Ep 338: The Midlife Plot Twist: Rewriting Your Money, Relationships, and Life Story with Lindsay Goldwert

Midlife comes with plenty of taboo topics that rarely get discussed together: money, sex, and the fantasy of burning it all down. Melissa Joy, CFP® sits down with Lindsay Goldwert, a writer whose work has appeared in The New York Times, New York Magazine, Slate, and MarketWatch, and the author of Bow Down: Lessons from Dominatrixes on How to Be a Boss in Life, Love, and Work, a Glamour Magazine Best Book of 2020.

Lindsay is now the co-author of The Midlife Plot Twist: How to Reboot Your Life Without Burning It Down (Even If You Really, Really Want To), out this September. She and Melissa talk about why it is so hard for women to ask for what they want, and why that difficulty tends to build up quietly until it boils over.

The conversation covers why financial planning benefits from a therapist's sense of empathy, how couples can use a financial planner as a neutral party for hard conversations, and why proactively involving a financial planner before a relationship ends, not after, tends to lead to better outcomes for everyone.

Lindsay and Melissa also get into how small, incremental investments in friendships, hobbies, and curiosity pay off over a lifetime, why knowing what you do not want is just as valuable as knowing what you do want, and why midlife deserves to be treated as a plot twist worth celebrating rather than a crisis to survive.

What You'll Learn
Why asking for what you want is especially hard for women, and how that difficulty compounds over time if left unaddressed

Why a good financial planner should function like a financial therapist, holding space for feelings as well as numbers

How bringing a financial planner into a relationship can give every partner's voice a seat at the table, and why that matters most in unequal power dynamics

Why getting financial planning support before a relationship ends, rather than after, tends to lead to fairer and faster outcomes

How to have tough money conversations with aging parents about wills, executors, and financial oversight before a crisis forces the issue

Why small, incremental investments in friendships, hobbies, and curiosity are a legitimate use of money for long term health and longevity

Why knowing what you do not want anymore is just as valuable as knowing what you do want

Why midlife deserves reframing as a plot twist to celebrate rather than a crisis to survive

Guest Bio:
Lindsay Goldwert is an editorial director and writer whose work has appeared in The New York Times, New York Magazine, Slate, MarketWatch, and many others. She is the author of Bow Down: Lessons from Dominatrixes on How to Be a Boss in Life, Love, and Work (Simon & Schuster, 2020), a Glamour Magazine Best Book of 2020, and the co-author, with Gabrielle Moss, of The Midlife Plot Twist: How to Reboot Your Life Without Burning It Down (Even If You Really, Really Want To) (Running Press, September 2026).

Connect with Lindsay:
Website: lindsaygoldwert.com
Instagram: instagram.com/lindsay_goldwert

Melissa Joy, CFP®, is the founder and president of Pearl Planning, a fee-only financial planning and investment management firm based in Dexter, Michigan. Pearl Planning is a registered investment advisor with the Securities Exchange Commission. Information presented is for educational purposes only and does not intend to make an offer or solicitation for the sale or purchase of any securities. This podcast offers news, commentary, and generalized research, not personalized investment advice. Nothing on this podcast should be interpreted to state or imply that past performance is an indication of future performance. All investments involve risk and unless otherwise stated, are not guaranteed. Be sure to consult with a tax professional before implementing any investment strategy. Mellissa Joy hosts the Women's Money Wisdom podcast, where she talks with experts and everyday women about the real financial questions and challenges women face. Lindsay Goldwert is not a client of Pearl Planning and is not being compensated for sharing her opinion and experience with our firm.

The previous presentation by PEARL PLANNING was intended for general information purposes only.  No portion of the presentation serves as the receipt of, or as a substitute for, personalized investment advice from PEARL PLANNING or any other investment professional of your choosing. Different types of investments involve varying degrees of risk, and it should not be assumed that future performance of any specific investment or investment strategy, or any non-investment related or planning services, discussion or content, will be profitable, be suitable for your portfolio or individual situation, or prove successful. Neither PEARL PLANNING’s investment adviser registration status, nor any amount of prior experience or success, should be construed that a certain level of results or satisfaction will be achieved if PEARL PLANNING is engaged, or continues to be engaged, to provide investment advisory services. PEARL PLANNING is neither a law firm nor accounting firm, and no portion of its services should be construed as legal or accounting advice. No portion of the video content should be construed by a client or prospective client as a guarantee that he/she will experience a certain level of results if PEARL PLANNING is engaged, or continues to be engaged, to provide investment advisory services. A copy of PEARL PLANNING’s current written disclosure Brochure discussing our advisory services and fees is available upon request or at https...

Transcript

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Welcome And Why Money Matters

SPEAKER_01 0:00

Welcome to the Women's Money Wisdom Podcast. I'm Melissa Joy, a certified financial planner and the founder of Pearl Planning. My goal is to help you streamline and organize your finances, navigate big money decisions with confidence, and be strategic in order to grow your wealth. As a woman, you work hard for your money, and I'm here to help you make the most of it. Now let's get into the show.

Taboo Topics And Asking For More

SPEAKER_01 0:48

She is the author of Bow Down: Lessons from Dominatrixes on How to Be a Boss in Life, Love, and Work, a Glamour Magazine best book of 2020. And now she is the co-author of the Midlife Plot Twist, How to Reboot Your Life Without Burning It Down, even if you really, really want to, which is out this September. Lindsay, welcome to the podcast.

SPEAKER_02 1:10

Oh, I'm so happy and honored to be here. Your audience is the one that I love the most.

