Capital Investment Advisors

#173 – The Happiest Retirees with Ryan Doolittle

On today’s episode, Wes sits down with Ryan Doolittle, host of the Retire Sooner Team’s brand new podcast: Happiest Retirees. Ryan tells Wes that he originally came up with the idea as a way to talk less about philosophy and more about the actual people on the ground, living happy lives in retirement. How did they discover the core pursuits that gave them purpose and passion and how did they make them a reality? By going straight to the source, Ryan hopes the show will shine a light on the road map and provide inspiration for others looking to find happiness.

Read The Full Transcript From This Episode

(click below to expand and read the full interview)

  • Wes Moss [00:00:00]:You. I’m Wes Moss. The prevailing thought in America is that you’ll never have enough money and it’s almost impossible to retire early. Actually, I think the opposite is true. For more than 20 years, I’ve been researching, studying, and advising American families, including those who started late on how to retire sooner and happier. So my mission with the Retire Soon podcast is to help a million people retire earlier while enjoying the adventure along the way. I’d love for you to be one of them. Let’s get started. The original name for the book that I wrote called You Can Retire Sooner Than You Think, which is again a big inspiration, of course, for the Retire Sooner podcast. The original name. And I just pulled up the contract recently, or the original manuscript and still on the manuscript, or when I pitched it to McGraw Hill who published You Can Retire Sooner Than You Think, the name on the proposal was still Happiest Retirees on the Block. And I’ve always loved studying this connection between money and happiness. It was probably not, though, back until it was probably not until 2013 that I moved beyond just being interested in money and happiness in the relationship to actually starting to study it and do our own research and our own surveys and our own analysis. Because back then I was a new dad and I think my oldest son was probably five or six years old, which means I would have had another child at probably age two or three because my two oldest are about two and a half years apart. And there was a really popular book that was popular with parents. And I remember learning this from a waiter. Actually, it was a server at a restaurant who before I think we ended up having kids, I started hearing about this book called Happiest Baby on the Block, and it was all about of course, it was a recount. Of parents that in some way, shape or form had cracked the core or figured out a way to have it so that your kids were not crying all the time and they would sleep through the night and making it a little bit easier on everybody. Happiest baby on the block. So it was the parenting habits and how we got our kids to be maybe a little easier to raise. No, I still to this day don’t know if that book worked at all, but that’s a whole nother story. But the name Happiest Baby on the Block really is what for some reason subconsciously got me thinking about, well, what does it look like if you’re the happiest retiree on the block, what are those habits? So over the course of about a year, I dove into the subject, which at the time was called the Money Matters Team. And now that has grown into not just the Money Matters Team, but the Retire Sooner podcast team as well. So the study, though, through now multiple surveys over the last decade or so. And the original survey that got all of this started was over 1350 households that answered a series of questions that helped me identify their life habits, their consumer habits, their financial habits. And then we were able to, through study, isolate the Happiest two quintiles, the least happy two quintiles, and then compare all of those habits, whether it was lifestyle or financial. And the data that came back was so compelling, was so interesting, that it really became a book. The book wrote itself, originally titled Happiest Retiree on the Block. Now, just so happened that many of the financial habits identified in the first book were also the same habits that helped people retire a little bit sooner. But as we all know, it’s difficult for anybody in the United States to be able to have enough money to fully stop working. It’s a huge feat for anybody to be able to do it. So if we were able to help our readers retire even three months sooner, a year sooner, five years sooner, then I think we were doing our job. And putting all that together really helped families ensure that they’re doing both the money and the lifestyle piece of the equation to end up with a happy retirement. So sooner and happier, really ambitious goal, but it really has become a life’s work now for me and our entire team. Speaking of our entire team, one of the very original people that helped me put all this together because it was six months worth of research and then a year worth of writing was the very talented Ryan Doolittle. Ryan Doolittle, when I first met him, he was, and I guess still is, a wonderful writer, an actor, and a comedic actor to boot. So he’s actually a really funny guy to be around and to talk to and get to know and a genuinely curious individual who really, just by his nature, never stops learning and diving into things that he’s interested in. So over a decade ago, Ryan Doolittle helped me research and ultimately organize. You can retire sooner than you think. So he has been part of the Retire Sooner team from really the very, very beginning. That’s why when he came to me this past summer and he pitched me on the idea of a new podcast where he just focused on gathering the stories of the Happiest retirees that he could find, I jumped up and down. I thought it was an amazing idea. So I’m so happy to have him here on the Retire Sooner podcast to talk about his new podcast called Happiest Retirees. Ryan Doolittle. Welcome to the retire Sooner podcast.Ryan Doolittle [00:06:08]:Hey, thanks for having me, Wes. I’m really excited to be here. And speaking of learning, I just want to thank you for teaching me what the word quintile means.Wes Moss [00:06:17]:Quintile. That along with basis points, those two very important words in both statistics and financial planning very much.Ryan Doolittle [00:06:27]:

    Every time I hear the word basis points on the news now, I think of you.

    Wes Moss [00:06:31]:

    I always think of it as a great name for a Wall Street bar. Hey, guys, we’re going down to basis points. Of course, basis points. For those who don’t know basis points, of course, they’re just the fractions of a percent.

    Ryan Doolittle [00:06:43]:


    Wes Moss [00:06:44]:

    100 basis points is just 1%.

    Ryan Doolittle [00:06:46]:

    But if you use basis points, you get to sound smarter than saying it does sound smarter.

    Wes Moss [00:06:53]:

    Yeah, I’d much rather say percent, but it does sound a little smarter for basis points. So give us an overview of the show. Explain your mission for Happiest retiree podcast.

    Ryan Doolittle [00:07:04]:

    Well, okay, so after so many hours spent listening to you speaking to the best and the brightest, the retirement gurus, I just thought, well, it might be of value to talk to the actual people on the ground, the actual happy retirees, to get their story. And so that’s what this has become. Our mission for the Happiest Retirees Podcast is to inspire 1 million families to find happiness in retirement. And we’re getting the stories straight from the source, straight from the happy people.

    Wes Moss [00:07:41]:

    What was the naming of the podcast like? Did you go through a bunch of I remember when you first pitched me, I thought it was so clever, and I hope this doesn’t get lost, of course, in the podcast, but you at one point said, I want to be the core pursuit finder. Right. So core pursuits hobbies on steroids and Ryan Doolittle. The thought of him looking like Carmen Santiago running around or Sherlock Holmes with a magnifying glass and a funny little hat, which you would probably have in your closet, ready to go as a prop for Was. I love that idea. Oh, he’s the corporate fighter. He’s going to go find people that are doing a bunch of new things. What were some of the names you were thinking?

    Ryan Doolittle [00:08:23]:

    You know, I was about 5 seconds from hitting click on buying the Sherlock Holmes outfit because yeah, I thought I was so clever. I thought the core pursuit finder, I’m out there like, I’m a detective. I’m hunting for these happy retirees and finding what these core pursuits are. It ended up changing to Happiest retirees. We just thought that was a way to bring more people into the circle and get the full story, the full three dimensional journey.

    Wes Moss [00:08:57]:

    Yeah. Happy retiree hunter sounds It could also be like, one of those serial killer podcasts.

    Ryan Doolittle [00:09:04]:

    Yeah. We don’t want to actually hunt the retirees down. We want them to remain living and being happy. Yeah. So that would have been a little confusing.

    Wes Moss [00:09:14]:

    So, Ryan, the mission for the Happiest Retirees Podcast is to inspire a million families to find happiness in retirement.

    Ryan Doolittle [00:09:23]:

    Correct. If we can do that, we’ll know we’ve been successful. I just felt like as kids, we’re all asked what we want to be when we grow up. And that makes it seem finite. Like, that’s it. But we on the Happiest retirees podcast. We refocus this lens. Now that you’re grown up, what do you want to do? Because life changes so much when you leave this career, in a way, you have so many more opportunities, and now you might actually be able to do what you want.

    Wes Moss [00:09:57]:

    All right, you’re talking to happy retirees. Are these, like, celebrity guests that you’re having on the show? Are they totally normal people? How do you know if they’re happy retirees? Why are we listening to these people, and how are you finding them?

    Ryan Doolittle [00:10:14]:

    Well, we have a minimum of you have to have won two Academy Awards to be on the show.

    Wes Moss [00:10:21]:

    It’s a good entry point.

