Women's Money Wisdom

Episode 287: Gen X High Achievers & Redefining Retirement with Joy Levin

• Melissa Joy, CFP® • Season 4 • Episode 287

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Gen X may be the “forgotten generation,” but they’re shaping retirement in powerful new ways.

Melissa Joy, CFP®, sits down with retirement coach Joy Levin, founder of GenX Encore, to explore how high-achieving Gen X professionals can prepare for what’s next. With longer lifespans, fewer pensions, and careers built on resilience, Gen Xers are facing retirement unlike any generation before.

Joy shares her research and coaching insights on navigating the identity shifts, social transitions, and planning gaps that often go unaddressed in traditional financial prep. Together, they unpack how to reframe retirement as an encore—a purposeful, fulfilling new chapter.

💡 Key Themes:

  • Why Gen X resilience is an asset (and a challenge) in retirement
  • The risks of skipping emotional + lifestyle planning
  • How to align with your spouse/partner on retirement goals
  • Avoiding social isolation in retirement and building new connections
  • Encore projects: turning passions into purpose
  • The power of holistic retirement planning—beyond the numbers


Connect with Joy: www.genxencorelife.com

Linkedin: www.linkedin.com/in/joyatallium

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:...

Speaker 1:

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. Welcome back to the Women's Money Wisdom Podcast. Today, we're going to be talking about all about Gen X high achievers and what they need to be thinking about, and I've got an expert here, joy Laben, who is. This is what she does. This is her life's work. Joy is the founder and president of Gen X Exec Encore, and she works with Gen X high achievement professionals, recognizing them for their needs and helping them with what's next. I'm going to let Joy start, first of all. Welcome to the podcast.

Speaker 2:

Joy, thanks for coming. Thank you so much. Yeah, thank you, melissa. I'm so excited to be here and I love talking about Gen X so Well.

Speaker 1:

I do too. I feel like we're I say we. I am a member of Gen X, I just turned 50. We're kind of, you know, the forgotten generation, but we are very relevant, especially now, especially today, and I would love if you, you know, just talked a little bit about your origin story, of why you do this work and how you found yourself doing your work.

Speaker 2:

Yeah, I'd love to do that. So I can start by saying you know, this is something relatively new, not just for me but for the world, like most people don't have never even heard of retirement coaching, because it's a fairly new thing. But so for a long, long time, for decades, I've been a market research consultant, so I've worked with companies and organizations doing focus groups and surveys, which I love and I still do. But a couple of things happened over the last few years that made me realize or made me get to this point. So one of them is I started thinking myself about what would be next. You know I've been doing this for 30 years. You know, what should I? What else out there? What else is out there? What else can I be doing? I've always been like one of those naturally curious people Like I wonder what it's like to be a doctor or, you know, a cop or whatever.

Speaker 2:

So I just started looking around and thinking about what else could I do? And then the other thing that happened is, as I got to know my clients, well, they started talking about like I don't know what I would do if I retired and I'm not sure what would be next, and should I, and maybe I shouldn't, I should just keep doing this because I don't know what else I would do. And so those two things kind of motivated me to kind of do some soul searching and thinking. And so I came upon retirement coaching and I particularly liked it geared toward Gen X, because I think there are some differences. I mean, every generation is unique, right, but I think there are some things about ours that you know have gone, have gone, ignored or overlooked, that I think are important to understand as we reach retirement years and, you know, think of them as kind of an encore and not a an ending, but a really new beginning, of an exciting new chapter.

Speaker 1:

I love hearing that and I guess I'd like to start with your research. So you know you don't just kind of vibe it. You've spent your career, your life's work, really getting to know the facts and the figures. So what? What have you found? Distinguishes Gen X from everybody else?

Speaker 2:

Yeah, there are a number of things. So, first of all, when you think about what we grew up with and in our environments, you know we were latchkey kids a lot of us for the first time ever. You know we saw things like the energy crisis in the seventies. Some of us we saw, you know, the challenger disaster in the eighties. We lived through like the dot com, but I mean like all kinds of things influenced us and I think they made our generation very adaptable and just kind of flexible and resilient.

Speaker 2:

So those things kind of matter when you're thinking about the future.

Speaker 2:

You know we want to come up with things or think about things in a way that kind of celebrates that resiliency way, that kind of celebrates that resiliency.

Speaker 2:

And then another major change is you know we're one of the first generations that won't have pension plans, right For most of us.