SPEAKER_01 1:15

Well, our audience is Gen X and Millennial Women. We are serious about money, but also about life and how money can be a resource for your life. And you're talking about all the taboos. You're talking about sex, money. Throw death in there, and we've got them all covered. Um, tell me a little bit about what inspired you to write this book, which I am so excited to read and promote.

SPEAKER_02 1:41

So um the cliff notes is that um I'd always been interested in taboo topics. Always, always, always. Um, I started out in news as a journalist in various newsrooms, and then I sort of toppled um very randomly into working for some investment startups. Um, one was called uh Stash, which is a big one, um, which did I did great work for them and they were a wonderful place to work for, and um another app called Zeta, which I think was acquired by Acorns. And um, and I just found that writing about um feelings and finance were really important. I felt that that was missing from some of these apps was that a lot of them were very male focused and they didn't really understand how the things that um motivate our decisions are so much based on emotion.

SPEAKER_01 2:29

You're preaching to the choir right there, so in the perfect spot. We're always talking about feelings.

SPEAKER_02 2:34

All about feelings and finance. And I became friendly with some behavioral um economists, and you know, I some of that stuff was proven out, some of it hasn't, but I really genuinely I love I loved all that, those conversations. And then I had the opportunity to write um an a book, but I decided I didn't want to write a money book um at the time because there were so many beautiful money books being written by women already at that time.

SPEAKER_01 2:59

Fantastic.

SPEAKER_02 3:00

It was a gift, what was going on around 2018, 19. And I said, I want to do something interesting. I want to write um a book about how to ask for what you want. And I had this idea that I would follow around a bunch of dominatrixes, and it ended up being the best year of my life. And I learned a lot about myself um in and out of the bedroom and um a lot about why it's so why it's so frightening to say I want something, whether it's I want to raise, whether it's I want to have this, I want to have a more equitable relationship with my husband, whether it's I want to put down boundaries, why why all these things are very hard. So the funny thing is.

SPEAKER_01 3:37

Do you find can if we if we can pause there? Is that a female, like as you studied this, do you feel like that's uh specific to women that it's difficult to ask for what you want? Or is it like kind of across society?

SPEAKER_02 3:52

I I feel like it's hard for everybody, but I feel like for women, I have found that it's especially difficult because we a lot of us, even someone like me, who I feel like is a pretty powerful person at this point, I'm still a nice person and I'm still I don't mean to be a pleaser. Like I hate that word people pleaser, but I like to make people around me feel comfortable. It's not fun to, it's a lot of labor to create a really a conversation that's comfortable for everyone is a lot of labor, you know, and sometimes it's worth it, but and it it's always almost always worth it, but it's not I don't know. I think for women, a lot more women I know just be like fine, like I'll just I'll just do it. Yeah, it's not a big deal.

SPEAKER_01 4:35

The passive aggressive, the passive aggressive.

SPEAKER_02 4:37

Um but just in the end, when you get to be our age, it builds up, it builds up, and then we start to really freak out, and it's that's when things start to become very toxic for ourselves.

The Midlife Plot Twist Origin Story

SPEAKER_02 4:48

So the way that this came into how so there's I I was um I was hired by Naomi Watts, the actor, to work for Stripes, which was her um menopause uh skincare and wellness company. And she's a very nice person. I I don't have any gossip about her, she was very nice to me, and she wanted me to launch an online magazine for her. Interesting for her brand called Adulted, uh, which doesn't exactly exist anymore. But um I I ended up hiring another woman who is now my co-writer, and we we wanted to do an online magazine about everything that wasn't perimenopause. You know, like yes, that's a whole section, that's your health, lots of health can get can go kind of haywire, you know, reproductive wise, everything wise in midlife. But there's 90% of everything else that happens with your family, with your money, with your friendships, with your partners, with dating.

SPEAKER_01 5:48

And we just I with your relationship with yourself, too.

SPEAKER_02 5:51

Oh little that's it. Your relationship with yourself, with the self-discovery and evil and how you how you have changed, you as a you, you're not the same person you were at 20 when you are 45 or 50. And luckily, Naomi was like, she got it right away, and she that's what she wanted. So um it didn't work out. Um, the brand ended up getting, she ended up buying the brand back, and now it's in a different um, it's still around. And uh, I'm very grateful to Naomi and the team. It was a great group of women. But my co-writer and I were were so mad that we didn't get to really do what we wanted to do.

SPEAKER_01 6:23

You had this project that needed to be birthed, Tom.

SPEAKER_02 6:25

It needs it needed to be birthed and needed to be realized. And we um pitched it as a book, and we just that was like our you know, we just had to get it out there, just all these things we were so passionate about because this is a book about my friends. This is a book about your friends. Like it's not even about an audience, it's about it's about it's about us. Like who's this audience? It's our friends, man. You know, like it's it's the the the girls I used to party with who are now, you know, now they're going through what I'm going through. Like they're still my sisters, you know.

SPEAKER_01 6:58

So when we get together, my friends, you know, we talk about those old times, we still have fun, but also bedtime might be like 9:30, because that's like the most fun on a Friday night. Something nowadays.

SPEAKER_02 7:10

And the the conversations have evolved, but the feelings haven't. We haven't changed as human beings. We are still the same goofballs, but the stuff that we're going through is changing. And I have a real thing about when people say, Well, who's your audience? And I'm I guess I'm such a type B kind of creative person. It's like my audience is my friends, and I know my friends, and I know my friends' friends, and their friends, and I and they're gonna dig it, you know. So that's where this book came from was really wanting to write a book for my, we want to write a book for our friends about how to feel better, about the fact that they have changed. We didn't have a crystal ball when we were in high school and college, when we picked our majors. We couldn't have known about certain technology. We could have known that, you know, we we talk in the book about how we were young, you know, we you printed out your resume on a laser printer, and then you wore and then you wore your like good express pants to your first interview.

