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

Single Retiree Shares Surprising Truth About Retiring Earlier Than His Peers | Retirement Reality

• Ari Taublieb, CFP®, MBA • Episode 302

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David’s story feels familiar to a lot of people in their late fifties and early sixties. After a long career in asset management, a role change and pandemic burnout became the nudge he didn’t know he needed. At sixty, he finally decided to stop working not because he had to, but because he could.

He describes retirement in one word: possibility. Time with friends, hikes during the week, early dinners without rushing, and yes, plenty of pickleball. The new rhythm isn’t about adding more activities. It’s about having choice. He’s still curious, still learning, still pushing himself with new skills and fresh goals, just without the pressure to perform.

David also talks about what made the decision easy and what made it hard. Leaving a good job wasn’t simple. Letting go of structure took practice. But he found freedom in quiet mornings, long walks, and realizing he didn’t need a title to feel fulfilled.

The conversation turns to money, too. The reality of how decades of steady saving built flexibility, how modest spending supports a rich life, and how “enough” means something different now. He’s planning thoughtfully for Social Security, Roth conversions, and even legacy for his daughters, while still reminding himself to enjoy the present.

If you’re in your fifties or sixties wondering what’s next, this episode is for you. You’ll hear how stepping away from work can open new space to live, learn, and move at your own pace. Sometimes the next chapter isn’t about doing more. It’s about finally breathing.

Interested in a custom strategy to retire early? 
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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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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 cannot wait for you to hear today's interview because this is a fun one, but a few key announcements. The first one being, as you can tell, if you've been listening to the podcast for some time now, it's been over five years since I started posting these podcast episodes every single week, and I rely on you guys to tell me what resonates most. You have told me the past month it has been awesome to hear these interviews, and many of you have shared, you already saw them on YouTube. It was nice to listen again. A lot of you have told me, hey, I really don't tune into YouTube. I prefer listening on the podcast app. It's easier for me while I drive, while I work out, whatever it is you like to do. So this is not going to stop. In fact, starting in March, I'm going to start to double up. So for the month of February of 2026, if you're listening to this, this is going to be a month of more interviews because you guys have all shared how much they have resonated with you, which is once again my ultimate goal to give you confidence to retire. And maybe you heard one thing that was a big takeaway, such as, wow, if I didn't have this superhero account, I couldn't have retired early. And boom, that prompted you to take action. So now you go get that superhero account. Or maybe it was someone explaining that they're paying 200 bucks a month for healthcare before Medicare kicks in, and you are thinking, wow, I couldn't retire because of healthcare. And now you're thinking very differently. So this is going to be a fun series. We're going to continue. I'm going to also do separate episodes. So it will become a podcast that you'll get episodes twice a week. That's going to start in March. So for the rest of February, we are going to continue these interviews. A few other announcements. I have started a new one-page plan series. And what this is, is if you follow me on Instagram at early retirementari or TikTok or on uh Facebook or YouTube, what I'm doing is I'm doing a sample, one-page plan in less than three minutes. So if you were to tell me your goals, such as I want to retire in three years, I have 1.2 million in my 401k, 200k in a superhero account, and I want to spend 6,000 a month. Am I on track? I will then record an episode very short, three minutes or less, because that's what the platform allows. And I give you my yes, you're on track, or no, you're not on track. And there's also a way for you to leave a voicemail. And so this is going to be a fun series because what I'm going to be able to do is respond directly to you guys. So if you want, you can of course um email me and just put in the subject line me, literally those two letters M E, and then I will send you the link where you can submit the information so that I can do this for you. And once again, that is my complete goal, ultimate goal, is to give you guys the easy ability to be able to find out are you on track or are you off track? And I'll be very honest and transparent as I always am. Now I do have over a thousand submissions, and I try to do one to two episodes every single day. And I post those daily on my various social channels, so make sure to check those out. But if you want a faster response, the best thing you can do is call into the show and leave me a voicemail. So if you want to write this down or if you want to just somehow tell your spouse or someone who's working out next to you, if you're at the gym, uh that would be very weird. But the number is 213-316-8397. We're going to put that in the description below. So if you're like, I missed the last number, no worries. We're going to drop it below. But that's how you will get the fastest response because what I'm going to do is a series where I respond directly to your voicemail. So it's the same thing as the one-page plan. The difference is you're actually explaining it to me via voicemail as opposed to me reading it on a screen and then writing it down and doing a review. So that can be a more interactive way for you to get to hear my guidance. And once again, it's never going to be financial advice. It's just a quick review, but it's a really fun way for me to feel like I'm close to all of you, getting to really share with you, hey, here are my thoughts. This is something you're worrying about for no reason. Or you know what? You're actually in a spot where I don't know if it makes sense to hire an advisor. Or you know what? This is a great example of why we need to bring your spouse in earlier than you think because it sounds like you're more stressed than you even know. And it's my job to be able to read in between the lines, and I feel like that is what I'm good at. So thank you for allowing me the opportunity to showcase my ability to hopefully help you retire with confidence. Now, with that being said, my final request here is if the content resonates with you, everything I do is for all of you, once again, to retire with confidence. So please leave a review if you listen on iTunes. If you're on Spotify, please just give it five stars if you think it's worthy of five stars, of course. And then if you're on YouTube, I love seeing your comments. My team does an amazing job of saying, all right, you got to check out this comment. And I will personally respond to so many of them. So I will respond with a video message or an audio message. I can do that directly in YouTube. It's very easy for me to do so. The podcast platforms don't make it as easy. So if you haven't been feeling as much love as you feel you maybe deserve because you've been listening to the show for a while, or you submitted a question and it hasn't quite been addressed, I'm gonna do this forever. So I it if you're wondering, hey, when is it gonna get to me if I had a specific question on superhero accounts or what can I do if I want to look if there's a case study for people like me? I'm currently working on a new app that hopefully can organize all the content I've done so that hypothetically you could search, hey,$1 million 60, and you'd see a bunch of case studies for people like you. You can do this right now on YouTube, but it's not going to exclusively bring up my content. And there's tons of awesome other creators out there, so maybe you'll you'll catch someone else who you find resonates with you. So my hope is that you enjoy these interviews, you resonate with them. Once again, if you want me to interview you on a future show, all of this is available in the description below. And then finally, you know, I exist and make all this content so you can truly enjoy your retirement. My hope is that you don't listen to the podcast forever unless you really love it, in which case awesome, with this stress or thought is a better word of should I be doing that? Well, you already just talked about Social Security. That is one strategy I didn't consider. I I always thought I should collect early because then it would take less pressure on my portfolio. And then really I'm talking about how that can ruin a Roth conversion strategy. And now you're thinking, oh, should I worry about that? And now I'm retired. Did I screw up? I don't want you to worry about any of those things. So that is why we exist, to be able to play the role as a true partner. I am that one weird advisor that says everyone doesn't need one. It's all about timing. So if you're five years out from retirement, wondering, hey, should I have a conversation to even see if an advisor can help? We would love to have that chat with you. And we might just tell you it's too early and we can't help. We might say, nope, it's a great time. We might say, you know what, you're very close, and here's what I would think about. We are very honest and transparent, and we hope everyone in our industry can follow in those footsteps. So, with that being said, let's listen to the interview and enjoy this month's worth of episodes for February 2026. Thanks, guys. 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 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 that? Please talk to your financial advisor, reality preparator, your estate attorney. Please be smart about this. But fun and everything. Once again, you want to do that. There's a lot of submitted a question on my website where you can retire the podcast. Go enjoy episode. If you, of course, want me to address a specific study or topic, all the requirements I can get. I respond to everyone personally and pick up. And if I find it will be helpful for all play. I will absolutely make an episode on it to him. At the very least, if you said a ball. David, thank you for joining another episode of Retirement Reality. This is fun for me because for those who don't know, when you apply to be on the show as a guest, which all of you can do in the description below, I'll ask one question here. And I'm going to your survey right now, and I just say, hey, is there anything else you'd like me to know as a guest? And David, you said, I need help convincing my friends to retire. So with that being said, it sounds like we already have a fun conversation planned. And hopefully, for those who don't know, how could you? David is going to a pickleball game or tournament later? Just a game. Just a game, okay. Um, have you ever played in a pickleball tournament, by the way? A couple of times. We might have to get into that and what that's really like. So today, a fun chat. If this is your first time here, guys, this is not my normal video where we have a big case study and Roth Conversions and healthcare. I have tons of content there. This is where David is kind enough to share his story, what retirement's really been like, and we're gonna get into it. I ask all my guests the same question first, which is if you had one word to describe retirement so far, what would it be?

