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A
What can I practically start doing to start that identity shift or start that change of mindset?
B
I really 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 saying how did those things then how can I fulfill those same needs but in this different arena?
A
All right, I think you're really going to love this conversation I 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 this 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. Ken, thank you for joining me on today's retirement reality. How long have you been retired for?
B
So I retired February 4th of this year. So I've been coming up on eight months or I guess moving into ninth.
A
Month of retirement nine months in. And if you could describe that retirement so far in one word, what would that word be?
B
Freedom.
A
Freedom. Now, you retired at 50, correct?
B
Yes, sir.
A
I am very curious about that because I think that for a lot of people that feels 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 that time. So I would love to explore with you, what was it like leading up to that decision? 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 and what maybe concerns do you have about the future of being young, not working? See things around that. So 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?
B
A little bit of each of those. So I. Growing up, my grandfather was a real big, you know, emphasis on, you know, saving, saving, saving. And so, you know, retirement saving. And specifically my grandfather retired in his mid-50s. So kind of set the example of what I was looking, you know, what I was looking at. So early on, at 18 years old, I was already, you know, putting into a 401k, made a couple of bad choices along the way in that of, you know, taking, taking a loan out and, you know, and what, what that looked like. But, you know, since I've been 18, I was, you know, retired, saving in my, you know, 401k retirement savings. And then later, you know, in my 40s, you know, I probably got into a couple of spots where I had done a couple investments. You know, I, you know, looked at some of the Tesla stuff and, you know, kind of thought, yeah, man, this really makes, makes a lot of sense. And so I got lucky on, on some spots there. And then in, you know, part of the full story is, is that, you know, my grandfather had, had done well and you know, you know, and my father, who would, would have inherited, you know, a lot of what my grandfather left behind. He wasn't, he passed away a year after my grandfather passed away. So there was a, a bit of, there's a trust set up that was meant to solve just for paying for great grandchildren, but it end 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, you know, that's been one of the hard ones, is actually trying to separate or accept that, right, to accept that, you know, this wasn't just by my doing. So you talk about identity, you know, the identity. 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, trying to almost justify or put forth, you know, that well, I could have done it anyways. 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 that came through, great loss.
A
Why do you think it's so difficult to accept that?
B
I think because we just weren't conditioned to kind of, you know, be our own man. 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? You know, it's kind of even goes, you know, you know, probably into. Deeper into even faith stuff is like, man, why me? Why, 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. So it feels, you know, almost a little bit of guilt, I think, probably around that.
A
And when that happened, can't wait. Did that change? So you're tired at 50. Was that always the goal or was this something that just accelerated the time horizon for you?
B
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, 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, you know, taking, you know, withdrawals out of my retirement, that that was going to happen. So this really kind of accelerated timeline on that happening both, you know, on, on multiple fronts. Right on, on the, you know, the, the stock, you know, the individual stock stuff that. That happened and that, 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, so there. It kind of still put a little bit of a uncertainty in there, but in the end, you know, it was kind of new, especially one of the motivators. Yes. You know, kind of one of the things that drive. My dad passed away at 62. So when we talk about healthspan more than lifespan, it. It rings very true for me. My wife's father passed away at 52. My grandfather lived 85, and my great grandfather lived to be 99. So I've kind of always had this joke if we, if we plot it out in Excel, I've got about three good years left here. So.
A
Ye.
B
Yeah.
A
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 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?
B
Well, 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 I wanted to retire comfortably. Right. It actually wasn't until probably 20, 20, 18, 2019, 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? So we actually started. We actually got caught up in this idea called the Great Loop, which is taking a boat and circumnavigating the eastern third of the U.S. 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. And then my wife came back, said, well, what if we did it now with the girls? And so we end up doing that. We left in 2021 and finished in 2022. 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. That we want to spend our time and our money on 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 at, 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. To that it's not a 65 plus, you know, type of future that I was looking at that, that we really needed to kind of probably bring that in sooner.
A
What broken your thinking? So 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?
B
Well, it was even in planning the trip. So even, even just the thought of it, like, first thinking about 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, you know, need to do that? And, and I do think that doing the trip, you know, I. When we went on that trip, I worked full time while doing it. And so we, you know, my wife and I joked.
A
I.
B
Or not joked, but we. We reflect that. I. I probably spent about 30% of my, you know, I probably experienced about 30% of it versus the standard retiree that might do it, right? Because, you know, if I wasn't working, you know, and I kind of felt that I needed to prove to people at work that wasn't slacking off. So I probably worked even a little harder, not less, while we're doing the trip. And 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, it started really getting into, like, my daughter, my youngest or my oldest daughter turned 16 in June. And just that mindset of, oh, my goodness, I've got two years left before she's going to be out of the house. And what does it look like to have some intentional moments, much more intentional moments over the course of the next two years with her that I wasn't able to do a real good job of doing Work life balance in the past.