SPEAKER_01 8:01

You know, we all had this, and I got my first job in financial planning from a one ad in a classified newspaper, which how do I even explain that to my kids?

SPEAKER_02 8:11

I mean, all these stories are so incredible. So these but we all but when we were doing all that, like we didn't could if you someone had come down and said, one day you will have something called Slack and you will be checking it from the toilet, you know, while you are and he'd be like, What are you talking about? Like when we went out, I'm not trying to get nostalgic, I'm not a nostalgic person. No, please, let's go. But but I will say that when we were coming up and as professionals, you know, we could leave our work and you know, we would work hard hard all day and then we would leave and it would be waiting for us the next day, yeah. Yeah, and maybe we could have access to email a little bit later on, but you could always pretend that you didn't for a little while.

Anticipating Change Without Dread

SPEAKER_02 8:53

So um, I just didn't we just have to not feel bad about ourselves for not seeing the future because we no one told us we were not prepared, our parents couldn't have been prepared for the future that we were going to face, and we just wanted to write a real like hand-holding love letter to like it's gonna be okay, we're gonna support each other, we're gonna be in this together. Um, and it's not over.

SPEAKER_01 9:13

It's I love the ambition of your project because it is. I've interviewed so many experts on portions or areas of a woman's midlife identity. And I feel like what's missing is that interdisciplinary conversation of how to how to go in and maintain control when um life is full of change, surprise, uncertainty, um, and pivots. So I think that we need more of these conversations that are proactive, that are um anticipatory and and so anticipatory with but you said the right thing.

SPEAKER_02 9:58

You said control and anticipatory as opposed to dread. And like, of course, it's gonna be a little dread. Your parents are gonna get older. Like, uh like let's not, I'm not gonna, it's all gonna be amazing.

SPEAKER_01 10:07

It's gonna be hard if you have aging parents and your kids are going to college, like things are gonna be like kids have bigger adult problems as yes, emerging adult, you know, emerging adults and yeah, things are things.

SPEAKER_02 10:17

Things are going to get gnarly. That is, you know, life has always been gnarly in different ways, you know. But think things are gonna get a little gnarlier as as we get older. But at the same time, I think that we're teaching people to to dread some of the wrong things, like, or to like it's everyone's it's like I we don't have to get into skincare and face stuff, you know.

SPEAKER_01 10:36

I mean, we can.

SPEAKER_02 10:36

Let's we can, or okay, you know, but I'm saying like the dread of aging and the dread of like perimenopause symptoms, this like you know, they you know, the Instagram ads that we're seeing for perimenopause products. There's I know for a fact that they're aiming them at people, women in their late 30s now. So yeah, because so now there's a whole generation of women who really aren't there yet, who are really should be focusing on their obviously on their health, but also on how their own their prime, like their embracing their youth, their their youth, their prime. Like you are every year you get smarter, every year you learn something you don't like, every year, you know, you you process something new. And I think that the things that people really need to think about, also knowing that every no one's doing it right necessarily, but for sure a little bit.

SPEAKER_01 11:25

And it's an experiment because nobody's an expert on this area either.

SPEAKER_02 11:29

But I think that there's this difference between anticipating and dreading, and there's a difference between fear, like I'm gonna get old, I'm gonna live, you know, we always joke, you know, from Saturday Night Live, I'm gonna end up living in a van down by the river, you know, like we joke about these things because you have to joke, you have to laugh, otherwise forget it. But there's also like, well, what are we what are we gonna do about these things? How can we do some sort of thinking and planning while laughing and maybe crying a little bit? Um, and just and and also, you know, making peace with the fact that we we really weren't told what to do and we have to do it right now right now, and it's and everyone is stumbling through it together.

Joy, Boundaries, And Knowing No

SPEAKER_01 12:07

I think there's a lot of moments that are quite joyful and difficult to easy to miss um in middle age. I started a business at 43, um, kind of started over my career um in on my own terms. Um and I could definitely look back over the last decade, I'm 51 today, and say um that it was like, you know, full of challenges and disappointments. And yet it's not at all. And like one of the things I started to focus on over the last three to five years was like, what's going right? What how do I feel that I've changed that makes me better, a better practitioner, a better human, more comfortable in my own skin. I certainly feel more comfortable today than I ever did in my 20s and 30s or 40s um in terms of who I am and you know, like boundaries and all sorts of things. Um, you know, just being given permission to look for the positives, I think is something that we all need to be reminded about.

SPEAKER_02 13:18

This is the okay, my my 40s had been my best decade by far. And like three of them were in in New York in a pandemic. So let's see if that gives you any like any idea. Um, there's so I I I am living for my 40s and I'm gonna be 48 soon. So, or 49. One of those. Oh my god. Okay. And but and also happy birthday. Thank you. Um, but I think that finding joy in these moments, like I it's so hard for me because I find so much more joy in every moment now because I appreciate everything. I appreciate every good day. I appreciate like I like I this summer, uh, you know, I'm taking some time off the summer to promote the book and to do, you know, and I'm becoming uh certified as a sex educator so that I could become an even better sex and money writer, um, and I can make more friends and talk about all the stuff that I want to talk about, write another book. I hope. Um, so you it is essential to appreciate and find joy in what you do every day. Like it's so true.

