my life because I've been deprived."

So, we've gone from one extreme to the other. I think we're going probably towards the center now and I think that spending is really important. It's one of the few variables throughout our lives over which we can exert control.

And, the last step is something that's a little bit more emotional but it is also important and that is you really need to consider any obligation you might have made to someone else. And, let me give you an example. I go through the pandemic. I'm freaking out and I decide, you know, I don't want to be a corporate attorney. I want to be a dog walker. That's really what I want to do. And, I look at all the money I have and I realize I can totally do this. The one thing is that I had promised my kids that I'd help pay for college and if I'm a dog walker, I won't be able to.

Well, if you already made that obligation and you made that assertation to your kids or you and your spouse have done that, then maybe you're not going to be able to do this thing. Maybe you're not going to be able to leave your corporate life all at once and become a dog walker.

So, I think that obligations are incredibly important and I think sometimes it could just be obligations to a partner where you're saying you kind of started your lives together and you were on a certain pathway and you want to blow it up and you need to really take responsibility and say, "Well, is this ... ? Is this fair to do because maybe I feel this way but does my partner?"

Sean Pyles: So, let's go ahead and go into that chapter you mentioned about going deep into the step of considering your spending habits. And, this is somewhere where we can all get pretty stuck sometimes. We've all heard pretty much our whole lives that the key to being good with money is to spend less, consume less. And, yet, a lot of us find that really difficult to do. Why do you think that is and how do we change that so that we can do other big changes?

Jill Schlesinger: So, I think that the thing that we need to ask ourselves is a series of questions around our spending and we have the answers to these questions because we went through the pandemic, which is kind of cool. And, the first question is, "What do I really need and what do I only think I need?" I need to pay the electric bill. Right? I don't need to essentially let my kids go through these zillion soccer programs or coaching, or this, that and the other thing. And so, the questioning around that became a lot easier to answer because you found out very quickly when you didn't spend a lot of that money, that everyone was just fine. So, that's number one.

I do think this next question, which is, “Do you find yourself feeling guilty, insecure or anxious about a purchase you make?” I think that sometimes we can try to figure out what it is that's compelling us to do certain things. And I think that when you're having an emotional response to the way you spend, that that should be a little warning flag. “Wait, why I am doing that? Oh, wait. Why am I ... ? What am I doing here?”

And, I think the third question that we ask ourselves that's helpful is, "Do I find myself making an impulsive purchase and if so, when and why?" And then I think that sometimes relationship dynamics do actually change your spending habits, meaning you sometimes have to be able to say like, "I love you. This is a great friendship. But, let's go take a walk in the park because going out to your club or this thing, it's just like not in my budget." But, it's hard to say that.

And, similarly, if you are thinking about this as a partnership, like your life partner, maybe one of you earns a lot more and maybe one of you doesn't and maybe you haven't had a real conversation about the dynamics in your own relationship that cause anxiety for you. Just having the conversation can really be helpful.

Sara Rathner: So, you mentioned a couple times making less money than the friends that you hang out with and that sort of leading to weird social dynamic issues that you have to navigate. And, for some people, a big, sweeping life change can often mean lowering their income, which is a hard thing to wrap your head around if you are accustomed to living a certain way because of the income you've had. But, maybe you're leaving a bad job for a better one that pays less or you decide to strike out on your own and start your own business or you move somewhere where salary ranges are lower.

And, while that might seem scary, there can be some advantages. Right? Maybe you end up in a lower tax bracket, which affects your retirement options, something like that. So, can you take us through some of that thinking?

Jill Schlesinger: Absolutely. I mean, first of all, I think what is also interesting to me is there are people who are making a certain amount of money. Let's say you make a lot of money and you are a bit miserable in your existence. And sometimes what I've noticed is that when people say, "Well, if I could actually find a place where maybe I'm not working in this same way. I might make less money but I think I could work longer.” There are a lot of trade-offs that we make all the time and I would encourage people to say, "Well, hey. Wait a minute. If I'm going to a lower paying job and maybe I am willing to make a change in my spending habits but maybe I'm in a lower tax bracket. Maybe my benefits are really better. Maybe I'm moving from a sector that doesn't have a pension plan to one that does have a pension plan. And, maybe I could just work longer because I'm happier doing what I'm doing."

I don't really love — you know, I come from a different generation than you guys, and I feel like I've learned a lot in many ways from your generation because I feel like I come from the model of kill yourself and retire whenever you can, but don't stop working ever. That really feels like that's kind of like the messaging that we grew up with.

