Drama-Free Divorce Podcast
Hosted by attorney and mediator Cary Jacobson, the Drama-Free Divorce Podcast brings you practical guidance, real conversations, and expert insights to help you navigate divorce with clarity, confidence, and less conflict.
Each week, we break down the emotional, financial, and legal challenges of divorce and co-parenting, without the chaos. Through interviews with industry professionals, personal stories, and step-by-step strategies, you’ll learn how to protect your peace, communicate effectively, and make informed decisions that support your future.
Whether you’re considering divorce, in the middle of it, or rebuilding afterward, this podcast is your supportive guide to a calmer, more empowered path forward.
New episodes weekly. Tune in for tools, tips, and conversations that put your family’s well-being first.
Drama-Free Divorce Podcast
EP #14: Navigating Financial Transitions During Divorce with Guest Jennifer Lee
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Money and emotions collide during divorce — and the decisions you make in those moments can shape your financial future for years. In this episode of the Drama-Free Divorce Podcast, Cary Jacobson sits down with Jennifer Lee, founder of Modern-Wealth, to talk about what smart financial guidance looks like during one of life's biggest transitions.
Jennifer brings nearly 30 years of financial services experience to her work with clients navigating divorce, loss of a spouse, and major business transitions. She's also the author of Squeeze the Juice: Live With Purpose – Then Leave a Legacy — a book about living with intention and leaving a meaningful legacy.
In this episode, Cary and Jennifer cover:
• Why having a financial advisor during divorce is so important — and often overlooked
• How emotions affect financial decision-making during high-stakes transitions
• The key financial steps to take as you rebuild after divorce
• The concept of values-based financial planning and the "family love letter"
• How to live with purpose and think about the legacy you leave behind
If you're facing divorce or another major life transition and want to move from financial uncertainty to financial clarity, this episode is for you.
About Jennifer Lee: Jennifer Lee is the founder of Modern-Wealth, a Sarasota-based financial planning firm specializing in major life transitions. Learn more at: https://modern-wealth.com/
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The biggest blind spot going through divorce is when you just want it over. And a lot of times the women just want it wrapped up. Can we just be done with this? We know what we're doing with the kids. I don't want to argue about the money anymore. I just want it over. And sometimes that need to wrap it up might be a little premature. We haven't finished the parenting plan or making sure that you have the proper custody and all these things. So I just don't like them to give up too early.
SPEAKER_00Welcome to the Drama Free Divorce Podcast. I'm your host, attorney and mediator Carrie Jacobson. Each week we bring you practical guidance, real conversations, and expert insights to help you navigate divorce with clarity, confidence, and less conflict. If you're ready for a calmer, more empowered path forward, you're in the right place. Welcome back to the Drama-Free Divorce Podcast, where we talk about how to approach divorce with clarity, confidence, and less conflict. I'm your host, Carrie Jacobson, attorney and mediator with Jacobson Family Law. Divorce doesn't just mean a legal process, it's also a major financial transition. Many people suddenly find themselves having to make financial decisions, all the while handling the emotional side of the divorce as well. And that's why the right guidance during those moments can make all the difference. And so today I'm joined by Jennifer Lee. She's the founder of Modern Wealth, which is a Sarasota, Florida-based financial firm focused on helping individuals navigate major life transitions. Jennifer has nearly 30 years' experience in the financial services industry and specialize in helping clients through emotionally charged financial moments such as divorce, the loss of a spouse, and even major business transitions. She's also the author of a book, Squeeze the Juice, Live with Purpose, then leave a legacy. And she brings a unique perspective to financial planning by helping clients connect their financial decisions with their values and long-term goals. Jennifer, so thankful for you for being here today.
SPEAKER_01Oh, thank you so much, Carrie.
SPEAKER_00I really appreciate being with you today. Absolutely. Well, I always like to start with our guest, kind of giving a little bit of a background. How did you get here? And what really led you to work with people who are going through these major life transitions?