SPEAKER_01 14:20

Even if it's so much, yeah, you know, like even if there's a hundred things to write on the list of like wouldn't want that again, like still realizing the blessings of the day.

SPEAKER_02 14:29

Well, not knowing what you want is a blessing. Never having like we have a whole section of the book that's like, I'm never doing that again. It's like, what an amazing thing to know what you don't want to do anymore. Like, what a gift. Like, we don't always know what we want, but to know what you don't want, that's like you're 80% there. Yeah, so true. And that's true for if you just are dating again. That's true if you're, you know, taking a new job or if you are moving to a new home, you know. It's like I'm never gonna live in a house again. I can, I cannot deal with the upkeep. I've done that. It's like, that's right, girl, you did that and it stunk. And now you don't have to do that again. It's like I'm never gonna work totally remotely. Like, I need to be in a hybrid office. Like, yeah, you know that because you did it, you know, like own that experience. Like you're you're a genius for yourself now, or like more than you were when you were younger.

SPEAKER_01 15:16

It's so true. Like, you there's only one person who's gonna be like it's clear who the biggest advocate for you in your life should be. Um, and that is you. Um, and if you don't write your script, then you are left to formulas that are not built for you.

SPEAKER_02 15:33

Certainly not, and not but and not built for anybody right now. What's happening in our in the workplace right now, this massive shift that's happening with employment for women, I would say, I mean, women and people, but you know, women like 45 to 55, this like huge, all these layoffs, this restructuring, this AI and stuff, you know, like we're all in this in a little bit of a maelstrom right now.

Midlife Transformation Beyond Symptoms

SPEAKER_02 15:59

And one thing I do want to say is one of the big things that gets me very upset about the perimenopause conversation, because it's saying that perimenopause is the most important thing that happens to you in midlife. That's not what I'm seeing. I'm seeing that perimenopause is something that is definitely affecting us. It's a that it affects us, affecting our hormones. But transformation is what I'm seeing most. You look what you did. You started, you started a whole new career in midlife. You you had your you did it yourself. All my friends are doing what I'm doing. We're all writing, trying to write books, pivoting our careers. My friends going back to school to become a therapist. Another one of my friends might is just bought a business, you know. Like we're all like, what is like what is the way, what is gonna a life that can suit me now? That to me is the story of midlife, you know. And there's like I and you might be sweating and you might like forget your keys and stuff. But beyond that, it's just so insulting to let us be boiled down to our symptoms when we're the healthiest, wealthiest generation of women to ever grace the earth. We're doing we're doing so much better than we think. I'm such a cheerleader.

SPEAKER_01 16:58

But no, I love what you just said. Like we are, when we look um at you know the history of women, um, women in the US and modern times, we have so much to write home about um in terms of our success. And for your reader, I know in all likelihood, I know for my um clientele and the listeners on this podcast, um, your your perspective to invest and your in yourself, your um willingness to proactively um work on your money story and your money situation gives you more resources, whether it's between your ears or within your wallet and your accounts, um, to augment and change expectations. You may have had um a, you know, like a story you told yourself about where you needed to be career-wise that isn't working for you anymore. Yes, yes. Um, you may think that you can't, you know, like trade in the um, you know, the typical picket fence house for a condo, or you may be changing your relationship status or renewing your efforts on working on your relationships. But all of these, um, you know, like for me, the money is a resource to use now or later. Um, and so there's just so many fascinating like options and choices that we have today that we may not have been afforded in a past life where there weren't 401ks to divide and things like that.

SPEAKER_02 18:33

That we even understood what they were or when they were explained to us at our jobs, you know.

Why A Financial Advisor Helps

SPEAKER_02 18:37

But one thing I wanted to say, just that you just said, is that in the book, so when I was writing the finance chapters, I said, and I made it a choice. I said, I could either go into like ways to invest, to have you know, you know, you know, make sure you have a you have a rough, make sure you have this, you have a diversified portfolio. And I said, you know what? They said, I'm gonna assume this is a group of women who are reading this book who have tried a lot of things. They've read all the books, they have downloaded the podcasts, they have like floating 401ks, they they're they're doing better.

SPEAKER_01 19:05

It's not a starter's manual for how to invest.

SPEAKER_02 19:08

But I said, you know, if you are if you start to deal with some mental health stuff, you go to a therapist. If you sprain your ankle, you go to a physical therapist. If you are 50 and you really aren't quite sure what to do with your money, go talk to a financial advisor. So one who can sit with you and can listen to you, someone like you, someone who can you could have a little cry with, and someone who could say, I and can talk to you over time. What are your goals? What are your goals? Lindsay, what are your goals? You know, do you have are you gonna have grandchildren? It's like, Noah, I I I know I'm never gonna have grandchildren, but I have nieces and nephews. Do you think you want to do this? Do you think you want like I don't want that? And I'm pretty sure I'm never gonna want that. It's like, well, we're gonna design a life for you. We all need help. And people think you need to be rich to have a financial advisor. They're like, why am I paying money to take care of the money that I don't have, you know? Right. But at the same time, it's like, you know, you are making an investment in yourself because you could be getting because you've especially if you're paying down your debt and you can't, you know, your school debt. It's like someone can help you pay down your school debt while still saving for the future. We all need help. It's you know, we're such Gen Xers and we're so we're such DIYers in our own way, you know, because we're used to like, I could just do it myself. I'll just do it myself.

SPEAKER_01 20:23

You know, we're also told that we're behind, we're told that we're um like the generation that is the most messed up. We're we're smaller, so we just don't get as much attention. But it's it's I find Gen X clients to be so fun to work with. Obviously, they're my peers often.