SPEAKER_00:

I guess I'd say possibility. Um really being retired opens up my day and really my life to lots of possibilities. Um having done the financial planning, which I know is not gonna be their focus of our conversation, but you know, I got here for a reason, and uh it's just I feel like I have uh a lot of possibilities open to me, and sometimes those possibilities are just leisure, and uh it's given me an opportunity also possibility, opportunity to think about um what's important to me and focus on things that that matter the most to me.

SPEAKER_01:

Possibility, I love that. How long have you been retired? Just four years, almost uh this week. Wow, okay. So four years now. Let's talk about the possibilities that you are not able to pursue during your working years. So it sounds like pickleball is one of them. What else have you been able to spend time on that you just couldn't during your working years?

SPEAKER_00:

I don't really feel like it's opened up uh for me things that I didn't do before. Uh so maybe you know, maybe I think more about the choice I have on a daily basis. But um, you know, I fill my day with uh spending time with friends, going to visit friends and family, um, getting together with circles of friends in other places. Um and then, you know, on a day-to-day basis, a lot of pickleball, uh fishing, walking, hiking. Um really all of that's really kind of been accelerated over the past few years. Um Where where do you live, David? What's your exact address? No, don't share that. I'm just kidding. Uh but where do you live? I'm in Connecticut.

unknown:

Okay, okay.

SPEAKER_01:

So right now, you've been retired four years, pickleball, more time with family and friends, love here and that. Let's talk about the transition. So we're gonna go all the way back to when you started just your career, but before we even get to that, people love. I read all of your comments, you talk about the transition. What was it like actually telling my employer I'm done? How far in advance had you been planning for retirement? What was that transition like? Sure.

