Business Owner Near Retirement Reveals Difficulty Of Knowing How Much Is Enough | Road to Retirement

For so many people in their 50s and early 60s, the road to retirement doesn’t start with a perfect plan, it starts with fatigue. That’s where Shawn is today. After decades of running two small businesses, volunteering as a firefighter, and never really turning “off,” he’s finally asking the question every pre-retiree faces: When is enough… enough?

This episode dives into the real challenges people face when they’re 1–3 years from retirement: selling a business, navigating healthcare before Medicare, planning around a spouse’s job and benefits, understanding true retirement spending, and figuring out what life looks like when the work phone finally stops ringing. Shawn shares his dream of RV travel, more fishing, more freedom — and the mental battle between “one more year” and finally pulling the trigger.

You’ll hear how he’s approaching Social Security timing, retirement budgeting, burnout, identity, financial independence, and designing a lifestyle that actually fits who he is now. If you’re preparing for retirement and wondering whether you’re emotionally, financially, or physically ready to take the next step, this conversation is full of real-life insight — not theory.

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Shawn is not a client of Root Financial Partners, LLC and received no compensation for participating in this video. His statements reflect his 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 offered only under a written agreement with Root Financial.

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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.

Transcript

Work Optional Mindset\n

SPEAKER_02 0:00

Welcome back to the Early Retirement Podcast. I want all of you to know the earliest time you can retire. Doesn't mean you actually need to retire. In fact, most people think when I say, hey, you're in a position to retire, that people just do. That doesn't happen that often. Most of the time, people go, wow, that's great to know. I'm going to keep working another year for my team so I don't just leave them high and dry. Or I've got this project. Or I don't know what I'm going to do yet in retirement. But it's really nice going to work knowing I don't actually have to be here. If I have a bad day, if politics change, I have the ability to do what I want to do, which is spend my time on whatever it is I want to do. And that's once again where I want all of you to live. I don't want you in that I don't know phase. Many of you have heard this before, but I'm a soccer player, and my wife says I'm worse than hangry when I'm injured. If you don't know hangry, that's hungry and angry. A very dangerous combination. And she used to think right when I get my MRI, I'm going to be even worse than that. Why? Because I'm going to see the severity of my injury. But the truth is I relax. And I relax even if the injury is bad, because now I know the truth. I have a plan. Got it. I might have to do six months of physical therapy or a year to get back on the field. But I know what I need to do in order to once again play soccer, which is the goal in this case. I want all of you to know, wow, what if markets went down right when I retired? Or what if tax brackets change? Or what if my health changes? Or what if I live longer? Or what if, what if, what if, wow, I still see that I would be in a position if I were to make the following changes. Great, I still want to retire. So if you're wondering, okay, what do I need to know before I retire? Once again, guys, you can email me the word retire in the subject line, and I will respond back with a free guide. It's a checklist to make sure you don't forget anything. If you want to build your own plan, just make sure to put in the subject line the word optimize, and then I'll send you the software that I use to build financial plans. And then finally, we love to help people retire early. So you can go to our website, rootfinancial.com, and that's when people are like, wow, I get I need to be financially educated on all retirement topics, but I don't want to actually be the one in charge of implementing it because I want to be enjoying my retirement. And it's our job to make sure we're helping you get the most true value out of what you've worked so hard for. So many people just keep working until 60, 65, thinking, you know what, that's what I gotta do. That's what my parents did, but that that's not the reality. The reality is there's so many of you who listen to this podcast who go, wow, maybe I could retire earlier, but don't take action on it. And we want to show you, hey, here's when it could be possible. And we're not just gonna sugarcoat it, we're not gonna blow smoke, we're gonna show, hey, here's the reality based on your situation, how much you could spend, here's what's reasonable. So it might surprise you, but it also might be a little bit of tough love. And we believe in being transparent. So hopefully the podcast resonates. I do all of this for you guys for free, and I love getting to do it. So thank you in advance for letting me record these episodes, or else it just feels like I'm talking to outer space. So appreciate you guys emailing me for these free guides. That's a long intro. Let's get to the episode.

Road To Retirement Series Setup\n

SPEAKER_03 2:50

But here's something I wanted to bring up to you that I don't know if I heard it on your site or a different site. I'm thinking, like this last year, taking off a week a month. I I know I've got uh there's an electrician that lives here near me that uh his license plate reached three-day weekend. So I know that you know he did that for a while before he retired. But I'm thinking take a week off and and unwind, relax, try and get more, you know, a little more healthy. And if the you know the customers don't like it, too bad. I'm at the point now where I'm just fed up with people, fed up with people that that waste my time, that have no um no respect for it. So if you have to wait an extra week because I need to unwind and and and get back in shape or whatever, then so be it.