    Ryan Doolittle [00:10:22]:

    Yeah. So the search process could be defined as anything and everything from googling to using chat GPT to word of mouth. We’re finding anyone who knows a happy retiree, and then we’re evaluating if their story fits our criteria. And I would say our criteria is, are they truly happy? Are they living the life with multiple core pursuits? Some of them have rebranded themselves after retiring. Some of them were already happy. What were they looking for? How did they find it, and where has it led them? Anyone that can inspire other people to find happiness in retirement, that’s who we’re looking for.

    Wes Moss [00:11:10]:

    All right, so your goal then, for the audience is for them to walk away with some practical retiree habits from people who’ve either transformed themselves or maybe they weren’t happy and then they became a happy retiree, or they didn’t have core pursuits, and now they have a whole bunch of core pursuits.

    Ryan Doolittle [00:11:28]:

    Yeah, I’d say our first goal is to inspire people to think, wow, that person did it, and that means I can do it. And then the second part of that is to get some practical examples of things they could do. Maybe they realize, oh, my gosh, I’ve always wanted to play tennis four days a week, and I never did. I mean, that’s something that anyone could pull off other people. I don’t know. I’ve always wanted to hang glide naked. I mean, that’s not I’ve always wanted to hang glide, and I’ve never done it. I’m not verifying that hang gliding is safe for it isn’t. I’m just trying to say they’re getting some examples of these people who said, I’ve always wanted to do this, and I never did it, and I can do it.

    Wes Moss [00:12:17]:

    All right, so what’s your favorite or most surprising thing you’ve learned about happy retirees so far? What are they doing so different?

    Ryan Doolittle [00:12:24]:

    I was very surprised to find out that pickleball was the most popular sport and that it was invented in 1965 on Bainbridge Island, which I don’t even.

    Wes Moss [00:12:35]:

    Know if I realized it was that far back in the past.

    Ryan Doolittle [00:12:38]:

    Yeah, I thought it was a brand new sport. I never saw courts when I was.

    Wes Moss [00:12:41]:

    Younger and why are you saying that? So that is the number one happy retiree sport.

    Ryan Doolittle [00:12:47]:

    Yeah. Pickleball is the number one sport for retirees. And I think it has something to do with you get the joy of tennis without the agony of knee pain.

    Wes Moss [00:12:56]:

    Okay. And you still get to play with multiple people and it’s fun and social and it’s less running around. So I think people can literally drink beer while they’re playing. Exactly. Beer while they’re playing. Pickleball. I think that’s part of it.

    Ryan Doolittle [00:13:09]:

    I think adding if any sport where you can add beer definitely adds players.

    Wes Moss [00:13:13]:

    Yeah. It’s like softball. I remember growing up my dad, once a year, we had a big softball party and I was still a kid, I was still like ten to maybe 14. And I’m looking back on it, they got so excited about softball out in this kind of oddly shaped field. So it wasn’t like a great field for softball, but it was in our horse pasture. So I remember we’d have to clean it up a little bit before we’d have softball games. But I think looking back on it, is that all the parents were drinking, I guess a beer league softball, and I guess maybe that’s part of it. All right, so what else do you know about these happy retirees?

    Ryan Doolittle [00:13:55]:

    Well, some of the statistics are surprising. People who drive BMWs are statistically less happy, which was eye opening. I don’t know that it specifically has to do with the actual car, but I think some people pick that car because they want to show it off, and that’s not really a good way to go about your life.

    Wes Moss [00:14:17]:


    Ryan Doolittle [00:14:18]:

    The Happiest retirees average 3.6 core pursuits. And now you mentioned a core pursuit is like a hobby on steroids, something that can get you out of bed in the morning. The unhappiest ones average about 1.9, so the more the better. Another interesting fact was that the Happiest retirees, their alcoholic beverage of choice is either white wine or gin. So the clear.

    Wes Moss [00:14:45]:

    Okay, so speaking of the beer leagues, it’s not beer, it’s white wine.

    Ryan Doolittle [00:14:50]:

    Yeah, the chardonnay softball leagues.

    Wes Moss [00:14:53]:

    So what do you think listeners will get out of the podcast?