SPEAKER_02 20:37

Yes, there are peers, and but we all feel like because we're smart and we did read, we could still read books. Now I hate to talk about younger people because some of his my nieces do read, they're they're young and they do read, but we still read. We we really tried our best, and everyone, a lot of my friends are doing much better than they think.

SPEAKER_01 20:56

Oh, yeah. I all the time I I people come in and they're like, ugh, you know, like I'm such a loser, I don't know how I'm doing, or you know, not great. And it's like, okay, here's like five things you're doing fantastic. And here's three opportunities that can make it even better. My cost is finite. I'm always comfortable talking about it, transparent about cost, but like your assessment of the relationship with a good financial planner is about the compounding returns of making informed decisions that are personal to you. Um, and those that's more difficult to quantify, but it is easier to feel.

SPEAKER_02 21:33

Well, the feelings are everything. This feeling of that you're in control. It's like I'm working with a person who I understand their fee structure, I understand what I'm paying for. I, you know, I know that they're not gonna be making decisions that just to benefit them, their fiduciary, you know, they're gonna hold my hand through this in a way that a therapist can hold your hand through processing some, you know, a divorce.

SPEAKER_01 21:53

Which I also advocate for is therapy is wonderful in midlife.

SPEAKER_02 21:57

Well, financial therapy, I think if I had a clone, I Become a financial therapist because I cool because I think that that that is is is so important because when especially with you know when I talk a lot about couples and relationship stuff, you know, if money comes into the equation, which it always does, it has to, you know, then it can't be a moment where a therapist is like, uh, like I don't, I'm not really sure. It's like, well, you can't tell, you know, you can't say how to and tell them what to invest and stuff. But things get really people in midlife, especially if you know women go in and out of the workplace, you know. You know, we work really hard and then we stay home to have kids, we go back in, we go part-time, you know. So that we do have less financial equity, you know, if we are in a partnership, because we are we're gonna bring in less retirement. We might feel like we we have been certain, we haven't committed as much as other people. If you don't have that relationship with a partner where you can really talk about that, where there isn't an understanding of like who makes more, who makes less. If you don't feel like an equal partner, now is the time to have that conversation and to have it with a a financial planner who has a heart and some feelings and give you some tips on how to have that conversation. It's like we we need this support because and it because we're if you're the right partner, they're gonna be like, oh my God, of course we're we're in it, we're in it to win it together. Who cares who made more one year and who made less? But things get very strange, especially if you are thinking about leaving your partner.

Money Power Dynamics In Relationships

SPEAKER_02 23:18

True.

SPEAKER_01 23:18

And if I will say that um financial plan, what one note for people in um good committed relationships that there are sustainable committed relationships is that financial planning um often brings bringing a financial professional into the room gives space for everybody's voice if it's the right person. If you're working with someone who only makes eye contact with kind of the dominant financial decider in the relationship, then might not be a great fit. But that's weird. Um but otherwise it should be an opportunity for mediation on some of the things that like maybe more difficult to resolve in um a you know, like long-term relationship when it comes to money, because there's often, you know, everybody has their own money story and everybody has a different perspective, it might make different things.

SPEAKER_02 24:09

You just said something so interesting to me. You know, I didn't write this in the book, you know, but like maybe some women would be more comfortable with a female financial advisor, you know, and if they're gonna be the one to bring up the conversation of like, you know, then you be the one to pick the person that you think you're gonna have the most direct conversation with, that you'll feel the one that you can talk to. I know a lot of men tell me that when their wives tell them, like, oh, we have to go to marriage counseling, you know, they pick the counselor, and then the men will be in the room and they're like, I don't know if I really like this lady or if this lady likes me. Yeah, you know, it's like, well, if you want to have the conversation, then you pick the person that's gonna make you feel the most powerful. So it's these are all hard things.

SPEAKER_01 24:44

And the other thing I want to note though, sorry to interrupt, is like if you don't know if your relationship will endure, having like it's in my opinion, in most cases, I see I did a lot of divorce work over the last 10 years, um, divorce financial planning work. Um having a financial planner involved with both of you, like only like it only makes it better when you break up two, um, typically. Yes. Because like, and also it might make the challenges of the relationship less, you know, like it might resolve some of the challenges of the relationship if there's power imbalances or inequity when it comes to access to funds and things like that. So both can be true. You don't need to wait till you're like signed the divorce agreement and then hire the financial planner.

SPEAKER_02 25:32

No, do it before. Do it before so that you end up on your feet and the conversations are faster. Maybe you can even go to mediation. Maybe you don't like and then and you should I want to read that book. I hope you write that book.

SPEAKER_01 25:44

So true. But like I like, you know, so we um you don't just wait and say, Oh, I'm getting divorced, so I'm not gonna start working on that. Like, there will be more to divide if you're making better decisions, more informed decisions. You'll have more perspective. Um, and like I said, it could resolve some of the issues.

SPEAKER_02 25:59

And and know what's yours is yours, you know, get those questions of fear. Oh, I didn't contribute enough, or you know, he paid off my loans, or I stayed home and I did all this other. I did a I for the time when I worked for five years and he took time off. Like, you know, just you have to just you just get it straight before and any time is important. But you know, this emptiness time, people are people's kids are leaving the house and suddenly these couples are looking at each other like are we still in it together? Are we in it together? Are we still is our chapter finished? Like now that we've raised these cool kids, like are we gonna still but want to be together? And then it's like, well, who am I? Like, what is mine? And I think these are I think every conversation as a couple, you need to have with yourself first. That's like my big thing is that is before you go into couples therapy or anything, it's like, well, you have to do a lot of your own work too, before you like dump all the stuff onto another person, expect them to pick up what you're laying down. You need to figure out who you are first and what you want. So that's why if you are thinking about ending a marriage or just thinking about thinking, getting your your finances together, your financial confidence together. Like some people just don't know who, like, are you on the deed of the house? It's like, I think I am. It's not that we don't know, we just we're we're tired, you know.

