Early Retirement - Financial Freedom (Investing, Tax Planning, Retirement Strategy, Personal Finance)

Why Retirees Are Flocking To This One Special Community | Retirement Reality

• Ari Taublieb, CFP®, MBA • Episode 300

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After years of research searching for the perfect retirement community, Judy found Woodside. 

She visited the Villages, Del Webb, and so many others that she found didn’t fit what she was looking for - other active retirees of similar age. 

Now she’s IN LOVE with retirement and shared her entire story with me on my show, Retirement Reality. 

This NOT a paid advertisement. If you wish to reach out for a Discovery tour of Woodside, you can email David directly at dseawell@woodsidecommunities.com and if you let him know you found him through my channel, he’ll make sure to treat you well!

I’m flying from Los Angeles to Aiken, South Carolina to visit the Woodside community next month myself to do a full review of the community (similar to a restaurant review, but for retirement communities)!

Is there a retirement community you’re excited to go to? If so, let me know in the comments and I’ll add them to my list of communities to review!

For Judy, early retirement comes down to one word: choices. At 57, two years into life after work, she wakes up with the freedom to choose slow mornings, long walks, golf leagues, pickleball lessons, and spontaneous trips.

Her plan was always early retirement at 55, and she never lost sight of it... even when fear, routine, and the temptation of “one more year” crept in.

She shares how she built her “superhero account,” prepared for healthcare, learned to balance enjoying today with planning for tomorrow, and embraced the courage to leave a career she liked for a life she loves.

Want to be a guest on THIS show and help others by sharing your story? Complete this: https://vwo3759x8i7.typeform.com/to/gh00JmnZ 

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Judy is not a client of Root Financial Partners, LLC and received no compensation for participating in this video. Her statements reflect her own opinions and experience and are not indicative of any specific client’s experience and are not a guarantee of results. No cash or non-cash compensation was provided, and no material conflicts are known.

Advisory services are offered through Root Financial Partners, LLC, an SEC-registered investment adviser. This content is intended for informational and educational purposes only and should not be considered personalized investment, tax, or legal advice. Viewing this content does not create an advisory relationship. We do not provide tax preparation or legal services. Always consult an investment, tax or legal professional regarding your specific situation.

The strategies, case studies, and examples discussed may not be suitable for everyone. They are hypothetical and for illustrative and educational purposes only. They do not reflect actual client results and are not guarantees of future performance. All investments involve risk, including the potential loss of principal.

Comments reflect the views of individual users and do not necessarily represent the views of Root Financial. They are not verified, may not be accurate, and should not be considered testimonials or endorsements

Participation in the Retirement Planning Academy or Early Retirement Academy does not create an advisory relationship with Root Financial. These programs are educational in nature and are not a substitute for personalized financial advice. Advisory services are offere

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Ari Taublieb, CFP ®, MBA is the Chief Growth Officer of Root Financial Partners and a Fiduciary Financial Planner specializing in helping clients retire early with confidence.


SPEAKER_01:

I posted my first podcast episode December 19th, 2020, and we are in 2026, and because it's been over five years, I thought I would change it up a little bit. Not entirely with the style, but you've heard a lot from me on tax strategy, on healthcare, on things that hopefully you're no longer worrying about that was causing you a lot of anxiety when it comes to retirement, such as, have I saved enough? Do I actually know what I'm gonna do when I retire? How am I gonna make sure I don't ever run out of money? And is my asset allocation correct? And everything in between. Over the next month, you're gonna hear from real retirees. These are interviews that I held. They are live on my YouTube channel right now, but many of you have shared, hey, that's great. I prefer listening on the podcast app. It's just easier for me. I listen on Apple Podcasts or Spotify or Google or wherever it is that you listen, and you'll tell me it's just easier when you're going on a run, when you're doing chores, whatever it is you like to do when you listen to podcasts. I know personally, I listen to podcasts when I'm in the car and when I'm doing my warm-up for my workouts. So if you're like me and you're like it's just easier to turn it on on the podcast app, over the next month you're going to hear from real retirees. And this is not going to take over my style entirely unless you guys go, oh my gosh, this is so entertaining and the quality content here. Hopefully you do feel that way. But I'm also going to stick with my traditional kind of, let's call it five to fifteen minute. Sometimes I know that becomes 20 or 25 minutes, where I'm just going over whatever it is that I feel would be helpful for you guys, or what you tell me would be helpful for you. I am posting on Instagram almost every day. I'm on TikTok. I'm on YouTube. I'm on where else am I? I don't know where I am. But those are the places that I traditionally am posting, and I'm laughing because it feels like nowadays you've got to be everywhere all the time. What I will say is it's all fun for me because I make content that I feel resonates most for all of you based off what you tell me. So thank you in advance. If you have left a review on this show, I really appreciate it. It's fun to read those and see if it has helped. If you are commenting on YouTube, thank you for doing that. I hope that the content resonates, and I hope it always will. This, once again, is not my show, it is yours. I want you to retire early with confidence, aka really know when work truly becomes optional. That's my ultimate goal. So if you enjoy what you do, great, keep doing it. But you don't feel, oh my gosh, am I forced to be here? So over the next month, you're gonna hear from real retirees. They are going to be longer episodes. If you enjoy this style, send me an email, Ari at rootfinancialpartners.com. If you hate this style and you go, you know what, those guests are great, but I prefer the 10, 15 minute, which you often say becomes 30 minutes. If you prefer those styles, awesome. I'll do more of that. Ultimately, you are just getting the best content you're looking for. As a reminder, I post every day on YouTube, so that's where I post the majority of my content. If you enjoy listening on the podcast app, once again, it's not gonna stop here. I'm over five years in, and I hope to do the next 50 years. So, with that being said, I hope you enjoy this month's episode of Podcast with real retirees. These selfishly were so fun to record because all the stories are so different. And I thought, quite honestly, when I started this podcast, how different would it be? When I started this series, excuse me, where I interview retirees. And I talked to a friend who had told me, What they're all gonna say a similar thing. I want to retire and have purpose, I want to make sure I don't run out of money. And I said, No, I I believe you, but I think everyone does have a unique story, and I think it gets deeper, but maybe I'm wrong. And I thought that because I talked to my clients who are awesome people and tell me great stories. Now, what I found is it's beyond what I ever could have imagined, and I hope you guys truly hear from the variety of people I talk to. I talk to single people, I talk to people who want to die with zero. I want I talk to people who there's couples and they both view money very differently. And most of the time there's one person who spearheads the finances and they talk about how they got their spouse involved, but not in a nagging way of, come on, let's talk about 401ks. But hey, what do you really want to spend your time doing? There have been multiple people from different sectors. I've had so many people come on who are in the IT department. I've had people come on who are in public service. It's just so fun to get to talk to different people. So if you listen to this and you go, wow, I'm retired or I want to retire, I have a story I want to share. You can apply to be a guest just like those that you're about to hear from. And with that being said, the longest intro of all time, let's stop this so you can finally listen to the actual episode. Enjoy this month, January of 2026 episodes where you hear from real retirees. I hope you have as much fun listening as I had recording. Enjoy. Was it actually hard to retire logistically or was it not?