SPEAKER_00:

Um, I was working for a large asset manager and uh was in a role I absolutely loved. And I was kind of serving as a mentor to people starting their career out, but I didn't have people working for me, and it was a great job. If I was in that role still, I would probably still be working. Um right around the start of the pandemic, I got moved into another role that I didn't like as much, but it was working from home exclusively, and I made the most of it. And I think I did some really good work in that time. So that was about a year and a half. And then I decided, and just by the way, during that time, I was definitely thinking, I didn't like that I was forced into that role. I didn't like um, I didn't really feel like I had growth opportunities at that firm. Um, and I started to think about what it would look like to wind down my career. Um, and then I found another job within the firm, but things didn't work out as planned. I kind of did a little bit of a bait and switch. I ended up in a role I really did not like getting up in the morning to go to. And by the way, going to was still 100% work from home. Um but just even getting, you know, dialed in in the morning and my routine day-to-day work was for really for the first time in my career, I just did not like my job. And so it was very easy for me to make the decision at that point. I had already been thinking about the numbers, I already knew I didn't have to work. And uh that's when I made the decision to um to give notice. And I gave them, you know, the standard notice. My manager was not surprised at all. And uh, and it was a pretty easy um transition out because I wasn't, I had only been working for that team for about two months. And I think also coupled with uh, you know, the pandemic and everybody working from home, you know, from from when I stayed home in March of 2020 to when I uh went in to turn in my badge and my laptop, I hadn't set foot in the office even one time. So all of the things, the appealing things about going to work and being with people and working with colleagues, um and just those connections, uh, I really hadn't had that for a long time.

SPEAKER_01:

Okay, a few questions there. So first question, David, did it feel like you were joining and quitting at the same time since you were literally going to return your badge and laptop? Well, maybe normally you'd feel like that's when I get it. Obviously a joke of a question. But I really want to know, okay, so was it the task that you were doing that made you go, yep, this is not the role I like, or was it the people you're working with or both?

SPEAKER_00:

Oh no. I at that firm the people were quite good, you know, smart, accomplished, um, dedicated. I didn't have any and fun many times. But um but the work that I the role that I had ended up in, the work that I was being asked to do was just it just didn't align with what I had done my whole career, um, what I wanted to be doing, why I was leaving the role that I was in, and uh it just didn't seem like that was fixable. That kind of thing can happen in big firms, I guess, sometimes.

SPEAKER_01:

Yes, it definitely can. Now, I hope please take this question with complete sincerity, okay, and take it, sincerity is not even the right word, take it as a compliment, truly, okay, David. So to me, you look, I know your next birthdays you're gonna be 30, okay? But a lot of people will talk about ageism in the industry, and they will often say, I got moved to this role because they just didn't think I had it in me anymore. Was that what you think happened, or was it just complete? I mean, who knows?

SPEAKER_00:

Well, all right. I mean, I'll speak candidly about that. Um the firm was um paying a lot of attention to um pay disparity, promotion disparity across gender, across other types of uh groups, um, protected categories. And I thought all that was pretty good. I was supportive of that. Um I certainly wouldn't want my two daughters to have the same opportunities as um their male peer group. And yet I did feel that um the firm was not interested in having another older white guy in um in more senior positions. Uh I don't think there was any deliberate effort to force me out or anything. I just don't think I was um particularly attractive to the firm for where, you know, as they were chart charting out their future. And I will say that firm was pretty dedicated to hiring really uh very often straight out of college, very smart people, hard workers. Um, and that was part of what made it a pleasure to work there initially.

SPEAKER_01:

Well, I appreciate the candor, David. And if they saw your pickleball skills, which I have not seen yet, but I'm sure if they saw that, they would have uh put you in a different role. Now, one thing you you said here, and you're a very nice guy, which is why you said it the way you said it, which makes perfect sense. You said, Look, I just didn't like the new role as much. I'll joke with people who start working with us and they go, Yeah, you know, I don't hate my job, it's not the worst. I'll go, if you could be done yesterday, would would you? They go, Oh my gosh, of course. And I'll say, you know, you go to a restaurant and they say, Hey, can I get some feedback? And sometimes I'll go with my brother, my mom, who's very nice, maybe nice like you, David, and they'll go, you know, the the food was interesting, and I'll go, that means it was bad. Okay. That's just them being nice. Okay. And then of course I'll smooth it out from there. But the reason I bring this up is it's one of those things that is hard for a lot of people to walk away when you're in a role that you're like, I don't love it. I know financially I'm in a good spot, but look, I just don't know what I'm gonna do when I retire. It doesn't sound like that was your problem. Is that right?

SPEAKER_00:

Well, I think you hit a few questions there. And one is like, what am I gonna do when I retire? Um Yeah, maybe let's maybe re-ask the question. I mean, do you want me to focus more on what I was leaving or what I was going to? Because they're very different ways of thinking about it.

SPEAKER_01:

Yes, thank you for clarifying that. Let's I'm more curious, and I feel like this is a selfish interview because it's just what I'm legitimately curious about. I'm more curious when you were working, if there was any hesitancy about financially, I know I'm in a good spot. Yes, I don't love my role right now, but I'm scared to retire because I don't know what I'm gonna do. Or did that not enter your brain and you're like, I can't wait to have pickleball and family time. I'm not worried at all.

SPEAKER_00:

Um, well, I will say, like, I did have immediate plans for right after I retired. So I knew I wasn't gonna like on Monday morning um be on my couch wondering what to do. And I'm not really that way anyway. I oh I have no trouble filling my days. Um but I had some travel plan, including a month away and um visiting my mom and uh doing a back a short backpacking trip with a friend. So I have things going on. Um but I do feel like uh the whole way of thinking about like, am I gonna be bored as like the fear of going into something new? Um, I do think that's something to overcome. I've that's as I've tried to persuade my friends to finally uh pull the trigger, um, I've talked to them about that. Like people that say, what would I do? I think they have an impression, I mean, it it's very much of an individual journey, and I can't speak for I can't generalize too much, but I could say that fear and that uncertainty of what are my days going to look like definitely seems to be a theme that I've heard from people. It's holding them back from making the move. Um and I have a lot of thoughts about that, about how to approach that. Um so and maybe I can get more tips from you on convincing people.