SPEAKER_01 27:14

It's like among Well, people some people never see their accounts. Like there's one person who has all the logins, and um, you know, I uh whether you're committed to each, like whether you're gonna stay in the relationship or not, like changing those dynamics would be, I think, helpful and healthy.

SPEAKER_02 27:32

Yeah. And but how but how do you do it? I I you know, ideally, someone like you, someone, you know, you know, would be like, well, here's like a separate plan of how to have these conversations. My big thing is tough conversations. That's like my tough money conversations. And then I don't have the answer, so I bring in people who can help, you know, whether it's what are some of the other tough conversations you had in the book and brought

Sex, Aging Parents, And Hard Talks

SPEAKER_02 27:53

light too?

SPEAKER_01 27:53

I know it's a very like, you know, uh funny, fun read too. Oh, not just a downer.

SPEAKER_02 27:59

Well, just is there's so many things that we we bring up. Well, the idea of do you, you know, people's do I want to open up my marriage? We don't get into that too much because the book is it would be an encyclopedia. But you know, do I still want to, do I still want to be in a monopulous relationship with my partner? Does he still want to, you know, what do I do with this person? We I don't think we're attracted to each other anymore. How can we, I don't want to like I don't feel like we have any chemistry. I don't want to have sex with him, but I love him, you know, or I love her, but I, you know, it's how can we have these conversations where like I love you and I'm still in it to win it with you, but I just I'm not feeling it right now. It's like, well, how do you put that out there? What do you and what do you want back from that person? Do you have any solutions? Like maybe we can open up the marriage. That's very is a very intense conversation for people to have because that might not go the way you want it to go. Doesn't mean you shouldn't try if you, but you have to spend a lot of time in yourself knowing what you what you want. You know, do you want to have a threesome? It's like, oh my God, like life life is yours. Do what you want to do, you know. But if you want to have these conversations, you have to really think about what you're unhappy with in your own self, you know, and what that's a conversation with yourself. That's a conversation with yourself, but and then having a conversation with your partner about um, but you know, there's so many, I mean, conversations. I mean, talking to your, you know, there's this great um woman, I don't know if you ever had her in her pocket, your podcast, her name is Cameron Huddleston. She has a book called Um, I think it's called Mom and Dad, We Need to Talk.

SPEAKER_01 29:22

And it's I've heard of that book.

SPEAKER_02 29:23

Yes. She's a wonderful person. And she talks about how when her father passed away, he didn't have a will. And it was like, it's a buckle beyond. So she's so converse tough conversations to have with your kids, you know, like, you know, like this is our financial planning. This is like both up and down. So my friends now, my friends who I used to go to the clubs with and party with and do all this stuff, they're saying that like now I have to sit down with my parents and like have them chase down their will. Like, oh my God, they had that, they still have this person as the executor of that person, died like 20 years ago. Like, so it's these are hard conversations talking to our own parents about money. It's like, how can we sit down with them and say, like, we need like make our lives easy. We're gonna help you make, we're gonna help you help us, you know. And no one told us how to have these. There's there's that's a great resource, is how to talk to your stubborn, I love that, anxious, resentful parents. Not all of our parents are like that, but a lot of people's parents are. They don't want to show with their kids what's under the hood because they don't they don't have what's there or they don't want to be judged and they don't want their kids to say, how could you have not taken this pension, or how could you have like, how do you have this much?

SPEAKER_01 30:32

Or sometimes it's like dad was such a great investor. So, and like, but I opened the investment portfolio and was like, that was great for like 2005 and hasn't been maintained or managed since then. So that can be the other, like, we don't, you know, like dad is so smart in this stuff, but dad's like 92 and can't file a tax return anymore. And you know, like, how do you go and be like the equivalent of like hand of driver's license?

SPEAKER_02 30:59

That's a certain kind of financial therapist that someone needs for like intergenerational stuff. We all need generational support. Someone could sit with your parents and like sit with you and say, like, it just try to like be gentle, but you know, I'm I have so much empathy for our older parents, yes, for sure.

SPEAKER_01 31:14

You know, like my when my grandmother came and so much empathy for the people that are caregiving for them as well, our peers.

SPEAKER_02 31:20

But my grandmother wasn't able to write checks anymore, it was just so devastating for her. I bet my mother, yeah, and my grandmother was very independent, she was very sharp, she was a bookkeeper, and my mom had to do all that for her. So my mother was like, my mom, my parents dealt with so much with their own parents. So I watched them. They were they, and it's you know, you can no matter what, you don't think you've done done enough and you've done anything, you know. So it's not the kind of thing where it ends and you're like, I did a great job. Okay, just you're not gonna feel that way. But I think they did. Um, but I I think that if I could, if this book is gonna go where I want it to go, where my my colleague and I wanted to go, we do want to create like this like network of helping people, of like, like, oh Melissa can help, like she she can, she can have uh I could help, she can talk about this and she can recommend some people, she can give tips and oh, we can talk with this other, this great marriage counselor, and she's got great ideas on how to maybe if you decide you're ready to come out in mid-life. Like we want everyone to be like, you're not expected to know how to do these things. Why would you think you had to as a place?

