
Loading summary
A
Let's assume your last day of work was on a Friday. You have the weekend. We've always had weekends. There's nothing different about that. But Monday rolls around, the first Monday of no work. What did you do?
B
One thing I always like, I would walk into work and when I walk to work, I always, if it was a beautiful day out, I'd be like, I just want to keep walking. Like, I want to like, spend the day exploring and like going out and do things. So I think, you know, in that first week I did a lot of walking and during the day, you know, like, I would walk around outside, like with like a huge, like a dumb smile on my face. I was like, just so happy and like, couldn't believe that, like, this is basically what I'm going to be doing now. I'm just going to like, whenever I want. I can just go out, walk around, go anywh, do anything.
A
For decades, retirement was just a theoretical number. Until one day it wasn't. Darren hit his target retirement number. He paid off his mortgage and then he waited for the right moment. A company reorg that opened up a window for him to retire. Eight months later, he's in phase one walks on Tuesday afternoons. Health first in a life full of small joys. But what's interesting about Darren is he's proof that you don't need a grand passion just to get started. In today's episode, we dig into health care worries, solo trips when friends aren't free during the week, and a very helpful reframing of the word retirement in the first place. Enjoy today's episode with Darren. Darren, thank you for joining me on today's episode of Retirement Reality. I would love to hear from you. If you could describe your retirement in just one word, what would that be?
B
Yeah, I guess I would probably say it's kind of surreal. Yeah, I find it very, very like after all these years of planning, just surreal to be able to actually do it.
A
Surreal. Okay. How long have you been retired?
B
Eight months.
A
Eight months.
B
So, yeah, it's still pretty fresh. I'd say I'm in the, in the honeymoon phase. I'm kind of just figuring out how it goes and so.
A
Yeah, yeah, so let's, let's dive into that. You've been retired for eight months and sure, retirement eight months in could look different potentially in the retirement three years and five years and 10 years in, but surreal. What was surreal about retirement to you?
B
Yeah, I guess, you know, like, you know, I had worked for 30 years and I had been saving for Much of those. Many of those years, for decades. And kind of over the years, you just kind of watch this number go up and down until they go up. And it's this theoretical number that you're just kind of looking at. It's very abstract. I always treated my investments as, like, I could only put in, I couldn't take out. So I was like. It was kind of like I didn't touch it once it was there, so I never saw it as kind of real thing. It was just a number.
A
And.
B
Yeah. Then one day, number says, you don't need to work anymore. And then you're like, oh, wow, okay. This theoretical money now is something that's actually became very tangible. And then one day, you know, when I finally pulled the trigger, then, you know, then my life is just, you know, completely different all of a sudden because of this, like, magic number that was. I had just been watching for all this time. So, yeah, it was just very, like, you know, I had a. The plan was always there. I was, you know, thinking about it. But then one day, the plan became reality. I'm like, oh, okay. Well, that just kind of happened. Kind of, like, surprising.
A
I won't ask you what the specific number was, but did you have a number in your mind where you said, once I hit this number, that's my trigger to operate?
B
Yeah, yeah, yeah, I did. And I was working with a financial advisor for some time as well. So I. Before I started working the financial advisor, I had a number. And then as the years passed, that number kind of just changed a little bit. As, you know, the world changed. And as. And my gut feedback from the financial advisor. But yeah, I always kind of had, like. Always had pretty much like a number that I was shooting for, whether that's sometimes a change, but I always had a number.
A
When you hit that number, the day you hit that number, either because a 401k contribution went in, or you had a bonus that you put in, or the market took it to hit that number, did you feel significantly different than before, or did it feel like maybe I need a little bit more?
B
I think probably the big thing for me was that, yeah, the number was looking good. I had a mortgage, and I kind of felt like I didn't want to retire with a mortgage. So that was a big, like, kind of thing on my back. I was like, I want to figure out a way to get rid of the mortgage. It doesn't take from. From my investments. I don't want to retire with a mortgage. And so I think that was probably the biggest switch. The day I was able to get rid of that mortgage, that was like, a huge weight off my back. I'm like, okay, now I have done. That was my last financial goal that I had, which was not having to deal with that. And that was the day that I could really, really felt, like, very confident that I was ready to go.
