Ready For Retirement
Ready For Retirement
Retired at 50 Freedom, Guilt… and What No One Tells You | Retirement Reality
Retiring at 50 sounds bold, almost unthinkable for most people, but for Kent, it was the only decision that made sense once life, loss, and perspective pushed everything into focus. In this conversation, he sits down with James Conole, CFP®, to share the honest story behind leaving work two decades earlier than expected.
Kent talks about saving from age 18, building a plan long before he knew what retirement would look like, and the complicated mix of discipline, luck, and family legacy that helped him reach this moment. He also opens up about the emotional side: the guilt of inheriting wealth after losing both his father and grandfather, the fear of telling coworkers and his mom, and the surprising relief when everyone responded with encouragement instead of judgment.
Nine months into retirement, Kent describes the freedom that comes from being fully present with his daughters, traveling on his family’s terms, rediscovering community through pickleball, and learning how to redefine productivity when your time finally becomes your own. And he doesn’t sugarcoat the harder parts — the identity shift, the loss of workplace validation, and the work it takes to build purpose outside of career.
This is what early retirement looks like when you stop planning only with your brain and start planning with your heart: more time, more presence, and a life shaped by intention instead of inertia.
Watch this episode of Retirement Reality — where real retirees share the highs, lows, and turning points that helped them choose a life they don’t want to postpone.
Want to be a guest on James’ show to help others by sharing your story? Complete this form: https://vwo3759x8i7.typeform.com/to/IwyScIeR
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Kent 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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What can I practically start doing to start that identity shift or start that change of mindset?
SPEAKER_00:I really you know thought as going through this process said is what am I retiring with? Right? What are the things that that did fulfill me in the workplace? What are the things that did fulfill me with my coworkers, you know, and and saying, how did those things then how can I fulfill those same needs, but in this different arena? All right.
SPEAKER_01:I think you're really gonna love this conversation I had today with Kent. Kent retired at 50, which sounds amazing, but he also shares some of the challenges, the guilt he felt telling people, specifically his mom, that he was retiring early. He shares the things that are different than what he originally expected retirement to be. And finally, he shares the things he's now able to do, the memories he's able to make with his family that he never would have been able to do if he was still working. Enjoy today's conversation with Kent. Hey, real quick, make sure you hit that subscribe button if you haven't done so already, and please give us a like if you're enjoying this content. Every week we're putting out a couple of videos to make sure that you have all the information you need to retire with confidence. Want to make sure you don't miss a single thing. Kent, thank you for joining me on today's uh retirement reality. How long have you been retired for?
SPEAKER_00:Uh so I retired February 4th of this year. So I've been coming up on eight months, or I guess moving into ninth month of retirement.
SPEAKER_01:Uh nine months then, and if you could describe that retirement so far in one word, what would that word be?
SPEAKER_00:Freedom.
SPEAKER_01:Freedom. Now you retired at 50, correct?
SPEAKER_00:Yes, sir.
SPEAKER_01:I am very curious about that because I think that for a lot of people that feels uh too young. There's maybe social pressure, family pressure, other pressures of why I'm guessing you're maybe in some of your peak earning years at a time. So I would love to explore with you what was it like leading up to that decision, uh, what was it that finally caused you to make that decision? What was it like telling your employer, what's it been like these first nine months? Um, and what maybe concerns do you have about the future of being young, not working things around that? But to start though, retiring at 50 is no easy feat. That takes a good amount of either saving, investing, starting and selling a business. How did you get to the position? Were you just a saver from a young age? Did you get lucky with a certain stock? What was that journey like for you?