SPEAKER_02 3:37

This series, Road to Retirement, is designed to hear from people like you. You're going to hear from real people who want to retire early, and they're sharing what's worked well for them so far. How close are they? Some people you're gonna listen to are a month out, other people are 10 years out. So there's a wide range of people, and all of these different people are gonna help you retire early from them kindly sharing their story. Now, if you haven't seen it already, I have another series here called Retirement Reality, where people who have already retired will share here's what worked, here's what's actually been more difficult than I thought, and so much more. Today's episode is a road to retirement. So if you're on your way to retirement, this episode might resonate even more. Enjoy. My guest on the Road to Retirement show is a business owner who says he's tired, he is ready to go. He has a son and an office manager that runs the business. He experienced having employees, went, yep, that's not for me. It's not worth the hassle. I don't want to have to rely on people who I feel might not do the job to the degree that I want to see it being done. And I want to retire at 60. Now, him and his wife have very different goals for retirement, which he shares in great depth, but ultimately his advice I think is very powerful, which is run those numbers, make sure those are in line and prioritize yourself, which is hard to do. He goes on to talk, and you'll see and maybe laugh when I guessed how much I thought his uh camper, you're gonna see what I mean by that in just a moment, is going to cost because I could not have been more far off. So when I ask the question if I can guess how much his RV is, I invite you to think about what that number is because I bet it's going to surprise you. Now, this show is very different from my other show, Retirement Reality. That's where I'm speaking to people who are already retired and they're sharing, and you can see there's a glow behind them. There's a their shoulders are down, they're just so relieved and excited to be in retirement. But some of them are very honest and they go, look, I wish I did retire a few years later because I really financially would have benefited from it. Other people have shared, I don't know why it took me so long. I would have retired at 50 if I knew what I knew now. So every experience is different. This new show is designed to highlight people like you who maybe haven't retired yet, but you're you're close. Maybe you're five years out from retirement, maybe you're longer, maybe it's 15, 20 years out, but you're wanting to hear from other people. And what's cool about this episode is our guest today shared, you know, he's not a W-2 earner in the traditional sense. He didn't actually start saving aggressively until his 40s, and he's gonna retire, hopefully, before 60. So this is a fun episode. If you do want to be on this show because you want to share with others who you think might benefit from it, please do apply in the the show notes. You'll be able to see in the description, excuse me, here on YouTube. You'll be able to see a link where you can apply to do just that. Regardless, I'll reach out and thank you for applying to come on the show because I don't take it lightly that you're willing to share and help other people. You don't get any financial benefit from it. I don't send you a paycheck. I don't get a paycheck from you. All I want is to help people understand what they need to do to retire early. And I think these conversations help explore that. So with that being said, I hope you enjoy today's guest, Sean.

Sean’s RV Plans And Timeline\n

SPEAKER_02 6:41

Sean, thank you for joining an episode of Road to Retirement. This is fun for me because I get to talk to people who are on their way to retirement. And you are transparent and you're formed with me, going, hey, I'm looking forward to peace of mind. I've got a few different businesses and things going on. So I ask all my guests the same question first, which is what are you most excited to spend your time doing once you retire?

SPEAKER_03 7:02

Relaxing.

SPEAKER_02 7:03

Relaxing. So what kind of relaxing? We're talking travel, we're talking just phone off, off the grid.

SPEAKER_03 7:09

Going tomorrow to pick up another RV, trading in the first one, going to pick up a much nicer one uh to uh get into traveling a lot more with the RV.

SPEAKER_02 7:20

Love it. One of the segments I'll do on the show is I'll I'll call it guess the RV. Now the truth is I have no idea and I'm not an expert, but if I were to guess, would you tell me? Sure. Okay, let's say 85,000.

SPEAKER_03 7:35

No, that's a camper. That's not RV.

SPEAKER_02 7:37

Okay, so it shows what I know right there. So do you mind sharing? And the reason I ask is a lot of people want to buy an RV right when they retire, but they're wondering, okay, how much do I really need? How much is the one that you're about to get, the one you're trading in for?

SPEAKER_03 7:52

Uh six figures.

SPEAKER_02 7:53

Okay. And is that like, wow, you're really balling? It's the dream retirement, or even that is like, hey, it's good, but I wish I could have this other one.

SPEAKER_03 8:01

This is low six figures. Uh, the first one I had was even lower six figures. The baller is high six figures, shy of a million.

SPEAKER_02 8:13

Okay.

SPEAKER_03 8:13

If you really want to get into, you know, the retirement one that you drive down south every year and stay there for three, four months. And uh I'm not at that stage and don't know if I'll ever get to be there, but yeah, we'll we'll we'll talk about some of that fun stuff today.

SPEAKER_02 8:28

So I appreciate you sharing that. Now you shared on the forum, hey, I'm thinking maybe I'm a year and a half away from retirement. Why that time frame?

SPEAKER_03 8:36

58 years old, and I kind of just picked the number 60. Been working since I was 14. Uh, you know, first job was the lifeguard, my my local beach that that we were members of and been working ever since. Basically, right now I'm tired.

SPEAKER_02 8:54

Wow. 46 years is a long time. Now, what's stopping you from retiring tomorrow? Is it financial? Is it the business?

SPEAKER_03 9:02

I've got two small businesses, and by small I mean me and my son and an office manager. And they're really niche businesses. And my son's probably gonna take the one over. Um, that's the plan, and the other one I'm gonna need to sell. So it's a matter of getting to the point where I want to sell the other one.

SPEAKER_02 9:22

Now I know selling sometimes is hey, who do I want to sell it to? Then there's the financial side of okay, I could go to this person and the business would run a certain way, but that's maybe not exactly how I envisioned it. Are these businesses more of look, they're babies? I want to make sure they go to the right person. Is it a combination of yes, I want it to go to the right person, but financially I also want to make sure it's very profitable. How do you view that?

SPEAKER_03 9:42

If you got a blank check, I'll sell you the business.

SPEAKER_02 9:45

Okay, understood. So um, yeah, I'll see what we can do at root, depending on the business. Um, jokes aside, uh, I would love to hear about why you decided to enter this field as being a business owner, because I've had multiple people on the show who go, Yep, business owner sounded sexy and fun to me. Didn't realize I would really never not get to work. And then there's other people that go, look, it's what I want to do anyway, so I love it. What's your relationship being a business owner?