SPEAKER_01That's a great question. I'm actually originally from Maryland. I have lots of family there and many clients and friends who are in the area. And I've been in Florida now 14 years. So go back and forth to see clients and it's fun. But in terms of getting involved in really in the divorce space, you know, when I relocated, sometimes you have to readjust and look at your practice and look at who you really serve and who are those clients that you love to work with. They happen to be women in financial transition. Okay. So these are people who were in the middle of big, chaotic, stressful, emotional points in their life where they have to make a lot of decisions and it's overwhelming. And so really what I did was I narrowed my focus. Of course, I work with happily married couples. I work with men, but my real niche is working with women in financial transition because I find that women have a lot of balls in the air and they may or may not have been the money person in the relationship. So I really try to help them create a path forward that they can go in confidence, right? And with confidence and know what their life's going to look like post-divorce.
SPEAKER_00And are there other financial transition points where you may be working with clients as well?
SPEAKER_01Sure. I mean, we work with clients all the way through their life, from marriage to having kids and into retirement. Major transition points typically are divorce, loss of spouse, retirement, buying or selling a business. That's when you need some advice, some perspective, uh sounding board, really.
SPEAKER_00Absolutely. Both from the financial standpoint, but also as you were saying, the emotional impact and where those often collide with one another.
SPEAKER_01It's like the perfect storm, right? Right. So, and a lot of times, you know, you might experience this, have experienced this in your own life. When you are in a particularly emotional space, your executive function is not as masterful as it is on a day when you are at the top of your game. And we have to understand that we're human and we have to understand that we need those people in our life that can help give us direction, perspective, guidance, and help us make good decisions. When it's so chaotic, you have the a really huge chance of making a big mistake.
SPEAKER_00And that that's why working with someone like yourself during this divorce process can be helpful because you're really providing that guidance.
SPEAKER_01That's what we try to do. I tell clients that, you know, it's not my job to tell you you can't keep the house, but it is my job to tell you the consequences. If you do X, here's what is gonna, you know, financially look like for you. And you decide. It may be that it's more valuable for you to be done with the process than it is to fight over $50,000 more of money. That's up to you where that perspective is, right? So we talk about that and really break that down.
SPEAKER_00So yeah, and I would say that we have the same type of conversations from the legal perspective, right? And I've always kind of explained it like this client may have a different perspective of whether or not to pursue that $50,000. Whereas the other client may say, you know, it's just not worth it. I'm ready to move on. I know I can make that up somewhere else, or it's just not worth it in the grand scheme of things. And I don't feel like as the even the attorney that I can make that decision for them, it's really giving them all of the information and then them making that decision.
SPEAKER_01I mean, that's really what it's all about. We're we're that's that counsel.
SPEAKER_00So right. Absolutely. Now you have said that the relationship between your financial advisor is one of the most important when those emotions do collide with financial events. Can you talk a little bit more about how that comes into practice when you're working with a client?
SPEAKER_01Sure. I think the biggest area, blind spot, I think that we have going through divorce, the big biggest opportunity for mistakes is when you you just want it over. Right. Right. And a lot of times, as women, not exclusively, probably because sometimes it is the men, but more times than not, historically, in my experience, yeah. The women just want it wrapped up. Like, can we just be done with this? I don't want to fight about it anymore. We know what we're doing with the kids. I don't want to argue about the money anymore. I just want it over. I want to move on with my life and I want to have some peace. Right. And sometimes that need to wrap it up might be a little premature and you're leaving money on the table or you're leaving pieces. And I'm sure you know this as well. On the legal side of things, that's happening in your world too, where they're frustrated, they just want it over. It's like, but wait a minute, we we haven't finished the parenting plan or making sure that you have the proper custody and all these things. So I just don't like them to give up too early. And we were talking about this in the pre-call, just it takes a village to get through divorce, right? It takes oftentimes it takes a divorce coach or a therapist and certainly some best friends. Right. It takes the financial person to give you perspective on which assets you should take. And it absolutely takes the attorney to either navigate the toxic personality or help to mediate. Look, we're fighting over little things here, right? The real priority is the kids and what happens with the assets, you know. Right.
SPEAKER_00Absolutely. And for those clients that we've worked with who have given in, you know, somewhat prematurely, I often hear them come back later and say, I wish that I had pursued it, right? Or wish I had not given up so easily, because now they're in a situation where maybe they're not in the best financial situation and they can't undo that decision.
