Richard eisenberg Richard eisenberg
Podcast 285

285: The Path to a Purposeful ‘Unretirement’ with Richard Eisenberg

Today I’m talking to Richard Eisenberg. Richard started his career as a finance writer at Money back in 1978 and has been writing about personal finance, money, and retirement for decades.

He recently left his post as the Senior Web Editor of the Money & Security and Work & Purpose channels for Next Avenue. However, in what he calls his “unretirement,” he’s started writing a new column for MarketWatch, contributed to Next Avenue, and become the co-host of the Friends Talk Money podcast.

While some finance writers want to help rich people get richer, Richard has focused his career on helping others manage their money better and make smarter financial decisions. In a world where there’s so much more information, financial products, and opinions than ever before, Richard has a wealth of knowledge and a proven track record at sifting through the data to provide sound and relatable financial advice.

In this conversation, Richard and I discuss how to make sense of the tremendous amount of financial information and articles available today, the 5 keys to a successful semi-retired or unretired lifestyle, and how to discover new meaning and purpose in the next stage of your life.

In this podcast interview, you’ll learn:
  • How finance–and finance education–has changed over the course of Richard’s 40+ year career.
  • How to identify whether you can trust the author of a piece of financial writing and what to look out for.
  • The difference between a midlife crisis and a midlife financial crisis.
  • How Richard defines unretirement.
  • Why Richard decided to “unretire” and what fellow “unretirees” should be looking out for in their own lives.
  • The 5 keys to a successful ‘unretirement’.
  • How Richard defines purpose–and why he believes that everyone who can should unretire.
Inspiring Quote
  • "Not everything you do in unretirement or in life can bring you joy, but the more you can find that does give you joy, the happier you'll be. And the more you can get rid of the things that don't bring you joy, the happier you'll be." - Richard Eisenberg
  • "There’s no right way to unretire or to retire today." - Richard Eisenberg
Interview Resources
Offer valid in the 50 United States and the District of Columbia, to first-time requestors. During the offer period, receive one (1) in-stock book per request. Limit (1) book per week per household. Limit three (3) books total each calendar year, between January 1 and December 31. Offer valid while supplies last. Howard Bailey Financial, Inc. reserves the right to cancel, terminate or modify this offer at any time. Void where restricted or otherwise prohibited.
Read the Transcript

Casey Weade: Richard, welcome to the podcast.

Richard Eisenberg: Thank you, Casey, great to be here.

Casey Weade: Richard, I’m excited to have you here. I have followed you for quite some time. We’ve included many of your articles over the years from Next Avenue and beyond in our Weekend Reading email series, an email that goes out every single Friday. So, there are many individuals listening right now that have read your articles who are familiar with your background, but they don’t know Richard personally. So, today, we get the opportunity to learn a little bit more about you personally and find out what it’s now like to be actually retired.

But before we get there, you’ve been writing on personal finance and money and retirement for decades. What was it that has you today so jazzed up about personal finance as you continue to write in your retirement years? Right now, you continue to write these articles on this topic, but what originally got you interested and why are you still jazzed up about it?

Richard Eisenberg: Well, sure. First of all, thank you so much for having me and thank you to your audience for reading any of the articles that I’ve written. I started at Money Magazine back in 1978 as a fact-checker, and those of your audience who may know Money Magazine, which unfortunately no longer publishes a print version but does have a website. But when I started Money Magazine, it was right after college, and I knew I wanted to work at a magazine and I wanted to work in New York City and I was interested in personal finance a little bit. I didn’t know a whole lot about it because not many people in their 20s, early 20s do, but I was lucky enough to get a job offer there and started, and I just loved it.

And so, over the years, I spent 19 years at Money as a fact-checker, as a writer. I was the Washington correspondent for five years. I was a senior editor. And when I left, I was the executive editor, and I learned a lot and I tried to share what I learned with our audience. And it’s service journalism and what I like about it at Money Magazine and what I did at Next Avenue, later on, was to try to help people manage their finances and learn a little bit more. What I didn’t want to do is work some personal finance writers do, which is to help rich people get richer. I’m happy people are rich and I hope they do well. But mostly what I want to do is help people who are not quite there yet, but would like to be doing better than they are or just feel like they’re doing the right thing. So, that’s what I’ve tried to do my whole career.

Casey Weade: Did you feel like that was missing for you, that education, those outlets were missing for you when you were younger?

Richard Eisenberg: Yeah. When I started out, this is back in the late 70s and early 80s, there wasn’t a lot of personal finance information out there for people. There were some books. There were some magazines. There were more magazines than there are now. There was Kiplinger’s, at that time was called Changing Times, and there was Money Magazine. That was mostly about it. Sylvia Porter had a magazine for a while. Of course, there was no internet.

And so, I felt like for a lot of people who didn’t have a financial advisor, they were on their own and they were trying to figure it out, and there wasn’t a lot that they could go to to learn that. So, I wanted to do what I couldn’t and I got lucky because it was a great time to be a personal finance writer and editor because it was the time where we started seeing a lot of changes, new types of mutual funds and ETFs, and savings accounts, 401(k)’s. None of those things existed when I started in 1978. There were mutual funds, but not that many of them. So, over time, things changed, and I got to tell people about it. And of course, there’ve been a lot of tax laws over the years, and that’s changed a lot. And every time there’s a new tax law, it’s a lot for people to know and do better their finances.