SPEAKER_03 10:12

Well, way back uh when I was working for my uh then father-in-law, I read one of the trade magazines in the business that that he's in, and it talked about a much larger operation on the East Coast that only lets their family members come in after they've done something out in the real world. Okay, you don't just graduate college and come into the business and start taking over, you know, lawyer, doctor, whatever it is. Kind of gave me the um entrepreneur bug. Um I left that business figuring it'd be a few years. The business I bought um is an invisible fence dealership. I had been a customer at the time. The the current owner wanted to sell. Again, I'm looking to get out from from there and figured that'd be a nice little transition. I can start doing what I want to do. And, you know, young, silly, and stupid, I'll be out golfing every Wednesday, you know, and I'll just do what I want to do. Well, 32 years later, I'm still doing it, and you don't get to go golfing every Wednesday. Okay. Um years into that, I I try to sell it once or twice. Um, that didn't work. A deal fall through on me. Um but at that point I also bought into another product, a fire retardant product, that really interested me because I've been a volunteer firefighter since I was 14. And this other business floundered, sat there for years until 2011 when uh I was able to help uh code get passed here in Pennsylvania that my

How His Businesses Shaped Retirement\n

SPEAKER_03 11:52

product would be used on new residential homes. So that took off, and um I'm at the point now where I'm just tired.

SPEAKER_02 12:03

Wow. Well, first of all, thank you for being a volunteer firefighter because so I grew up originally in Malibu and there's been some wildfires going around here, and the amount of support that comes from volunteers is incredible. Now, on top of being a business owner, not only are you doing volunteer firefighting, is there anything else you're doing?

SPEAKER_03 12:22

Not right now. Um, I've really cut back the last couple of years. I was really involved with the Builders Association in Pennsylvania on the local and state level. Um used to do a lot more work with my fraternity back in the day. Um, but the last few years I've just cut back on a lot of that stuff just so I can start planning and um looking forward more to retirement. And, you know, I've always taken vacations around business trips, you know, because you go somewhere for a couple of days for seminar, whatever it is, stay for an extra couple of days, make it into a little vacation, and uh just want to go out and just do vacations now. And I've done that for the last year.

SPEAKER_02 13:09

I hear that all the time, and I love that you just mentioned that. Let's talk a little bit about those vacations. As, you know, let's pretend you were retired tomorrow, business sold, son's now running the other business, and you're good. Are you going for a week? Are you going for three months? What do those trips look like?

SPEAKER_03 13:25

Yeah, that's hard to say. Uh with with the new RV and um if I get my wife to retire as well, um, then then we're looking probably at a month at a time to really get out and see the country, uh, maybe longer over the summers. Um right now it's it's four or five, maybe six days uh that I try and squeeze out over a long weekend. And and just go where we can go that where I can drive and and 300 miles a day and and for a couple of days and and go with that.

SPEAKER_02 14:00

Are you truly turned off on those days? Or are you still checking the phone and making sure things are I'm never turned off?

SPEAKER_03 14:07

Laptop goes with me, the phone goes with me, and you know, we'll be driving down the road and the phone will ring from a builder who needs a job done or something, and you know.

SPEAKER_02 14:16

Do you recall, and I'm not bringing this up just to bring tough conversation, I think this is very real and relates to a lot of people. Do you recall the last time you've turned off? Was it 13 years old?

SPEAKER_03 14:27

No, if I've gone if I've gone to trips like in the Caribbean or something like that, then then yeah, that gets turned off because I don't want to be bothered then. I'm trying to think the last couple of vacations we had, I really haven't had many calls, thank God. But um yeah, just it it just never gets turned off because that's just not my personality.

SPEAKER_02 14:48

Yeah, me either, by the way. Um, which has created other issues, but I I hear it.

SPEAKER_03 14:52

Well, as a as a newlywed, you're in trouble, man.

SPEAKER_02 14:54

Yeah, you know, you're aware. Look, guys, I'm three months veteran, okay? So um, yeah, and I love what I do, but look, if there's a day where that changes, I want to have the freedom to do what I want to do, which is the whole purpose of why I do what I do today, is I want everyone to know when is work optional. So if you knew you did not have to keep working, you could still work. Maybe you do another project, maybe you volunteer more, but it's more of what Sean wants to do, and it's hard to be selfish sometimes. I want to know about your wife, though. You mentioned her retirement. Is she in a completely different field of work?

SPEAKER_03 15:24

She's a pharmacist at a hospital.

SPEAKER_02 15:26

Enjoys it?

SPEAKER_03 15:27

She's a pharmacist at a hospital.

SPEAKER_02 15:29

Okay, you said it right there. Now, is she thinking retiring the same time based off benefits? How is she looking at it?

SPEAKER_03 15:36

Yeah, we've got um we've got some stuff coming up in the next year. Uh, we've got a second grandchild coming in March and a wedding um in October. So

Training For Retirement With Time Off\n

SPEAKER_03 15:47

uh she won't be retiring this year.

SPEAKER_02 15:50

Let's talk, if you don't mind, a little bit about this theme that's come up in recent episodes, which is joy and security. And if you were to talk to younger self, or you can even answer for your wife if you think you know what she might say. You know, you mentioned, yep, she's a pharmacist at a hospital. Was that the dream? Was it, hey, from an early age, we were taught from our parents get a job that pays you and you can figure out purpose and what you really want to do later in life. That theme of joy and security, I tell through a story of my dad often. So to give you some time to think about the answer. My dad loves surfing and he grew up and he watched the movie Endless Summer. Have you ever seen that movie by chance?