SPEAKER_00:Um a little bit of each of those. Um so I growing up, my grandfather was a real big emphasis on you know saving, saving, saving. And so um, you know, retirement saving, and specifically my grandfather even retired in his mid-50s. Uh so it kind of set the example of what I was looking, you know, what I was looking at. Um so early on at 18 years old, I was already putting into a 401k. Made a couple of bad choices along the way in that of you know taking it, taking a loan out and you know, and what what that looked like. Um but you know, since I've been 18, I was you know retired saving in my you know 401k retirement savings. Um and then later, you know, in my 40s, you know, I probably got into a couple of spots where I uh had done a couple of investments, you know, I you know looked at some of the Tesla stuff and you know, kind of thought, you know, man, this really makes a lot of sense. Uh and so I got lucky on on some spots there. Um and then in you know, part of the full story is that um, you know, my grandfather had had done well, and uh, you know, I you know, and uh my father uh who would you know would have inherited you know a lot of what my grandfather left behind, um, he wasn't uh he passed away a year after my grandfather passed away. Uh so there was a uh a bit of there's a trust set up that was meant to solve just for paying for great-grandchildren's you know education, uh, but it ended up that it's been accumulating you know better than what it needs to go ahead and cover that. So that played another piece of it. And so as you're talking about the things that you have concerns around or the things that are hard to think about in retirement, uh, you know, that's been one of the hard ones is actually trying to uh separate or accept that, right? To accept that you know this wasn't just by my doing. Uh so you talk about identity, uh, you know, the identity I I would actually have a spreadsheet, you know, in my spreadsheets, I would have, well, here's what I would have if it was just me alone. And then this is the piece that that contributes. And really, you know, uh trying to almost justify or put forth, you know, that well, I could have done it anyways. Um, and it's been a hard part of just kind of really kind of moving into and accepting, you know, that that was a a great gift uh that came through great loss.
SPEAKER_01:Why why do you think it's so difficult to accept that?
SPEAKER_00:Uh I think because we we just weren't conditioned to kind of you know be our own man. Do we do I have what it takes? You know, what did what did I accomplish? What was you know, who who who you know, who am I to to to be able to you know receive this? Um you know, it's kind of even goes, you know, uh, you know, probably into deeper into even faith stuff is like, man, why me? You know, why why do I get this? You know, I say if I could live life a thousand times and and never end up back in this spot again. Um so it feels you know, almost a little bit of guilt, uh, I think probably around that.
SPEAKER_01:And when that happened, wait, did that change? So you're retired at 50. Was that always the goal? Or was this something that just accelerated the time horizon for you?
SPEAKER_00:I had planned an early retirement. So I I probably knew even a decade ago, decade and a half ago, that I was probably on track. Um, that you know, by 55, you know, I was looking at the rule of 55, knew by 59 and a half once I was able to start, you know, uh, you know, taking you know withdrawals out of my retirement, uh, that that was gonna happen. So this really kind of accelerated the timeline uh on on that happening, both you know, on multiple fronts, right? On on the you know, the the stock, you know, the individual stock stuff that that happened and that um you know there was also some potential on the work side that there was some work stuff that might have delivered on that as well, but that didn't work out. So uh so there it kind of still put a little bit of a uh uncertainty in there. But uh in the end, it you know, it was kind of a new uh, especially one of the motivators, yes, you know, kind of one of the things that drive uh my dad passed away uh at 62. Um so when we talk about health span uh more than lifespan, uh it rings very true for me. My wife's father passed away at 52. Um my grandfather lived at 85, and my great grandfather lived to be 99. So I've kind of always had this joke if you if we if we plot it out in Excel, I've got about three good years left here.
SPEAKER_01:So yeah. How much of the why changed for you? So you started saving young, and it sounds like you wanted to retire at an early age, even when you started saving. But my guess is the reason behind that, the why for that maybe you started shifting from your 20s to your 30s to your 40s, getting married, having a family. How did that why change, if at all, that led you to an early retirement?