Casey Weade: Those outlets were maybe not quite what they are today back when you first started writing. In addition to just the number of tools that are available to us today, we have an abundance of tools, we have an abundance of resources. There are millions of articles being published and there are millions of outlets that we could go through to consume information and to learn and grow. And I don’t know exactly how to present this question. I’ve thought a lot about it. It’s just one of my frustrations. I guess sitting in the chair that I’m sitting in, I’m visiting with families, individuals that are coming in, and they’re overwhelmed with the amount of information that’s been thrown their way. They’re paralyzed by the amount of information that’s been thrown their way. Quite often, they’re bringing to the table things that have been generalizations that are made, or there’s been actual misinformation that has come their way through the media. And there’s just a dichotomy of opinions out there today.

So, I’m wondering, how does someone discern whether what they’re reading is valuable and insightful? Where do they go? Where do they look? I mean, even some of my favorite writers, they can make generalities, and those generalities can lead to mistakes as an individual. I’m just wondering how you sift through all this and if you have any insight you can provide to those that are attempting to do so for themselves.

Richard Eisenberg: It is very challenging because the internet is a double-edged sword. On the one hand, there’s lots of great information out there. On the other hand, there’s lots of bad information out there, and it’s sometimes hard to tell which is which. And there are fewer magazines and actually not that many books these days being written about personal finances. So, that is kind of going by the wayside to some extent.

My advice for people in terms of just whether to trust the information they’re reading is to start by learning about the person writing it or the outlet that’s providing it. And it’s usually pretty easy to find out what the background of that person is or that website or media outlet and see if that’s trustworthy if they have a good background. And you can pretty quickly tell the ones who don’t have much experience knowing about this or might have a point of view that they might not be telling you about.

One of my big pet peeves is the writing. Sometimes they see this in books, sometimes online, where it seems as though the writer is independent and objective, but the more you look into it, what you find is they’re really trying to sell you their product that they sell, like insurance or stocks or whatever it may be, and they’ve got a vested interest. And that’s really what you have to be careful about.

Casey Weade: Alright, and one of the reasons that I’ve included so many of your articles in there, and just Next Avenue, in general, I think does a wonderful job of coming out finance and retirement and other topics from a place of unbiased. I don’t see that level of bias in a lot of those articles as Next Avenue is not trying to sell you on an individual product or strategy or anything like that, but then I also see a lot of lines being drawn in the sand by other authors. And in reality, finance is just so nuanced. How hard is it for someone like yourself to write about financial strategies, write about financial tools and products, given that things are so nuanced?

Richard Eisenberg: Well, if you do it for a while, as I have, now you start learning which types of people and sources are trustworthy and knowledgeable and useful and which ones aren’t and then you start going either back to them or finding new ones. So, I like to think that the work that I’ve done, other articles on Next Avenue, in other places like that, I’ve started writing for MarketWatch, and they do great work also in personal finance and retirement. Those are places where you can feel that you can trust the people who are writing them because those outlets have vetted the people who are writing for them.

Casey Weade: And Richard, I really want to make sure we get to your retirement because that’s just going to be, I think, some of the most valuable content that we can provide to our audience today. But as I was doing my research, I’m going back and looking at Richard as a two-time author. And my initial thought is, oh, I want to talk about one of these books, let’s focus on these. And then I go, oh, well, one was published in 1987, one was published in 1998. But that’s wonderful because now we get to see what’s changed for Richard, the way that you think, and how you might rewrite those books. And I want to kick this off with the first book, 1987, How to Avoid a Mid Life Financial Crisis. I want to ask, why did you write this book? And what’s the difference between a midlife crisis and a midlife financial crisis?

Richard Eisenberg: I wrote that book because it came out of an article I wrote for Money Magazine back then. It was about how the Baby Boomers were just starting to turn 40 of all things. Now, some of them are in their 70s. But at that point, they were just turning 40, and I thought it was a good time because a lot of them had not thought a whole lot about their personal finances, and 401(k)’s were fairly new that maybe they could use some help in just sort of getting on track for their financial future and to avoid some of the mistakes that a lot of them, I think, were making at the time, whether it was about debt or budgeting or saving taxes. So, that’s why I wrote the book.

And a midlife financial crisis, I think, is a little different from a midlife crisis. The midlife crisis, we all know that phrase, and that’s usually about you feel like in your 40s or 50s that you want something new, and so, you’re going to go out and buy a red convertible or something like that. A midlife financial crisis is more about, oh my goodness, I’m in my 40s and I haven’t saved enough for my kid’s college education or my own retirement or the possibility of long-term care, that sort of thing. So, it’s what can you do in your 40s around then so that you can get on track, and if you’ve made some mistakes to correct them because there’s still plenty of time to catch up? And that’s what I was trying to do with that book.

Casey Weade: As a 40-year-old today, I’d say, I don’t feel like I’m at my midlife. I feel like I’m maybe at a third life and I’m not ready for that crisis yet. Do you see that the midlife crisis has shifted with longevity, that that point in time is happening in our later years? And if so, where do you see that landing today?