SPEAKER_01:

Yeah, I've got some tips for sure, but let's do this because sometimes I'll like to do a little bit of root theater. And what I mean by that is I'll pretend to be a character. So, David, I'm almost in this short example. I'm gonna pretend to be your friend, but I'm not allowed to talk back. Okay, I just have to say, yes, tell me more. So pretend I'm one of your friends and you want to tell me about why retirement is so great and why I should consider retiring. What would you tell me?

SPEAKER_00:

Well, I have a friend in mind. He was the one that said to me at least a year before I was really thinking about it, he said, Why am I still working? I have more money than my parents ever had. My house is paid off. My kids have launched. Their loans are paid off. Like, I'm in a I I don't need to work. Why am I working? And then the pandemic hit, and maybe like a year later, when I was really starting to think about it, I went back to him and he said, Um, I have too many clients and I don't know what I would do with myself. And I reminded him that he likes to make those YouTube videos where he plays the guitar and the sacks and the ukulele and the mandolin and blends it all together and does a great, you know, cover song. And I just reminded him like you have things you love to do. Like you could focus on your real passion in your life and fill your day with things like that. Um, I haven't yet convinced him all the way, but he has reduced his uh client load. And um I think it's you know it's in his future. But that's the kind of argument I make is like to just step back and think about um, you know, what do you really care about? What do you really take pleasure from? Uh, you know, where's your where's your joy? And and to realize that you could uh you could really fill your days with that. I think there's another point I often make, which is I mean, every people have different careers. My career was in corporate America, and my days, like many people, were filled with, you know, conference calls, Zoom meetings, uh in-person meetings now and then, and just like the emails to respond to, like the constant churn and the feeling of being busy. And one of the things I think people think is that they need that, that they feed on that. But once you step away from that, um, like try to think about like a time you've really been on vacation where you didn't have your phone with you and you weren't checking email. And when you really tuned out, I think you got into a different like pace of living. Um so I feel like that was big for me to just realize that uh as soon as I dial down my days, you know, I still get up, you know, at a reasonable time and uh, you know, spend time right sitting where I am right now and having my coffee in the morning and having some breakfast, and then, you know, going to find a pickleball game or a friend to walk with. Um, but I just don't feel like the urgency, like I need to be doing, doing, and accomplishing in the same way that I really did during my work life. And I think that's, you know, going back to, you know, really what I think about what it's all been like is just not having that kind of feeling of having to accomplish things.

SPEAKER_01:

You convinced me. Let's play pickleball tomorrow. No, that was really wise, David. So there's a fun little thing, and apologies for the visual in advance to all the listeners, but I have people that will say the same thing. They'll say, I'm scared to retire, I don't know what I'm gonna do. I have so many clients, and they want to scratch that productivity bias that you just alluded to. And I'll say, okay, here's what you're gonna do to practice. You're gonna go to the bathroom, and you're not allowed to bring your phone. And you're just gonna, you're gonna be there. And how often do you go to the bathroom? And they'll be like, pretty often. And as people get older, they tend to go a little bit more often. I go, well, you're gonna have tons of time to practice. Okay. So all that being said, it's one of those things that, and I talked about my partner James, who has just one of the most brilliant phrases to talk about this. He goes, When's the last time you did something for the first time? And it's probably been a long time. Like I just got married for the first time, and hopefully final time. But there are a lot of people out there that go, you know, I don't know. The last time I did something for the first time was 20 years ago when I graduated school, or when I asked someone out on a date or whatever it may be. And retiring is a big transition. So now, if it's okay with you, David, can we go to the from? What were you retiring from? Since I feel like we have a good sense of what you retired to.

SPEAKER_00:

From meaning, what was I leaving when I left my job?

SPEAKER_01:

Mm-hmm.

SPEAKER_00:

Well, I mean, I think I talked somewhat about that, that um for me, it would have been a very different experience if I had was still working for the group that I really enjoyed working with. Um and like I said, maybe I wouldn't have retired at all, but even if I had stayed there for a longer time and eventually decided, hey, I'm ready to stop working and you know, explore another part of my life. Um, I think that would have been um, you know, very different experience. They were that was a very supportive team. Um, and I just think, you know, it, you know, uh, I might have gotten a party thrown for me, I might have gotten a nice card. I actually did get a card, come to think about it, when I finally left. Um but uh but yeah, I don't, I feel like uh it wasn't so hard for me to leave because in a way, you know, I talk a lot about fulfillment. And this is a little bit of the flip side of what I was just talking about in retirement. And maybe I'm talking about retirement still and not working. But there was an aspect of my job that was very fulfilling. I was good at it. I'd done it for a very long time. Um, that was why I really enjoyed that one phase of work there. But um in retirement, I do feel like I say to people, I'm never bored. I'm great at keeping myself busy and filling my day, but there's times when I feel a little bit unfulfilled. And maybe uh, you know, a fixer upper house or a boat that needs work or just some projects help helping somebody out. There's you know a lot of ways to go, big and small. You know, some people have bucket lists. I think people that have a real clear bucket list, which so often is travel, um, they hit the ground running. You know, they know what they want to do next. And I don't think like the lack of a bucket list should stop you, but I think you know, spending the time to think about, and I talked about what's your joy, what's your passion, like what is going to make you feel fulfilled, uh that's a that's an important thing to think about. And I still don't think you need to wait to figure that out and then retire. I think it's okay to retire and you know, have that be part of your retirement journey.