SPEAKER_03 16:26

I believe so, yeah.

SPEAKER_02 16:27

Okay, so it's like a fun surf movie, lighthearted. And my dad's dad, so my grandpa, was a CPA. And my dad saw Endless Summer and saw my grandpa's life, and he just thought for no good reason they paid the same. You could be a CPA or a surfer. And he thought they both, for some reason, made the same money. So he said, I'm gonna be a surfer. Like, why would I be a CPA when I could do this? And then he realized, wow, that's not real life. But his whole point of life was not, I want to have security and I want to have a family and I want to have kids, and I'm lucky that he had me. But his whole life was built by I want to live a life where I could go surfing if I want to. So he chose to be a business owner because if waves were up, he was leaving to surf. And that's really what shaped his life. Now, my mom was the exact opposite. It was times were tougher. I want to grow up and have money and not have to worry and work till I'm 80. What was the approach that you took?

SPEAKER_03 17:19

Well, that's hard to say. I can remember as a kid, my grandfather, both of my grandfathers were coal miners here in Pennsylvania. I can remember my grandfather who lived with us uh telling me, get a desk job. Don't beat yourself up out in the field. You know, get a desk job, sit, you know, do that kind of thing. I can never see myself doing that. I'm not that kind of person. You know, I I've I've done physical jobs my entire life, you know, and and physical sports and and working out and exercising all that stuff my entire life. I just I enjoy numbers. Um actually when I first bought my first business, um had no business skills at all. You know, I we got a history degree, political science minor, so I had no business classes at all. Went back to school at night, got my MBA, and I I do enjoy running numbers when it comes to PLs and stuff like that. Um I'm the treasurer of my fire department. You know, I enjoy running all these different things like that, but I can't do more than a couple hours. I can't sit at a desk all day. It's just not me. You know, I've got to be out doing something. So that's got me to the point now where, you know, not much works anymore. Every joint hurts, and you know.

SPEAKER_02 18:39

Yeah, we're gonna talk about health, but I appreciate you sharing that. What do you think your wife would say? And I imagine she's thinking, you know, maybe this isn't my dream job, so to speak, but it is secure and it's what I studied, so I'm gonna do it. Do you think she would have changed anything if she could go back 30 years?

SPEAKER_03 18:56

She told me um when when I guess when she first got out of high school or whatever, she wanted to be a hairdresser. And somehow ended up going to school for pharmacy. I don't get the connection or what happened there, but uh, you know, that's what happened. And, you know, 30, how long has she been doing? 35, 36 years, something like that. You know, she's been working at hospitals.

SPEAKER_02 19:20

Do you think that, and I hope not, but I hope you end up making the call you want. When it comes to retirement, there's a lot of people who do the one more year of, yeah, you know, the business just not ready to sell yet. I don't really think it's the right time. Or your wife goes, you know, if I work just two more years, you know, the benefits get way better. And yeah, I know you want to travel, Sean, but the truth is, look at these benefits. Do you think you guys might fall subject to that one more year, or do you feel you've got it pretty dialed in?

SPEAKER_03 19:44

I believe I have it pretty dialed in. Um, like I said, she wants to work the one more year because of the baby and the wedding to pay for. Um but here's something I wanted to bring up to you that I don't know if I heard it on your site or a different site or if it just popped into my head. I'm thinking like this last year, taking off a week a month. You know. I I know I've got uh there's an electrician that lives here near me that uh his his license plate reached three-day weekend. So I know that you know he did that for a while before he retired. But I'm thinking, you know, take a week off and and unwind, relax, try and get more you know, a little more healthy. And if the you know the customers don't like it, too bad. Yeah, you know, I love that. I'm at the point now where I'm just fed up with people, fed up with people that that waste my time, that have no um no respect for it, you know. Um so if you have to wait an extra week because I need to unwind and and and get back in shape or whatever, then so be it.

SPEAKER_02 20:54

100%. And yes, that was me, and I'm very transparent about that. I even go further and say, I think you're training for something you don't know you're training for. And I've had people go, I don't know what you mean. And what I mean is it's more fun to train for a marathon. You know it's coming up. Now I've never run a marathon, I'm never going to run a marathon, I have no desire. But I play soccer and it's I don't go to the gym going, wow, this is gonna be just a blast. And people say, I have friends that go, you're so disciplined. I go, I'm not disciplined. I want to play soccer. It's fun for me. So I do this gym thing so I can play soccer. My clients and viewers, you guys are doing the same thing. It's time to train for retirement. If you're driving all day, 300 miles a day, you've got to be sitting there in comfort or you are not gonna be happy. So I would say, can you take off a week? Yes, but can you also go, you know what? Instead of having a 24 hour rule, which maybe as a business owner you live by because you want to provide good service because you're a good person, maybe that becomes a 72 hour rule. And if people don't like it, well, guess what? They're not gonna be someone you're thinking about when you're in retirement two years from now and you're sitting there feeling good. So, what can you do to start training for retirement? That's

SPEAKER_03 22:00

Well, you know, you you talk about uh people retiring to something, okay, um or being bored. Well, there's your chance to take a week and see if you're gonna be bored.

SPEAKER_02 22:13

Yeah.