A
So you hit your number, you paid off your mortgage. How long between doing those two things did it take for you to actually stop working?
B
About four years, actually. Yeah, once I. Once I paid off the mortgage, I was like, I can go anytime now. So that was kind of nice, kind of that, you know, having that independence at work, because I didn't feel quite as tied to it as I did. But, you know, I still so had stress with everything, but I did like my job. And so I kind of just kind of kept working for another four years because I liked it and I was enjoying it and kind of just waited for the right moment to. To where I felt it was, like, the best time for me to go. So. And, like. So that could have been any time, but it ended up being, like, four years.
A
I'm curious to know what that moment was, because I think for a lot of people, that's a similar experience where they have maybe a number. They have these financial checkboxes. It might be paying off a mortgage. It might be putting a child through school. It might be whatever it is, and they hit it. But that doesn't necessarily. It feels good, but it doesn't launch them into retirement. It tends to be something else that actually is the impetus to make that decision. What happened four years after you hit those numbers that prompted you to retire?
B
Yeah. Yeah. I guess one thing I'd say, you know, I've heard people say things like, you know, you shouldn't retire away from something. You should retire towards something. And I felt like I didn't have either. Like, I wasn't. I liked my job. I didn't want to leave it. I didn't have a big, like, other than kind of, you know, a lot of various little things I want to do. I didn't have, like, a huge passion that was trying to go to. So was kind of like, well, I'll stick around at work while I'm enjoying it or while things are kind of going well. And then we had a reorg, and I got moved into a different division, and I kind of saw basically a good time for me to. I was kind of looking for the best time to leave that would cause the less disruption to My teammates and stuff. So when we did this reorg, I moved to a different team and I like handed off all my work to somebody else that I was starting to pick up new work, but I wasn't really embedded that deep into that work yet. So I thought there was a window there where I felt like if I leave now, first of all, you know, if I go to this new team, I probably am signing up to be there for a little while because I don't want to go to a new team and then like leave, you know, half a year or whatever. And I've also hands off my old stuff. It was a like, nice window where I, I, I felt it was like not going to be disruptive. And also coincidentally, that was right around my like exact 30 year working time. So I felt like everything lined up. It was like it was 30 years. It was like at the end of the year. So it was coming into the new year, I was changing teams, I'd handed everything off. I was like this like just feels like the time to do it. So everything just kind of like aligned in retrospect.
A
So, you know, at the time everything aligned. A reorg was happening. You hit your 30 years, you had already hit your numbers you wanted to hit. Knowing what, you know, now, being eight months into retirement, was that the right time? Do you wish you had retired sooner? Is there any part of you that wishes you had stayed on? How are you feeling today?
B
I actually feel like it was pretty perfect. Like, you know, yeah. Since I didn't have anything like I was really going towards, I didn't feel like a retiring tutor would have like helped me too much more. That would have been maybe nice. But I guess probably the main thing is that the working, the extra four years that I did, you know, was four years less than I have to support myself in retirement and four years more income that I made. So that like also cushioned things a little bit. Also gave me like padded my numbers a little where I felt even more confident. And yeah, so I think just because of that situation, I felt like it's kind of like the perfect timing.
A
You, you mentioned before, you said a lot of people, they have a passion, they want to retire too. There's something that they really want to do that works, maybe preventing them from doing. And, and correct me if I'm wrong, it sounds like there wasn't necessarily something, one specific thing that you couldn't wait to do once you stopped working. So what happened? Like, has it been an adjustment? Has it been hard to adjust to the New reality.
B
Yeah. I think a surprise that I found is that I like settled into not working very easily. Like, I talked to many people before I, you know, stopped working. And you know, many people are like, oh, it's going to be so different. And it is very different. And you know, you're going to have to, you know, you know, you could be bored. You know, my dad, he retired and then kept going back to work and you know, you see that kind of happen. So like, I didn't know. It was like uncharted territory. I'm like, I don't know what's going to happen. I was telling people that like, I don't know, in a month I could be bored and I'll be like coming back, trying to come back to work or looking for another job or three months or six months. And yeah, probably that was the biggest surprise was that for me, I mean, everybody's very different. I have, you know, my way I work and the way I like approach things and I just like loved it. I was just immediately like waking up every day without anything that you have to do specifically. And I didn't have one big thing I wanted to do, but I'd like, I have like lots of little things. So I've like always, like, I always have things that, that kind of keep me busy and none of them are like important or earth shattering. They're just like things I like to do and things I had on my list of things to do for years. And now I just kind of work my way through them and like, yeah, just kind of do whatever I feel like on the day.