SPEAKER_00:Well, the the the I guess I would say is I didn't know when I started at 18 that I wanted to retire early. It's just that I wanted to retire comfortably, right? Um, it actually wasn't until probably 20 nine 2018, 2019, uh, that that I was always prior to that, I was always in the accumulating mindset. I never really even asked the question about like, what is my retirement going to look like for for for my wife and I? You know, what does that look like for us? Um, so we actually started, we actually got caught up in this idea called the Great Loop, uh, which is taking a boat and circumnavigating the eastern third of the US, uh, basically Great Lakes, inland rivers, Gulf of Mexico, East Coast, and even down, we went down in the Bahamas. And we started looking at that and said, wow, that'd be a really cool thing to do in retirement. Um, and then my wife came back and said, Well, what if we did it now with the girls? And so we ended up doing that uh in, we left in 2021 uh and finished in 2022. Uh, but it was in the planning of that, in the even thought process of doing that for retirement, that broke something in my brain about moving from this, hey, to save for retirement to what does retirement look like? What would we be doing? What are the things that we want to spend our time and our money on uh as we move into that? So that was really the thing that really kind of made, I think, the biggest shift on that. And then going back and looking at the, you know, like, yeah, you know, that my dad had passed. I think for since my dad, he passed away in 2012. So I think ever since then, it was that, you know, and he was only, you know, only retired for two years before he passed away. So that kind of stuck in there, and it's like started kind of making all these things make sense to that it's not a 65 plus, you know, uh type of uh future that I was looking at that that we really needed to kind of probably bring that in sooner.
SPEAKER_01:What broke in your thinking? So you you take this trip early, this trip that you thought would be a cool retirement thing, you do it earlier while you're still working, you do it with your girls, with your family. What was the shift that happened that made you think differently after taking that trip?
SPEAKER_00:Uh well, it was even in planning the trip. So even just the thought of it, like first thinking about for retirement, it was really as simple as like, oh my goodness, I've been so focused on accumulating that I that that I didn't that I didn't think about the stop. I didn't think about when do we stop? When do we when do we know need to do that? And and I do think that doing the trip, you know, uh I when we went on that trip, I worked full time while doing it. Um and so we, you know, my wife and I joked, I or not joked, but we we reflected I I probably spent about 30% of my, yeah, I probably experienced about 30% of it versus the standard retiree that might do it, right? Because, you know, if I wasn't working, uh, you know, uh and I kind of felt that I needed to prove to people at work that I wasn't slacking off. So I probably worked even a little harder, not less, while we're doing the trip. Um I mean, so there's stuff I missed in that. Um and also I just kind of after we finished, I realized, man, I was there, but I I wasn't as present with my girls as I wanted to be. Um, so that was probably kind of moving forward after getting back from the trip and over the last you know 24 months is started really getting into like my daughter, my youngest or my oldest daughter turned 16 uh in June. And just that mindset of, oh my goodness, I've got two years left uh before she's gonna be out of the house. And what does it look like to have some intentional moments, uh, much more intentional moments over the course of the next two years with her uh that I wasn't I wasn't able to do a real good job of doing work-life balance in the past.
SPEAKER_01:Let's let's dive a little bit deeper into that. So even going back to your your financial journey to get where you are, sure, maybe there's some people won't say good fortune, because that good fortune came at a cost of losing a grandparent, losing a father. But there there was also a very significant amount of that. If you started early and you prioritize saving, it sounds like you're a planner, it sounds like you're someone that this didn't just fall on your lap out of no, like this was something additional on top of work that you have been doing since the age of 18. You knew in your mind you wanted to retire early. There's maybe some pivotal moments along the way that really brought that even into sharper focus. What was it that finally prompted you to say, you know what, this isn't just thought in my head that I want to retire early, but I'm actually gonna make the decision and tell my employer?
SPEAKER_00:Uh yeah, so that's a good one. Um probably two parts to it. One was, you know, uh did have you know um some headwinds on you know, some on the financial front. I've kind of made it to some numbers where I'm like, oh yeah, that's that's that's like it's not comfortable that I can move, you know, we can move forward and and you know, not feel that it's a you know a giant leap. Um so probably numbers that I got comfortable with uh on the first part. And probably, you know, honestly, we you know, I was at a job. Um we had a um, you know, we went through a bunch of layoffs, you know, in 2023, uh and then got acquired in 2024. Uh and really just kind of the job front is like, you know what? Um I'm just not as you know, we got we went from being, you know, kind of a startup mentality to a you know a large you know, 4,000 plus employee company. And I just started looking around, just said, man, I just I just don't know that this is where I want to put my time anymore. Um and so that and there was you know probably even some kind of uh uh leadership, you know, vacuum of leadership and things. It was like, you know what, um this kind of it made me take a step back and say, well, wait a second. I I this doesn't have to be it, right? This doesn't have to be my priority, this doesn't have to be the thing that I'm spending my time on. And then combine that with like, and I could be doing these things with my girls, doing things with my wife, being present, you know, more. Um, that was really kind of the thing that, you know, those two things come, you know, were were what probably was hit the tripwire to to to move into retirement.