SPEAKER_01:

I like that. And one thing that just makes me feel so good about this chat, and I would tell you, David, if if I didn't feel good, but I feel very good because I love hearing when people go, look, I like my job. Yeah, I got moved to a different role that I didn't love as much, but I liked what I did and I was fulfilled for many years because I talked to a lot of people that didn't love what they did for 35 years, and now they're like, I found my career that I want to do, but I'm 65, and I don't feel I can even enter because of the barriers. So, first of all, just it makes me happy. But what I want to do is a few rapid fire questions, if that's okay with you. So, how old were you when you retired? 60. 60, okay. When did you know financially you're like, look, I I'm only here because I want to be here?

SPEAKER_00:

Well, maybe a year before. Um, I mean, I have been uh, you know, a saver my entire career. Um, from my very first job, I was putting into the company um retirement plan and you know, rolled that over many times. So I knew I had like done the work to um to prepare for you know eventual life of leisure. Um but that was not something I was actively thinking about, like moving to retirement. I think it really only surfaced, honestly, when that friend mentioned it to me, which was uh, you know, really just like a year or so earlier. So I think it was only in my late 50s that I really started to think about um, you know, leaving the workforce. So running. I should mention also when I when I left that job, I didn't really say to everybody that I was retiring. I didn't make a big show about this is retirement. I didn't update my LinkedIn. Um and in fact, uh I didn't really look too much, but I had in mind, and eventually I did get a job offer, and um it was appealing because it was going to be working at a university, and I had a feel like a good feeling about kind of giving back and going back to um, you know, working with young people. But there were many aspects of that job that were just have not been suitable for a person at my point in my life. Um, for example, 50 weeks a year working on site did not sound appealing anymore. And at that point, I I just realized I really should just acknowledge that I'm retired. Um so yeah. Good insight there.

SPEAKER_01:

Are we still in your rapid fire questions? Yeah, no, are you kidding? This is great. I love just going off the cuff. Okay. If someone were to come to you and say, David, I'm at a university, but you can work on your own schedule, it's virtual, and you're doing one class this quarter, then you're off next quarter. Whether you do good or bad, you still get to do it. Would you be like, oh, that's of interest? Or would you say at this point, I've got my schedule, I don't want to entertain that?

SPEAKER_00:

No, I think um, I mean, every once in a while I talk to somebody who um, you know, a friend or a friend of a friend or somebody I meet socially or on the pickleball court, and they'll say, Oh, you know, wouldn't your skill set be great for a late-stage startup? And the answer is yeah, it would be. And it would be interesting to me to do that. Um I would find that like that would appeal to my passions, and it would be something that I would definitely consider. But I'm not seeking it out now, and I don't think those kinds of things like just fall in your lap. And one thing I've learned is like, you know, many companies when they think of looking for a real seasoned professional are thinking somebody like maybe 42, 45, and I'm 64, gonna turn 65 uh soon enough. And uh I just I don't think there's like that many great opportunities.

SPEAKER_01:

Yeah, it's interesting because I've had clients share similar feelings and I'll say, let's look at Angel List together. And we'll be on Angel List and they'll go, that looks interesting. And what I find, I'm not saying this would be you, but I had someone who I could tell they weren't fulfilled, they didn't have pickleball, like there was a sense of what am I gonna do for fulfillment. They weren't, I like your word fulfillment because they weren't really bored. They're like, hey, I could fill my day, that wasn't the issue. It's I just don't feel fulfillment. And by them going through the application process, it reminded them, wow, I really don't want to do this. And they kind of thought they did. They're like, I feel like I miss it, but I don't.

SPEAKER_00:

Yeah, that was a little bit of my experience. You know, let's talk a little bit more about pickleball for a moment. Yeah, please. Um you know, you talked about learning something new, and for me, I played racket sports like my whole life, but um getting into pickleball, besides it being a social activity, uh, and you know, fun exercise, being outdoors, for me, it was a new skill that I could kind of get my head around and really think about. So I'm not a player that just goes out and like hits the ball and you know has fun. I'm thinking about what are the tactics, what are the strategies, how to improve, what's weak in my game. And part of that is, you know, I can now have the time. And uh, but it really is part of what appeals to me. It's part of what like why I got into fishing when I got into fishing 20 years ago was just the range of skills to learn and the challenge of uh learning it all and getting good at it. And so that's some that's an ongoing thing for me. It could be cooking. I I'm a sourdough bread baker. Um you know, there's just there's always new things to learn.

SPEAKER_01:

I'm gonna give you some kudos because if you remember the question earlier, David, when's the last time you did something for the first time? You entered a pickleball tournament. Let's hear about how you decided when you started playing pickleball to go, I'm going into a tournament. How did you decide?

SPEAKER_00:

Oh, well, my friend made me do it. It was a fundraiser. And yeah, I was happy to do that.