A
A list of things that you've had on your list for years. How did that. Was this a physical list that you kept, that these are things I want to do or was it more of a mental list of a mentalist?
B
Yeah, yeah. Like, for example, like, I had many video games I wanted to play. So I have been sort of starting to play video games, books I wanted to read. I had like all sorts of projects around the house that I wanted to do. Actually, probably my number one, you know, thing I started doing when I, when I stopped working was basically focus more on fitness, like health and fitness. So working out more I had, you know, in the, in the past few years with work being kind of busy, I had allowed myself to like, not, you know, do as much health, like exercise as much. So I basically, I really, that was like, probably my number one goal when I stopped was to like get into regular exercise routines, eat better and like now my job Essentially is, you know, to be as healthy as I can be. That's like my number one job. And then so that, that kind of was my main focus. And then doing all these kind of other things as well.
A
Yeah. I'm curious, Darren, what the last eight months has been like. So let's, let's assume your last day work was on a Friday. You have the weekend. We've always had weekends. There's nothing different about that. But Monday rolls around. The first Monday of no work. What did you do?
B
Yeah, well, yes, for me it was, I think Monday was a holiday. So I made a mistake. I should have resigned on the Monday and then got the pay for that last day. So Monday was. I didn't consider that my first day because that was actually like a long weekend. But yeah, I think the first day, yeah, I just, I. Yeah I probably got up and just like one thing that I always like I would walk into work and when I walk to work I always, if it was a beautiful day out, I'd be like, I just want to keep walking. Like, I want to like spend the day exploring and like going out and do things. So I think, you know, in that first week I did a lot of walking and during the day, you know, like being able to go like go around and like take, take a big long walk on like a Tuesday afternoon or Wednesday afternoon when it's like nice out and instead of being like stuck in an office, I was like, I think for that first month or two, I would walk around outside like with like a huge like a dumb smile on my face. I was like, just so happy and like couldn't believe that like this is basically what I'm gonna be doing now. I'm just gonna like whenever I want I can just go out, walk around, go anywhere, do anything. So yeah, I think probably just getting out a lot more in that first while and I still do that a lot. But that was like a big one, was like, okay, now I'd like I can just do anything during the day. I don't, I'm not in the office like nine to five all the time. And if it's a beautiful day and I'm not looking at a window wishing I was outside.
A
Does your day to day look the same today? So, so first Tuesday after retiring, you're just walking in your smiling the whole time because it's just so new. You're eight months now, eight months in now. Are you still waking up and walking? What does the routine look like today that it' maybe didn't look like day one.
B
Yeah, yeah, it's probably like pretty similar. I think I kind of feel like, you know, I'm still like maybe this would be like. I imagine probably as I am not retired for longer, I'll be going through phases. This is, I feel like still I've been at that first phase of like, I kind of do the same things. Like I get up, I usually, you know, do some exercise in the morning, work on the computer. I've got lots of like, you know, like computer projects, like programming projects and things that I kind of work on and then, you know, have some lunch and then go for a walk and yeah, so I kind of like. So. And yeah, and go for a walk and yeah, maybe I'll go see a movie in the afternoon, stuff like that. So I think it hasn't changed significantly. I think maybe it's become. I'm definitely very like routine oriented. So I kind of follow kind of the same routine kind of every day or variations of routines on certain days and stuff. So yeah, I feel like it hasn't actually evolved significantly, but I do feel like probably there, you know, will be a time when, you know, basically maybe I go to some other phase or maybe I change some other things. Some of the ways I'm operating.
A
If you can rewind 12 months ago, so you weren't yet retired, you're about four months out. Is what life looks like today what you imagined it would look like going into retirement, or did you have a different vision for what the day to day might look like?