SPEAKER_01:Yeah, the three big ones of financially, of course, you need to be financially prepared to do this, especially if you're gonna retire at 50. And so feeling like you're in a good spot there. Internally, feeling like I've only got a couple, few I don't say few good years left, but few years where the girls are still at home and I can see them all the time. And then externally, of course, the job feels a little different. Maybe it's not what I want to spend my days doing. Despite all that, walk me through. Was it difficult to take a step back and say, man, I'm 50 years old and I'm about to go retire? Was there any feelings of what's my boss gonna think? What are my coworkers gonna think? What are my friends and family gonna think of me retiring at 50?
SPEAKER_00:Absolutely. Um I dreaded it. Um and again, it goes back to that whole feeling almost not worthy of it, right? Not not being, you know, uh, I I still say that I still feel like there's days where I feel like I'm uh an 18-year-old or a 22-year-old, you know, caught in this surreal moment uh where it's it's almost, you know, we talk about imposter syndrome in the workplace. It almost feels like imposter syndrome in the retirement workplace, right? That it it it was, you know, it's like oof. And because of the conditions that kind of afforded it, uh it also made it, you know, kind of a little bit weirder to explain. And I honestly went into it thinking that everyone was gonna be bitter or resentful or like envious, jealous, you know. So whether it was at work, at church, at, you know, um with friends, um, even my mom, I was afraid to tell my mom because it just didn't feel right because she worked till she was in her 60s. Um, and so yeah, uh, you know, putting together the the letter to you know, kind of engage with my boss on uh was you know, was uncomfortable. And it was like, okay, let's let's see what happens. And then that was the first instance of like, man, sorry to sorry to hear you, you know, that you won't be with us, but so happy for you and the decision and the opportunity that you have. Um, and that's probably the biggest thing that uh the biggest thing that shocked me the most is I had so many apprehensions about telling people, uh, because of just feeling like it was gonna, you know, like it was almost um it felt that it felt like going into this that this was something, again, if I if I felt I didn't deserve it, then I felt like it was almost boastful or or kind of like, you know, hey, look at me, or you know, look look what I look what I had the grace of receiving that you don't get. Like, especially with people at church, it's like, you know, God is good. Well, he's even gooder than me, right? Like that was uh uh that was a hard one to kind of start, but man, every interaction was man, that's so awesome. Um, you know, I can count on you know one hand the number of people, and probably on just a few fingers, the number of people that even even in the statement of saying, like, man, I'm I'm envious of you or I'm jealous of you, everyone else has just been like, man, that was that's awesome. So whether it was my boss or even the you know, the the engineers on my team, um, they were all just like, man, that's that's so awesome. You know, uh glad you could, you know, glad you're able to have this opportunity, uh, especially in in regards to being able to spend the time with the girls over the next couple of years.
SPEAKER_01:Thank you for sharing that, Kent. Well, I think one of the things that surprises people is the difficulty when you actually start thinking about retirement, the actual, I gotta tell my boss. I don't think people think about that being one of the almost like roadblocks to getting to their side and the dread of that, or the, oh, what are they gonna think? Are they gonna be mad at me? Am I letting the team down? Do I not deserve this? I'm really curious, though, by that conversation with your with your mom. I know a lot of people where there's a sense of, my parents raised me, my parents worked so I could have the life I have. My parents worked until they were 65 or 70 or whatever it is, and to feel like worse to happen way sooner almost feels like this the guilt of, am I standing on the shoulders of giants, so to speak, and taking this easier path because of what whether that's accurate or not, I think that's a feeling that people have. Walk us through how what was your feeling going into that conversation? How did the conversation happen? And what was your mom's reaction?