A
Let's dive a little bit deeper into that. So even going back to your financial journey to get where you are, sure, maybe there's some, I won't say good fortune, because that good fortune came at a cost of losing a grandparent, losing a father. But there was also a very significant amount of that. You've 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. No, 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, this isn't just thought in my head that I want to retire early, but I'm actually going to make the decision and tell my employer?
B
Yeah, so that's a good one. Probably two parts to it. One was, you know, did have, you know, 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. So probably numbers that I got comfortable with on the first part and probably, you know, honestly, we, you know, I was at a job, we had a, you know, we went through a bunch of layoffs, you know, in 2023, and then got acquired in 2024. And really just kind of the job front is like, you know what? I'm just not as, you know, 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. And so that, and there was, you know, probably even some kind of leadership, you know, vacuum of leadership and things. It was like, you know what, this kind of, it made me take a step back and say, whoa, wait a second, I, I, this doesn't have to be it, right? This doesn't have to be my perm, 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. That was really kind of the thing that, you know, those two things, you know, were, were what probably was hit the tripwire to, to, to move into retirement.
A
Yeah, the three big ones of financially, of course, you need to be financially prepared to do this, especially if you're going to retire at 15. So feeling like you're in a good spot there internally, feeling like I've only got a couple, few, I don't say a 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 co workers gonna think? What are my friends and family gonna think of me retiring at 50?
B
Absolutely. I dreaded it. And again, it goes back to that whole feeling. Almost not worthy of it, right? Not, not being, you know, I, I still say that. I still feel like there's days where I feel like I'm a, an 18 year old or a 22 year old, you know, caught in this surreal moment where it's. It's almost, you know, we talk about imposter syndrome in the workplace. It almost feels like imposter syndrome in a retirement workplace, right? That. It, it was, you know, it's like, oof. And because of the conditions that kind of afforded also made it, you know, kind of a little bit weirder to explain. And I honestly went into it thinking that everyone was going to be bitter or resentful or like, envious, jealous, you know, so whether it was at work, at church, you know, with friends, 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. And so, yeah, you know, putting together the letter to, you know, kind of engage with my boss on 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. And that's probably the biggest thing that. The biggest thing that shocked me the most. It's. I so many apprehensions about telling people because of just feeling like it was gonna, you know, like, it was almost. 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 it felt like it was almost boastful 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. To me, that was. That was a hard one to kind of start. But, man, every interaction was, man, that's so awesome. 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 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, they were all just like, man, that's. That's so awesome. You know, glad you could, you know, glad you're able to have this opportunity, especially in. In regards to being able to spend the time with the girls over the next, you know, couple of years.
A
Thank you for sharing that, Kent. What? I think one of the things that surprises people is the difficulty when you actually start thinking about retirement. The actual. I got to tell my boss, I don't think people think about that being one of the almost like roadblocks to get into the other side and the, the dread of that or the, oh, what are they going to think? Are they going to be mad at me? Am I letting the team down? Do I not deserve this? I'm really curious, though, about 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 we're stepping away sooner almost feels like this. The guilt of, am I standing on the shoulders of Giant, 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?
B
Yeah, so I avoided telling her for a while. I mean, it was probably, probably a couple months into retirement before I actually, you know, she called one day and, you know, she always like, oh, 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 while you're working. And, you know, I meant to just leave a voicemail and I said, well, Mom, I answered the phone, 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, was it. 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 kind of, the opportunities that it unlocks, you know, she was very excited about what that looked like. Yeah, I, you know, I, I, I process after the fact of just saying is like, you know, gosh, how would I feel about my kids, my girls going through that situation? Of course you'd be excited for them, regardless of what your circumstances are. Right. Why would you. But, yeah, the but it was, you know, but she, she didn't have those opportunities in her life. And so it kind of felt like, again, it was probably the piece of just wanting to do it with humility that it didn't seem as, you know, you Know, putting something on, something in someone else's face that says, look what I've got. But really just trying to say as, 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, that I'm, I'm able to, to get here.
A
Yeah, Very cool. So we've talked so far about the kind of, the build up 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 retired so you could have more time with your girls. I know you said you're, I think you said your wife's homeschooling them right now. So you want more time. They're not going to be in the house forever. Has the reality of retirement so far matched your expectation of what it would be?