B
Yeah, I think probably the biggest thing that hasn't really come to fruition the way I thought it would was travel. Like I do travel, like usually once a month I'll travel somewhere like in North America or you know, something kind of small. But yeah, before I, before I left my job, I was like, I'm going to do all the travel. I'm going to go to Europe for a month and I'm going to like go here, I'm going to go there. And I had really big travel plans, so I would have envisioned I would be like living somewhere or like staying somewhere overseas for like a couple months. And I haven't really done that yet. That's kind of still on the plan. That's when I talk about the phases, maybe the next phase. I'm doing more traveling, but I've been happy just because I've really enjoyed kind of decompressing from work, doing all the things around, kind of where I live in my, in my home and in the city that I kind of had wanted to do over over the past many years, I'm kind of just like, enjoying that and not, like, pressuring myself to go and, like, jump into doing a bunch of travel just yet and, you know, that'll come. But right now I'm more just like, kind of doing, you know, stuff around. Around locally.
A
Yeah. How old were you when you retired, Darren?
B
54.
A
How many of your friends or people that you worked with are retired, given that you're retired at a young age?
B
Yeah, maybe two. Not that many. I know maybe two people directly that kind of my peers that. That have. Have retired.
A
Has that been a challenge, being retired, having all the free time in the world? But a lot of your peers are still working?
B
Yeah. Yeah. It definitely means, like, the weekdays and the weekends are different because weekdays everybody's kind of working, so you kind of are on your own a lot, which I'm fine with. I like just being with my thoughts. But, yeah, it's definitely harder to find people to do things with. And if I go on trips, I can go in the middle of the week. I can go anytime. But not everybody can do that. People want to do things over the weekend. So, yeah, so it does mean kind of weekdays and weekends. I sort of have kind of some different activities because it's. There's more people available to hang out on weekends. So, yeah, it's been a little bit of challenge, but like I said, it doesn't really bother me. I don't mind doing things on my own. I'm pretty happy doing that.
A
Yeah. I want to go back to what you said at the very beginning about surreal being the word that you would describe? Retirement is surreal to you? More of the. The life that you get to live and how happy you are. Or is it just surreal, this fact that you spent 30 years building up this portfolio planning for this moment, and now that moment's arrived and it just is hard to fully grasp that.
B
Yeah, I think. I think it's just. Yeah, that, you know, I guess more. More above my life, like, now my. You know, the plan that was so theoretical for so long now is basically this. And, like, this is what my life could be like forever, if I want it to be. So it's very nice. And I can craft my life to be whatever I want, whatever I want it to be now, you know, I have the freedom to kind of do whatever I want. So, yeah, I think that's kind of like just the.
A
Yeah.
B
Just feeling very lucky and, like, privileged that I'm able To was able to retire so early and now I just kind of do what I want.
A
Yeah, I know you mentioned that there's the reorg and that's what was the final thing that pushed you into retirement. But you enjoyed work. Is there any aspect of you that misses work or misses the structure or misses coworkers or misses any aspect of that previous job?
B
Yeah, I think not as much as I would have thought. I would have thought maybe I missed like a bunch of things about like, you know, seeing people every day being in a workplace because I did go into the office and I liked going into the office seeing people but I still do meet up with my co workers. I go back into the office actually like once, once a month usually to see them. So yeah, probably the biggest thing is like not being able to see my co workers as often because I did, I did like my co workers but other than that, nothing, nothing really. I did like my job and I felt it was, you know, I like the type of work I did but like I didn't feel like, you know, it wasn't fulfilling in a way that feel like I'm missing some, some, you know, some piece of my life of the actual work that I was doing. So. Yeah, so not, not that much actually. Surprisingly that is a surprise too.
A
Yeah. One thing that you said earlier was it sounded like you talked to a lot of people before actually retiring and they gave you feedback of oh, are you going to be bored or oh, are you going to miss a structure or did you feel like you got how, how accurate was a lot of advice that you felt like you got from friends or co workers or whoever you are speaking to.
B
Yeah, I think probably because I got not a lot but a couple warnings of people like oh, you know, you know it's gonna, you're gonna be bored or you know, or like you could be bored or you know like people that were hesitant like so and were.
A
These retired people, Darren, were these people who'd already retired or people started a mix?