SPEAKER_00:Yeah, um, so I avoided telling her for a while. I mean, it was probably a couple months into retirement before I actually, you know, she called one day and sh, you know, she always like, Well, I don't want to bother you at work. You know, she every time she calls, it's like the first words out of her mouth, and uh and while you're working, and uh, you know, I meant to just leave a voicemail. And I said, Well, Mom, I answered the phone. Uh, but just so you know, you're not bothering me at work anymore because I'm I've retired, right? So really just trying to give her the freedom to call me uh was it. And and she was, you know, she was happy for me. She was, you know, she it was, you know, she was excited to hear, and you know, and again, the you know, the the um kind of the opportunities that it unlocks, you know, she was very excited about what that looked like. Um yeah, I you know, I I I processed after the fact of just saying it's like, you know, gosh, how would I feel about my kids, you know, my girls going through that situation? Of course you'd be excited for them, regardless of what your circumstances are, right? Why would you um but yeah, the uh but it was, you know, um, but she she didn't have those opportunities in her life. And so it kind of felt like, again, it was probably that the piece of just wanting to do it with humility, that it didn't seem as uh uh, you know, you know, putting something on something in someone else's face that says, look what I've got. But um really just trying to say this, you know, like, you know, you know, you you you helped raise me, man. This is partially, this is your this is partially your victory, mom, uh, that I'm I'm able to get here.
SPEAKER_01:Yeah, very cool. So we've talked so far about the kind of the buildup to retirement, the decision to retire. How did that go? How did the conversations go? I'm curious how the first eight, nine months have been. You know, you were tired so you could have more time with your girls. I know you said you, I think you said your wife's homeschooling them right now, so you want more time. They're not gonna be in the house forever. Has the reality of retirement so far matched your expectation of what it would be?
SPEAKER_00:Um mostly. Uh so I I uh was listening right after I had uh retired. I, you know, I still still listening to the podcast, still listening to things. And uh one guy got on and said, Well, you know, I took a sabbatical. And I don't know if I really turned or not, but I took a sabbatical. And he says, and uh so I could spend more time with my family. And of the the five lessons I learned uh of things that went wrong, is he said, I didn't realize my family didn't want to spend more time with me. It's like, oh uh and he said, but what what they really want is um you know uh moments, right? They want to have you know uh meaningful you know experiences together. And uh it has truly unlocked that, you know. And I would say again, the the going back to that word freedom is man, having a schedule freedom, um a schedule that frees you up to be able to make decisions in ways you wouldn't when you have you know a set block of PTO, right? Um that in itself has has unlocked a lot of opportunities. So we've we went to uh we did a uh five-day family marine science camp down in the Gulf of Mexico, uh, which again, if I went back to working, it's like it would have been really hard to say, oh, I'm gonna take you know five of my 20 days of vacation to go do this thing together. And so I probably would have sent my wife with the girls to do it and went and joined them. Uh we bought some season tickets for uh amusement park, uh, and we've been there three times already. And again, we might have gone there before for two days, but we wouldn't go back multiple times and use up all of our time for that. Uh we were able to just do a 16-day road trip up to the northeast, and you know, again, something that never would have been done had uh I still been working. So it's really, you know, unlocked a lot of opportunities. Even even now with the girls, I said one of the probably the the things that that shows you know just the freedom that comes is we had a a couple, an elderly couple that was moving to be near their near their daughters to North Carolina, and uh and they got a preliminary house um inspection report, and they're like, wow, oh my gosh, we got this list of like 40 things, and I'm like, hey, I can come over. And so I end up spending four days over there doing stuff. And there's no way I would have taken the PTO to go do that. Um because I would have been feeling like I was robbing from my family by by using that time for that. So it just really is really has opened up the opportunity to just kind of be present and and be available and not having to think about like, you know, what's what's my time worth? You know, is is this a you know, is this is this really a good trade-off? Um, you can be a lot freer with your time uh once you stop putting it in in stop having those same constraints around it.
SPEAKER_01:Yeah.