B
Mostly. So I was listening right after I had retired, I, you know, I still, still listening to the podcast, so listen to things. And one guy got on and said, well, you know, I took a sabbatical. I don't know if I returned up, but I took a sabbatical. And he says, and so I could spend more time with my family. And of the five lessons I learned 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. And he said, but what, what they really want is, you know, moments, right? They want to have, you know, meaningful, you know, experiences together. And it has truly unlocked that. You know, and I would say again, going back to that word, freedom is man having a schedule. Freedom, 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? That in itself has, has unlocked a lot of opportunities. So we've, we went to, we did a five day family marine science camp down in the Gulf of Mexico, which again, if I went back to working, it's like, it would have been really hard to say, oh, I'm going to 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 wouldn't have joined us. And we bought some season tickets for amusement park. And we'd 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. We were able to just do a 16 day road trip up to the northeast, and again, something that never would have been done had I still been working. So it's really unlocked a lot of opportunities. Even, even not with the girls. I says 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, near their daughters in North Carolina and, and they got a preliminary house 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, right? 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 because I would have been feeling like I was robbing for 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 be available and not having to think about like, you know, what's, what's my time worth? You know, is this a, you know, is this really a good trade off? You can be a lot freer with your time once you stop putting it in and stop having those same constraints around it.
A
Yeah, yeah. What, you know, 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?
B
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. So. And I've done that with a group of guys. You know, we probably got eight or 10 guys that, you know, you 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 is kind of doing that with them. I still kind of think of it as we're almost in, we're phases of retirement because the girls are still working right now, because my wife or the girls are still in school right now and my wife's working with them. It kind of creates a little bit of a weird balance of most of what I'm doing right now is kind of working around the house, getting the backlog of tasks, you know, completed and projects. So probably not as much of the unlocking of like doing woodworking or doing, you know, this or that or the other. 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. Well, we are going to, you know, do more traveling by boat. I think is, is kind of what our dream is when we get to really retire.
A
Yeah, yeah, yeah. The time and financial freedom to do that. Um, what's been hard, you know, hard whether it's I lost structure from work, I lost purpose. I. My impression was I was going to 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?
B
Yeah, I think that probably one of the items is the. I, I heard someone talking and say about, you know, even doing like projects at home becomes more enjoyable because you, you have, you have the time to do it and 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 9:00 o'clock to 11:00 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 and less productive. 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. But also you don't want to get so sluggered that you're like, hey, you know, 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 is probably one of them. Yeah, I would say it's been, you know, again, it's, it's. I probably idealized a little bit what the extra time would look like with being present with my girls. So it's still hard, you know, at 16 and 14, they're, you know, still. It's still hard to, you know, probably connect as deep as maybe I, you know, thought would happen just by being more present. So that's, that's probably been a, you know, probably the ideal is, you know, kind of come back to, you know, on the curve of normalization on that one.
A
Did you have specific thoughts? Can't. 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.
B
Yeah, probably was more of a, you know, more of the open ended. Right. One of the things that was kind of on the plan is, you know, is picking up is being a kind of helping out on the homeschool co op and you know, so I'm teaching a physics class for my daughter and some of the other kids in the co op, which I've never taken physics before. So it's been an interesting, an interesting one. But that's, you know, so that's one of those kind of things that was on the plan of doing. But there haven't been as many or it's been harder to, you know, when I look at my schedule and openness, I look at theirs 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 present at youth group, you know, in, in, you know, I, 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 it's, it's nice just to evil able to even be in the room, you know, with them at times. 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.
A
Yeah. Is there any part of you that fears, you know, the, these next two to five years you are home with your girls, there, 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?
B
I don't think so. 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, you know, seeing them, you know, kind of launching them and then after that, you know, dependence, if you talk to me or talk to my wife, I have a, you know, like a ten 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. Before she reevaluates and says, is this really what we're gonna do? So there's a, there's a lot of that that would, you know, kind of fill in, you know, probably the late 50s to mid-60s. And then after that, you know, she has her dream of having, you know, grandma's lake house. And so, you know, what does it look like to establish that, you know, after that?
A
So, yeah, yeah, you, 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 you've taken from other people with all that, both your experiences and things you've heard from others. Are there some things that, like, what would you want people to know? People who are in this position where they 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?
B
Yeah, definitely. I think it's, it's really like, it's, it's, I think that I said, you know, kind of thought about it in the passive is 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. Where is your heart? You know, what is it that you, you need to, you need to, you know, kind of understand that so much of it is about how you think of yourself and how you think of others. Right. Identity. Right. You know, am I getting all my fulfillment through my, you know, the way that my co workers applaud me when I come up with great solutions? Well, 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, attractant. Right. If, if you, if you allow that to be the, the penultimate fulfillment, then you're going to work to your, you know, 99. Right. Or work till the day you die. 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. You really get to have so much freer of a, of a time and experience by not carrying that, that with you. 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.