    Ryan Doolittle [00:14:55]:

    I think they’re going to get a chance to hear from people who are either in the same situations they’re in now or the one they’re going to be in within a few years or maybe even further down the road. But they know they want to get there. And this is a way to listen and find out some ideas for how to go, what direction to take, maybe what the first step was. Because I think some people get overwhelmed and they think, well, I just can’t do it. And if they can just take that first step like these people do, they can get there. They can be happy retirees. So you asked, do I really think there’s anything that the listeners can learn from these happy retirees, and I really do. There’s a great quote from Margaret Mead. She was an anthropologist and she said, never doubt that a small group of thoughtful, committed individuals can change the world. In fact, it’s the only thing that ever has. I know for myself, I read over that quote quite often because it sort of gets me back on track when I’m feeling a little discouraged. But I think it really applies to this situation because happy retirees, you listening? You are important and you can do this.

    Wes Moss [00:16:06]:

    That’s inspirational. I like that. The S and P 500 fell nearly 20% in 2022. Inflation jumped to double digits, and the Fed has continued to relentlessly raise interest rates. It feels like chaos, but at Capital Investment Advisors, we take a disciplined approach to investing to help our clients find happiness in retirement. Regardless of the scary headlines, we can’t control the chaos, but we can control what we do about it. If you’d, like, help with your disciplined retirement strategy, reach out to our That’s Y-O-U All right, so you’ve already released now several episodes. I think you’ve released three episodes, and I know that you have several more in the works. So you’re already doing this. What are some of the themes you’ve noticed from some of your guests so far?

    Ryan Doolittle [00:17:06]:

    So, yeah, I’m noticing some themes, and it’s very much in line with some of the themes from the book the Five lifestyle Habits that happy retirees tend to have. They focus on marriage, family, faith, health, and as we talked about before, core pursuits. So those are really key categories that need to be in check to keep the happiness levels high.

    Wes Moss [00:17:33]:

    So let me ask about some of those lifestyle habits. When you say marriage and you say faith, is this that the happy retirees have to be married? Do they have to be faithful in some way, meaning they have to go to church? What do those look like?

    Ryan Doolittle [00:17:48]:

    Well, the happiest retirees tend to be married. Now, that’s not to say you have to be married to be happy. And in fact, it’s not even statistically so bad to be in your second marriage. We call that sort of the marriage mulligan. Now, if you’ve been married eight times, that’s not really a good sign.

    Wes Moss [00:18:07]:

    Talk about that’s over par.

    Ryan Doolittle [00:18:09]:

    Exactly. I think you need to, at that point, turn the mirror to yourself and think, maybe I’m the problem. But now, secondly, family. Our research shows that happy retirees live near at least half of their adult children. Now, we say near because I think that’s a very important word. You don’t want to live in the same house as I think probably most of us would realize that doesn’t usually go very well. The next faith would be a lot of these retirees, they have a faith in some religious or spiritual area, and that is also mixed with the community that going to church services can lead to a lot of times that’ll also lead to volunteering, which is also a very popular corporate suit for the happy retirees. Health, I think, is kind of self explanatory because if you’re not healthy, you don’t have much of a chance to be happy. So you have to take care of yourself, eat right, drink right and exercise.

    Wes Moss [00:19:06]:

    Wait, did you say eat right and drink right? Is that meaning that you should only be drinking gin and white wine or is it okay to be in the softball beer league?

    Ryan Doolittle [00:19:15]:

    I will also allow water. That’s also okay. Water, white wine and gin in moderation. And then the final category, core pursuits we sort of got into, you need to average around 3.6. You need to find something that you’re passionate about and you need to do it. And I think once you find the thing you really like, it’s not going to be that hard to get yourself to do it.

    Wes Moss [00:19:38]:

    So who’s the audience, ryan, who do you hope listens to this show?

    Ryan Doolittle [00:19:43]:

    Well, in addition to saying I hope, everyone does. I think specifically millions a big goal, buddy.

    Wes Moss [00:19:49]:

    I mean, you get a million is.