SPEAKER_01It's frightening. Whenever I do a talk like this or a podcast, I will have women come to me and say, Where were you when I was going through my divorce? I didn't know. I gave up too soon. I only got five years of alimony. I was married 30 years. I should have gotten more. I just didn't want to fight about it. Those are consequences that last the rest of your life. Now, maybe, you know, maybe you can recreate assets because you're, you know, this dynamic and independent individual. And I hope that you are. Maybe there's enough money where it doesn't matter that you fight over the last 500,000. But I'd rather you get your money and give it away. You want to give it away, let's get it. And then you give it away where you want to give it away. So that's just my personal perspective. Absolutely.
SPEAKER_00No, if you've got someone who's going through divorce, what are some of the most important financial steps that they should be thinking about before they move forward? Someone who's kind of at the beginning stages of the process.
SPEAKER_01Yeah. I think that the illusion is that you're just going to file for divorce, you go to the attorney and you file for divorce, and that's how it goes, and you figure out the rest of it later. Well, the reality is you're taking one household with maybe two incomes and only one Netflix account and one gas bill and one utility bill. And now you're going to split it into two households. Well, it costs a lot more to be divorced and run two households. I think that you really need to have some clarity as to what those resources are and what it's going to look like. So maybe you have a big, beautiful house and you think you're going to be able to stay there. Maybe you are, maybe you're not. Right. But are you going to be willing to? Are you going to be able to move into a two-bedroom apartment with your kids? Right. What does that look like? So I think having a financial reality check is definitely helpful because you could go all the way through the divorce process, be on the other end, okay, here's what you get, and now what? I mean, we wouldn't let our clients do that because we're trying to make sure that they're knowledgeable all the way through, but it happens.
SPEAKER_00Yeah. Yeah. And I think when they're doing that inventory, it's also thinking about what are those things that are my non-negotiables, like the things I absolutely have to have, and whether that's stay in the same school district that my kid is in, you know, whatever that that may be. And then finding those things that are more negotiable because you're gonna have to give something up along the way and figuring out how can we work around that. Yeah. Yeah.
SPEAKER_01I mean, you're talking about your practices in mediation, and in a perfect world scenario, we have a couple that says, Look, I'm just not in love with you anymore. We had kids together. I did love you. Well, I was crazy about you at one time. We built a life, it's just not working. How do we unwind this? Right. And that's the perfect scenario. Maybe you're able to see that more in the mediation space, I hope. But it is a terribly emotional time. Sometimes there's narcissism, sometimes there's addiction, sometimes there's affairs, you know. Right. You just don't you just don't know what's bringing you to the table for divorce.
SPEAKER_00Absolutely. And in the mediation space, you know, while many of them are very amicable, you know, there are times where there's all of those layers of the emotions. But I try to do my best to focus them on, well, this is where we are now. How do you want the next chapter to look like? And what are you guys going to do to move forward in a way that addresses both of your goals and needs? So, you know, but also having someone like you that they're working with individually can really guide them to figuring out what that looks like. Yeah.
SPEAKER_01I mean, I love the idea of educating each party in advance as to what you could typically expect. You've been married X number of years, you have kids, here's the expectation, here's your income, here are your assets, they're marital, non-marital, generally what you can expect. And then have them really understand what that looks like with a financial person. And then you can really narrow down to my non-negotiables and hopefully get back to the center line.
SPEAKER_00One of the things that I find really interesting about your work is how you encourage clients to communicate their values. And I think there was something that you've mentioned, which is a family love letter. Can you talk more about that concept and why it's so important?