Speaker 2:

There are some who do, but you know we've had to sell fund for 401ks with supportive employers and so that made us think differently about retirement and what will come next.

Speaker 2:

And then a third major thing is you know, because of medical advancements, when social security was first started, you know way back, people were expected to use it for like two to five years, but that was their lifespan. Now we're looking at potentially 10 or 15,000 days of our next chapter, and so to think of it like just playing golf or whatever, that's just not going to happen, especially for these Gen X high achievers who are so used to, you know, having a strong identity in their work or, you know, having a lot of purpose and relevancy. So we need to start thinking differently about how retirement will look and the support that people will need as they move into retirement. You know it's certainly the numbers and the finances are extremely important, but there are others, there's a whole other side of it that typically people don't think about or talk about, and that can lead to a lot of issues. You know where people are. Like gosh, I must be the only one thinking these things and it's just not true.

Speaker 1:

I couldn't agree more I. I want to go back to something you said in the beginning, because there's just so much to unpack with each little section. First of all, I not only are we an incredibly resilient generation, you know there's all this emphasis of how. You know how difficult it is for the baby boomers, or how difficult it is for millennials or Gen Z. You know they skip right over Gen F, but we were. You know, we, we did get a lot more exposure to the world's events than kids do nowadays. It was a lot more, you know, kind of independence You're on your own, lack of parental supervision. Helicopter parenting I don't think had been invented.

Speaker 1:

So that resilience is both an extraordinary capability.

Speaker 1:

But it is also so important because retirement itself relies on resilience and it is something where, if you can access your flexibility and your resilience, you will be so much more successful. Because I think people assume, hey, I'll need six months to kind of get ready for retirement, and then I put in my notice and we're off to the races with our feet up and there's nothing to do in retirement except for enjoy it. You know, I put in my notice and we're off to the races with our feet up and you know there's nothing to do in retirement except for enjoy it. But for people whose identity, especially high achievers, which I know we both work with, where your identity is so intertwined with your work life, you know, a six month runway with, just you know, hanging up the work hat and and putting on you know, the leisure, athleisure, whatever, is not going to cut it. You need to do some more soul searching and some more preparation and you really need to pull out that resilience that you were, was put into your DNA and get ready to use it.

Speaker 2:

I totally agree and I think there's a flip side to it too, where you know because we know we're resilient and we've been kind of in that mindset for so long when you get into retirement and you start kind of facing these issues, there's no guidebook on how to navigate that, and so while there's this resilience, there was an expectation that, oh it's, yeah, I shouldn't be bothered by this and I'm going to power through, and just a lot of the skills that we've used in our work lives don't really carry over into retirement, so we need to harness that resilience to find new skills and new ways to become, you know, stay relevant and have a purposeful life.

Speaker 1:

Yeah, so some of us listening who are Gen X and I often include older millennial, because I, maybe because my siblings are in in that cohort Some of us are, you know, kind of planning for a retirement in our 60s. Others of us are retired or getting ready to retire much sooner, and I think that's one of the other key distinguishing factors is when you're disconnected from that pension. It's not a 30-year clock, it could be very different for different people. So perhaps we could start with that cohort that knows retirement is on the horizon, let's say in the next three to five years. What is your work with them in terms of how things they may not have considered or may need to work with a professional to prepare?

Speaker 2:

Yeah, that's actually the best time to start working with somebody like me. Is that three to five? You know time horizon, because what happens is, you know, first of all, there's been research done about three quarters of retirees say they have seen somebody struggle with the transition to retirement. So you know, if you can head that off and plan for it, you're that much ahead of the game. You know there are all kinds of things and we can talk about that come up in retirement.

Speaker 2:

So the planning is the key and so what we do is we go through a series of exercises and I have tools and worksheets and it is having those conversations that people are not having. You know, just one example is the issue of if you have a partner or spouse. Right, you're probably not talking about very specific things, that what retirement will look like, and so it. You can find this disconnect where a spouse thinks we're going to travel and the other spouse is like, okay, now we're having grandchildren and I'm not sure I want to travel that much or move to this other location that we've been thinking about.

Speaker 2:

So that planning is so important in heading off some of the disagreements and issues that people have, and another big one is social life. You know, being in retirement can be very isolating. You know a lot of people, in fact, who are retiring earlier. Their friends are still working and so all of a sudden they're like nobody's around to hang out with during this, all this time I have now, and that can really lead to isolation and that can lead to depression and all kinds of issues. So you're right, that's why the planning can be so important and that's some of the things that we kind of work on.