SPEAKER_00:

It was not really hard because I had been planning to retire since I was probably 22. So when I started, in my mind, I kind of knew like at some point, like I'd like to retire early. You know, I didn't want to make work, you know, forever and have to, you know, just go forever. And so when it got really close, I would say, you know, I think you use the, you know, pushing the goalpost back. And I did that for like a little bit, you know, I was like, well, maybe I should go till 56. That'd be one more year salary, one more year of the, you know, and then I'm just like, but but why? Like, why? Why work another year? You know, it's just more time, you know.

SPEAKER_01:

What I'm doing in this new show, Retirement Reality, is having heartfelt, candid conversations with people who have already retired so you can hear from them what worked well, what didn't, and everything in between. I hope you enjoy. And if you're retired and you want to personally come share your story on a future episode, there's a link right below this in the description of this episode where you can apply to be a guest. Now go enjoy the episode. My guest today is the poster child for an early retirement. She started saving and maxing out her 401k right when she got her first job, and she stayed at that job for 32 years, retired at 55, and talked so much about the importance of making sure that, yes, you save for retirement, but that you enjoy life along the way. And I'll talk to a lot of people who I find stave so much and they're in such a good position, but look back going, well, I should have maybe enjoyed life more, and other people that are not in a position to retire because they're maybe enjoying it a little too much. She has a great balance and she talks transparently about what it's like living in this community where it's not your standard retirement community because a lot of communities have people who are kind of the majority in their 60s, 70s, 80s. This community, yes, there's people that are older, but there's also people like her. And when you retire early, you want to be around people that oftentimes are in a similar age range because of health and energy, and she's golfing all the time and just has great stories. So really hope you enjoy this episode. Judy, thank you for joining the Retirement Reality Show. Now I can already see your beaming to be here, which makes my job way more fun. So thank you in advance for having that smile. I ask all my guests the same question first, which is if there was one word you could use to describe your retirement so far, what would it be?

SPEAKER_00:

I would say so far, um choices.

SPEAKER_01:

Choices. I haven't had that word yet, and I've recorded like 20, 25 of these. So why choices? Now you have unlimited words.

SPEAKER_00:

Right. Um, for me, I feel like it's your ability to choose whatever you want to do. So if you want to go golf today, or if you want to go hiking, or if you want to plan your next vacation in a couple of weeks, it's just you get to choose whatever you want to do.

SPEAKER_01:

Let's get the whole Judy story. I like that. So, Judy, how long have you been retired? How old are you today?

SPEAKER_00:

Um, I've been retired for just over two years, and I'm 57.

SPEAKER_01:

Wonderful. Now, I imagine, and for some people it's not a big deal, but certain people retire, they're this is so great. Oh my gosh, I retired at 55, but my friends haven't retired. So, like, who am I hanging out with? So, before we get into the full Judy story, how you transitioned, what you did for work, all of the good stuff, who are you hanging out with today since you retired so early?

SPEAKER_00:

Right. Um, that's a very good point. Um, so I moved uh about a year ago, so from Illinois to South Carolina.

unknown:

Wow.

SPEAKER_00:

And so, yes, while I spent my whole career in Illinois, um, I was pretty much, well, I am the only one of all my friends that retired. Everybody else, right, is still working. And so, um, but prior to that, I always knew I wasn't gonna stay in Illinois. I didn't want to shovel snow, I didn't want to be in the cold. Um, so here in South Carolina, I've been here about a little over a year. And um, so the people that I hang out with are the people in my community here. So I'm not, it's not a 55 plus, but it's a planned community. So it's very 55 plus-ish. So everybody, I would say 90% of the people are retired. So the people that I go walk with or golf with or hike with or play pickleball or go to the trivia night with are all here in the community.

SPEAKER_01:

Very cool. Now, Judy, we're gonna I want to talk offline about this after because right now I'm actually visiting various communities to highlight them to show, hey, here's what certain people love and don't love. So maybe I'll make a potential visit out to you soon. Yeah. Why South Carolina? Was it this community or was it just I wanted to go?