SPEAKER_03 22:14

You know? Um, like some of your other guests, you know, I want to do a lot more fishing. I I fished every day when I was a kid because we had a cabin out near a lake. I fished every day, every morning before we went to the beach. And I want to get back and do a lot more fishing. Um taught myself how to weld off YouTube a couple years ago, you know. I want to do a lot more welding and that kind of stuff. Um so do that for a week, you know, instead of worrying about paying the bills or anything else like that, and get used to getting into that retirement mode so that you're not bored, so that you know, you especially not if if you and your wife are in the same house all day. You know, I got a bunch of friends that retired that the wife said, Go out and get a part-time job. You ain't staying here all day.

SPEAKER_02 22:58

Oh, yeah, I've heard that many times. Hey, I love you, not this much. Um, now I have heard a lot of people, a lot of you guys will tell me, and I like that you're bringing this up, Sean. I'm worried about being bored. I don't think it's something you should worry about. Now, I know a lot of you, I can already hear it. You're going, well, I might not have the luxury Sean has of just taking a week off. If it's a day off, if it's taking an extra Monday, if what can you do to practice retirement so that when you get there, you go, wow. Well, first of all, it does a few things. Number one, it makes it way easier to save money because you're like, yep, I'm saving and I'm more motivated to pay off that principal of the mortgage or save to that 401k because I see that's more time fishing. Or you're able to go, you know what? By me doing this, turns out maybe Sean, I don't think this will be the case. Maybe you're like, look, fishing wasn't the same. I don't know why, but for whatever reason, and I know nothing about fishing. What if it just isn't giving you the feeling it used to? You're still gonna want to retire, but now maybe you're gonna prioritize some other things. Now, what I've never seen is two spouses that like the same exact things. And I'll have people come to me and go, what do I do? My retirement vision is very different from my spouse. And I've had people potentially talk about while I'm live with them, going, you know, maybe we're just not a good match. And I go, I don't think it's that. I think you work together for 30 or 40 years for a reason. It's just now you have different goals. Maybe Sean's taking a trip and wife is deciding not to go on that trip and you're doing something else. But that will cause some issues naturally if they're not discussed. Is that something that you discuss with your wife, or how do you guys talk about that?

SPEAKER_03 24:28

Oh, she'd she'd love for me to take the dog and get in the RB and go.

SPEAKER_00 24:31

Yeah.

SPEAKER_03 24:31

Leave her alone, you know?

SPEAKER_00 24:33

Yeah.

SPEAKER_03 24:33

Uh she uh I've told her because she's not into the studying the YouTube videos and stuff like that that I am about retirement or whatever. I told her she has to have something to look forward to, you know, that that she just can't sit around and watch Colombo all day.

SPEAKER_02 24:51

Yeah.

SPEAKER_03 24:51

Um she loves to bake, you know. And I told her, well, then maybe you can do more bacon, you know, and and certainly you can you can do that in the RV as well. Um things like that. So so yeah, you you've gotta you've gotta talk about it, you've got to get used to to going somewhere. Like we're going to pick up going to pick up this new RV tomorrow.

SPEAKER_02 25:11

Yeah.

SPEAKER_03 25:11

Um I'm gonna be spending the weekend at a campground with a dog because she's going wedding dress shopping.

SPEAKER_02 25:16

Yeah. You know, so well, kudos to you guys for having those conversations. And you're a great example of yeah, different goals, still love each other and have a great life. Now, does she watch, and if not, ignore this question. Do you know if she watches something called Great British Bake Off?

SPEAKER_03 25:31

Uh no, more just Colombo and Murder, Murder, Kill, Kill. I figured she's trying to figure out a way to sneak up into me, you know.

SPEAKER_02 25:38

It's crazy how much how many shows out there right now are murder. I'm like, what is this country doing? Um, but regardless, I I'm curious because you brought up the financial side and I always like discussing

Saving Late And Still Retiring Early\n

SPEAKER_02 25:48

it. Naturally, there's one person who takes more of an interest, but let's just assume for whatever reason you were not here, which hopefully you're here a very long time. Is she going, you know what? I'm gonna start to figure this stuff out. Is she going, no, no, no, that's just not my thing. Finances have been Sean's thing. Like, how would she approach retirement?

SPEAKER_03 26:05

You're gonna get me in trouble now. No, the the money aspect really isn't her her angle. Um I'm obviously more into it being a business owner and and and running PLs and things like that, but I don't know how she'd do if I wasn't around.

SPEAKER_02 26:26

Yeah. My wife's the same, by the way.

SPEAKER_03 26:28

Had the scare, you know, had the 80% blogged on the widowmaker.

SPEAKER_02 26:31

Yeah, yeah. Look, my wife, if I said Roth conversion, she will fall asleep. Like that is her trigger word. So I I get it. But those conversations obviously are important to have, and it's one of those things that you can't quantify exactly, but there's a peace of mind knowing if there wasn't now, maybe it's your son, whoever it may be, but I do recommend having those conversations. Now, in terms of the financial side, obviously you're savvy to the point where you like these things. And, you know, running PL statements isn't something that most people go, that's not top of my list. My wife was a history major as well, so that tells me you're very intelligent. You like looking at the YouTube videos and studying these things. I'm curious when, and it's okay if you don't want to share the exact number, but when did you first realize that maybe I should have a superhero account, which is what I call a brokerage account, by the way, because of all the different benefits that come with it? Is that something that, yep, my dad told me about that early age? As soon as I heard about that in a 401k, I got on it. Was it I started in my 30s because that's when finances really were allowing me to save money? What was your process to save for retirement?