B
A mix? Yeah, I think one, I think one retired person said something along those lines and, and other non retard people. Like two or three people said, you know, or raise those kind of sentiments as well. So yeah, I think there would. Yeah, so I think that kind of was a pretty common piece, piece of potential feedback which why is why I was concerned about it. But I think like I say for me personally that hasn't been a problem. I certainly could see that being a problem for some people but for me that I was like yeah. And I also felt like if that's going to be the case, the sooner I find out about it, the better. Right. The only way to really. I don't know if that's going to be a problem is to just jump into it. So I'm like, I'm young now. If I did start getting super bored, I could just go back to work or I could find some other thing to do. And so I'd rather know now that I need to readjust myself, because at some point, I'm gonna have to stop working. At some point, I'm gonna have to be prepared for this. So might as well figure it out now.
A
Well, I think you're starting to answer my next question is how did you emotionally prepare for that? You know, this moment's gonna be surreal. You know, you've been planning for this moment for 30 years. There's aspects of your job that you truly did enjoy. You have friends or colleagues giving you feedback that you're gonna be bored. Don't do it. I would imagine you're too young. You got. So you got good earnings years in front of you. How much more could you. How did you emotionally prepare yourself to say, you know, I'm just gonna do it? When it sounds like there's maybe a good number of voices and rational reasons not to do it?
B
Yeah. Yeah. I wouldn't say a lot of people saying it, but they're definitely that kind of feedback. But, yeah, I think mainly I. I think emotionally, or I guess because of this window, this, like, good timing for me to leave at work, I just really felt like that was. That was kind of giving me, like, calmness or, like, confidence that it was the right thing to do. Because I'm like, if I don't do it now, it's. It's. I'm going to miss the window and I'm going to. I'll regret it. Like, I. You know, I. You know, I didn't know I was actually going to, like, resign until, like, the day I booked the meeting with my manager. I was like, you know, I was always like, I'm 90% sure. I'm 90% sure. But I was like, I'm just pulling. Actually pulling the trigger is, like, really difficult. So, you know, it's obviously a big decision to make. So, yeah, it was kind of like, until I actually booked a meeting and sat down and told my manager, I wasn't actually sure I was going to do it, but I really had a feeling that if I didn't do it and take advantage of this opportunity and I would be kicking myself in two months or three months. So, yeah, I kind of felt like just everything was aligned enough that made me feel confident that it was the right decision to make and, you know, take the risk.
A
How did your manager take the news?
B
Good? Yeah, she was really good about it. Yeah, she was of course disappointed but that I was leaving. But yeah, was like, you know, very supportive about, you know, basically the, you know, me not being, having to work and stuff. So, yeah, it was quite good. They did ask me to stay a little bit longer than I had anticipated, but since I didn't really have any specific place to be, I like stuck around a little longer than I had expected. But that was great because I had lots of time to say goodbye to people and to wrap things up even more instead.
A
You know, one thing that, what was interesting to me as I started working with clients in this phase of life is there's the fear of retirement that people have. But then once they make the decision to do that, there's a real fear of letting your boss down or letting your team down or letting your company down that a lot of people feel. Did you feel any of that? Of what are they? Am I letting them down? How did, how, how did you wrestle with those emotions?
B
Yeah, that was tough. You know, really my 30 year career, I only had two jobs, so I only ever resigned from two jobs. So I wasn't like very good at it or wasn't very used to having to resign. So I was very nervous about it and I was moving to this new project that was kind of a high profile, important project and my manager was really relying on me to work on that project. So I knew that would have been, that was like not ideal. So I was like, yeah, I was quite nervous coming into it, but at the end of the day knew it was the right thing to do. And then like I said, she was very supportive and like, you know, it went quite well. It was, it was, you know, you just helped, helped me a lot through it to make sure that it was as smooth as possible.
A
Yeah, I think this is an important theme to pick up even as people are listening is you had these fears, you had these concerns, you had these unknowns, whether it's about retirement, whether it's about the finances, whether it's about how do you let them know. But there is a sense of what I'm hearing is if not now, when type of a thing, or I can always go back if this doesn't work out. I can always make, you can't get these years back, though, if you don't do that.
B
Exactly.
A
Yeah.