SPEAKER_00:

Um I would say about two years before I retired, um, I started like planning of where I knew it wasn't gonna be in Illinois, I knew it was gonna be somewhere else. So um uh my boyfriend, I've been with him for now for about six years, five, a little over five years. And so we knew we wanted to get out of Illinois, and so we started what I'd call like a two-year tour. So we started in Arizona and looked there, we looked at Dell Webs, we looked at 55 Plus communities, we looked at regular communities, we used a realtor, we did South Texas, we did North Texas, we've done Alabama, we did Florida, the villages, like we did two years worth of vacations. But while you're vacationing, you're looking to see is this the right fit. And then, yeah, and so spent a couple of years doing that, and then finally, towards the end, North Carolina, South Carolina, and um this was a community um in South Carolina that just kept coming up on all of the like great places to live, you know, with retirement, tax purposes, this, that, you know, income, just all of the different things. Um, we knew we didn't want to be really close to the ocean, but we wanted to be close enough that you could go to the beach for the day, or you could go to the mountains. And so it kind of had it like a spreadsheet, you know. I kind of checked all the boxes of needed to have like neat needed to be near some airport so that you could fly out, needed to be not too far from the ocean, but not too far from the mountains. Um, you know, just a lot of different things. Needed to have culture, needed to, you know, I just had kind of like a list of all the things that you would want in a community. Um, we're big golfers, and so we wanted, we were looking, you know, for golf community type things. We wanted a planned community. So since we knew we were gonna be uprooted and have to like make all new friends somewhere wherever you go, kind of wanted somewhere where people were gonna be maybe about your age and had other activities. And so this community just kind of fit right into like what we were looking for, checked all the boxes, um, you know, has all of the things that you could imagine, you know, the the pickleball, the tennis courts, the pool, the workout centers, the hiking, you know, the social director. You know, it has all of the things that you kind of just want when you're retired to do. Um, so yeah.

SPEAKER_01:

Beautiful. Sounds like you really hate it. No, I'm just kidding. But um, okay, Judy, I'm gonna ask you a very honest question. I'm gonna give you a second to think about it. Okay, I've never asked this before. Okay. But my question, and you can be totally honest, don't answer directly when I ask the question, because I'm gonna tell a little context, okay? Okay. What percentage of the decision was financial to go to South Carolina? Okay, don't tell me, okay? But if you're thinking, eh, maybe 20% of my decision, eh, maybe four or forty percent. The reason I bring it up is I had a client once who said, Oh my gosh, I want to retire in Florida, look at the tax implications. I said, it's significant. We went through the analysis and I showed them they'd be fine either way. And they said, Okay, well, I mean, look at the tax savings. Like, what am I, an idiot? I'm not gonna not do this. I said, Well, do you have friends there or family? They go, nope, I know nobody. I go, do you think uh you'd like it? They go, No, I wouldn't like it. There's nothing I like there. I go, then why would you do it? And they go, well, you just showed me all the tax savings. I go, well, that's a piece of it, but that shouldn't be driving the decision. So if you were to put just a number, even just for fun's sake, what would you say?

SPEAKER_00:

Yeah, I would say it was still a pretty low percentage, um, maybe 20% or so. I I don't know necessarily that I was basing everything because Florida does have better, you know, for retirees. That's why there are a lot of retirees that go there. There are a lot of retirees that go to Nevada, you know, with no state income taxes and and various other things. Um, so yeah, you got you kind of have to look at the whole picture of everything too.

SPEAKER_01:

You do. Um, and I like the way you're looking at it. And I'll joke with clients and say, I have a better idea. And they go, Oh, is it like, should I go to like Cyprus or something like that? I go, don't go to Cyprus. Work forever. And they're like, What did you just say? I'm like, well, you can work till 100 and then you'll never run out of money. And they're like, Yeah, I'm not doing that. And I go, well, that's what we get to talk about. And there's clients who I've also said, look, I can tell you hate your job so much that based off what you want to spend, Florida is really the only state that's gonna allow you to do it. So we're married to nothing, just whatever gives you a good life. So with that being said, Judy, I want to touch more on communities later. By the way, everyone in the comments, if you're listening to this going, yep, I just say no value in a community. I'm gonna be living at my home till I die, great, let me know. If you're like, nope, this sounds cool. I want to see you investigate more where Judy's living, great, I'll do that too. So let us know in the comments. Now, Judy, let's go back to just kind of your work transition. One of the things that comes up often in these episodes is hey, it was really hard to retire because I didn't know how to tell my boss. Or, you know what, my team, they relied on me so heavily, and there was a project I was working on. There's other people that go, it wasn't hard. I prioritized me. I told them I'm done, and I was done. So before I get to learn about what it is you did for your career and kind of what the transition looked like, was it actually hard to retire logistically or was it not?

SPEAKER_00:

Um it was it was not really hard because I had been planning to retire since I was probably 22. Wow. Like when I started my career, I worked at the same corporation. I worked at a large insurance company in central in Illinois for my whole career. So for 33 years. So when I started, in my mind, I kind of knew like at some point, like I'd like to retire early. You know, I didn't want to make work, you know, forever and have to, you know, just go forever. So um, but when it got closer, like when I got to 50, you know, I'd always had in my head, I knew I was gonna retire at 55. Like that was the that was my goal. That was always been my goal because I knew it uh where I worked that you could retire at 55 and get your pension, get your health benefits, you know, get all of the package, right? And so I knew, okay, 55 was the goal. But when I got close to 50, then I kind of knew like, all right, well, um, I'm getting closer. And so I started telling like my team, my co-workers, not that I was going to retire, I was just always, you know, very much. Um, I was I was a leader in this area. I was always, you know, very much giving advice on, you know, hey, make sure you're trying to max out your 401k, or hey, you know, if you're getting this bonus, don't forget, you know, you might want to put some money in your in your Roth or in your IRA. I was always like sharing things that I'd always done for 33 years. I I was sharing it with other people, kind of saying, like, if you ever want to retire early, these are the things you want to do. And so I was kind of like leaving hints of things throughout several years that, hey, I was going to be retiring because these are things I've done and it's gonna set you up well to retire early or whatever. And so when it got really close, I would say, um, you know, I think you use the, you know, pushing the goalpost back. And I did that for like a little bit, you know, I was like, well, maybe I should go till 56. That'd be one more year salary, one more year of the, you know, and then I'm just like, but but why? Like, why? Why work another year? You know, it's just more time, you know. Yeah, I could get another bonus, I could get this, but you know, I eventually um that was like the hardest thing because I'd already had like my boss was already putting in for like new projects and like management leadership courses for me to take and things like that down the road. So finally I was just like, I've got to tell her because she keeps scheduling me for all these things, and I'm not gonna be here for them because I'm gonna be leaving.