SPEAKER_00:Yeah.
SPEAKER_01:What are you know are are there things on that note? Are there things that you always have wanted to do, but just you haven't had the time? And when you did have the time, when you were using PTO, obviously that goes right to family stuff. Are there things, simple things, that you're now able to do and you find yourself doing far more frequently that you maybe even didn't anticipate before?
SPEAKER_00:Uh so the one I probably wasn't expecting is I am you know I've joined the old man club, so I've started playing pickleball. Uh so uh and I've done that with a a group of guys, you know, we've probably got eight or ten guys that, you know, you know, randomly, you know, different different guys will show up on different weeks, but we've been doing that, and that's been a a great source of you know connecting. And and I was just telling everybody the other day, it's like that's become my workplace, you know, relationships uh is is kind of doing that with them. Um I I still kind of stay kind of thinking as we're almost in we're phases of retirement, you know, because the girls are still working right now, uh, because my wife or the girls are still in uh school right now, and my wife's working with them. It kind of creates this a little bit of a weird balance of is uh you know, most of what I'm doing right now is kind of working around the house, you know, getting getting the backlog of uh of tasks you know completed and projects. So um probably not as much of the unlocking of like doing woodworking or doing you know this or that or the other. Um and then eventually we're you know, we kind of see that as the the the plan until the girls are gone, and then once they're gone, I'll probably uh well we are gonna you know do more traveling by boat, I think is is kind of what our dream is. When we get to really retire, yeah, yeah, yeah.
SPEAKER_01:The the time and financial freedom to do that. Um what's been hard? You know, hard whether it's I I lost structure from work. I lost purpose. I my impression was I was gonna spend all the time in the world with my girls. And my girls' impression, my wife's impression was no, we're still doing school, and we we can't was what's been the hardest part, if anything, in these first several months?
SPEAKER_00:Yeah, I think that um probably one of the items is the I I heard someone talking and say about, you know, uh even doing like projects at home becomes more enjoyable because you you have you have the time to do it and you you're not you know, I always say is you know, I used to, you know, if you had to paint a room, you do it from nine o'clock to eleven o'clock at night, right? And trying to try to whip it out and get it done. Well, now you've got you know a whole day to do it. It probably is that you become less focused uh and less productive. Um so I think there's that that part of still trying to trying to measure your productivity, right? You don't want to, I don't, I don't want to be seen as like, you know, my identity is in how well I complete a task list. Uh, but also you don't want to get so sluggered that you're like, hey, you know, I'm it doesn't matter if I do anything. So I think just trying to find that healthy balance in that and in the and the motivation on you know, kind of like, you know, having having a sense of urgency on some things to get done uh is probably one of them. Um I I would say it's been, you know, again, it's it's I probably idealized a little bit um what the extra time would look like with being present with my girls. Um so it's still hard, you know, that at 16 and 14, they're you know, still it's still hard to you know probably connect as deep uh as as maybe I you know thought would happen just by being more present. Um so that's that's probably been uh you know, probably the ideal is you know kind of come back to you know on the curve of normalization on that one.
SPEAKER_01:Did you have specific thoughts, Kent, on okay, I'm retired. I have specific things I think I'm going to do with my girls, or is it more just I'm retired? Of course that will be filled with something, although I don't know what specific things probably something.
SPEAKER_00:Probably was more of a you know, more of the open-ended, right? Um uh one of the things that was kind of on the plan is you know, is picking up is being a uh kind of helping out on the homeschool co-op. Uh and you know, so I'm teaching a physics class uh for my daughter and and some of the other kids in the co-op, uh which I've never taken physics before, so that's been it's been an interesting one. Uh but it that's you know, so that's one of those kind of things that was on the plan of doing. Um, but there haven't been as many, or it's it's been harder to, you know, when I look at my schedule and openness, I look at theirs as like, oh, well, they're actually at school, or they're you know, doing dance, or they're doing, you know, youth group, and it's like, oh, but things like being president youth group, you know, I'm in in the you know, I uh you know attend their youth group, I you know, you know, go to the co-op. So just kind of being, I kind of say is it's it's nice just to able to even be in the room with them at times. Um so yeah. And then the travel stuff, I've been you know, kind of trying to, you know, kind of lead on that of being intentional about how do we get out and kind of have these meaningful experiences together.