Speaker 1:

Well, if you're listening and you're like, oh, I won't be lonely, just do a little project with yourself and evaluate how much of your time is spent with your coworkers. And for me, you know, my coworkers provide an outlet for social life. I have a long list of friends but because life is busy and hectic and planning ahead is difficult, some I may only see once or twice a year, and so you may have on a pie chart more than 50% of your kind of social engagement with other people that you know may feel like work but also brings a lot of, you know, the psychosocial benefits of being around other people is coming from the people that you work around, especially if you go to the office versus working from home?

Speaker 2:

Yeah, absolutely, you know, and there's actually been research that's been done where about 40% of people before they retire think my social connections are going to increase in retirement, I'm going to have more time, I get to pursue my interests and meet all these people. But in reality, once people do retire, more than 80% say their interactions socially actually drop off and about four in 10 say those interactions drop off by more than half. So there is and that's research that's been done by the Retirement Coaches Association, so there is, you know this this big difference in what people think and the reality they're going to face. And so by doing that planning they can sort of lay the groundwork for not really experiencing that disconnect and, you know, being able to make sure they have those relationships going before that happens.

Speaker 1:

Yeah, yeah, that is an excellent reminder I. I guess the other part is like how much time do you spend with your spouse if you are in a relationship or partner, and how do you enjoy that time together? And you know again, that might be too much of one thing where you need to make plans for one or the other of you to find another, you know, kind of access point to getting out of the other of you to find another, you know, kind of access point to getting out.

Speaker 2:

Oh yeah, there are a lot of couples where one spouse will say you need to do something else and sit on the couch. You know, it's like we marry for better or for worse not to have lunch every day together. Once in a while it's nice. But yeah, we need to have our own tribes and our own activities because that just makes the relationship that much more rich. Right, most spouses or most couples don't have the same work life. They bring their own work lives into the relationship and that makes it more better. You know, that makes it just the more better and more interesting to talk about.

Speaker 1:

Yeah, absolutely so. And how do you prepare people? Is your, are your agapeness primarily with one person, or sometimes are they with couples? Because how do people get prepared if one person's retiring and the other one's going to keep working?

Speaker 2:

Yeah, that's a great question. We definitely see that. You know I work with individuals, I work with couples. You know we can do group sessions.

Speaker 2:

So, yeah, when it comes to couples and they're on different timelines, it really makes sense to think about. You know, planning it in chunks, like you can ask each one of them okay, what am I going to get done by the end of this year, what do I want to get done? And for the one person it might be okay, I want to, you know, start taking guitar lessons or whatever it is I want to do in retirement. And the other person's thinking, well, I want to do something career related. And it's so, it's having those conversations, so you can make sure that both needs get addressed and it's not just somebody feeling like, okay, I'm pulling them along into retirement, it's still having those fulfilling lives that are full of purpose and being able to navigate them together. So that is definitely one thing we see a lot where people are on different timelines. You know easily, you know even just like four or five years make a huge difference. That's perfect.

Speaker 1:

And then do you have some recommendations for people after you know the big day hit, you know they've crossed the finish line, which you and I both know is really just another phase it's. It's a starting line for a huge phase of many of our lives. It's getting bigger and bigger as people live longer and retire earlier. What are your recommendations for once you are retired? So you've assessed, hopefully you've prepared, but there still may be surprises, and I love we recently interviewed Dan Halit who wrote a book about retirement and he mentioned like the worst day of retirement is like day 115. You have the, you know the highs have kind of evaporated, all the endorphins are gone and you're like, is this all I have to look forward to? So how do people kind of nail after they put in the intention and the preparation for getting to that point of retirement? How do they make it so that they have more probability and possibility for success? Yeah, that's a great question.

Speaker 2:

Yeah, a lot of it is, you know, having somebody like me, a coach, that can say, okay, you might know what you want to do, let's work on how you're going to get from point A to point B. I mean, cause just people just don't have these conversations and so they just have no idea how to do it in a realistic way. So that's part of it. It's about talking to other retirees, sometimes like kind of having a retirement mentor, you know where. Yeah, yeah, so you know somebody who's been through it.

Speaker 2:

You know, in the last couple of years how did you make the change? You know, how did you kind of set your plans in motion? And I love you know that's one of the things I want to start doing is connecting people in that way. I think that's such a powerful thing Because when you think about, like, in work life we have mentors like that, but in retirement that's like unheard of, like why would you do that? But it can make such a huge difference to hear from somebody who's done it in a way that succeeded, for them to be able to help somebody else. They benefit, and the new retiree benefits clearly as well.