SPEAKER_01:

Okay, Judy, I'm fascinated right now. Okay. If I were to go outside right now, I live right by UCLA because my wife teaches here. If I were to go outside and ask a student at 22, hey, what are you what are you thinking about right now? They would not say retiring early. They would say retirement, I'm gonna be dead by 40. Okay. So what was it that made you think I want to retire by 55? Was it your parents who worked way too long? Was it, you know what, I just want to golf so badly, I can't golf when I'm working?

SPEAKER_00:

No, I you know what? I think, well, if I back up to like college, I was a finance major. And so I was big into, you know, finance and savings and things like that. But when I started my career at State Farm, I had um my uncle, actually, my my grandma's brother, so my great uncle, he just said, like, right when I started at my insurance company, he said basically, like, well, the first thing you should do is max out your 401k. And I was like, max out my 401k, like, ah, you know, I need money, you know, whatever. But at that time in 1992, um, it was like$8,500. Okay, that was the max you could put in your 401k. And he's just said, just do it. You're not gonna regret it, you won't miss it, you know, whatever. It'll be fine. It might be hard for a little bit, but just go ahead and do it. So I back then you got it was a piece of paper that you filled out, not automatic, and you filled out the paperwork, you turned it into human resources, and they did the paperwork for you. And so I remember being in the orientation, and they said, you know, the earliest you can retire is 55, and you can get your pension, you can get your benefits, health benefits, la la la, all this kind of stuff. And I thought, you know, I want to get out of there at 55 because I did see like grandparents and parents like live and work really hard and long and long into going right up to Medicare and things like that. And I thought, you know, I really want to be able to leave when I want to leave or whatever. But then also I will say, during my career, um, about 10, 15, 10 years into my career, one of my friends, their father, also worked at with me at the insurance company and retired at 62 and passed away at 65. And that was kind of an aha moment of like, wow, you work all these years, all these years, 30, 35 years. No one's guaranteed anything. And then all of a sudden you pass away. And so you didn't get to enjoy that that retirement. And so that always kind of resonated with me until later on in my career when I was a leader over several people, and one of my employees was fifty nine and got leukemia and passed away. And he'd been there longer than me, you know, thirty five, forty years, and didn't get to. even retire. He was still working. And so, you know, it kind of puts things in perspective of when things like that happen, you're just like, you know, you just you can't buy back your time. Like you have to go. And that's why I think, you know, I watch a lot of your videos. I watch a lot of YouTube videos. I watch, I listen to a lot of, you know, you um podcasts. But I think people have a lot of fear in retirement. There's a lot of fear. But and I I had that, but I would rather take my chances, I guess, because I want you want to enjoy these go-go years, you know? You don't get them back.

SPEAKER_01:

So I I love the way you're thinking about it. I love the transparency. Yeah, there's so many things that could go wrong when you retire. And all of you guys that have those rational thoughts of well what if I retire and markets do bad? Or what if I retire and I have to go back to work. Oh my gosh, I told my boss I quit. I can't go in and beg for my job back. If you didn't have those thoughts, that would be weird. So Judy, you are living proof to say, look, there's no guarantees. There's no guarantee I couldn't get hit by a bus if I go outside and a guarantee that, you know, vice versa. So I love that you're sharing that. Now here's something that I've only talked about recently in a few episodes, but I'm curious your take. So there's a word joy and a word security. And I'll use my dad as an example before I get your thoughts on it. So my dad is a big surfer. And he grew up, he watched the movie The Endless Summer. Have you ever heard of this movie?

SPEAKER_00:

No.

SPEAKER_01:

Okay, big surf movie. Okay. And kids having fun and that's the gist of it. Um shows I'm a good son and watched it all, right? So here I am my dad, he loves Endless Summer. And his dad was a CPA. So my grandpa. And my dad watched this movie Endless Summer and watched his dad as a CPA and he thought they paid this thing. He goes here's the guy surfing and here's his CPA. He didn't know that surfers didn't make money. He's like eight years old going well I'd just rather be a surfer. So when he saw that his life was oh my gosh, I don't care if I make money, I don't care if I have a family, I don't care, I'm surfing. So my dad was the best dad ever, but I did not get picked up from soccer practice when the waves were up. And there were multiple um events when waves were up where other things did not occur. And once again best dad ever. But his viewpoint on life was I saw my dad live a life that in his opinion was mediocre or maybe not to the fullest extent. So he was like I'm going to be a surfer, what job can I do that lets me surf? Because when the waves are up, I'm going. So he was a reporter and he made movies and he transitioned and eventually he built security over time by realizing I'm going to need financial resources to have a family, which I do want and I do want to do more than just surf. There's other people that have shared on the show, you know what? I really enjoyed my job to an extent and I really didn't know what else I was going to do and now that I'm retiring now I'm really living the dream life I want. So yeah maybe it wasn't my dream job but it allowed me to get to this point. How do you view joy and security up to retirement if that makes sense?

SPEAKER_00:

Yeah I mean I I enjoyed my job um I I liked it. I was obviously there for you know I had lots of different jobs within the company but I mean I was there 33 years or whatever. But again I think along those lines it was just a a means to the security of it. You know I I had a really good job. I knew how to save you know and I knew how I really wanted to make sure that I balanced it though. I didn't want to just like save save save save save and not enjoy life. So there you gotta have a little bit of both you got to be able to you know save knowing that you're maxing out your 41k you're maxing out your Roth you're doing all the right things but you want to take the kids to Disney you want to go to Hawaii you want to do all the you know fun things and trips.