Richard Eisenberg: Well, it’s true that people are living longer in general than they were in the 80s by a few years. You can argue what is exactly midlife, but by and large, the average life expectancy of people these days is in their 80s. Some live longer than that, some don’t. So, I feel like 40s is still more or less midlife for a lot of people.

Casey Weade: Don’t tell me that, Richard.

Richard Eisenberg: But I wouldn’t get too hung up on that, definitely.

Casey Weade: And did you experience this? Did you have your very own midlife financial crisis of your own? And is that kind of part of the reason for the writing?

Richard Eisenberg: I think I did not, and I hope I didn’t because I feel like I knew enough to do what I had to do to avoid. So, I’ve been saving furiously since I started working both for myself, and then we have got two sons now and we started saving for their colleges as soon as they were born. And I’ve been careful about spending and debt over the years. I’ve made mistakes, everybody does, but I don’t think I had a midlife financial crisis because I feel like I knew how to avoid it.

Casey Weade: I’m curious, did you ever feel like you had enough? Did you ever feel like you saved enough as a great saver? Did you always feel short? Did you always feel in balance? Did you feel like you always had this job optional status? What’s that felt like for you?

Richard Eisenberg: Well, I think most people don’t feel like they have saved enough because you just don’t know what the future can hold. There are going to be the Elon Musk’s of the world who don’t have to worry about that so much. But most of us, we just don’t know what the future will bring in. Are we going to need long-term care for ourselves or our partner or parents? That’s very expensive. What’s our health going to be like? How long are we going to live? So, I feel like I’ve saved well over the years. I wish I had saved more because I think it’s always better to have more than less. But I felt like, and we’ll talk about my own retirement, I felt like I’m now at a point and I met with a financial advisor to help confirm this that my wife and I had done enough of the right things that we were in a good position right now. Things can change, but for now, we’re feeling okay.

Casey Weade: Well, with about 30-plus years of experience since you wrote that book, would you change anything? Or would you update anything? Would you add anything to it?

Richard Eisenberg: Well, the biggest change since I wrote the book, and that was true for the other book, too, the money book or personal finance is that there have been a lot of tax laws since then. And every time there’s a tax law, that means people need to change the way they manage their money to relate to that. And it could be about the savings for retirement because the IRA rules have changed over the years, the 401(k) rules have changed over the years. So, that’s been the biggest change, and I’ve tried to adjust my personal finances accordingly. When I started freelancing, I set up a simplified employee pension plan, an SEP plan, for my self-employment earnings, so I had them tax-sheltered. I continued to segment my 401(k) through my jobs. I’ve had a bunch of different jobs and different employers, but luckily, they’ve all had 401(k)’s and a couple even had pensions. So, I tried to take advantage of those as much as I could.

Casey Weade: What do you think the best place is for someone to start if they’re heading down this road of, hey, I really want to understand finances, financial planning, retirement planning? What do you think that first stop is? I think the first, and for most, is Google, but there might be a better place.

Richard Eisenberg: Well, no, that’s a good place to start if only because everything is there. And then you’ve maybe wanted to start thinking about, well, what are the areas of personal finance that are really either don’t know enough about or aren’t really want to focus on? For some people, it’s debt. For some people, it’s saving. Some people, it’s taxes, insurance. Pick one and start with that. Don’t try to understand everything at the same time because that’s too much but to do it in bits.

There was a great book that came out a couple of years ago by a writer named John Schwartz. And I may have to tell a little bit wrong, but essentially, it was like how I put my financial life together in a year, more or less, that’s the book. And he was in his 50s, and he felt like he and his wife had not done everything right, and there was a lot they were doing wrong and didn’t know. And he spent a year trying to learn. And in the book, he tells you how he went about learning that, what he learned, what he did wrong, what he’s doing right. And I really recommend that book because I feel like he does a really nice job of helping people get on the right road. And then the articles that we published at Next Avenue, the podcast, you mentioned there are lots of great places for information on particular topics.

Casey Weade: We’ll make sure we have links to all of those resources in the show notes at You can check it out there. Let’s talk about your retirement and kind of your journey here, Richard. How did you decide? First of all, how did you make this decision to retire from Next Avenue? And is this really retirement? You’re still writing.

Richard Eisenberg: Yeah. Well, I call it unretirement. Some people call it semi-retirement, but it is retirement. It’s just not the retirement that people described 20 or 30 years ago. Back then, retirement meant you quit working your job full stop and you don’t do any work and you spend the rest of your life at leisure. And if you’re well enough, you try to take advantage of the things you can do that you had no time for before. That’s changed. And for me, my definition of unretirement or semi-retirement is one that I think a lot of people have these days, which is you’re not working full time, you’re working part-time in retirement pretty much as much as you want to, but where you want to and how you want to. So, I’m not working full time anymore, but I am working. And I just started writing a new column for MarketWatch about unretirement. And I’ll be doing that every other week. And I’m writing for Next Avenue and I’m still doing the Friends Talk Money podcast.