Speaker 1:

So if you're someone who doesn't know when they're going to retire, you know, maybe retirement might be 10 years out. I mean, one of the things that you and I both know is that it can be a surprise.

Speaker 1:

You can have a game plan and not have a game plan, but just think I'm going to work forever. But people don't always retire on their own terms, sometimes due to health or career changes. You don't necessarily have a choice or the needs of others. But if you're that person who's like, oh, maybe I should start thinking about retirement, like it feels like I'm at the age where I need to get more serious about this, and I often these people, these kind of people you know that might be the first time they engage with a financial planner in addition to learning about a retirement coach.

Speaker 1:

But where would you have those people you know kind of get started when they say, okay, I've always, you know, saved a little bit of money, but now I really want to understand what I, what it takes to retire, but I don't know when that date is going to be.

Speaker 2:

Yeah, you know, for a lot of people, I think it starts like almost with the financial planner saying, okay, so where do I need to be financially so that they know what's realistic, and you know maybe what's a stretch or that they have to save more for whatever it is. And then you know we there are some books out there that can be helpful, but I think it's really starting to think about working with a coach or, you know, being able to, at least in your own head. I mean, one of the things I do is we look back in time. You know, what did you used to enjoy that you haven't done in 30 years?

Speaker 2:

You know there was a reason you enjoyed it done in 30 years. You know there was a reason you enjoyed it. So it might be that you want to do that same thing or you want to do something that has similar traits. You know, maybe it was, oh, I really enjoyed, you know, having a paper route like back in the day or whatever, and so there were things about that. It was interacting with a lot of different people, it was having some structure. So it's, you know, it's kind of thinking through what did I used to enjoy and why did I enjoy it and then how can I carry that back into my future?

Speaker 1:

life is one, you know, concrete way that sometimes people can start that planning process it is important to start with a financial planner and hopefully you're able to work with someone who not only is you know kind of managing the dollars and sense and accounts. I've had people come to me in the past who said my advisor told me I could retire but not like how to retire, for example, not like where I would take money out. Maybe I need to hire a financial planner on top of that. And I'm like, well, if you work with someone who's trained in you know kind of the big picture of financial planning, you shouldn't need a second engagement on that side. So then you can use you know the costs you would have done to pay for somebody to plan on top of your investment advisor to reach out to a retirement coach, or you can spend that time kind of building the social connections. You need the plans for the hobbies.

Speaker 1:

I've had some, some clients who've done wonderful encore projects, whether it's make a movie with a friend or write a book or continue to create art, with kind of no expiration date but a lot of flexibility, and I guess that's where we might go for the next portion of our discussion. I know you talk about the encore. So are some of the people that you work with still doing things, but just in a different way.

Speaker 2:

Yeah, you know, they're all kind of like every situation is so different. So like, for example, I worked with an attorney who realized I want to write a book, just like you were saying. And you know, or it could be, a lot of people say I want to serve on a nonprofit board, and so how do I get there? It could be, you know, I want to do a passion project, like you were just saying, and so how do you structure that So's sustainable, so that it is meaningful to you? Or how do you create a legacy? Is this other big thing that we often work on? So, yeah, there's a lot of different parts of it, but I think you're right.

Speaker 2:

I think that retirement planning is traditionally thought of in the financial realm, but what I think we're finding is that it's really a holistic approach. That is the best way for somebody to make sure, or have the greatest chance, that their retirement will be fulfilling, will be purposeful, that they're not just sitting around counting money or wondering what else they're going to do or, you know, arguing with their spouse or whatever it is you know, to make sure that they have an enjoyable time Because, like I said, to have 10 or 15,000 more days, 30 years in which to look forward to, you know, a whole other chapter of your life. Like I said, it's it's really not an ending, it's a new opportunity, yeah.

Speaker 1:

Yeah, and I I think what I would take from would take from what you just said was retirement is multidisciplinary. Certainly, if you don't have the finances nailed, then everything else can come crashing down. But the same goes for your psychology, your health, your well-being and so many other things. And you know the degree of difficulty is increased when you add a partner. You know a co-pilot, when you're in a relationship and if you're not in a relationship, the degree of difficulty increases because you need that. You know whether it's social life, but also the resources and people to take care of you if you can't always take care of yourself. So both, both have their own complexities and challenges.