SPEAKER_01:

So there is trade-offs to it and there's balance in that so you should have been a CFP Judy I think that's your next stage of life if you want I would love that yeah there are people that take the classes or just become a CFP for the sake of it. So maybe in the future uh maybe we'll do collaboration videos in the future. Okay. Judy one of my favorite questions which you might think okay this is dull but it's not people love hearing it what does your day look like so during your working years like what time were you waking up? You know it we all prioritize our health but naturally it's less when you're working unless you're really disciplined and I'm getting the vibe you are. But there's like working Judy and now there's retirement Judy. So do you mind starting with what does your day look like today? Obviously it's going to differ a little bit but what time are you waking up? Are you taking a nap? Do you do no TV until it's dark?

SPEAKER_00:

What's your day look like yeah um it it varies but I would say like back in the working world right you're getting up at 5 30 six in the morning getting ready going to work 6 30 you know whatever corporate life um but in retirement life yeah it's hard to get up kind of sometimes I mean you're getting up like I would say 7 30 you know and it's I like a slow morning. That's just who I am. I like to have my coffee I like to you know um I might read my devotionals and things like that um watch the news I'm usually looking at looking at the stock market seeing what's happened overnight checking checking in on all the different you know stocks mutual funds doing all that um I I love to read I like to read a lot of like the Kipling's magazines go into maybe read a look at a couple of you know podcasts or something and then um usually then I work out um at some point I work out for probably about 45 minutes an hour or so give or take um I like to get in my 10,000 steps um do the walking getting all that done and then I would say most days I live on a golf course here so I'm just looking out um uh probably I have a tea time maybe at some point I I might just play nine holes might play 18 um depends if I've got league that day I'm in a ladies league a couples league I've got the neighbors down the street here there's six or eight of us that play on Saturdays together. So you know depending on the day I've got tea time set up or um trying to get into pickleball lessons um we have you know go to the pool if it's hot out nice um it just it can it can really vary um there's we have what we call like a social director so like Wednesday nights or trivia nights I'll go up to the clubhouse and we'll do trivia and dinners and I don't know there's just always something going on. So it it can vary but that's kind of a typical typical day.

SPEAKER_01:

Seems like you really hate it. No it it's amazing. I I love getting to hear about because it seems like it's minute details but there are people right now when you are speaking that I can promise you were thinking how do I get there? That's what I want to get to the fact that maybe you got them at don't have to wake up at 5 30 but I know a lot of people are thinking wait a second so the slow morning not having to rush I can have my coffee then I can work out and then golf this is something I heard a lot I went to school in Puget Sound which is Tacoma Washington. Some people called it Tacompton Washington but that's a separate story. And it was I was near Chambers Bay so a lot of people would come in it's a famous golf course and a lot of people would golf that I went to school with and they would always say how difficult golf was because they said it took a toll on their body and I'd be like well don't you work out as well and they're like well I don't have time for that I have to pick do I work out or do I golf so they're just golfing and then they're retiring because naturally I always talked about this stuff and they would say well when I retired my plan was to golf and then all of a sudden I hurt my back and I couldn't golf anymore. And I was like well that's a real bummer because like if you're not prioritizing your health to do what you want to do it it's kind of difficult. So how did you prioritize your health leading up to retirement because I know a lot of people will talk about it's so difficult because I'm so busy.

SPEAKER_00:

Yeah um well I've always kind of been a little bit working out and trying to get steps in even when I worked um so when I worked I either probably just would walk during my during lunchtime or something or I would just get a quick little workout in maybe after work or something. So I I worked out a little bit but you're right like when you retire I mean you have a lot more time you know if you don't golf that day and you want to volunteer in the community because we like to volunteer and help others or whatever and then you want to you know get to the gym work out you know eating healthy and all of that I think when you turn about it seems like 45 50 people really start taking priority in their health because they really want to make sure like you're good for those you know 10, 15 those go-go years. You know, you we why everybody watches all the videos of you guys and it's like you really want to be ready to go because if you're going to we went to Italy um last year right after retirement for like a month we went for about 27 days like you're walking 25 30 steps a day and you're going up the cathedrals to the top and you're climbing you know 400 steps you better be in shape so that you can do all these things um so yeah I call that retirement fit certain certain clients will need motivation and I go you're training for retirement that that is just the same reason people sign up for marathons or at 5K's or whatever I love that.

SPEAKER_01:

Now Judy I'm not gonna ask for your boyfriend or partner's name but if I were to ask him because he was with you before retirement correct six years or so if I were to ask him how do you think Judy has changed since she retired what do you think he would say um he would probably say um I'm probably more relaxed and I'm you know because having a corporate job you're a little more stressed out and like the you know trying to get everything done and accomplished um a little more relaxed a little more slow paced and probably a lot more fun because and my golf game's gotten a lot better because you have a lot more time to do what you want you know to play golf compared to just on the weekends.

SPEAKER_00:

You know before we could only play on a Saturday or something. Now you're playing whenever you want to play as much as as much as you want.

SPEAKER_01:

So incredible and this is a dumb question but I'm curious and I'll probably ask it when I eventually go out to that community to see it. My thought is if you live on a golf course now I'm clearly not golf savvy which you're about to tell from the stupidity of my question but you're on a golf course and you're in a community that allows for golfing you still have to set tea times you can't just like go golf and I imagine that's correct you do have to set tea times.

SPEAKER_00:

Oh absolutely how far in advance is that day before or like week before um I would say a week to two weeks before um but definitely a week before yes even in the community it's a pretty large community um but like for tennis or pickleball you kind of have to you know set some times as well for that as well because everybody's pretty active actually.

SPEAKER_01:

And if you thought that was a dumb question get a load of this if you're outside of the community can you go to that golf course?

SPEAKER_00:

It's a it's a private community. Okay. Correct it's private.

SPEAKER_01:

I'll hear now some of my clients are you know gigantic golfers and I'm clearly not but they will tell me there are certain communities that they're like I need friends in that community because then I can be a partner and do is that a thing where if you had friends you could like bring them with you or is it like you have to no no like I I have guests come in I've had my my college roommate was just here a month ago or whatever and we've had family in and we've brought them and they've golfed with us and you could have guests.