SPEAKER_03 27:34

It probably wasn't really till this other business took off. Um both of us had previous marriages that cost a lot. You know, the only people that make out there are the lawyers. So after the other business took off, that it it really became a cash cow because there's no overhead, there's no advertising, it's it's all word of mouth that I've built up. And I was able to put a lot aside. And what age was that uh approximately? Wow. 15 years ago.

SPEAKER_02 28:05

So really not till your you know 40s where you've started to save aggressively.

SPEAKER_03 28:09

Yeah. Yeah. Wow. Wow. I mean, don't get me wrong, I wasn't broke. I mean, I still had the toys, you know, still got the Harleys. I, you know, I had a fishing boat, sold that. I wasn't I I wasn't living high on the hog, and I certainly wasn't living paycheck to paycheck, but uh it wasn't until then that I really started getting a lot more serious about putting money away because I finally had some coming in that I could do that with.

SPEAKER_02 28:31

Right. And for all those out there who are going, well, I can't retire early because you know I didn't start saving until my 30s. Here's a great example of someone who is actually on track to retire by 60, potentially even sooner, who still lived his life and had the toys. And I'm happy to hear that because I'll see a lot of people that will make the mistake of saving so much that they don't buy toys or enjoy their life at all, retire and go, now I don't know what I want to do because they never really realize what they love doing because they're working so much. And then there's the flip side of people who spend so much that they're nowhere on track to retire and they're going, why me? And the why me is, well, you didn't do the hard work to save for future you. Now, one thing I'll see a lot of people do is they'll push back retirement because it turns out that one toy they want is just so luxurious, it's what they want. And I'll be the first person to go, great, I want you to get it. But we got to understand these trade-offs. Were you thinking there's one RV I really want? I'm not retiring until I have enough to get that. And if that means I'm working more, so be it. Or are you more so, hey, look, maybe it's not the dream one, but it's gonna be a good RV where I'm still gonna enjoy.

SPEAKER_03 29:36

Yeah, I'm I'm not gonna be that lady with the extra million dollars.

SPEAKER_01 29:38

Okay.

SPEAKER_03 29:39

And if she wants to give it to me, she can give it to me. You know, I'll take it off her hands for her. But uh, yeah, I'm not working the extra year for a toy. No way. Yeah, you know, I just I I I just believe I've worked long enough and hard enough that uh I want to be able to do those uh the trips and everything else like that. Um the Dream RV, I don't know if I'd ever get it, you know. I mean, I don't know how long I'd have to work or get into some other business to to do that as well. Right. Realistically, you know, what we're getting is way more than most people, you know. Um I understand that. And I understand that, you know, looking at some of these other RVs or or whatever it is, whatever toy it is, it's a toy, you know. Do I really need it? No. Do I want it? Yeah. Have I worked my butt off for it? Yeah, I have, and I'm gonna enjoy it. And I'm not gonna, you know, let anybody take that away from me.

SPEAKER_02 30:35

I like your mindset. And the happiest people in retirement don't have the most, they make the most of what they've got, and you've got a good head on your shoulders.

Healthcare And Real Monthly Spending\n

SPEAKER_02 30:42

Now, one of the things that causes a lot of people to not retire early, and you probably can guess it, is health care. What is your plan to approach healthcare until Medicare?

SPEAKER_03 30:51

Well, my wife's a couple years older than me, so she should be able to get into that um in the next two years, I think. Myself probably still be part of the buyout deal with my son.

SPEAKER_02 31:03

Okay. So interesting situation where we can stay on there, be involved in some capacity. Was that something that worried you, just healthcare as a whole? Was that like a potential stop, or did that not even cross your mind when it came to retirement timing?

SPEAKER_03 31:16

It really didn't cross my mind. You know, it's just gonna be another expense. You know, I like my like my my dad, my mom's 86, my dad's 85, and I can remember 20 years ago or better, whatever, when when he probably should have retired, you know, he's taking part-time jobs to help pay for the health insurance, you know, before he can get onto Medicare. Like, yeah, I don't want to do that. Yeah, you know, yeah, yeah. I I I need to be able to get out now while I can still move around.

SPEAKER_02 31:45

Yeah. Well, kudos to you once again because it's hard to make that call. And I'll see a lot of people who just keep working because I mean, maybe it's not easier in your case because you're tired, you're ready to go, but there's lots of people who find it actually easier to work because this unknown is too scary. Not the case here. Now, I would love to hear a little bit about just general spending on a monthly basis. How much do you find, like keep toys separate, keep a big trip or a wedding or a remodel separate? But how much every month do you anticipate you're gonna be spending in retirement?

SPEAKER_03 32:16

That's gonna depend on how well the other business gets sold.

SPEAKER_02 32:21

How much would you love to spend? Let me say that.

SPEAKER_03 32:24

How much would I love to spend?

SPEAKER_02 32:25

Yeah, love to spend. Not toys, though. This is just every month, you know. Sean, here's $10,000 a month. Do you hear $10 a month and go, oh, I don't know how I'd spend that? Or you go, oh no, I could double that easily.

SPEAKER_03 32:35

I I really, I really surprised myself when I sat down and started doing the the um how so the the budget work um for my my my uh my accountant who's who's uh uh CFP as well, who who's doing my planning and stuff. And when we started doing the actual expenses and everything and and laying out the budgets and whatnot, I was like, wow, I do spend that much a month. I can't believe that, you know. I'm like, where the hell's it going? You know, what do I have to show for it? You know? Grammys, you you you you go to the you go to the grocery store and you look at the bill, I'm like, it's me and my wife, you know, what's a family of four doing right now? How are they affording all this? But I I think 10 is on the high side.