SPEAKER_01:Yeah. Is there any part of you that fears, you know, the the these next two to five years, you are home with your girls, there's time together, there's presence. They're out of the house in a few years. Does the fear ever cross your mind of, oh, will I get to the point where I feel bored or like I need more structure or like I do want to go back to work, or is that not something that you feel that you need to worry about?
SPEAKER_00:Uh I don't think so. Uh yeah, again, it kind of goes back to our our strategy of like, you know, we've got this short term, which is you know, hanging with the girls, uh, you know, seeing them, you know, kind of launching them. And then after that, you know, dependents if you talk to me or talk to my wife. Uh, I have a you know, like a 10-year plan of how we're gonna live on a boat and go to many places. And she says she's given me three years of uh before she reevaluates and says, is this really what we're gonna do? Uh so there's a there's a lot of that um that would you know kind of fill in, you know, probably you know the late 50s to mid-60s. Um and then after that, you know, she has her dream of having grandma's lake house. And so, you know, what does it look like to establish that, you know, after that? So um yeah.
SPEAKER_01:Yeah. You um you've mentioned a couple times, backtracking a little bit, of things you've heard or podcasts you've listened to, or but so you have both the lived experiences of having gone through this, you also have the learnings that you've taken from other people. And with all that, both your experiences and things you've heard from others, uh are there some Some things that like what would you want people to know? People who are in this position where they're saying I've saved my whole life, I prepared, I thought this was just a financial math problem. I'm I'm I've arrived. I know I can do it, but I still can't bring myself to retire because I'm learning there's this whole psychological aspect to it as well. Any common or kind of foundational things that you would want to pass along to those people?
SPEAKER_00:Yeah, definitely. Um I think it's it's really like it's it's uh I think that I said, you know, kind of thought about it in the passive as like, you know, the accumulation stage is the brain, using the brain. And then like right as you're ready to flip the switch, it moves to the heart, right? Um, where is your heart? Um, you know, what is it that you you need to you need to you know kind of understand that uh so much of it is about how you think of yourself and how you think of others, right? Um the identity, right? You know, am I getting all my fulfillment through my, you know, the way that my coworkers applaud me when I come up with great solutions? Well, you you kind of need to figure out, you know, how do I how do I realize that that's in some ways almost an empty or a false you know uh attraction, right? If if you if you allow that to be the penultimate fulfillment, then you're gonna work till you're you know 99, right? Or work till the day you die. Um and there's just so much more to be had when you're able to say, you know what, I'm not I'm not defined by the things I accomplish in a given day. Um you really get to have so much freer of a of a time and experience uh by not carrying that with you. Um so I think it's really kind of working through, you know, just make sure you're working on the heart as much as you're working on the brain.
SPEAKER_01:Are there any kind of practical tips you have to go that that person says, okay, yeah, Kent? That makes complete sense. I'm that person. I I I get validation from my coworkers. I get validation, accomplishing things on time. I hear you, I know that's empty. What can I practically start doing to start that identity shift or start that change of mindset?
SPEAKER_00:Yeah, um, I would one of the things I kind of process through in that is this is um a lot of people say, you know, you know, oh, what are you retiring from? And then people think that, well, you you remake it really smart by saying, what are you retiring to, right? You need to have something to go to. And I really you know thought as going through this process said is what am I retiring with? Right? What are the things that that did fulfill me in the workplace? What are the things that did fulfill me, you know, uh with my coworkers, you know, and and saying, how did those things then how can I fulfill those same uh needs, but in this different arena? And so just for example, you know, I was in a leadership role. I I love trying to help other people kind of experience their best, right, in the workplace. Um, and so okay, well, how do I bring that with me? Well, the pickleball thing was a bunch of guys that you know that that weren't doing anything, uh, that were looking for to you know engage relationally, to act competitively, um, and to have good fellowship. And so I said, hey guys, man, we're gonna we're gonna start doing this on Tuesday mornings. And and so just bringing that same you know act of of serving others, uh, but just in a different venue. Um, and so I get the same joy out of it because, you know, just like me, you know, helping an engineer, you know, kind of be his best, uh, I'm helping, you know, these people that maybe otherwise would have just been sitting at home on that Tuesday morning. Uh, and so get to see them experience you know the fun of the competitiveness, the fun of the fellowships. So I think, you know, just doing root cause analysis of what are the what are what's the actual thing behind that accolade that fill that's that's speaking to your heart. What are your desires that are that are there? And how do you kind of find those desires getting filled uh in other venues? Hmm.