So, I’m still in the game, but I’m just not doing it all day, every day from 8:00 in the morning till 6:30 at night. So, yes, for me, this is unretirement. I decided to do it because I had just turned 65. I’ve been at Next Avenue for 10 years. I was part of the launch team. I thought this seemed like a pretty good time to step away from that job, but somebody else got a chance to do it and look at it with fresh eyes and have a chance to explore my own Next Avenue and have the time to volunteer and to mentor and do freelance and travel and see my kids in Los Angeles, which is where I am today. Those kinds of things that I couldn’t have done three months ago.

Casey Weade: Well, how many weeks are we into retirement right now, Richard?

Richard Eisenberg: Gee, I guess I’ll say six.

Casey Weade: About six weeks into retirement. So, we’re still in that honeymoon phase, I’m sure.

Richard Eisenberg: Yeah.

Casey Weade: I don’t want to talk about what that transition and kind of where you find yourself at today mentally, but this kind of brings me back to a previous guest, Bruce Feiler, which you also referred to in your last article at Next Avenue. You talked about Bruce Feiler and the impact that he made in your life. And in our conversations, one of the things I found most intriguing was transition periods, his three phases of a transition, the long goodbye, the messy middle, the new beginning. If you’d like to catch the full-length episode, that’s Episode Number 267 of the podcast. But I’m wondering, Richard, where are you in this process, long goodbye, messy middle, new beginning? We’re probably in one of those two later stages.

Richard Eisenberg: I think I’m probably in the long goodbye. I don’t think it’s going to be that long for me. I let people know, I let my employer know back in November that I was going to be leaving in early January, so that’s when the goodbye started. And then I gradually started telling sources and friends and family members in December that this is what I was going to do starting in January and then went public in January, saying, “Hey, I’ve unretired, and here’s what I’m doing.” And I’m still figuring things out. I’m going to be doing that for a while. I’m hoping that I’m not going to be in the messy middle, if at all, or maybe not long. I feel like what I learned from Bruce Feiler’s book may help me prevent that, but I could be wrong about that. So, we’ll see. So, that’s kind of where I feel like I am today.

Casey Weade: That’s interesting. I would have thought, and I think most sort of thought, well, it’s really a three-stage process, right? Long goodbye, that’s everything that happens before I actually cut the cord. And then the messy middle is while I’m figuring out this next transition period. And then once I finally eliminated all of those major decisions that I need to make and I know where I’m at today, now I’m at the new beginning, but it sounds like you see it a little differently.

Richard Eisenberg: Yeah, I mean, as I say, I’m only six weeks into it and I’m making mistakes and I’m going to make plenty of mistakes. And there’s no right way to unretire or to retire today. So, I don’t want to say, make it sound like I have all the answers. I don’t because nobody does, but I do feel like I thought about it a lot, planned for it a fair amount. So, that not only was the long goodbye not that long, but also, I feel like the messy middle I feel is from people who really didn’t think about it very much, and now they’re sort of at sea because they don’t know what they’re going to do with their time, where are they going to find meaning and purpose in their lives, what are they going to do with all their free time, who is their new identity? So, I can see why a lot of people have that messy middle, and I may have some of that. I don’t think I’ll have a lot of it.

Casey Weade: Well, that’s the goal of most, to free ourselves up so that we don’t have to spend too much time in that messy middle and squish that together. And you’ve come from a great position with all the decades of research that you’ve been doing over the years, making that pretty simple. However, even with all of the knowledge that you have, there were probably some surprises that came up along the way. What were some of those surprises, maybe things that were more challenging or even easier than you thought they would be?

Richard Eisenberg: I’ll say two, one of them I think has to do with scheduling. So, when you’re working full time, you don’t have to think much about your schedule because your employer has pretty much figured that out for you so you know what you’re doing more or less every day, all day. Now, every day is a little different, and there are meetings and things you schedule, but you pretty much know what the routine is going to be. When you retire or unretire, you don’t have a schedule, it’s up to you. And so, you start thinking, what am I going to do every day, any day? And so, you still have to figure that out and start filling it in, but you don’t want to overschedule yourself, either. So, that’s sort of been one challenge that I feel everybody has to deal with, and I’m working on it right now. And the other is there are always going to be health issues that surprise you. So, one of the things I thought I was going to do when I unretired was learn how to play pickleball because it seems like everybody is learning it, especially a lot of people on retirement.

Casey Weade: I was going to ask you how the pickleball game was going.

Richard Eisenberg: Yeah. And I thought my wife and I would learn that sport. I bought the paddles and the balls and I figured, well, we’ll be in California for a month. This will be a great place to do it. But soon before I started my unretirement, I had a rotator cuff injury and tendinitis in my right arm. And I’ve been going to physical therapy now every other day for it. And so, I’m almost at the point where I feel like my arm is strong enough to do it, but not quite yet. So, that was a surprise and a change, and I feel like everybody’s going to have something that will sort of keep them from doing all the things they thought they do when they thought they do them, but you deal with it.