SPEAKER_02 33:17

Wow.

SPEAKER_03 33:18

Realistically.

SPEAKER_02 33:19

Yeah.

SPEAKER_03 33:20

Because I don't, I don't, I don't we go out once a week, twice a week, you know. It's not like we're out every night eating, eating, eating out at dinner. And um I don't buy the high-end clothes or anything else like that, you know. Um I'd rather buy a high-end fishing rod than some high-end clothes or something.

SPEAKER_02 33:39

So I'm the same way. By the way, look, I have 10 pairs of soccer cleats because when the cleats come out that I want, I want to make sure if that model goes away, I've got them and I'm happy to do that and not buy wine. So that's my thing. In terms of well, I gotta buy gin.

SPEAKER_03 33:51

Sorry.

SPEAKER_02 33:52

Say that one more time.

SPEAKER_03 33:53

I gotta buy gin.

SPEAKER_02 33:54

Yeah, well, look, hey, we've all got our things we need. In terms of spending, so let's just say, hey, here's $8,000 a month, $96,000 a year. That's excluding taking, you know, additional trips or what have you. That's just the basics. Now, pretend I were to say you have to spend double that, but it can't go to you know, fishing rods or travel, but it must be spent just on uh sometimes it could be uh what are examples I've shared in the past? It could go to a charity, um, it could go to children, it could go to um just additional groceries. Would you find that would increase quality of life? Or would you find, look, if I had more money to spend, but it really was only going to charities or children, it's hey, that's really not a priority for me. Like my kids have time to save and make their own money, or charitable giving is something that maybe I want to do at the end of my life. Is this something, and it's not a great question now that I'm saying it out loud, but I'm curious. Um, because certain people will tell me, if you gave me more than that, it would just get saved. Like we're spending what we want to spend. Other people say no, if you really doubled that, life would look very different. So, how would life look like if I were to double that number?

SPEAKER_03 35:07

Well, if you're restricting toys, yeah, then what else are you gonna spend it on? I mean, how many pairs of shoes does she need in the closet? You know, I mean, how many pairs of clothes or sets of clothes or whatever can you wear? Um, you know, yeah, I'd I'd set up probably set up some accounts for my kids and the grandkids. Okay. Um I I I try and I I try and make meals that are as healthy as we can right now. You know, could I do that a little better buying some better cuts of meat or something like that? I mean, but when it when it gets to a point, how much more do you have? And what can you do with that if you're not buying, like I said, toys or non-necessities?

SPEAKER_02 35:47

Right.

SPEAKER_03 35:48

You know? I mean uh not gonna buy a better quality toilet paper. What the heck, you know?

SPEAKER_02 35:52

Right. No, no. Tuply is fine. And I I bring it up. Oh, twoply, that's on holidays. Um, the Jewish digestive system needs it, not to give you that visual. Um, but I want to bring it up because it's something that a lot of people will go, uh, 8,000 a month, yeah, that's what I'm planning for. But the truth is, what if I get it wrong? Oh, maybe I need 15 a month or 20 a month. And the truth is you have to do the exercise that you did, which is sitting down and going, wow, maybe it's more than I thought, but it's less than I thought you were gonna say. I thought, Sean, you were gonna say, Yeah, you know, we need 15 a month or something. You so it's all relative. And if I were to give you more money, but say it can't go to toys, you're going, well, what good does that do to my life? Nothing really changes. So the point of me bringing it up is I don't want to see you working longer than necessary. Now your situation's different. You're a business owner. It's gonna come down to is that business gonna sell? Is it a valuation that's attractive to you? There's more that goes into it. But no matter if you're a W-2 earner or you're a business owner, there becomes a point where having more really doesn't change life in a big way. And that trade-off of do I work longer or do I, you know, decide I'm gonna prioritize me is not something that's always easy. But this is one of the things I love about math. So I'm not obsessed with Roth conversions or healthcare subsidies. I'm obsessed with you knowing the earliest time you can walk away. And if you love what you do, great, keep doing it. If you don't, you're just working more and adding more anxiety. So, what I hope you can do, Sean, is get real clarity, and it sounds like you're pretty much there, to understand, you know, you said a year and a half, 60. Why 60? If the right valuation came in next month, do you feel that you could walk away? So, just a question for you. You mentioned 60. I'll see people who will say January, you know, 2020, my dog's name is 2020. I'm just gonna do that's when I'm gonna do it. And I'll say, look, if you want to do it because that's when the stars align, or there's a purpose that you're worried to go to, that's one thing. But if you're just picking something just because it's an arbitrary number, I last thing I want to see, which unfortunately I see more often than you'd imagine, is a healthcare event a curse or something that really doesn't allow you to enjoy what you've worked so hard for, which is why I get emotional in these cases. So once again, is 60 something that you're thinking just works out timing-wise? Pretend an offer came in tomorrow. How would that change things?

SPEAKER_03 38:06

Oh, I'd I'd sign the I'd sign the paperwork and and

Return On Hassle And Employees\n

SPEAKER_03 38:10

walk away.

SPEAKER_02 38:10

Okay.