    Ryan Doolittle [00:19:50]:

    A that’s right, right. It’s a big goal, but I think it’s a reachable goal. I want people who are thinking about retire and wondering if they can be happy, what they’ll do. I want those people to listen to this and get on track and start the journey of finding happiness. It’s a major transition. We don’t realize that when we have a career, that becomes a big part of our identity. I mean, we spend more time there than we do at home. So when you stop that career, you lose those social networks, you lose the identity of who you were or are. So this is a way to find a new identity. Now, some people love their job and maybe they want to just do it a little less and then they can have more time to do community theater or hang glide naked, whatever it takes. But it’s a major lifestyle change, and the earlier you start thinking about that and planning and having a purpose, finding that purpose, the better off you’re going to be.

    Wes Moss [00:20:52]:

    I find it daunting. Again, I host the Retire Sooner podcast, but if I’m thinking about early retirement, just on the surface without thinking about the habits of happy retirees, which again, I’ve written about, you’ve written about, and we probably understand as well as anybody, but when you’re thinking about that much change all at once so no more work. And I’m a guy that has always had at least two jobs or so, and that in itself is daunting. And even though I know that I need to have close to four core Pursuits and be a member of a faith community and have a certain amount of social network, it still is a little overwhelming to think about actually doing it. You’re trying to help your listeners understand all of that and remove the daunting nature of stopping work and still being a happy retiree.

    Ryan Doolittle [00:21:45]:

    Yeah, I really am. And I have to say, Wes, you have a motor and you’ve been inspiring to me to work harder and to focus on what I want to get accomplished. In addition, you’re a master of what it takes to retire. But I think you are someone who’s going to have to work hard figuring out how to relax or figure out what else you want to do. So in a way, I want you to listen to the show, even though you’re the master here, you’re the guru. Because I think someone who is such a hard worker and so willing to keep pushing and accomplishing things, sometimes it’s hard for them to switch gears and think, now what?

    Wes Moss [00:22:29]:

    Yeah, I agree. It can be a little daunting to really think about it. All right, how about you? Do you think you’re on track? I know you’re a brand new dad, Keaton’s, still not even one. How much are you thinking about being a happy retiree?

    Ryan Doolittle [00:22:43]:

    Yeah, I think if I tried to be a happy retiree right now, keaton wouldn’t have a big college fund by the time he got older. But I do think, and a lot of this is because of working with you. You’ve got me thinking about it. I am on track. I need to solidify. I’d say I’m a late bloomer on the financial aspects, but I now know what I’m supposed to do and I’m trying to do it. I have a situation that I think a lot more people have than I realized. I had a severance package from a previous job and I rolled it over into an IRA and I thought that just meant now I have an IRA. Now it’s invested. It was just sitting in cash at the brokerage house doing know. As we know, cash doesn’t keep up with inflation, so I’ve got that now invested where I wanted it, marriage wise. I married way up, so I’m on track there. Kid. I have one kid. He’s nine months, Keaton, so statistically, I’m supposed to have at least one more. You went one above, you did extra credit.

    Wes Moss [00:23:50]:

    Yeah, I think it’s 2.5 is the average number of children for the happy retiree, I think it’s 2.5. So you do have a little work to do.

    Ryan Doolittle [00:23:58]:

    I do. And I remember when you had your fourth, I thought I was, again, so clever because I was going to say, but, Wes, you went over and you’d already thought of that. I’m around halfway there with children core pursuits. I have a lot of interests. I’m not really very worried there. I have a lot of things I like to do writing, tennis. I’m starting to get into golf because I think I’m more mature now and I’m not going to get so angry. I have a little bit of my dad in me. One time I asked him where his sandwich was, and he said it was in a tree back on the 6th hole.

    Wes Moss [00:24:33]:

    Oh, did your dad used to throw his clubs?

    Ryan Doolittle [00:24:35]:


    Wes Moss [00:24:37]:

    Have you ever thrown a golf club?

    Ryan Doolittle [00:24:39]:

    I’ve never thrown a golf club. I’ve thrown a tennis racket.

    Wes Moss [00:24:43]:

    Okay, I can see that, actually. No, I can’t see that. I can’t see you getting that. You’re so patient and kind.

    Ryan Doolittle [00:24:52]:

    Well, it’s nice of you to say that. I have my moments. I’ve come a long way. I think I have a natural temper that I don’t like about myself, so I’ve been able to work on that.

    Wes Moss [00:25:02]:

    You’ve tamed your temper.

    Ryan Doolittle [00:25:03]:

    I have, yeah.