A
Are there any kind of practical tips you have to go that that person says, okay, yeah, Ken, that makes complete sense. I'm that person. I, I, I get validation from my co workers. 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?
B
Yeah, I would. One, one of the things I kind of process through in that is, is a lot of people say, you know, you know, oh, what are you retiring from? And then people think that, well, you make it really smart by saying, what are you retiring to? Right? You need to have something going 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 did fulfill me in the workplace? What are the things that did fulfill me, you know, with my co workers, you know, and saying, how did those things then, how can I fulfill those same needs but in this different arena? And so just for example, you know, I was in a leadership role. I love trying to help other people kind of experience their best right, in the workplace. And so, okay, well, how do I bring that with me? Well, the pickleball thing was a bunch of guys that, you know, they weren't doing anything that were looking for to, you know, engage relationally, to act competitively and to have good fellowship. And so I said, hey, guys, man, we're going to start doing this on Tuesday mornings. And so just bringing that same, you know, act of serving others, but just in a different venue. 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, I'm helping, you know, these people that maybe otherwise would have just been sitting at home on that Tuesday morning and so get to see them experience, you know, the fun of the competitiveness, the fun of the fellowship. 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 speaking to Your heart and what are your desires that are. That are there and how do you kind of find those desires getting filled in other venues?
A
I really like how you're framing that and just kind of 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 you put in your thought and your energy. But it's the you that should be the focus. You're. You are the. The constant in both of those equations and what's bringing you fulfillment and what are you doing to 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.
B
Yeah. You know, and, and for me, part of it was even just trying to take pressure off myself because everyone says, you know, well, what are you going to do now? Right. Like again, people want to put you into the box of, you know, what are you checking off, what are you doing? And it's so much pressure on thinking you have to kind of reinvent yourself in retirement. And it's not, it's moving with yourself in retirement. 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. Yeah, yeah. That made it so much more, you know, give, give more freedom in it.
A
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 you would like to leave the audience with any major learnings, lessons, challenges, or just quite frankly, 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?
B
Good question. Yeah, I think that it's just the. For me it's. It just feels like such a, you know, an anti. Pattern of like that we so many people just go through the ropenness of like, hey, I'm have this job and hey, I'm get fulfilled by. And hey, you know, you know, continue to accumulate more and accumulate more. And even for us, we had, we had to make a decision, you know, you know, 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 going to have of having good health, of saying, like, you know, what a two and a half star, three star lifestyle is, may, is, is enough for us and therefore not making, you know, the continuation of work to be an idol 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, you know, that, that would have, you know, that we would be able to enjoy that in a way that wasn't, that was kind of on our terms rather than on the terms of our current health condition at the time.
A
Yeah.
B
Love it.
A
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, there's 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, the challenging conversations, the challenges you've wrestled with, with identity and other things and the benefits of it too. And just that shift of what are we here to prioritize, what are we here to spend our time doing? And thank you for sharing that. I think that's going to help a lot of people who are in that same position wondering what's next for them. So, Kent, thanks for joining me on today's episode of Retirement Reality.
B
Awesome. Thanks, James. Appreciate it a lot.
Host: James Conole, CFP®
Guest: Kent
Date: December 3, 2025
In this episode, James Conole sits down with Kent, who retired at 50 — a milestone that, while enviable, comes bundled with emotional complexity, identity shifts, and unanticipated challenges. The episode delves into practical steps, emotional hurdles (like guilt and imposter syndrome), changing family dynamics, and the realities (both freeing and challenging) of early retirement. Listeners get deep, actionable insights about what it actually feels like "on the other side" — well beyond the basic financial calculus.
Financial Preparation & Family Influence (02:25 – 04:47)
Struggle with Guilt and Worthiness (04:47–05:28; 14:31–17:14)
Motivations Evolve Over Time (06:59–09:24)
Realization from Life Events (09:40–11:20)
Sharing the News: Anxiety & Reality (14:31–18:13)
Telling His Mom (18:13–19:49)
Newfound Freedom, New Opportunities (20:18–23:33)
Unexpected Joys and ‘Old Man’ Transitions (23:33–24:49)
The Hard Parts (25:18–26:59)
Identity and Self-Work (30:22–31:49)
Practical Transition Tips (31:49–34:13)
Letting Go of Pressure to Reinvent (34:13–35:33)
Final Reflections (36:01–37:20)
Freedom Defined:
On Accumulation vs. Enjoyment:
Imposter Syndrome in Retirement:
On Support from Others:
Philosophy Shift:
Letting Go of External Validation:
For anyone considering (early) retirement, this episode provides a candid, heartfelt look at both the liberation and the emotional recalibration that real retirement requires.