SPEAKER_01 32:23

Um, as you were, you know, like you had your vision of the book. Did anything that you assumed would be one way you like get get into the weeds of the topic and are like, oh my God, I had no idea that this is what we needed to be talking

The Burn-It-Down Fantasy Exercise

SPEAKER_01 32:37

about.

SPEAKER_02 32:37

Well, it's really funny, you know, just talk about like knowing your audience. Like, um, so we put out a poll on LinkedIn and it got shared pretty widely, which was really wonderful. Um, so it wasn't just like our friends or anything. And we said, How have you ever considered, did you ever fantasize about burning it down? And 80% said yes. And they and we said, Well, like, give us examples. And they were like, they were like running away, like leaving my my family and like opening a bakery on like a desert island. They're just like quitting my job, getting leaving my husband, you know, like we have all this, you know, we're keeping the world going every day, but within us is like a volcano of energy that um if allowed to explode, you know, could really do the world, do the world some damage.

SPEAKER_00 33:24

Yeah.

SPEAKER_02 33:25

Um, which uh so the world should be grateful to us. Um, but I think that was the why it kind of showed us that we were our idea that, you know, you know, how to reboot your life without blowing it up, unless you really, really want burning it up, unless you really, really want to. So we're saying don't burn it down, like singe it, light it on fire a little bit, you know, but don't like you don't have to change your name and fake your death. Like you don't, you don't have to do that, you know. Like what do you think?

SPEAKER_01 33:47

Well, if we're for our listeners who are sitting in their car, like, I wanted to burn it down this morning. First of all, they everybody needs to read the book, but then what would you tell them to ponder when those moments come where they're just like, I'm done with this?

SPEAKER_02 34:02

I think you can make two lists in your head. You can make it you can make it the list of the things that you actually would would would miss about your life if you, you know, faked your death and moved to move to Guam and opened up, you know, a juice, a juice shop, you know. Like, well, what would I miss? And again, these conversations are very fantasy like, but they're fun. Because in fantasy, you can really like you, you don't have to have guilt. You can have real, like, I'm a very big believer in the cinema of the imagination. So you can say, well, say I did this, like, who would I miss? Like, well, I guess like I miss my kids, you know, after a day or two, you know, I guess I'd miss my friends, and I guess I'd miss it. It's like, okay, so there's still some things to live for in this realm.

unknown 34:37

Yeah.

SPEAKER_02 34:37

It's like, okay, maybe maybe it's not all bad. And you know, but then you often have to think, but this is why I really, really do want to burn it all down because I'm tired of X, Y, Z.

SPEAKER_01 34:47

And yeah, what is like in in the way of your contentment?

SPEAKER_02 34:51

Yeah, and but and your comfort. With and take over, take out the because you look when you live in a world of this fantasy world, it gives you a freedom from shame and guilt. It's like, oh, I know I should feel grateful. It's like, yeah, yeah, yeah, yeah, yeah. You are grateful. It's like, stop saying I should, should, should. Of course you're grateful. Of course you're a good person. It's like you're not a bad person for saying that sometimes you want some alone time, and you're not a bad person for saying, because you we all have so much to be grateful for. It's like, yes, like that's a given. Like put it aside and be real. And say, what are three things that are probably a good reason to not burn it all down? Like, you know, you you kind of do like your family, you don't mind your friend. Yeah, you know, there's some things that are still, you know, that you you might miss if you go into liquid disprotection. And then think of three things that are like, but you know, but this is what's really making me bad. Yeah, you know, and it's like, well, like how, and it's about small changes. We don't burn this book is not about like simple tricks and quick hacks, and there's no quick hack to getting to understand yourself, also because your your landscape is always changing, but getting in touch with your essential self, because you really haven't, you are still the same person. Like when we pitched the book, we said, like, save and you remember you know in the magazines like new year, new you, you know, the new you is gonna go to the gym, the new you is gonna be organized, the new year is new, and we're like, F that, like new year, like new year, old you, you are great, you're great as you are. Like, do you want to improve some habits? Great, great, great. That's not what we're talking about. You do know yourself and you and you know at this point in your life what you don't like and when you're over. So instead of just trying to change who you are, figure out how you can change this thing, you know, whether it's maybe taking on a different role at work, or maybe it's figuring out how you can just like put some money aside to get someone to help you like clean the house like once a month. Just like, how can you just offload, use your money to like just not that much money when you're in the old folks' home, you know? Like it just how you can like like I cannot handle just having to clean the whole hat, blah blah blah. It's like, okay, well, don't don't pretend to be a clean person tomorrow. That's not gonna happen. Be like, what can I do? How can I reallocate my resources so that I don't have to think about this so much? And now I have more time. It's like that, that's what we want people to do.

SPEAKER_01 36:56

And so many of our Gen X peers are have nailed retirement already and they need more resources for this stage of life, which involves more people's needs, less time. Yes, uh um, you know, peak earning years where you like why not have permission to enjoy a little bit of it. Um, so I love the idea of incrementalism and also like make lists that are add edits and delete. You know, like what do you want to keep a change? What do you want to add? But also like that to don't list of like, you know, whether it's like people in your life or things that you're doing that just do not serve you anymore, like feel free to cross them off the list.

Spending On Friends, Hobbies, Longevity

SPEAKER_02 37:40

The other thing about longevity, everyone's obsessed with longevity now. We all want to live longer, healthier lives. Yeah. Absolutely. So the way to do that and how to start and to use your money now is to invest in like in things that grow your friendships, things that grow your hobbies, things that grow your, your your explanation of all these things will extend.