    Wes Moss [00:25:04]:

    Well, if you’ve never thrown a golf club, that’s good. They’re easy to throw. I’ve never thrown a golf club either, and I’m not going to break that streak. I’m not going to break that streak.

    Ryan Doolittle [00:25:13]:

    It’s not worth it. I played golf recently, and I was really impressed with my peace of mind. What do I care? I’m not trying to make the PGA. I’m just out there having fun and again, drinking a beer. Sorry, it wasn’t gin or white wine, but I was still happy. My health, I think, is in check. As I got a little bit older, in my 20s or maybe my early thirty s. I ate fine, but I didn’t really have to worry about it. Then I think I got a blood test in my mid thirty s, and my doctor said, you better change this and this and this. It was kind of eye opening. So now I’m on track with that faith. I feel like I’m on check. I think we all have our own journey there. I feel pretty good about it. Friendships, I will say. And we did a little research on this, and you had a guest on the Retire Sooner podcast, an expert who was saying that males, especially.

    Wes Moss [00:26:08]:

    Dr. Michael Platt, the head of neuroscience and sociology at Wharton.

    Ryan Doolittle [00:26:14]:


    Wes Moss [00:26:14]:

    Such a great guest.

    Ryan Doolittle [00:26:15]:

    Oh, my gosh. I think about him all the time. He even related it to, I think, the monkey family, or maybe it was apes, but that males in that species have the same problem, where as they get older, they get more solitary. And I feel that in myself, especially having a kid and working, you’re just so focused, you forget to go spend time with your friends.

    Wes Moss [00:26:41]:

    Yeah. I mean, you’re protecting the family, right? Yeah. It’s food and shelter for the family. And it’s so easy to dismiss the frivolity of socialization.

    Ryan Doolittle [00:26:52]:

    Yeah. And I think that females, for some reason, understand that more. Either that or maybe they need it more, or maybe they’re just smarter and they realize that we all need it. I don’t know. But they tend to keep their friends stimulated and that sort of thing throughout. I’m a little worried that I’ll be 65, and I’ll realize I haven’t done anything with any of my friends in five years. I’m going to definitely keep my eye on that.

    Wes Moss [00:27:25]:

    So what I’d love to do is hear a couple of clips, too, from the new podcast.

    Ryan Doolittle [00:27:30]:

    I’m glad you said that. I brought a few clips in. I want to go through them and so we can point out specifically what these happy retirees are doing right in their lives.

    Jill Smith Entrekin [00:27:39]:

    I had an English teacher’s daughter in my class, and the English teacher came to me the next day with the essay I had written, and she said, Jill, this is good. You really need to expand on this. And I laughed. Put it in what we teachers call file 13, because I’m grading hundreds of essays and research papers. I didn’t have time for that. But when I retire and I read that book about how to write the novel, the first thing I did was to get out my essay and think, okay, let’s get started.

    Ryan Doolittle [00:28:13]:

    That was Jill Smith intrickin. She is a retired school teacher. She taught English literature for 30 years, and once she retired, someone said to her, why don’t you write it yourself? And she realized, yeah, I have always wanted to do that. She’s now published two books, and she has a third one on the way.

    Wes Moss [00:28:34]:

    Post being a teacher. So she was not a writer during her career? No, her main career.

    Ryan Doolittle [00:28:41]:

    She just taught students how to write and never did it herself. I mean, just in the classroom she would, but she was never pursuit it. And now she’s published, which is just amazing.

    Wes Moss [00:28:51]:

    What kind of writer is she?

    Ryan Doolittle [00:28:53]:

    She writes fiction. She writes a lot like Southern fiction. I would say her favorite book is To Kill a Mockingbird, and she says it’s the perfect book. So she’s sort of writing towards that. But she has more core pursuits than maybe anyone I’ve interviewed. In fact, she had to skip yoga just to do the interview with me, and she said her friends and her family are a huge part of it. They’ve encouraged her. She does a lot of social activities and family activities. So she is just hitting all the notes.