SPEAKER_03 38:11

Are you kidding me? I mean, yeah, you talk about you know working longer or or whatever. And I've got a lot of clients myself that have got some good businesses, some really big businesses, and make a boatload of money. Okay. I mean, more money than I can imagine, okay. But at what cost? Okay. And and how do they get to that point? The one thing you didn't ask me, or maybe I didn't I didn't say enough, is that I don't have any employees other than my son and my office manager. And that's why I'm at the level that I'm at. Could I grow the business more? Yeah. Could I continue to own the business into semi-retirement and get employees? Yeah, I could do that. But guess what? I hate having employees. Okay. Had them in the past, did nothing but babysit, and um, you know, just was even more stressed than a regular business, just business part of the day.

SPEAKER_02 39:06

You're right. I have not asked you, and there's a phrase that I've brought up. You may have heard it in a video, but I think you're gonna love it if you haven't heard it yet. And it's on my list and you're already ahead of me, which is why I like you. History majors, I have a thing with my wife, and now you. Um, have you heard of my phrase ROH? No. So ROI, return on investment, is very different from ROH. Return on hassle. Is it worth the hassle? And you just brought up a great point, which is look, could you grow it? Of course. And now you're managing hassle. And I'll bring this example in a lot with rental properties because I have clients that love rental properties. And I go, great, I love them too, if they make sense for your plan. But what if you're now traveling and you're worrying about, oh, yep, roof just leaked. So now you got to call the property manager. Oh, they're actually off because they're on vacation. So now all of a sudden you're not really retired. You're now running a different business. So I like that you actually are looking at it and deciding what you want to do, which is I've got myself, office manager, and my son. Great. Now you might find that's where you're at in your stage of life and that works best. I'm curious because I think there's other business owners who are going to watch this and go, I feel just like Sean. And I wish I could ask Sean what I should have done earlier. If we went back 10 years, 15, 20 years, do you wish you never hired employees? Do you think you never would have had the perspective you had today unless you have done that? What would you tell other business owners?

SPEAKER_03 40:28

It it's certainly certainly something you have to go through. You know, there are other people out there that love their employees and love having employees. Okay. My mindset that that I learned a long time ago getting in when I first got into the business from some other colleagues was you know, you got to put as much money in the bank as you can today. Because once today's gone, it's gone. Okay. Bob doesn't show up this morning. Well, that means I gotta go jump in the truck. So whatever I had planned for the day is now out the window. Okay, because I gotta get out there and do his work because that's what's putting the money in the bank today. And I just got so fed up with that. I got so fed up with just sitting there waiting. Uh, are they gonna show up this morning? Are they gonna even bother calling to say they're not showing up, you know? And when you're talking small business like that, you know, whether it's you know, uh a landscaping crew or or whatever, somebody's gotta pick up the slack. And it's not to me, it wasn't worth a headache. To me, you know, being the the physical kind of guy that I am, I just finally got to a point where I said, I'm gonna do the work, I'm gonna keep all the money, and I'm gonna just stack it away and I'm gonna quit when I want to quit. You know? And other people don't want to do that. You know, they they want to have employees because they want to go golfing on Wednesday or whatever, you know?

SPEAKER_02 41:48

Yeah. Well, you built the life that's a fallback. Yeah, yeah. You you built the life that made sense for you, and that's what's important. Now, Sean, I don't think you're alone in saying a lot of what you've shared today, which is yes, I am tired. Yes, I do want to go fish. I cannot wait to have time to just do what I want to do and be off for more than a week because I've been working since I'm 14. And I'm excited and appreciate you coming on because a lot of the other episodes I record are, you can tell, very different. People retired. I'm loving life. So I'm excited, and if you're willing, I'd like to do a follow-up interview with you in a few years to be able to go, okay, what's changed? You might go, look, I'm just, I can't believe I waited this long. I wish I had done this. You might go, you know what? That sense of purpose and fulfillment, it's missing a little bit. We'll be surprised to see what you say. But if all of you out there resonated with what Sean shared today and you feel similar, yep, I'm tired. I just want to call it quits. I'm, I feel like I've done my part now. It's time for me to enjoy me. Let Sean know in the comments if you enjoyed this because we do this all for you. Sean, you just took an hour out of your day to talk to some guy you just saw do some YouTube videos. So I appreciate you doing that once again. I end these shows the same way, which is by shutting the heck up myself and letting you talk to someone. You've already done this a little bit, but someone who's five years out from retirement, and this can be anyone, it can be a friend you're thinking of, it can be um really anyone that you think might resonate with someone who has the experience that you've had over these amount of years, and five years they're away from retirement and they know it. Meaning five years they are retiring, but they're worried. They're worried about health, they're worried about identity, they're worried about what their spouse is gonna think, finances. You can tell them anything that comes to your mind for the next minute. So I'm gonna shut the heck up and give you the floor here.

Sean’s Advice And Closing Notes

SPEAKER_03 43:32

I'd say uh study, educate yourself, get your numbers in line. All right. Once you realize that the numbers are in line and you believe that you can live with those numbers, then you pull the trigger. All right. Don't be your client with the extra million dollars, a lady with a sciatica now. I got sciatica too. But I'm still going hiking and I'm still gonna go fishing. Okay. Um And and I'll get I'll get out and get in the RV and get on the road as soon as I can.

SPEAKER_02 44:05

Love it. Great advice, Sean. Once again, I appreciate you coming on and sharing all of this and hope to do a follow-up with you in a few years and that we can see some photos of that RV and you fishing. Great. Appreciate it. Thanks, Sean.

SPEAKER_03 44:16

Thanks, Ari.

SPEAKER_01 44:18

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.