SPEAKER_01:

You sound like me on the soccer field because I I always tell my wife, I go, it still feels odd to say wife. We're a month in, and sometimes I'll still forget and say fiance. Congratulations, Ari. Thank you very much. So um I'll say, hey, uh, she'll she'll say, Why do you love soccer so much? I go, I'm just playing chess with my brain. That's all I'm doing. It's just, it's so stimulating to me. It's my flow state. I can't think of anything else. And I'll have friends that go, hey, you want to go kick the ball around? I go, to be honest, you're not gonna like me. They go, sure I will, you know? I go, no, no, no, trust me. To me, fun is when it's serious. And you're not gonna like me. So I'm not if you want to go just casually talk and have a ball nearby, that's different. But if you're expecting me to kind of be in this middle ground, you're just not gonna get the RE you're thinking you're gonna get. And they'll be like, that's kind of weird. And I'll say, I'm weird. You know I'm weird by now. And so I like that you're like, hey, if you want to go kind of casually hit, you know, maybe we could, but like I am here to play, I want to learn, and so that's really cool. So what I want to shift to a little bit is something that might not be bothering you, might not be bothering anyone listening, but when it does come up, there are some really helpful tips to navigate it. So we're gonna talk about your spouse. Are you married? I'm divorced. Divorced, okay. So I'll have a lot of people who will say, I am worried when they're married to spend a lot of time with my spouse because it's been 30 years and we're haven't really spent a lot of time together. And I'll have divorcees or widows who share, you know, I'm gonna be alone, but I know myself, I know I like being alone to this degree, but I just don't know how to join a new community. I've kind of got my virtual water cooler, you know, chat and when I'm in the workforce, but when that's no longer there, my best friends that I thought were best friends aren't really hitting me up as much as usual because I'm not there all the time. So, how are you outside of pickleball, outside of your friends, how are you finding community?

SPEAKER_00:

Tell us a little bit about that. I mean, I feel like this is a little bit more about my divorce journey than my retirement journey. But um, when I when um my marriage ended, I got into hiking. And I had done a little hiking before that and a little walking, but um I live in an area where there's a lot of good hiking nearby, and I joined a meetup group, actually, probably half a dozen different meetup groups, okay, and started really regularly hiking, tough hikes, um, you know, starting out a few miles, working up to eight, 10, 12 mile hikes, lots of elevation gain, fast, but with a group of people. And um, that was a great step in the in that transition for me. And I feel like um when I retired, I got right back into that. Like I would do that on weekends before, but you know, suddenly I found it was available to me to do, you know, a few times during the week. And it's exactly what I did. And it was, you know, again, I've talked a lot about the pandemic, but it was really I retired kind of as we were coming out of the pandemic in 2021. And um it was great to be outdoors and great to be seeing people and being in, you know, with groups of people.

SPEAKER_01:

Um is it true the trails are way more enjoyable during the week when there's less people?

SPEAKER_00:

Oh, yeah. Yeah.

unknown:

Definitely.

SPEAKER_01:

Because I hear that a lot from people. I have people who go, I wish I retired earlier for that reason solely. And in my head, because I'm not a big hiker, I go, that mountain looks pretty giant to me. So I feel like there's enough space for everyone, but they're like, you don't get it.

SPEAKER_00:

Yeah. No, and there's lots of things like that. Like I do feel a little bit um, I don't know, like a caricature when I say, hey, I can meet at five for dinner or drink. But um the fact is I could. Like I'm, you know, my days are free, and you know, five o'clock is a good time at, you know. But uh, but yeah, certainly meeting, uh being able to park at the trailhead and being out on trails that are less crowded is a is a nice advantage.

SPEAKER_01:

If you're open to sharing, David, I would like to get a little bit into the finances to the degree you're comfortable, of course. So I start by asking the following question. Certain people will say, look, Ari, I spend a lot of money.$3,000 a month, that's a lot. Other people go, you'll never meet someone who spends more than me. It's$8,000 a month. So what I'm finding is everyone's definition of a lot is different. Do you mind sharing? Every month is, of course, a little different, but is there a general range where every month you find, hey, I'm generally spending this amount of money?

SPEAKER_00:

I think I'd rather not share a number, but I would be happy to share that my number to me, and I think in my community of friends, which are I have a big circle of friends that I have known since kindergarten, and an even larger circle of college friends. And I think like my spending is pretty low. And one of the reasons for that is um I just feel like I've lived a modest life and uh I get pleasure from, well, let's just think about the things I talked about. Uh, you know, time outdoors, time in or on salt water, breaking a sweat. Uh, these are not expensive things. I don't do a lot of luxury travel. Um, I don't, you know, get a new car every couple of years. So I think my spending is really modest. And I think one of uh I'm one of those people that you talk about on your on your shows that you know you're trying to convince them to spend more. And I think um, you know, I feel like uh I don't deny myself. Like one of the things growing up, we would go out to dinner now and then, not too often. Um I eat a lot of meals out now. And uh I've just like it took me a while to just accept that that's the luxury such it is that I'll allow myself. But um it's really, you know, it's not it's not the same as a payment on a on a luxury car going out to dinner. So um, yeah, so I I think I I live comfortably within my means. Um, I think I have you know the possibilities open to me um for you know being living a little bit more luxurious and doing a little bit more um, you know, travel and splurging a little bit more.

SPEAKER_01:

Beautiful. And please continue this candor because David, I love this. And my dad used to always say, he goes, look, you're at no if you don't ask. So I'm always gonna ask. So I appreciate it. I love, and I feel the same way, like my sweat when I'm playing soccer, my stimulation, my happiness level, there's no money that can possibly replace that. So I love that things you love doing fortunately don't cost a lot of money. At the same time, I don't want you to be mad at me if you are 85 in what, 50, 55 years now when you have six, seven, eight, ten million bucks and you have regret. The good news is you're like, look, I'm not feeling like I can't do what I want to do. But is there a dollar amount that you think about where you're like, look, if I were to pass with this amount of money, I would look back and go, you know, why didn't I do XYZ? Or do you go, look, I live in the moment, I see my portfolio is still growing, and whatever's left over is left over.