SPEAKER_01I think writing your family love letter, whether you're married, whether you're divorced, whether you're a single mom or a single dad, whether you're an aunt like me, it's important because money is just a tool. People get anxious about money, and that's why I love what I do, because I don't get anxious about money. I get excited about it. I want to talk about what it can do for you, how it supports your own particular values and your own lifestyle and what you want for yourself and for your kids and your family. So writing your family love letter is a couple things. It's the easiest way to describe it is if this is the last conversation you have to have with one of your children, you have to tell them everything. You have to tell them everything about what your feelings are about marriage, you have to tell them what you hope for them in a relationship, you have to tell them what you would aspire for them in a career and contribution to their community. And then you tell them about money, you know, here you have this money. Don't spend the principal, right? Spend the earnings, you know. If you want to get educated, go back to school, if you want to, you know, experience things, travel, do the things that we would have done, you know, as a family. If you're a business owner, there's a lot more, right? What's that last conversation you're having with your spouse if you're the business owner and they're gonna need to sell the business if you're not there, right? So it can be as simple as that. What is it that they need to know? And it can be as complex as, you know, how do you want your funeral services? What are the, what did they mean to you? Who do you, you know, my dad gave his love letter in person to us because he got diagnosed with a brain tumor. And so he literally gave it to us and said, Here's who I want to speak at my funeral. I mean, to have the ability and the capacity to have that conversation is crazy and it's incredible. So I always encourage people to really think about the people they love that are in their life, because it's a lot.
SPEAKER_00It is a lot. The logistics of things, right? This is these are where my accounts are, this is what you need to do, as well as as you mentioned, the values that you're trying to pass along, especially if you have children.
SPEAKER_01Who you trust. Right. You know, yeah. I mean, there's layers upon layer. So yeah, if you have small children, I did this talk with a group of men who were insurance people, and I had them crying. And I and I love that because they heard me, right? Like they they got it. They're like, this is important. We need to make sure that we communicate to our kids what it is that our values are and what we hope for them. Yeah.
SPEAKER_00Now I mentioned in the intro that you are the author of a book, squeeze the juice, live with purpose, and leave a legacy. And it really focuses on living intentionally and thinking about the legacy that you want to leave behind. So kind of along those same lines as your family love letter. How does this philosophy influence the way that you guide your clients through financial decisions?
SPEAKER_01It's really everything, it's kind of the center of the relationship. So I need to understand and get to know my client to understand what's important to them. What's important to you may be different than somebody else. And that's okay. I I'm not here to judge what's important to you. My job is to help fulfill those things and facilitate them if we can do it financially. So, really, when we're meeting with new people, there's a couple conversations. The financial side of things, the first conversation is what do you have? What's your income with your assets? What are your resources? And what do you want? Well, then what do you want is a little harder for people to come up with, right? Oh, yeah, I want financial freedom or I want uh to take off on Fridays. They can't necessarily articulate it, or I want a nice retirement. Well, what does that mean? What does it look like? Are you running an RV? Are you going to Europe? Are you sitting at home and nobody's bothering you and you're reading books? What is a nice retirement, right? So when we gather as an advisor those things, what do you have and what do you want? We can figure out how to make what's in between as efficient as possible. And that's really what we do. So we first try to understand that. And then as life goes on, we're always talking and evaluating and adjusting things that are going to be more strategically beneficial for the client. So you may have somebody who is a business owner and they're just starting to save money in the beginning. And 20 years later, they're five years from exit. So it's planning those, those kinds of things. Now, what's important to you? Well, now I'm divorced. Now I've got grown kids who want to join the business. What does that look like? So if I do my job right, if I do the relationship right, it's a lifelong experience. So yeah.
SPEAKER_00And that perspective can be so meaningful when you're helping clients who are rebuilding after divorce, right? So now they're going from this is the life that I had before, and it's like that transition point and having another conversation of what do you want the next portion of this to look like?
SPEAKER_01Yeah. And it could be scary, right? It can be scary, particularly if you if you weren't working and now you need to figure out what your life looks like. Or you are working and now you have a huge alimony payment. So it's an adjustment, you know? Right. So those are times where you have to evaluate and make decisions, financial ones, that are going to impact your life and your future. And sometimes it's really meaningful to have those conversations with somebody like me. At least I hope to think so. Like think so.
SPEAKER_00Absolutely. For someone who may be listening today and is facing a divorce or some other major life transition, what advice would you give them when it comes to navigating the financial side of that change?