SPEAKER_00:

Oh yeah you can bring your guests in and family relatives oh absolutely they could use the pool the amenities oh yeah they just have to pay a minor price of course no I'm just kidding yeah yeah yeah just a minor mild$10,000 fee.

SPEAKER_01:

Okay let's shift gears financially a little bit. Now I don't need your net worth social security number any of that crazy stuff. But you know I've had certain people go, look, Ari, I'm just a modest spender.$20,$25,000 a month, I'm comfortable I'm like, well certain people might not call that modest and I've other people go I spend a lot I don't know why what am I doing wrong? I spend$3,000 a month I go well it's all relative so it's not right or wrong but is there a month let me ask is there a general amount in any given month that you go I try to target this as a minimum or maximum or how do you even think about it.

SPEAKER_00:

Yeah um you know I think before we retired I really was trying to get a handle on the monthly expenses like I feel like everybody you need to know how much you're spending um each month and you probably need to know that even before years before but I really tracked and kind of was getting an idea now obviously leaving Illinois and moving and building a house and doing all of this like that kind of changed a little bit of it but you still kind of have to know now that we've been here a year like you know you get it down to the penny like I know what we're spending each month right but before that I knew so yes I mean I target like 8,000 sometimes it's 7,000 sometimes it's 10,000 you know if we're gonna go to Savannah Georgia for four or five days if we're going to Charleston or for you know taking a couple of day trips I mean you're gonna fluctuate because you got hotels you got this you got that you're spending here and there. But if we have a month where maybe we're not really traveling we're just kind of staying put for a little bit and just kind of doing our normal things yeah I mean we can you know I get it we get it down but it's you know I just I I know with the max I kind of want to spend every every month um and then you're just like oh we're getting close to that we've taken like three trips or I mean we're going to Hawaii in like nine days we're gonna probably blow it out of the water in nine days or whatever. But you know that's what you've saved all these years for I mean like you work really hard and you figure out a way of how to save that money. You know everybody's always just like yeah but you have a you know my kids will say oh but you've got a pension and you're gonna have Social Security you know we're not gonna have a pension we're not gonna have social security and I was like here's what you're gonna do and I tell them and they do exactly what I've said. So they're gonna everybody's gonna be fine you know but yes I mean we do the old people we do have a pension and we do have social security but I would be fine without the pension and the Social Security. Like I knew what I was doing way back you know when I was 22 23 um and it really it just comes down to and I told like I tell every young person this just max out the 401k as much as you can if you can't max it out at least just try to max out every year for 30 years and and a Roth or whatever or an IRA like something just try to and do it every month in dollar cost average over the whole 35 years.

SPEAKER_01:

You'll be fine you know you have such a healthy outlook on it. We could clip that two minutes right there and I feel like that's what should be played before every like presidential debate like hey before politics go on just hear this two minute clip from Judy okay you're all gonna be fine okay this is what you're gonna do. And the people that go I can't max up my 401k I'll I'll joke with clients and I'll go there's different versions of can't and I'll go like this I'll go look I'm five foot five okay I can't become six seven that surgery doesn't exist yet you can max out your 401k now maybe there's some spending happening otherwise that's not letting you but it's humanly possible. My favorite joke on this and I I do all these dopey jokes for a reason because I'll get really into the weeds because I love this stuff. I had a mentor who once said all right yeah I get you love this stuff but other people financially just might not as much so you've got to find ways to make sure their brains can go off and on then they'll actually take in your info. So I'm like okay so my favorite quick story here and then I have a question for you I promise and many of the viewers I know you guys have heard this before but my dad and I I I would go to soccer tournaments as a kid so my dad's driving me all over and it's hard to get a hotel room so we get one hotel room and the AC does not work. And so my dad calls and goes can we change rooms and he heard at the front desk that there were other rooms. He was just being nice to say can I have another room he wasn't saying are there available rooms we knew they were available. And they said no it's not possible. And my dad was I think he's trying to teach me a lesson but he said watch this I'm like okay he goes we put a man in a rocket we shot him into outer space he landed on the moon we flew him back home and he's still breathing and I can't have another room is that what you're saying to me right now and the guy goes you know I think there's another room available and it was my dad sharing like look no means get to work. No is go deeper. Don't just give up. So it's a stupid story. But it was fun and I think about it a lot. So my question to you because when it comes to the finances that monthly amount just so everyone's clear what you are saying and tell me if I'm wrong$7,000 a month that's after taxes. That's just what you're spending that's adjusted for inflation. Guys it's not some magical number that's the same every month. So I love that I'll see a lot of people make the following mistake that I can tell you're not making so kudos to you which is this you know I don't want to spend too much these are the years where yeah I've got my energy and my health but what if I overspend? What if I run out of money I don't want to spend too much and then you've got the other part of your brain going hey but isn't this like what I save for when I'm 80 I'm not gonna take the same trip. So like shouldn't I do this? And what happens is people have those two thoughts clash and then underspend. Then they're mad at me when they're 80 with too much money, wishing they enjoyed you know more of their earnings. So that balancing act not always easy but it's one of those things that I'll say look it's all about probability and confidence and that's what retirement's about. It's not like there's some magic number but I want to go back to something you said. You brought up goalpost planning which is that phrase I talk about of one more year, one more project and I'll ask you guys in my videos, I'll say hey would you please close your eyes, go to your partner and ask them, don't ask yourself ask them how many times have you said you're gonna push it one more year? And they might tell you it's more than you even remember maybe it's not that many but getting to hear it from them sometimes helped. But you had said something that struck me that I've not forgot about which is wait a second I knew I could retire before 55. I even thought about pushing it to 56. So do you remember the first time you went wow if I did walk away now maybe it's not full benefits of healthcare but if at 52 I did walk away would we be okay do you remember doing that analysis?