Sean Pyles: Mm-hmm.

Jill Schlesinger: And, I've learned a lot about, even in my own reset, I don't make as much money as I did when I was a money manager and an investment advisor and a financial planner. I just don't. I have — but, I am so much happier, so much more fulfilled. I'm OK saying I don't need, I don't really care. I don't need as much money. It's fine.

Sean Pyles: Yeah. Well, one of the big life changes that a lot of people did over the past couple of years was leaving their jobs. We've all heard about the "great resignation," the "big quit." So, all of these people did that, but it's still one of the toughest things to do.

You suggest something called bullying your boss. And, Jill, I need you to explain what you mean by that because I hear the word "bully," and I think you're going to get yourself canceled. So, please explain yourself.

Jill Schlesinger: I know, I know. You know what? Here's the problem. Remember that we started and I said I really shouldn't curse in this book.

Sean Pyles: Yeah.

Jill Schlesinger: My girlfriend was like, "Don't curse in the book." Because, in my first book, I threw a few F bombs. Listen, my first job on Wall Street, I was a trader on the floor of the Commodities Exchange, so "the" and the F word are sort of interchangeable for me.

So, when I was thinking about the book, I was thinking about a lot of people were understanding that the power of the relationship between employer and employee was shifting. And, it's different in every industry. I know. If you work in technology right now, you don't have as much bargaining power. But, oftentimes there are little slivers where you do even then.

So, I came up with this thing called "bullying your boss." And “B” is button up your ask. If you're going in and asking for a raise, I want you to do your homework. What is it that I seek out of this conversation with my boss and what it is that I want? So, that's buttoning up your ask.

The second thing is the "U," which is understand the full picture. This is an "OK boomer" moment. So, right after the financial crisis, I knew a ton of people who work in the banking industry and I always would laugh. So, this is already a long time ago. It's 2009. It's 2010. And, one of my friends and then another one of my friends and another one of my friends — so, we're all the same age — “My God, my young employees are asking me for a raise. Do they not understand we almost went broke six months ago?”

And so, I think that understanding the full picture before you — when you think about what it is you want, do you really understand what's going on at your company, in your industry? You don't operate in a vacuum. So, be careful as you walk through this process to understand what is the landscape that is ahead of you.

The third step is to lose your ego. Don't — I found it quite worrisome when I heard people go toe to toe with their bosses, like high pandemic when the labor market was shifting. And I think that it's important to not go in just being like a bang on the desk, demanding person or even just being like, "I can go anywhere I want." And, you know, you run the risk of really burning a bridge.

And, step five is don't yuck it up, the "Y." You know what? You don't know how all this is going to go and you don't know what's going on in everyone's life always. So, I just think that it is important to just make sure you understand. Don't put some sort of marker. Don't draw the line in the sand and don't make an ultimatum unless you really want to and if you — but, generally speaking, ultimatums are not great. They really aren't. And, what's better to do is to just say like, "You know, I guess that this is not the right time." And, you go back to your desk and you just kind of like let it be. Don't let things inflame.

Sean Pyles: Well, your approach can make or break your relationship with your boss and I think by taking that really hard-line tactic, you can burn through a lot of goodwill.

Jill Schlesinger: Yeah. And, you know, I am — I am somebody who like — I am very comfortable making changes in my own personal life. I think that we sometimes minimize how hard that is to do.

Sean Pyles: Mm-hmm.

Jill Schlesinger: I really do. And, I think that you're right. You don't want to necessarily — A, you don't want to burn a bridge because life is very strange and you'd be surprised where people end up. You know? Like, “Oh, I told this boss off three jobs ago and now they're in your organization.” And that's a — oof. It's so awful.

But, you know, the other piece of it is that sometimes you may find that it's really good to stay, that the anxiety of leaving, even if it's for a little bit more money, may not be worth it.

Sara Rathner: So, let's say, Jill, that we've gone through all of the steps you've outlined in your book and you realize you're actually not in a position to make the big change that you were hoping to make. And, what can you do then besides just getting really, really upset and sitting with those feelings? What can you do that's productive?

Jill Schlesinger: You go sit in the corner, suck your thumb, and then you sit on your pity pot for a little while, then you come back out. And, you realize that maybe there are some half steps to make. Is there a — is there some interim step that we can make to get you to that final step but maybe delay it by a few years? Or, maybe that you would go to your employer right now and instead of saying like, "I really want to quit," to say, "Here's what I'm thinking. I'm thinking that I'd love to be a consultant or I'd love to help you part time or I'd like to help you on a project basis." And, that when you have the flexibility of thought and you conceive of different ways to do what you want to do, you give yourself more choices.