Casey Weade: Well, you had just released an article, and this is one of the points that you made in there, the fourth key to a successful unretirement is to make a schedule. And so, this was released just three hours ago on MarketWatch, 5 keys to a successful ‘unretirement.’ Let’s go ahead and stay on that topic for just a moment when it comes to your schedule. What types of tips or insights might you have for individuals that are at that stage where they go okay, I need to make a schedule? How far out are they thinking? Are they looking at it day by day, hour by hour, year by year? How do you go about making that schedule?

Richard Eisenberg: Well, it’s a very personal thing. I think everybody will figure out what works best for them. For me, I like to have a four-week calendar but really focus on the next two weeks. And of course, I have an iPhone, a smartphone, and so, a lot of it’s on there. But I also do what my younger son, Will, calls my analog calendar, which is very old school. I took out a piece of paper and I literally wrote it out so day by day, date by date, for the next few weeks. And it was blank when I started and I started filling it in. And I fill it in with both things I’m going to be doing for work, podcasts I’m going to be on, but also medical appointments I have dinner, dates I’m going to have, and lunches and coffees with people, that sort of thing.

So, what I’m trying to do is I don’t want to fill up every day, every hour of every day, but I do want to fill up most days with enough things going on. There may be some days, probably weekends that are completely free, but most of the weekdays I’m trying to fill up with something is going on just because I’m the kind of person who likes to keep busy. And I feel like if I was looking at a calendar that nothing on it, I would get nervous and bored. And I just feel like I want to know that I’ve got something going on.

Casey Weade: Yeah, it’s interesting. For me, my goal over the last couple of years has been to have as little on my calendar as possible. I want to have a clean calendar so that I can do the things that I want to do that I find are most impactful on a day-to-day basis and I can see transitioning in retirement. I might have to look at that a little differently. Maybe I would actually have the desire to have more things on my calendar, but I’ve always been very goal-oriented and I’m sure you’ve been as well with all of your accomplishments. I’m wondering how goals get incorporated into this schedule. I think many of the families that we work with, they struggle with setting goals. It’s always been about the career or financial goals, and now, they go, okay, well, I have all the money I need, did the career thing, and had all the accomplishments I needed to make there. Now, how do I go about setting goals in retirement? Can you speak to that?

Richard Eisenberg: Yeah. Well, I think it’s a good idea to always have goals, but there are different kinds of goals when you’re retired. So, for me, one of my goals was I want to do more volunteering and more mentoring. I knew that was generally what I wanted to do. Now, I’m thinking about how I’m going to go about doing that. And the gentleman who runs the MIT AgeLab, Joe Coughlin, just was on a podcast all about preparing for retirement, and he talked about the difference between planning for retirement and preparing for retirement and thought he made an excellent point.

So, for example, when it comes to volunteering, he says, “Don’t just think that you want to volunteer but think about, well, where do you want to volunteer? And how do you want to do it?” And that’s what I’ve been working on. So, I think I have a few ideas of places I want to volunteer. In fact, I reached out to one of them a few weeks ago and I said, “I think I’d like to be helpful for you if you’d like me.” And he was very excited about me doing that. So, once I’m back in New Jersey at the end of February, starting in March, I’m going to reach out to him and figure out ways to do it. And I know, he said the best times for his charity are weekends, so I’m going to plan to spend many of my weekends volunteering there. And I know I’ll find other places too.

I signed up for something called Cirkel, C-I-R-K-E-L, which some of your audience may be familiar with, but if not, it’s a really great initiative that brings together younger people and older people to mentor each other and help each other out with whatever it is that they would like help on. So, I signed up for that and I had my first Cirkel session a couple of weeks ago with a wonderful young woman who is really a dynamo when it comes to social media and the internet, and she’s running what’s called the feminist community. And I was learning about what she’s doing and how she’s doing it and what her challenges are. And I was telling her about what I’m doing and what my challenges are. And I think she’s going to be helpful for me, I think I’m going to be helpful for her. And I would encourage other people to try, if not Cirkel, then something like that to see how can you be helpful for people and maybe how can you find people who can be helpful for you.

Casey Weade: I think there’s a surprising number of resources out there that fall into that realm that many are just unaware of, but they’re out there, much like that. One of the keys that you have on your list was the third key to a successful unretirement was not being afraid to say no. Can you speak to that and how that showed up in your life?

Richard Eisenberg: Yeah. So, that was something new for me and maybe another one of the challenges because it was so different. When you work full time for your career for a long time, you’re used to saying yes all the time because you have to, your employer tells you you need to do something, you do it, or you volunteer for things. Well, when your unretired, then it’s up to you to figure out, well, how am I going to spend my time? If I’m going to do part-time work, what part-time work am I going to do? Where am I going to do it? How much time we’re going to spend on it, that sort of thing?

And so, now, I’m finding myself in the position of saying yes to some things and no to some things, and that’s been a new experience for me. And I’m not sure I’m making all the right decisions, but I’m hoping I’m making enough of the right ones. I’m saying yes to the things that I feel I really want to do, that I’m going to enjoy doing them, I’ll learn from. So, like, the new MarketWatch column is something I’m excited about doing and a few other things that I’m doing.