Speaker 2:

Absolutely. I mean that's. Those are such realistic scenarios. I mean they really do happen. And also, you know, just like you said, when you're single, what are you going to like, what is your social life can look like? How are you going to get out there, how are you going to nurture those new relationships and find old ones or whatever it is. And you're right, like thinking about all these different parts of it. You know we talk about the financial portfolio, but I like to say there's really a retirement portfolio there's. You know it could be, you know, part social life, it could be a passion project and, of course, the finances. So it all kind of. That's why I think it's like more of a holistic approach now.

Speaker 1:

I have a retiree. He's been retired for five or six years and I met with him recently and he said I feel really good about the money that I spent this year. He had done some exceptional travel, kind of bucket list travel had big celebrations for an adult child's wedding and bought a car he loves and we were discussing doing some charitable giving, and so I just loved that perspective of talking about what he invested in during this retirement. Like you know, he saw kind of saw that spinning not as like oh my. He saw kind of saw that spending not as like oh my gosh, I can't believe that went down the drain and instead said that the way I chose to spend money brought me a lot of joy.

Speaker 1:

And so that's a goal for those of you listening who think that retirement may be within the next decade or so to say. Could I build a life and and create experiences? Hopefully, because we know how experiences are can be so powerful um in terms of um wellbeing, um to see if you can um spend with joy um, not spending is free, but right, right, no, yeah, and you know it's, it's.

Speaker 2:

It can be a real psychological struggle. I'm sure that you see for people to go from accumulating to decumulating, right to letting go of some of that money. But you're right, I mean you're not going to take it with you you know at the very end, using in a purposeful way that gives you that joy and enjoyment and that meaning for your life, and those experiences are just so much more valuable than anything material that you know you can really acquire in a lot of cases.

Speaker 1:

Yeah absolutely Well, what are some of the resources that both you have, and I would love to also hear, like, what you think people preparing for retirement should be reading and thinking about.

Speaker 2:

Yeah, you know there's just some good people to follow. I would just look on Amazon and find some of the good writers in the retirement category. You know the head of the Retirement Coaches Association, robert Lara, has published I don't know how many books it is now 10. And what he also does is he has retirement coaches like myself write chapters in these books. So you get all these different perspectives. That's one place I would start.

Speaker 2:

You know there are associations like AARP, I think it's. There's another one, amac, I think it is, and find out what they're writing about in their magazines. You know that's a good place to start. And just some of the trades, the financial trade magazines they do occasionally more and more have kind of like lifestyle articles and things that people should be thinking of beyond the numbers, and so those are good places to start. So I would look at some of those places, because it's hard to say which one resource is going to work for people, because there's such a unique combination out there of what's going to work for any individual. So I think it makes sense to look at all of these different things and find out, you know, what resonates with you, what seems to make sense, you know, and you know, there are people like me retirement coaches that can help you tie it together.

Speaker 1:

So yeah, well, if someone's listening and thinking, oh my gosh, I need a retirement coach, this is what I've been looking for. How do you work with people, joy, and where can they find you?

Speaker 2:

Yeah, yeah, so I work with people generally. One of the things I really like about retirement coaching, and the way it's different from sometimes other types of coaching or whatever other professions is it's fairly finite. So typically I engage with people either, you know, in six or eight sessions that's enough to kind of at least lay out a plan, and then we'll sometimes check in, like once every other you know, six months or whatever it is to see if the plan is on track. So that's generally how I work with people in those packages and so in any one of those packages we go through a series of exercises and tools to address all these different factors we've been talking about, and so that's the way I like working best with people.

Speaker 2:

I do workshops, you know, from time to time, like I said, I do group coaching. Sometimes I our couples. So there's a variety of ways, but the best way to get in touch with me is, you know, my website is genxoncorelifecom. You can reach out to me through LinkedIn. I'm on LinkedIn, joy Levin or you can email me, jlevin at genxoncorelifecom.

Speaker 1:

Joy, thank you so much for joining us. We'll have all of those resources and links in the show notes, but I love the work that you're doing and keep up the great work.

Speaker 2:

Oh, thanks so much, Melissa. This was such a great talk. I really really enjoyed it, and thank you so much for being such a gracious host.

Speaker 3:

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 proplancom 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 a receipt of or a substitute for personal investment advice from Pro Planning or any other investment professional of your choosing.

Speaker 3:

Copies of Pearl 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 pearlplancom. 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 proplancom.

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