SPEAKER_00:

Like, how do you look at legacy planning? I mean, uh just recently, you know, as I mentioned, I'm gonna turn 65 in a few months. And uh so I'm kind of doing a little bit of new planning around what that's gonna look like. Um and uh really for the first time I've thought about you know what I might want to bequeath to my two daughters. Uh before, and I I have a feeling they would agree with me, like just spend it, just go, you know, do your thing. Um but I do think it's possible for me to leave them something. And I think that's for the first time is something that I'm incorporating into my plan. Um, but I would say like the broader issue for me is you know, just what we were talking about is like um, you know, thinking about what I like to do and trying to make it possible um to do that on a routine basis. So I'll give you another example, and you did you threw in the word regret, although I'm not sure you're asking me what are my regrets, but I'll share one. Um I live pretty close to uh Long Island Sound, and there's you know a great coastline there, and I would love to own a boat or even a kayak. But when I first moved here, I didn't really know how long I was going to. Be here. And I kept on delaying that. And I was still working. But now I've been uh out of the workforce for four years, and I still haven't lived that dream of a couple of kayaks, a boat to get out onto the water in the way I said is something that I really enjoy. Um so I guess I feel like uh sometimes we might need to remind ourselves that uh you know what is it that I really care about, what gives me joy? Um, and to try to make it this is really the theme, I think, is to make it easy to do the things you like to do. And so for me, I have a great walking trail at the beach. That's readily accessible to me, and I could do that anytime. The pickleball community is very accessible to me. The hiking is very accessible. Any day of the week, I don't have to make an advanced plan. I can get up and do things I love to do. And I think it's about broadening that a little bit more to the things I just mentioned. Maybe a boat or a kayak, other things that I like to do. Um, so that's kind of the reminder is just to look at you know what you love and and you know make it part of your day.

SPEAKER_01:

I appreciate you bringing it up, and David, I already know the answer to the next question. I think all the listeners know the answer, and I think you know, but I'm gonna ask it anyways because I love hearing it. David, if you think, if you went to your daughters and you say, hey daughters, because I know that's exactly how you would say it, hey daughters, would you rather I leave you both a million dollars, or do you think I should buy a boat today? What do you think they'd say?

SPEAKER_00:

They would say buy a boat. Yeah.

SPEAKER_01:

And sometimes that is not the response, depending on the clients and the family relationship, which is I'm laughing because there are times where I'm like, I think daughters might say something different, which you know, everyone raises their children and however they choose to raise them, but it it shows you did a good job because they want you to enjoy it fully. And I I told my dad, I go, I my dad and my mom, look, I hope there's nothing, and if you want to spend more on yourselves, please do it. Now, what I want is more time with you. So if you're gonna spend on, you know, my dad, for example, he loves Porsches. I would say, Dad, if you love your Porsche, you work for it, you choose. Selfishly, I'd rather you decide to take me on a trip, because then I get more time with you. But that's me being selfish. So maybe you buy this level Porsche and then we take this level trip. But it's a conversation, and my family wasn't it was never this way. It wasn't at the beginning. We talk openly about finances and that it's it's taken time to get there. So if you don't mind taking me back, David, to when you entered the workforce, you said, hey, you've been in the you're in the financial services industry, you started contributing to your 40K, I imagine at the time. Who was the one that told you to do that? Did you just think that's a good idea? What was the relationship like with your parents and how they managed money? I'd love to get into that a little bit.

SPEAKER_00:

Sure. Um so I'm I'm actually not a finance person. My background's in technology and software implementation. It's really what I did for my career. And uh, but I was in a graduate program that was not related to that, in a doctoral program that I didn't like, and um left to work at the uh at the university and worked there for a few years in the same lab, but doing more computer-related things um in support of the research. Um, so that was really like a big decision for me to go from being in an academic environment from my career to really entering the regular workforce, even though I was at a at a university. Um so, but I do remember that the university had a a retirement plan. And like I can't really remember if it was called an IRA at the time, but there was definitely like a plan that I could contribute to, that they would contribute to. And when I left there, like I got a rollover and just you know put it into an IRA, and that was my first IRA at a bank. I knew very little at the time, but um that was definitely the start. And um, you know, by the time I got married, you know, 10 years after graduating from college, I had a little bit of an S Egg and I had a down payment on a house. So I had really been um yeah, focused on saving, and I definitely got that from my parents too.

SPEAKER_01:

Good. Well, David, I know we're already 40 minutes in. I have a blast doing this. I'm not gonna make you late to pickleball, and we talked about that before, but I have a few more questions if that's okay. Sure. Uh the first, some of these are silly, and then I have a few more real questions I just thought of. But do you have a superhero account today, or do you know what I mean when I reference that?

SPEAKER_00:

Um I feel like that's do you use that to mean like a regular brokerage account? Exactly right. Yes.

SPEAKER_01:

Do you have a brokerage account? I do. When did you start that? And the reason I'm asking and adding color there is there's a lot of people who go, I don't even know about this superhero brokerage. And I joke superhero because it's my favorite account. And I had someone who called Vanguard and said, Can I open a superhero hero account? And they laughed, going, What on earth are you talking about? So that's why I definitely preface it by saying, if you're it's a brokerage account, it's not a real account. So I bring it up because many people just think 401k, add there forever, but if they want to retire early, I mean really early, you might be paying big taxes or penalties based off when you pull it from. So when did you first learn about this brokerage account? Um, because it's just so often overlooked.