But I said no to a few things too because I felt like either I wasn’t that passionate about it or I thought I might not be as good at it as somebody else might be or I wasn’t sure if it was going to work or it just wasn’t the way I wanted to spend my time, so I said no. When I’ve been able to, what I’m trying to do is say no but offer the names of one or two other people who I thought they could do it. So, I feel like wherever I can be helpful to try to get them the kind of person that might be able to do the job, I want to do that. They may or may not use that person, but at least I feel I’ve been trying to help them with that. So, that’s been an interesting experience for me saying no.

Casey Weade: Well, I wonder how this ties into your fifth point. There must be a tie in here. Your fifth point to a successful unretirement is to be more like Marie Kondo. Can you speak to that? There must be some crossover here.

Richard Eisenberg: I think so. So, this is my wife’s unretirement tip for me, and I think it’s a good one. Your audience, I’m sure, knows Marie Kondo. She’s all about decluttering and downsizing. And she says, “Keep the things that bring you joy and get rid of the things that don’t.” I feel like in unretirement, I’m trying to do that too and I think that’s what people should try to do. Not everything you do in unretirement or in life can bring you joy, but the more you can find that does give you joy, the happier you’ll be. And the more you can get rid of the things that don’t bring you joy, I think the happier you’ll be. So, that’s what I’m trying to do is do more of the things that give me joy, seeing my family, traveling a little bit, doing new kinds of work, and less of the things that don’t give me joy, like administrative functions and scheduling things and meetings and all that sort of stuff. And so far, so good.

Casey Weade: You strike me as someone that has a lot to say no to. You have a lot of things that bring you joy. What would you say to someone that is struggling with that? Maybe a lot of their joy in the things that they wanted to do are now they feel in their past and they’re not sure what they want to bring with them. What’s that joyful thing that they want to do? Or what are those things that they want to use to fill up their schedule? If they’re struggling with this, where do you think they should be in?

Richard Eisenberg: I think it’s really a lot about introspection. Think about the kinds of things that really do bring you joy, and it could be a hobby that you have but haven’t had much time to work on, or a musical instrument that you’ve used to play but you haven’t been around, you want to pick it up again or you’ve always wanted to learn one, or you want to take a class and something you’ve never done, you want to learn how to paint. Think about those things, but also think about the things you did in your job that might be transferable skills so you may be able to do what you were doing before part-time, maybe even for your former employer. Some people do that, maybe for somebody else, but if not that, it may be that the kinds of things you were good at, you can use those skills in something else and you need to figure out what that might be.

So, keep your options open and say well, or even ask your spouse or partner or friends, what do you think I’m good at? Sometimes we need somebody else to tell us what they know or they think a person is good at in a way that you may not be able to see it as well. And then once you’ve heard that or you think about it, then you say, okay, now how can I put that to use and get joy out of it?

Casey Weade: Yeah, that’s wonderful. I wonder with all of the individuals you’ve talked to over the years, all the retirement, aging, financial influencers that you’ve had the pleasure of engaging with, who’s been most influential? Who stands out the most to you?

Richard Eisenberg: Yeah, I’ve talked to so many people who I admire that I’ve learned so much from. I’ll mention a few names and I apologize for the ones I’m leaving out because I can’t remember them all. But a few of them that I think are really great, there’s a gentleman named Paul Irving, who until recently had run the Milken Institute Center for the Future on Aging, and he is a very thoughtful man about aging and how things need to change, how we need to change ourselves for aging in the world. There’s a man named Ken Dychtwald, who runs a group called Age Wave, and he’s a really smart consultant and advisor and expert on Baby Boomers but also about aging in general. He’s written some terrific books. I would really encourage people to seek him out because he’s really great. A woman named Catherine Collinson with Transamerica. She runs the Transamerica Center for Retirement Studies. She publishes some terrific research all the time where they survey workers and retirees about retirement and working and what they want and how they’re doing and what they’re doing wrong and that sort of thing. And so, those are just a few names of people that I find to be really great.

Casey Weade: Now, who do you wish you would have met sooner?

Richard Eisenberg: Oh, I don’t know. I have to think about that one. There’s a writer who has written for me a lot at Next Avenue, two or three. One is Chris Farrell. And he wrote a book a few years ago called Unretirement. So, that’s where I got the word from. And he writes a lot still for Next Avenue and lots of other places. And he’s very thoughtful about what he calls Purpose and a Paycheck, and that’s the idea of in the second half of life, doing the kind of work where you feel like you’re finding meaning and it matters, but you’re also getting some money from that. Marc Freedman, who started a group called, who’s terrific. He’s all about giving back in the second half of life and particularly, the ways that older people can do that by mentoring and helping younger people and an intergenerational connection. So, those are a few people who I think are just really doing great work. And another writer is Kerry Hannon. She just started writing a column for Yahoo about personal finances. She’s written some terrific books about working over 50 and personal finances. She wrote a lot at Next Avenue for me, and I think she does great stuff too.

Casey Weade: We had Marc Freedman on the show a while back, and what an amazing resource, Definitely check that out if you haven’t yet. So, Richard, let’s talk about this transition from a financial standpoint for you. You have a wealth of knowledge. You’ve been studying this stuff for decades and decades, right? Most people would say, “Well, Richard’s obviously a do-it-yourself or he doesn’t need a financial advisor.” However, you mentioned a moment ago, you hired a financial advisor. I know you hired a certified financial planner practitioner. Why did you feel that you needed to do that? Why not just go it yourself?