SPEAKER_00:

Yeah actually I went when I was about 51 52 I went to like a financial consultant and um it was just a like a two hour session and that was it you know um paid like 250 for it and had had already given her all my information all my data all that and she said basically you could retire tomorrow and you'd be fine and that kind of was like the kickstart. I think I was 51. I was like okay I could retire tomorrow and she's like had confidence you know she'd ran all the you know did all the software and everything and I was like and I felt pretty confident that I could could do it. I'm not one of those people and I tell my kids and my kids know this as well like you know I'm not buying you know 25 pairs of Nikes and 20 you know 20 Louis Vuitton purses and this and this and this you know and what I think on one of your other videos one of your like keeping up with the Joneses like who are they what are they doing I mean you don't you don't need all this stuff I guess um in your 20s and 30s and 40s. You know people just want to like I gotta have 20 more of this and 10 more of this and a Starbucks every day and da da da and you said like you know you can max out your 401k if you choose because you could give up maybe some other things that you really probably don't need. So so yeah so I think when I was about 51, you know I kind of knew like I could go tomorrow but then I was like well I really just want to go to 55 because then I know I can get full pension, full you know health benefits, all of that, which I understand I've got lots of friends. I've got my siblings family people that are like well what are you doing for health insurance? What do I do for health insurance till 65? Like everybody's you know It's the whole health insurance thing, which is a big thing for a lot of people. Obviously, I'm fortunate, like my corporation, I have health benefits um each month till I'm sixty-five. Um and I but I pay a premium for it. But um but yeah, a lot of people, you know, that's that's a big concern, you know. That's that's one of the I think the show showstoppers for people, you know, is like, oh, I I can't do it because of healthcare.

SPEAKER_01:

Yeah, it's a valid concern. And I have a video I put out I don't even know how long ago, but basically saying why, not it shouldn't be a concern, but how if you plan around it intentionally, if you have that superhero account I talk about, if you're wise with making sure you're preparing ahead of retirement, that it's really not as much as you think. And if you're optimizing your income, I have clients that yes, they're spending 2,000 a month. So you're like$25,000 a year. Yeah, I have clients that are doing that for three years and it they hate doing it, but guess what? They have the money to do it, so it's not fun to do, but they would be okay even if that was 10 years. There's other people that go, that's just gonna crush me. I'd rather work another year. Great, that's your trade-off, and you get to decide that. So I'm glad you brought that up.

SPEAKER_00:

Now what I've told a lot of people is that I didn't even start my pension. So even though I could start my pension at 55, I deferred it and I'm just gonna let it ride and grow because a long time ago, you said, like hoard cash, you know, get this superhero account. So I just started loading up a superhero account years ago, knowing that I was going to need that when I turned 55 and then live off of that, so to speak, um, until I'm ready to turn on my you know, pension because you know, there's the whole you know, back in my day there wasn't a Roth, you know, you had the 401k when you started out. So a lot of us are gonna get dings later on. So it's like we gotta hurry up and try to figure out what to do with this 401. Yeah, and you've got this sweet spot between 55, 65 ish to like try to get it into a you know, more into a Roth. Um but a lot of window. Yeah, it's a big tax window. I will say one of the smart things though, when the Roth finally came out, I don't know, like back 20 years ago, I guess, I had a large IRA back in the day and moved that into a Roth. So I have like a Roth that's my Roth in this in Apple stock for like 20, almost 20 years, 18 years. And so that's the smart thing. So like I get the young people to just get the Roth because you know, we didn't have it back then, and then we have to hurry up and play catch up now.

SPEAKER_01:

Yes. Oh, you're thinking about it so well. And what you're really sharing for everyone who some people are like, yes, I'm advanced. Other people are listening, going, What did you just call me? Who's Roth? But for those people, just truly know Roth, think about it like tax insurance. That's all it is. So I have clients that they're in a high tax bracket, they're still doing Roth. They're like, I just like that I never have to pay taxes ever again on this money. The the window that we talk about is let's pretend Judy, you turned on your pension. Might feel good. You're like, well, I paid into this thing, so like I want money and I don't know how long I'm gonna live. But then what happens is when there's Social Security and a pension and RMDs, you might be like, haven't flown in all the money. And you're like, what's the problem? Well, the problem is you're getting taxed what I call up the wazoo, which is at your highest marginal bracket, which is not the most fun. So you've got these prime years to try to tackle paying Roth conversion taxes and okay, well, I still want to travel. And so there's this balancing act that's difficult where, and I've I've shared this honestly many times, where I did a really bad job for a client, Judy, early on in my career, where I showed them an analysis. The finances I thought were really well thought out. I'll give myself some credit there, but I missed something really big. And I showed, here's the value of doing these conversions, look at this fancy stuff. I thought I was a whiz kid, and I'm waiting for them to go, oh my gosh, this is brilliant. And they go, Oh my gosh, I see how smart. Okay, if I do the conversions, I'm in the 22% bracket now and I pay taxes now, and then in the future I'm at 32, and then Social Security, I'm gonna kind of defer mine, but my spouse is gonna take theirs. And we had it all, and then I said, Okay, guys, so like let's do it. And they said, I just have one question. I said, What is it? They go, I don't want to disappoint you, and I know you just built this whole report, but I think to be able to pay the taxes on some of these things, we shouldn't take vacations. I said, What do you mean? They said, Well, I I don't want to screw up the analysis, you're just so excited right there, and it made a lot of sense, and it looked like there's more money at the end, but to do that, it looks like I'm not gonna really be able to spend as much as I want today. I went, oh my gosh, I'm so sorry. They go, what? I go, this whole thing is irrelevant at this point. How much do you want to spend? And they told me and they dreamed big. And so in the initial meeting with them, I said, guys, how much do you want to spend? And I think they said like 7,000 a month. I said, Great, next question, okay. I I didn't go, why is that? Okay, what else? Um imagine one of our questions now is if we forced you to spend$200,000 a year, meaning if you didn't do it, it goes to your least favorite political party. That gets people talking. I'll say, What would you do? And then they'll say, Oh my gosh, I would do this and do this and volunteer and do charitable giving. And I go, Great. So 7,000 is what you'd like to spend, but it sounds like 12 is the dream. And they go, That's the dream. I go, great. Well, let's look at that. And why is that so important? Because their conversion recommendation would be smaller, but they'd enjoy their life way more. And the ultimate goal, the sign of a good plan, is a good life. It's not, did I do the best conversion at the X percent of blah, blah, blah. It's how did you live? So I love the way you're thinking about this, Judy. Here's how I like to end my episodes. I like to shut the heck up and give you the floor for one to two minutes to talk to whoever you want who's retiring, let's say, in the next five years. You can give them advice such as, you know, here's something I worried about that turns out is just not a big deal. Or, you know what, I don't have any advice for you because my life's completely different, and I recommend you do XYZ instead, which didn't work for me, but might for you. Whatever you want to do, it could be here's how I talk to my kids about money. Whatever you think would resonate with someone who's five years out from retirement and they're just looking for insight from someone like you who's living it. So I'm gonna shut the heck up and give you the floor.