SPEAKER_00:

Sure. Um well, when I first started making more money than I was spending, uh, I started to pay attention to that. And I found out about something called mutual funds. And at the time, um I remember, like I learned about it, and I was kind of so excited about the basic concepts about you know buying a share in something that was diversifying and you know, all of the benefits of mutual funds. But it was a brand new area. And I remember like writing down like uh on a sheet of paper, typing it on a typewriter, and sharing it with people that was like, oh, this is something interesting for you to know about. And I remember writing down, there are hundreds of mutual funds, just to give you an idea of the timeline. Um so, but I did start to learn about like the basics of investing. And I would say at that time, like, I I don't think my um thinking about the the nuts and bolts of investing, you know, buy and hold, invest for the long term, uh asset allocation, you know, all those kinds of um the the building blocks, uh that's really been my approach all along. So as soon as I had more than I could spend, I was definitely looking into um well, I don't I couldn't say a brokerage account. That definitely came later, but um I had mutual fund accounts and I was you know adding to them um really from when I was in my mid to late 20s.

SPEAKER_01:

Awesome. Another silly question. Have you eaten any cauliflower in retirement?

SPEAKER_00:

I have.

SPEAKER_01:

Okay. Now that is obviously a vegetable, but it's also an analogy I talk about in reference to Roth conversions. So I'll ask have you implemented any Roth conversions in retirement?

SPEAKER_00:

Right. So that's a great question. So um, I mean, without getting into too much detail, um, this year is a particular year for me to probably realize some capital gains. And then I'm thinking next year, I'll be 65, um doing a few uh Roth conversions, maybe for up to five years until I start taking Social Security. And all of that approach, which is not so revolutionary, but it is kind of it's it's one of those investing building blocks. I really only educated myself about that over the past year. That's really how I came to know about uh you and your firm. Um, was I felt it was time for me to learn about, you know, what was retirement going to look like in terms of not just, you know, pulling some money from here or there, but really having a plan and having a tax plan. And so it was really just this year that I learned, I mean, I knew what a Roth conversion was, but I didn't understand how to use it so tactically as part of my um, you know, retirement tax planning. Now that said, um I do think, you know, it's not like an automatic that it's the right thing to do, you know, and I know I don't need to tell you, and your listeners are probably very familiar with Irma surcharges and taxation of Social Security and Um, its impact on capital gains taxes, and um and even, you know, what's your tax rate gonna be in the future anyway? Um so I'm thinking about all of those things, and I'm not really sure exactly what I'm gonna do, but it's uh it's forefront of my mind.

SPEAKER_01:

I know what you're gonna do, David. You're gonna play pickleball. Okay, I'm gonna back up a little bit here so I don't hit anyone. You're gonna be like provisional income, okay? Then you're gonna be like, Irma surcharges, okay? So you're just gonna be educating the whole court playing pickleball. There's a risk of that. Um okay, let me end this with my question that I always like to end with now, which is I'm gonna shut up. I've done a lot of talking, more than most would probably want. One to two minutes where you just get to talk to someone. It can be a younger you where you're literally just telling younger you, hey, you did better than you thought. Like, remember when you wanted to buy that boat and you were thinking, could you be in this position? Like you're doing it. You can also talk to just anyone generally who wants to retire early at some point. Because whether you know it or not, and I hope you do know it, there are lots of people watching this going, I want to be David one day. The fact that he retired at 60, that's so awesome, and he just went for it. And oh my gosh, I'm divorced as well, and kudos to him. And there's a lot of people that you are helping. And it always feels weird because it's just us talking right now. But the fact that there are other people that are resonating, which if you are, please do guys go in the comments and give David some kind feedback based off him being willing to share today. So I will be silent for the next few minutes and let you talk to whoever you think would love to hear what you have to say.

SPEAKER_00:

Sure. Well, just as I'm convincing people about retiring, I often um say, look, if you love your job, like you don't need to retire. You if if it gives you fulfillment and you enjoy it so much, then just keep doing it. Or if you want to do something else, you can maybe scale it down a little bit. And um, when I say that to you know peers, um, it's brought to mind the one time that I said to my daughters, I think I just read something that got this into my head. And I said to them, as you think about what you're gonna do with your life to make a living, you should be thinking about how are you gonna support and sustain yourself through your whole life. Like that should be a key consideration. And two days later, I went back to them and I apologized for saying that. And I said, instead, what you should do is really think about what gives you joy, what's your passion, what what do you love to do? Um, and then figure out how to make a living with that or how to take care of yourself with that and sustain that. And that's what I would say to my younger self. Um, I had a really good career, and I wouldn't say I regret my choices I made in my career. Um, I worked with tons of great people, I worked with tons of great technologies, I was at really good companies at just the right time. It's like the internet was taking off. Um and it was fun, but I don't know that it was really my underlying passion. And um, maybe I would say to my younger self, um, just to consider more options and um really ask myself those tough questions about uh what really gives me joy.

SPEAKER_01:

Well, David, I'm so grateful. I feel like I have the best seat in the house because I get to get all the wisdom from all of you retirees who have done it, and it helps shape my life and all the viewers. So, David, truly, truly so grateful. Anything else? Because I only ask because a few people have been like, ah, why didn't you ask me that one question? Or I wanted to share this other thing that I have my list here, but it sounds like you're kind of ending the show, so I'm gonna let you do your thing. Was there anything else that you wanted to share, or do you feel that covers it?

SPEAKER_00:

No, I felt that covered it. Didn't we end on such a high note?

SPEAKER_01:

I know, and here I am going anything else, and you're like, we're good. So I thought, honestly, David, that was so fun. I really appreciate you coming on the show. Once again, guys, if you want to be a guest on the show because you want to share your story, you can go in the description and you can apply to be on the show. Thanks, David. Thank you, Ari. 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.