SPEAKER_01Just like anything else you're going to evaluate. You're going to buy something, you're going to, you're going to buy a new device for your home, buy a new TV, you research. So the first thing is gather as much information as you can, right? Gather your financials, gather your income, gather your assets, gather your resources, and then have a conversation about what that looks like, right? And then ultimately, once you know that you're going to go down that path and you're talking to an attorney, you want to understand. I'd rather them come to me first and be armed to come to you and say, okay, Carrie, I've been married 20 years. We have three kids. We both share a business. I'm the breadwinner. This is going on. I want a divorce. What does this look like? What's my exposure? How long is it going to take? What is he going to fight me on? And be educated and articulate about how to go about it logistically. Now, that doesn't always happen that way. Right. They come into your office first and they're probably very emotional. And that's why I say, you know, it's it's a team effort. And we all can have those emotional conversations. It's just maybe not as cost effective to do it, you know, starting with the attorney. Right. Yeah.
SPEAKER_00Yeah. Because many attorneys do charge by the hour. And so sometimes if you're working with a divorce coach or therapist, then that can help reduce your cost overall for what the process looks like.
SPEAKER_01Yeah. And in your case, you're probably your first conversation with somebody is is mediation right for you? Right. Right. And then what do you operate on like a flat fee? Or yeah.
SPEAKER_00So we actually offer flat fees for all of our clients. And so we do a start that conversation through a consultation. If it's mediation, we do a joint consultation with both spouses, trying to find out, you know, where are they in the process? Because sometimes they come in, they've already had a lot of conversations. They worked out a lot of those details themselves and they just need help getting it, the logistics figured out. And then there are other scenarios where they are at the very beginning stages and haven't had much of those conversations because either they don't know where to start or communication is not great between them. And that's what we as mediators also help do is facilitate that conversation. And so we have different packages that are available to them, but we charge, you know, a flat fee for those services. And then for our separation agreement clients, similar, we do it based on a time period, kind of where they are, how much time we think a process is going to take for them in negotiating the agreements. So we find that for us, the flat fee model works so much better for our clients because they know what it's going to look like going in. Every time we have a conversation with them, we don't want them to feel like they're, you know, being pressured and that they can't have a call or send an email because of what that expense is going to look like.
SPEAKER_01Yeah. And that's, you know, typically a big fear, right?
SPEAKER_00Anytime fear, you know, because you know, when those attorneys do work on the hourly model, getting that bill at the end of the month or every two weeks can be eye-opening for sure.
SPEAKER_01I love the idea of mediation, Carrie, as well, because everybody's motivated to solve the problem.
SPEAKER_00Right.
SPEAKER_01Right? Everybody's focused in the right direction to get to a solution where it's amicable. Like nobody's trying to create a dramatic scene. We're just trying to figure out can we agree to something? What can we negotiate? And that's a very helpful skill set that you have.
SPEAKER_00Thank you. Well, then having that financial clarity coming in is also big, you know, because it does help drive the conversations as to what that path is going to look like. Yeah. Well, Jennifer, thank you so much for joining me today and sharing your perspective. Obviously, financial transitions often feel overwhelming, but with the right guidance, such as yourself, a clear understanding of your values and goals, it's possible to move forward with confidence. Can you please tell our listeners where they can learn more about you and the services that you provide?
SPEAKER_01Sure. My website is my And a hyphen and the word wealth. And then I always like to say if we stimulated some thought and you have a burning question, you can certainly give you 15 minutes on a squeeze the juice call, no cost, no obligation. And that's on my calendar image Jennifer ModernWealth. So if you have a question, shoot me a message and I'm happy to get you an answer.
SPEAKER_00Absolutely. And thank you to all of our listeners for joining us today on a drama-free divorce podcast. If this episode resonated with you or you know someone who could benefit from it, please feel free to share. And until next time, I'm Carrie Jacobson, reminding you that divorce doesn't have to be chaotic to be effective. Thanks for listening to the Drama Free Divorce Podcast. If you found today's episode helpful, be sure to follow, subscribe, and share it with someone who needs it. For more resources or to work with us, visit JacobsonFamilyLaw.com. Until next time, stay grounded, stay informed, and stay drama free.