Richard Eisenberg: I’m a big believer in working with people who know more than you do in whatever it is you’re doing and learning from it. And yeah, I’ve written about it and I’ve learned a lot about personal finances, but I feel like a financial advisor, a certified financial planner, a fiduciary who does this for a living, that’s all they do is think about this, knows a lot more than I do, and I could learn a lot from them, and also, just to check to see whether I’m doing the right things. And they looked at the investments that my wife and I made and they thought we had made a lot of smart ones, but they had some other suggestions, and I thought they had some good ideas. And they’re just very helpful in keeping me on track and making suggestions about things that we didn’t know better or hadn’t thought about before. I feel like it’s just good to have a professional backstop.

Casey Weade: Yeah. And I think many don’t think about some of those elements that they don’t know, right? We don’t know everything. Let’s find out if there’s something that is underneath the surface. So, how about you and your wife interacting with this advisor? Let’s talk about you and your wife a little bit in that relationship. How do you and your wife interact with the advisors, say, on an ongoing basis or upfront? Do you have a strategy, maybe some practices you have prior to meeting with the advisor or meeting with an advisor? And can you speak to that?

Richard Eisenberg: Sure. Well, it’s been very important for us, and I think it’s true from all couples that we do it together, that we meet with the advisor together, that we have a chance that each of us asks the questions that we have to the advisor, that they ask us questions, and that we talk about things now. No couple is going to be in agreement on everything. And some people are more aggressive from an investment standpoint than others. That’s fine. You shouldn’t be trying to force somebody to change their ways that makes them uncomfortable. You just need to– both of you understand each other and what you’re doing.

Before we meet with our financial advisor, we usually do it quarterly. I put together a summary of where we are, how our assets are doing and our liabilities, and how they’ve been doing, what the performance has been over the past year or past quarter, and then we give that to our advisor, but we look it over before we go so we can sort of see what has it been going for us, what we’ve been doing right, what are our questions, what should we be changing. And then let the advisor look at it too and say to us how they’re seeing it and see if we’re in agreement, see if they think we should be making some changes. And that’s worked out pretty well for us, I think.

Casey Weade: Well, some don’t do that. Many don’t do that, right? They’re over-delegating, they’re saying, “Hey, here, handle this, and I’ll do whatever you say.” I think it’s so important for not just your financial well-being, but your financial confidence to actually know what’s going on and be able to ask great questions around that. When it comes to delegation, you’re delegating certain activities to the advisor. Do you and your wife delegate or have a division of activities when it comes to your finances?

Richard Eisenberg: Well, I guess I would say I tend to be the one who’s more proactive in our investing. I’ll always discuss with her when I’m thinking about us doing, and if she’s not comfortable with it, we won’t, but usually, she is. But she just is less interested than I am. It’s not like I feel like I’ve got all the answers where I need to bigfoot this. It’s just that she would rather I manage the investment side of things. We both, I would say, manage savings. We each are saving individually and we’re doing some savings together. Neither of us has debts right now other than individual credit cards. We’ve paid off our mortgage, we’ve paid off our car loans. We didn’t have any student loan debt. So, from that standpoint, that’s not an issue for us. So, I feel like some things we do separately, we each have separate bank accounts, and some things we do together, but every couple needs to find out what works for them.

Casey Weade: The average age of widowhood today is 59, right? 59 is the average age of widowhood. And you obviously understand the importance of having your spouse involved in this process, especially your spouse being a female. We want her involved in this process and we as a firm want them involved in this process. But many times, we’ll have a spouse that says she’s just not interested or he’s just not interested. And what would you say to someone and what kind of advice would you give to someone to say, alright, I know she’s not interested or he’s not interested in this financial planning thing? What could someone do? What kind of strategies or tactics might someone be able to employ in order to get that person more involved?

Richard Eisenberg: Well, there are a few things you can do, I think. One is if you see an article that you think might be of interest and useful for your spouse or partner, you might say, boy, I think you might want to read this. This could be interesting, or I found interesting, I like to talk to you about it. So, you can start with that. We talk about having meetings with a financial advisor together. I feel like this way, even if my wife isn’t as interested or even as knowledgeable, perhaps, as I am about investing, she’s been part of the conversation. And if I were not around, they would know her and they would be able to talk with her, and she could start working with them on it, and vice versa. I don’t think there’s anything I’ll ever be able to do to get her very interested in investing. Some people just aren’t interested, and I feel like you can’t force some people to do that. I’m doing as much as I can, but I know sort of the limitations. And that’s about all I can suggest.

Casey Weade: Well, Richard, let’s shift it back to the softer side as we wrap the conversation up here. You were the editor, the former managing editor of not just Next Avenue, but also of their Money and Work & Purpose channels. So, we would be remiss if we didn’t bring up the word purpose in this conversation. First, how do you define purpose? And what does purpose mean to you?