    Wes Moss [00:29:28]:

    Yes. So the other thing I think is cool about really diving into core pursuits as almost like this garden of multiple things you’re doing, maybe at any given time, you never know what’s going to grow up to be the tallest stalk of corn, if you will. And in this case, it was in the garden for a long time, and then it really blossomed. And then that became one of her writing became really one of her life core pursuits. And I think that’s a great lesson that your listeners are going to be able to take away from these is that maybe some of these are ideas that get planted in their garden, and maybe they’re fine for a little while and they don’t do a whole lot, but eventually they become a. Significant bearer of fruit in the core pursuit garden. And I think that’s why it’s so exciting to listen to these real life retirees on your show.

    Ryan Doolittle [00:30:19]:

    Yeah, it’s one of those things where sometimes something is so close to your face, until you get those retirement bifocals, you don’t see it.

    Wes Moss [00:30:27]:

    It’s hidden in plain sight. If you only had a core pursuit magnifier Hunter scope to find them. All right, let’s do another clip.

    Ryan Doolittle [00:30:36]:

    So why did you take so fondly to unretirement? And what does that mean for you?

    Richard Eisenberg [00:30:44]:

    Well, I guess I took fondly to it because I thought it gave me a chance to explore new avenues for myself. I’m learning new things. I’m writing for places I didn’t get to write before. I’m catching up with old friends who I hadn’t seen for a while. I’m the kind of guy who just likes to keep busy my senses. You are too. And so I felt like the traditional retirement just wouldn’t work for me. I would get too restless. And so the constant struggle and decisions that I’m trying to make are figuring out how busy do I want to be and am I spending my time the way I want to. And I don’t want to overdo it. And I feel like right now I’m in a pretty good place where some days I’m busy all day, some days I’m busy a little bit, some days I’m not busy at all. I feel like it’s pretty much what I was hoping it was going to be.

    Wes Moss [00:31:38]:

    Now, Ryan, are you projecting on me on that one to see if am I going to unretire if I try to retire?

    Ryan Doolittle [00:31:45]:

    I’m impressed you caught that a little bit. I mean, Richard has a motor, like he said. He’s still finding that balance between being too busy, not busy at all. I think he’s really doing a good job of finding it. He calls himself unretired, which means he’s not having the pressures of being the managing editor of Next Avenue for PBS. But he still writes for them sometimes, and I have to say, sorry, Richard, but I follow him on LinkedIn, and so I’ll check in on him sometimes, and I’ll notice in his banner it’ll say Open to Work. He changes his resume. He’s he’s a very active guy, and I think he’s finding that perfect balance, and I really do think he’s on his way.

    Wes Moss [00:32:30]:

    Let’s listen to our next Happy Retiree podcast sample.

    Ryan Doolittle [00:32:36]:

    Well, it sounds like you don’t really feel a whole lot of limitations in retirement. In fact, you seem to have less than you did when you were working.

    Ingrid Reckard [00:32:44]:

    Yes, for sure.

    Ryan Doolittle [00:32:45]:

    So how would you suggest other people get to that point?

    Ingrid Reckard [00:32:50]:

    Well, I think first is that they have to want it, because I have friends who are still working, and for whatever reason, that’s their life, and they’ll probably die at the job. They don’t want to leave the job. Okay, so if you want to retire, it’s a good idea to know ahead of time, what are some of the things you’re going to do in retirement? How will your days look? Because it is a difference.

    Wes Moss [00:33:25]:

    All right. So what’s this clip telling us, Ryan?

    Ryan Doolittle [00:33:27]:

    So, Ingrid is getting at if you want to be happy in retirement, you have to have a curiosity for it. You have to find a mean, I’d rather die hang gliding naked than sitting at my cubicle. I mean, that’s just but she she figured out that she wanted to do something, and she went about doing it. It doesn’t just happen. You have to make it happen.

    Wes Moss [00:33:51]:

    Wait, what is she doing?

    Ryan Doolittle [00:33:53]:

    She retired from being an executive at bank of America, and she loved to travel. In fact, the day she retired, she was on a plane to Costa Rica. But she realized, I want to do something. I love traveling. Oh, so now she’s a travel agent. In her retirement, she has her own company. She gets to keep traveling. She gets to write it off on her taxes. She gets the perks. It’s kind of a win win situation.