I am all about, that it's great to have money but it's not great to have money, to have a pile that is sitting in an account. It's great to have money because it actually increases the number of options you have in your life and if you haven't accumulated enough money to get to your most desired outcome, what is the next step that you could make? Could you maybe do something different and could you find a way to have something in between best case and worst case that will help you move a little bit more towards your goal?

And, I think that gets you off your pity pot pretty quickly because it feels action-oriented and it feels like you're moving in the right direction, even if you're not 100% there yet.

Sara Rathner: So, as a society, we — it feels like we are in this giant period of navel gazing and I wonder how long this will last. You know, we're talking about this great money reset, but does that have legs? Are we going to utilize this society-wide crisis to propel changes in our lives? Or, once things calm down, are we just going to go back to who we were and what we thought our lives were supposed to be?

Jill Schlesinger: Well, that's a great question that each of us needs to answer. I think that that is incumbent upon you to determine. If we all collectively went through this, there is some large number that will go back to the way things were, because maybe they liked the way things were. You know? That maybe it was just that I had a moment, I looked at these numbers, I looked at what I'd have to give up by doing, making certain changes, and I'm going to just stay with the course. But, I do so maybe with the knowledge, and that I've already gone through this process. I feel better about it. OK? So, I think that's one thing.

I think that it would be a shame if you went through this process and you could make some changes, you could reset, you could put yourself on the road to get something different in your life or you recognize something in yourself but you didn't act upon it because you were fearful or maybe you just — it was easier to go back to the way it was.

Then, I think that's a shame because I do really believe when I talk to people all the time and they come back on the air with me and they tell me their stories — it's like those old goofy shows about it's a makeover and it's like, let's do the reveal. And, what you find is that people really do make fantastic changes in their lives and they do so in a way I think that is really inspiring. They really do.

And, you know, so, I don't want to leave you on a down note. OK? But, I'm going to tell you. So, I want to, so, I want to bring you the bookend of the Maureen from the pink binder. OK? So, Maureen from the pink binder was a dear, dear friend of mine and we would always talk about our careers. She worked at Black Entertainment Television. I'm at — which is part of the CBS family. And, we would talk about media stuff and she would often say to me like, "I got a job offer to go here, and I did this but I really like where I am and I have the greatest job." And, she would always think about these things. Obviously, someone who always has a pink binder. You know? Come on. That's not somebody who's not thoughtful about what's going on in their lives. Right?

Sean Pyles: Mm-hmm.

Jill Schlesinger: And — and so, last year, she was diagnosed with an end-stage cancer at age 60, which is like, she approached it with this pink binder. She gets her pink binder and she starts talking about like, "What am I doing for the next six months of my life. I've just been given a death sentence. What am I going to do?"

And, I thought that what was so inspiring about her life and her death, frankly, because she died in November, is that she always was so thoughtful about her decisions. And, I keep thinking about that now as you ask that question. Well, what if you, what if we all go back to the way we were? I think that was the greatest shame in the world. I know Maureen would have hated that for me or for any of us.

And, I do think that we're only here for a limited amount of time. I learned that lesson all too well last year with Maureen's death, and I do feel like, don't sit around and fritter around. And be bold enough to consider it, make responsible decisions, but you have opportunity and you have agency and I really want people to feel that agency when they read this book.

Sean Pyles: Yeah. But, Jill, we are so sorry for your loss. Maureen sounds like a really incredible person.

Jill Schlesinger: Yeah. She's the best.

Sean Pyles: We're really grateful to have you on the show today. Thank you so much for talking with us.

Jill Schlesinger: Well, I am so happy to have been here with you and to experience the vibe. You guys are great and I really, really do appreciate it. So, thank you so much for having me.

Sara Rathner: And, that's all we have for this episode. To send the Nerds your money questions, call or text us on the Nerd hotline at 901-730-6373. That's 901-730-NERD. Or, email us at [email protected]. And, visit for more info on this episode. Remember to subscribe, rate and review us wherever you're getting this podcast.

Sean Pyles: Here is our brief disclaimer. We are not financial or investment advisors. This nerdy info is provided for general educational and entertainment purposes and may not apply to your specific circumstances.

This episode was produced by Tess Vigeland. Sara and I helped with editing. Kaely Monahan mixed our audio. And a big thank you to the NerdWallet copy desk for all their help.

Sara Rathner: And, with that said, until next time, turn to the Nerds.