Richard Eisenberg: Well, I think a lot of people, as they get into their 50s and 60s, start thinking a little bit more about meaning and purpose than when they were younger. And this has been true for me. They start thinking about, well, what am I doing or what can I do to be useful to my community, to the world? How can I be more helpful? And what have I done, what am I doing that might matter and might live on beyond me besides any kind of a financial legacy? And often, that means volunteering or mentoring. Where can you be helpful with a nonprofit that maybe could use some extra hands and some extra eyes to help people who are whatever, less fortunate in some way, or could use information or advice, that sort of thing?

And so, I feel like for me, finding meaning and purpose is just seeing will work. And where can I be helpful? And how can I do it? And that can be in person, that can be online, could be phone calls, conversations. There’s no one answer. And I think for me and I think for a lot of people, they find meaning and purpose in lots of different ways. I interviewed a guy for Next Avenue a few years ago who was a lawyer. He wasn’t very happy as a lawyer. He wanted to find more meaning and purpose in life. He decided to open a chocolate factory and make chocolate. And he’s doing that with his daughter now and he’s loving it. And that’s giving him a lot of meaning and purpose. And part of that is because he’s working with people who are growing the chocolate in parts of the world where he feels like he can help make a difference there, but he just finds it fulfilling that he’s doing something that gives him pleasure. So, for everybody, meaning and purpose is a little bit different.

Casey Weade: It seems like there is kind of this roller coaster of purpose or these peaks and troughs, we climb the mountain, we feel like we have the purpose, and then, all of a sudden, we go, I feel like I don’t have any purpose anymore. Do you have a method of staying in check with a level of meaning that you’re getting out of life, your level of purpose that you’re feeling on a day-to-day basis? Do you have a way to kind of check in with that and make sure you’re continually staying in balance?

Richard Eisenberg: Well, I think you kind of know it. If you have it or you don’t, the people that are most concerned about it, I wrote about this in the MarketWatch piece and also for Next Avenue, is people who retire without thinking at all about where they’re going to find meaning and purpose in their lives once they retire. It’s not to say that once you retire, you have to spend all of your time volunteering. But I think if you don’t think at all about this and then you retire, it can lead you to get depressed because you can feel like, well, I’ve lost my identity, I don’t know what to do with my days, I just don’t feel like I have any purpose myself in life. And I feel like anything people can do to avoid that from happening is helpful for them. So, I’d say if you’re not yet retired or if you are, to think about what can you do to find meaning and purpose.

And you may find that you want to volunteer somewhere, you try and it’s not a good fit, and that happens for people. That’s okay. One of the things you find in retirement, I think, is a chance to experiment. And if you want to volunteer somewhere and it’s not a great failure, you don’t like it or they don’t like you, whatever, just move on and say, okay, I try that. I’ll try another place. So, you don’t have to feel like everything is going to work out and that you’re not a failure if you try something and it’s not something you’re going to want to continue to do. It’s an experiment, it’s a journey.

Casey Weade: That’s the beauty of retirement. Dean Niewolny was on the podcast a while back, and he discussed low-cost probes. And that’s what you have the opportunity to do in retirement is test out different things and not feel bad about letting those things go. Well, Richard, we’re coming to a close, and if you just had one piece of wisdom or information or knowledge or one thing that you would like to communicate to the thousands of people that are listening around the world, what would that be?

Richard Eisenberg: I would say if you can afford to unretire and want to, you should absolutely do it. It’s not for everybody. Some people don’t want to do it, some people can’t do it, some people want to work full time until they drop or until they’re in their 70s, and that’s great. Everybody’s different. But I think more and more people are thinking, this idea of unretiring, semi-retirement, it sounds kind of good to me, I think I might want to try to do it. I would just say, think about it before you do it, plan it out as much as you can. Think about it financially, think about it emotionally, psychologically. If you have a partner or a spouse, talk with them about it because it’s a big transition, and you want to give it as much thought as you can so that you can help yourself to do it right.

Casey Weade: You said at the beginning that if you can unretire, you should do it. So, that begs the question what’s holding so many people back that could retire, and they’re not pulling the trigger? Why wouldn’t they do it?

Richard Eisenberg: It’s scary. I think a lot of people worry. Who am I in retirement? How am I going to spend my days? Where am I going to get my income from? There are lots of big questions, and it’s just a big change for people. It’s almost like adolescence. That’s a big change for people when you’re young, and it’s a little scary and all new. Well, it’s the same thing when you’re in your 50s, 60s, or 70s and you’re retired from a full-time job. It’s a whole new universe and often something that you don’t know much about. You haven’t gotten a lot of preparation for it. So, I can see that people will say, “Well, I’ll get to it one day, but I feel safer just continuing to do what I’m doing.” And that’s okay. But some of those people were doing that, and they’re also unhappy and they’re maybe frustrated and depressed or burned out and they’re not giving themselves the chance to try something new. I hope they do it.

Casey Weade: That can be paralysis by analysis just due to overwhelm, right? We have all of these different questions, all of these unknowns. I think the beauty of it is that there are answers to all of these questions that you have, but to your point, it takes time. It’s not going to happen today, but you want people to start the process. Richard, thank you so much for joining us here on the show. It’s been an absolute pleasure.

Richard Eisenberg: Thank you, Casey. Love talking to you.