    Wes Moss [00:34:19]:

    You know, what’s interesting about one thread through all three of these examples is that they’re all doing something that does relate back to some sort of a little bit of income. Maybe it’s not anywhere close to the big exact job in Ingrid’s case that she probably earned. But at least it sounds like there’s some income involved here in all three of these.

    Ryan Doolittle [00:34:41]:

    Yeah, I think so. And that’s another important part of happy retirement, is setting up your life so that you have multiple streams of income, because you’re not going to have that giant flood of income that you might have from your primary working years. So you’re getting these tributaries flowing in, and they add up to be enough for you to live the life you want to live.

    Wes Moss [00:35:04]:

    Tributaries of income that all come together as to one larger stream.

    Ryan Doolittle [00:35:08]:


    Wes Moss [00:35:09]:

    Ryan Doolittle where do we find the podcast? Where do we find the Happiest retirees podcasts?

    Ryan Doolittle [00:35:17]:

    Well, we’re everywhere you go to to listen to your podcasts. You can also go straight to our website,, that’ll have all the episodes there. Wherever you listen to podcasts, you will find us. Just search for Happiest retirees.

    Wes Moss [00:35:33]:

    Ryan Doolittle, host of Happiest Retirees podcast, a man unaptly named around these circles, we always say Doolittle seems to do the most. Thanks for being on the show, man.

    Ryan Doolittle [00:35:47]:

    Hey, it’s been a real pleasure to be here, Wes. I always enjoy spending time with you, and I’ll say that in high school. I won my class presidency by saying I won’t do little. I’ll do a lot. Hopefully, the same applies here. Hey, y’all.

    Mallory Boggs [00:36:00]:

    This is Mallory with the retire Sooner team. Please be sure to rate and subscribe to this podcast and share it with a friend. If you have any questions, you can find that’s You can also follow us on Instagram and YouTube. You’ll find us under the handle Retire Sooner podcast. And now for our show’s. Disclosure this information is provided to you as a resource for informational purposes only and is not to be viewed as investment advice or recommendations. Investing involves risk, including the possible loss of principal. There is no guaranteed offer that investment return, yield or performance will be achieved. Stock prices fluctuate, sometimes rapidly and dramatically due to factors affecting individual companies, particular industries or sectors, or general market conditions. For stocks paying dividends. Dividends are not guaranteed and can increase, decrease or be eliminated without notice. Fixed income securities involve interest rate, credit inflation and reinvestment risks and possible loss of principal. As interest rates rise, the value of fixed income securities falls. Past performance is not indicative of future results when considering any investment vehicle. This information is being presented without consideration of the investment objectives, risk tolerance or financial circumstances of any specific investor and might not be suitable for all investors. Investment decisions should not be based solely on information contained here. This information is not intended to and should not form a primary basis for any investment decision that you may make. Always consult your own legal, tax or investment advisor before making any investment tax, estate or financial planning considerations or decisions. The information contained here is strictly an opinion and it it is not known whether strategies will be successful. The views and opinions expressed are for educational purposes only as of the date of production and may change without notice at any time based on numerous factors such as market and other conditions.

Call in with your financial questions for Wes to answer: 800-805-6301

Join other happy retirees on our Retire Sooner Facebook Group:


This information is provided to you as a resource for educational purposes and as an example only and is not to be considered investment advice or recommendation or an endorsement of any particular security.  Investing involves risk, including the possible loss of principal. There is no guarantee offered that investment return, yield, or performance will be achieved.  There will be periods of performance fluctuations, including periods of negative returns and periods where dividends will not be paid.  Past performance is not indicative of future results when considering any investment vehicle. The mention of any specific security should not be inferred as having been successful or responsible for any investor achieving their investment goals.  Additionally, the mention of any specific security is not to infer investment success of the security or of any portfolio.  A reader may request a list of all recommendations made by Capital Investment Advisors within the immediately preceding period of one year upon written request to Capital Investment Advisors.  It is not known whether any investor holding the mentioned securities have achieved their investment goals or experienced appreciation of their portfolio.  This information is being presented without consideration of the investment objectives, risk tolerance, or financial circumstances of any specific investor and might not be suitable for all investors. This information is not intended to, and should not, form a primary basis for any investment decision that you may make. Always consult your own legal, tax, or investment advisor before making any investment/tax/estate/financial planning considerations or decisions.

Previous ArticleNext Article