SPEAKER_01 38:02

Your purpose outside of work.

SPEAKER_02 38:04

It'll extend your life. New friendships will extend your life. The more friends you have, the more the longer you're likely to live, is to have you have a more vibrant social life. That is 100% true. Making friends is hard for a lot of people. Making some time to invest in meeting new people is going to that is a very worth that that's a healthcare spend, it's a social spend, it's an everything spend. I love that. You know, like I would like to learn how to play the drums next year, you know. Okay. Because like, why is it because I have a vision of me when I'm like 75, being in like, you know, my senior group, I want to be in the battle of the bands. I want to be I want to be in a band at my old folks' home. Like that is a vision.

SPEAKER_01 38:43

What a great goal.

SPEAKER_02 38:44

It's a great goal. And I can do that. And so if I'm spending like if I spend $500 next summer learning to play the drums, like, is that an investment in the happiness of my older years? Um, yes, beyond how happy will I be when I've when everyone's like, when I'm playing, you know, I don't know what but what am I playing? I'm playing Liz Fair or playing something, what you know, to my great soundtrack. That sounds good. Yes, my my little fair soundtrack to everyone in the old folks. So that $500 I spend will be paid off in a million, because so that is what you need to do with your money is invest in the kind of life you want, how rad you are. What would your 17-year-old self say?

SPEAKER_01 39:19

Yeah, she would be happy that I was a lot more comfortable in my own skin doing things like that. Or, you know, like I took a jump off of a high dive, which I never would have done as a child when I wasn't visiting Europe in my late 40s.

SPEAKER_02 39:33

Congratulations. I'm learning how to ride a bike for the first time. Yay! I love that. You know, it's never just all these little things are gonna make you they just they do pay off in dividends. Now you could take a million high dives. Like, I'm gonna be able to ride a bike, like I'm gonna be able to like I these are these little things, all the things that I did, these the weird things are the things that paid off the most emotionally for me. So just have have faith in your goofiness.

SPEAKER_01 40:00

Yes, and and try new things, and it's okay to be like, well, that was that was a miss. Well, because but at least I tried.

SPEAKER_02 40:08

Well, when you're young and I could talk to you forever, but when this I spoke to this great uh therapist and she helps patients who are um her patients are retired and they're trying to kind of navigate their life after retirement, and a lot of them are struggle with purpose and all these things. Um, and she says that the most important thing to do is to keep discovering. She's like, when you're young, it's like you pick up a guitar, you play it for a year, then you put it down. You know, you play play tennis for a little while, then you switch to softball. You know, you do and and that's part of growing up, is you're just picking things up and putting them down. It's like, well, you can still do that as an adult, and you're and and you're not a quitter. Like, yeah, I you know, I decided I was gonna play the drums, you know, and then I now I can keep a basic beat and I'm gonna, you know, maybe like stop doing that for a while and now I'm gonna do this. Like, I think having a teenage attitude toward, except now you don't have to put on your college resume, now you can just do it for you.

SPEAKER_01 40:58

And you don't have to ask mom for permission to sign up.

SPEAKER_02 41:00

No, oh my god, that's my whole life. It's like, aren't you glad to be an adult? You don't have to like ask for permission to do things, like, but um, but just treat your treat yourself like a teenager more, like just let yourself explore and make time for friends, like all that stuff is like we weren't wrong. The things are important to us when we were young, we were right. Fun and friendships and keeps you young. Yeah, because we were right, those things were fun and we still deserve them.

Where To Find Lindsay’s Work

SPEAKER_01 41:25

Well, where can people find the book and any future projects that you're working on, Lindsay? I'm so excited for it to be out in the world.

SPEAKER_02 41:32

Oh, thank you so much. We can't wait. Um, you can always find me at lindseygoldworth.com, just first name, last name, and you can find the book. Um, you can find uh all my writing. And then I have a new newsletter which I'm very excited about. Uh, it's called Dear Star69, and it's going to be a sex and relationships advice newsletter with a little bit of other advice and tips and thoughts about um how to live a more sensual life um in yourself. Um that sounds amazing. Yeah, it's uh very it's it's it's it's very me. I just want everyone to have everyone to have a good time.

SPEAKER_01 42:06

Well, congrats on all of your success, and thank you for bringing the messy money middle into the conversation with the new book, The Midlife Watchless.

SPEAKER_02 42:14

Thank you. I know we're gonna work together soon.

SPEAKER_01 42:16

I can't wait. Collaborations on boarding.

Support The Show And Disclosures

SPEAKER_00 42:29

Thank you for listening to the Women's Money Wisdom podcast. If you found value in this episode, the best way that you can support the podcast is to forward an episode to a friend or leave a review. Go to ProPlan.com and the podcast link to get all the resources and links mentioned. This presentation by Pro Planning is intended for general information purposes only. No portion of this presentation serves as the receipt of or substitute for personal investment advice from Pro Planning or any other investment professional of your choosing. Copies of Pro Planning's current rent and disclosure brochure and form CRS discussing our advisory services and fees are available upon request or on our website platform at PerlPlan.com. The information that we share is meant to educate and inspire, not serve as personalized financial advice. Everyone's situation is unique, so be sure to consult with your own financial professional for guidance that fits your life. And just so you know, the opinions shared in this podcast are Melissa's own and those of her guests. They don't necessarily represent any organizations with which Melissa is affiliated. For more important disclosures, please go to our webpage at proplan.com.