SPEAKER_00:

Well, for my kids, I mean, I, you know, or the young people, I really try to stress to save your money, you know, but also enjoy life. You know, there's a good balance between, you know, taking the trip, having the experiences, um, doing all the things you want to do. But most important, you don't need to have everything right now. You know, if you buy a condo or whatever, you don't have to furnish it all in one day, or you don't have to buy the 20 pairs of you know Nike shoes or this or that. You just don't have to have everything. There's there's a balance, and if you do it over time, you'll be fine. If you're five years out, you know, that's when it's kind of like you know in five years you want to go, you're pretty sure, but you're worried. I mean, I have a lot of friends that you know are my age that would like to retire, but they're scared, they're nervous, and I'm like, you're you're going to be fine, but you need to like start planning or at least think about the bigger plan of you know, hoarding cash or have a superhero account, you know, have some of those things put in place. Think about how you're going to you know pay for health care, you know, various other things, but you know, and and also get your health in order, make sure that you, you know, are taking good care of yourself and all of those types of things. But I really think if people just kind of have a plan of what they want to do, where they want to go, they you know, have some things to look forward to or have a purpose. Um, I you know, there's a lot of podcasts out there that talk about that, but you you don't want to just retire just to retire, and then you're just like, okay, now what? Like, none of my friends are retired. What am I gonna do all day? Like, you gotta have kind of a plan of like, I want to spend more time with my kids or my grandkids or my you know, friends in a community, or or what that might look like, but just kind of like be very thoughtful in that over the you know the next five years. I know I really did when I turned 50-51. I was definitely on board with this is what I was gonna do. And I knew I was gonna move, so I knew I'd have to start researching that whole process and things like that. So just have a plan.

SPEAKER_01:

Judy, you are the poster child for an early retirement. I'm so grateful you came on the show. All your comments there, especially around health, remind me, I want to tell you guys one last story. And I know I've done it many times, so if you're like, oh my gosh, I've heard this 12,000 times, feel free to tune out at this point. But for those who have not, so the quick story is I had a woman, and this is really what made me fall in love with this planning. She said she was upset that she had three million dollars. I said, listen, lady, I don't want to be mean here, but there's a lot of people who would love to have three million dollars, so why are you upset? And she said, You don't get it. I go, that's correct, but I need to now know why I don't get it. So please share. And she's telling me about all of her big travel goals and how she's not really able to do it as much. And I said, Hey, what's the problem here? And she said, I didn't need three million. I said, How much did you need to retire? She goes, I needed two million, maybe two and a quarter. I said, Well, what's the problem? You've got more money. This was earlier in my career. And she said, Yeah, you clearly don't get it. I needed two to two point two five million, let's say, so I could spend and travel. Now I've got bad sciatica because I sat at work for three more years, and when I travel on these long flights to these spots I want to hike at, I'm in a lot of pain. So when I get there, I'm in a ton of discomfort, and I don't enjoy it nearly as much. And I was staying going, I need to do one more year because oh, three million is my new goal, and then shortly that was four million, and she was very kind to say, Hey, if you didn't really show me the numbers with the level of emphasis that you had of, hey, why the heck are you still working? I may have kept going. And so it's one of those things that everyone's pushing the goalposts back. And I forget who said it, Judy, maybe you know, but Rockefeller or someone fancy old said, look, everyone just wants a little bit more. People who have two million think they need three and three, five, and five, ten, and ten a hundred. So make sure you have enough and you have a good plan, but ultimately don't push it back just for the sake of it. And maybe Judy, people will watch this video and you'll have some more friends that retire after they see it.

SPEAKER_00:

Hopefully.

SPEAKER_01:

Cool. Thanks, Judy. If you enjoyed this episode of Retirement Reality, check out how we help people retire with confidence. You can see we have an FAQ section on our website. If you just hover over the resources tab, you can go ahead and see this FAQ section here and learn everything about what it's like to work with us, including our personalized planning process, a quick overview of how everything works, do you have enough money to become a client? Where will your money be? Everything from tax planning to fees. We are extremely transparent and want to make sure that you're working with someone that resonates with you. Hopefully you enjoyed this episode. And if you once again want to be a guest on a future show so that you can share your story, you can see that in the link of this episode. Thanks. Thank you all as always for listening to the Early Retirement Podcast. I love getting to host these shows and make different content for you guys every single week. I've not missed a single week in years, and that is because I love getting to do this. Now, please be smart about this before you actually execute any strategy that you see me talk about or hear me talk about, should I say, please talk to your financial advisor, your tax preparer, your estate attorney. Please be smart about this. None of this should be construed as financial advice. This is for fun, educational, informational purposes only. Once again, just quick disclaimer here, guys, please be smart about this. Appreciate you listening as always. And you can, of course, submit a question on my website, early retirementpodcast.com. If you, of course, want me to address a specific case study or topic. I will not promise I can get to it, but I respond to every single person. And if I find it will be helpful for a lot of people, I will absolutely make an episode on it. At the very least, give you some insight. That's it. Thanks, guys.