SPEAKER_01:I really like how you're framing that and just kind of uh articulating it kind of as I'm understanding what you're saying, is there's so much focus on the what are you retiring from to what are you retiring to, the from and the to become the focus, and where are you putting your thought and your energy, but it's the you that should be the focus. You're you are the uh the constant in both of those equations, and what's bringing you fulfillment and what are you doing to uh find that identity and purpose and meaning, not just in the external environment, the from or the to, but but you as a person. So I like how you frame that, and that's something I want to think about deeper, even as you say that.
SPEAKER_00:Yeah, you know, and and for me, part of it was even just trying to take pressure off myself. Uh, because everyone says, you know, well, what are you gonna do now? Right. Yeah, like again, people want to put you into the box of, you know, what are you checking off? What are you doing? And it it's so much pressure on thinking you have to kind of reinvent yourself in retirement. And it's not, it's it's moving with yourself in retirement. Um, yeah, that that was, I think, what helped me to you know kind of take some of that pressure, stress, or anxiety of you know, having to answer that question to people. Um, that that made it so much more, you know, give give give more freedom in it.
SPEAKER_01:Yeah. I like it. Well, Kent, thank you for sharing this journey and the transition. I know there's a million things that we didn't get to cover, but in the last minute or two, anything else that you would like to leave the audience with? Any major learnings, lessons, challenges, or just quite frankly, the what the benefits of, man, I'm so glad I did this. And I want people to know what it's like on the other side after making some of those difficult decisions. What would you like to leave the audience with as we start to wrap up?
SPEAKER_00:Uh good question. Um yeah, I think that it's just the uh, you know, for for me, it's it just feels like such a you know an anti-pattern of like that with so many people just go through the roteness of like, hey, I'm gonna have this job, and hey, I'm gonna get fulfilled by, and hey, you know, you know, continue to to accumulate more and accumulate more. And you know, even for us, we had we had to make a decision. You know, you know, I I tell people, it says, you know, I could have worked till 65 and I could have lived a five-star lifestyle. And we had to make a decision saying, you know, is that really what we want? And really with the emphasis of health span, of not knowing how many days we're gonna have of having good health, of saying, like, you know what, a two and a half star, three star lifestyle is may is enough for us. And therefore, not making, you know, the continuation of work to be an idol uh that would capture us, that wouldn't allow us to kind of experience our retirement and our, you know, the labor of you know, 40 years of work, um, you know, that that that would have, you know, that we would be able to enjoy that in a way uh that wasn't that was kind of on our terms rather than on the terms of our current health condition at the time.
SPEAKER_01:Yeah. Love it. Well, Kent, so much good stuff here that you've shared. I really appreciate this. And as I mentioned even leading up to this, there's this thought of retirement being a math problem, an investment problem, portfolio problem, until you get there and you realize, oh, it's it's this stuff that's actually bringing me the most consternation or the most anxiety. What's it actually like? So I appreciate you taking a few minutes to share what has it been like, the challenging conversations, the challenges you wrestled with with identity and other things, and um the benefits of it too, and just that shift of what are we here to prioritize, what are we here to uh spend our time doing. And thank you for sharing that. I think that's gonna help a lot of people who are in that same position wondering what's next for them. So, again, thanks for joining me on today's uh episode of Retirement Reality.
SPEAKER_00:Awesome. Thanks, James. I appreciate it a lot.