B
And the other thing was I had. I actually had a red line in the sand, which was 55. I said, I will not work past 55. Like, so regardless of how things are, like, timing at work or other things, I'm like, I just have to stop at some point, you know, like, yeah, it's, you know, since I hit all my financial goals, what is keeping me going, you know, and it's inertia just that's going to keep me going. And at some point, you really have no idea how long you're going to have your health, you're going to have, you know, things can change so quickly. So I'm like, you know, if there's no reason for me to financially be working, then, you know, I really owe it to myself to, like, take the. Take the jump and do it. And then, yeah, like I said, if it doesn't work out, I could always consider going back. And then I have to figure out what the future looks like from there. But, yeah, like I said, 55 was really the hard deadline. I'm like, I'm not going to go back 55. So even if I hadn't quit earlier this year, I would have. I would have quit, you know, later in the year.
A
How much? I've talked to several people who, that probably not too dissimilar from you have hit their number. They have enough. They run the projections. The projections look good. The Monte Carlo looks good. The stress test looks good. But there's something about retiring in their 50s that doesn't feel right because Social Security is not kicking in or they don't yet have Medicare. And it doesn't matter how much we model out, the fact that your investments can support this, you can get other medical coverage. There's still this mental block of it. It's hard to know that your investments are what you're fully living off of. Did you experience any of that or did hitting your number give you the reassurance that you were good regardless?
B
Yeah, definitely, that is a concern. I mean, you know, yeah, you don't have a paycheck covered every week or month and every time. And now you have to pay for healthcare. That's like a big. A big change. I think probably, like I had mentioned earlier with the mortgage, once I get rid of the mortgage is, you know, a big monthly payment that I'm like, well, once I get rid of the mortgage, that money that I would have been putting towards the mortgage now essentially will Easily cover my healthcare costs or my like insurance, health insurance. So I'm kind of like, I don't want to have too big this, I don't want to add another expense. But if I can get rid of the mortgage expense, then basically I feel more comfortable with having this increased expense with healthcare. But yeah, definitely, that's a bit of a. It's a tough one having to also pay for healthcare.
A
Yeah. Changing gears a little bit, Darren. I find that sometimes when people retire they're so used to the day to day, the busyness. They have deadlines, they have jobs, high stress. There's not a lot of time to just even explore the really bigger questions of life. Who am I, what do I like doing? Is there. They almost don't know who they are by the time they actually retire. Have you learned anything about yourself that surprised you in these past eight months of not having that corporate job anymore?
B
Yeah, I guess. Yeah. I, I don't think any huge surprises. I think I kind of, it kind of turned out the way I kind of expected, which is a surprise in of itself because I wasn't sure it was gonna. Was gonna turn out kind of. Well where. Enjoying it so much. Yeah, I think maybe one thing is that I, even though I, like I said, I'm generally pretty routine oriented, so I always do have like a list of things I want to do every day and I still find myself like rushing around to do. Like I have this thing to do and I have this thing to do and so I kind of make this like false stress for myself or some of these like false deadlines. So I often have to like stop myself and go like what are you doing? Like you're, you don't need to be stressed about things like don't like schedule two things to do and there are three things to do in a day. Like spread it out through the week. Don't meet somebody for lunch and you have to get a haircut and then you go to go see a movie. And I don't need to do three things a day. I can just do one thing a day. So I felt like, I feel like maybe one thing is I kind of am trying to subconsciously introduce more stress kind of back to my life and I have to purposely go like, why are you doing that? Just relax. You don't need to be rushing around all the time. Yeah. Just enjoy it and not, you know, not, not cause yourself unnecessary grief.
A
Yeah. Yeah. Love it. Going back to what I said a little bit before, one thing that strikes me about you is you, you have felt all the same fears and concerns, maybe anxieties that people lead into this position, feel, but you went ahead and did it anyways. Is there a piece of advice you would give to the audience or something you would tell them whether it's how to emotionally prepare, how to financially prepare, how to psychologically prepare. What advice would you give people who are sitting maybe in your shoes 12 months ago and knowing financially I can do this? I like work, I don't love it, but I don't know if I can bring myself to actually do the scary thing and tell my boss I'm gonna go retire.
B
Yeah, yeah, yeah. I guess I'd say like, you know, it's not, you know, I don't, I don't even really like, like to use the retirement, the word retirement. I generally tried to say stop working. And when I left my work, I didn't tell people I was retiring. I told people I was taking a year off, which was potentially true. I didn't know if I was only going to take a year off. So to me, I even do see a possibility of the future where I might work again in some capacity, like part time or contract work or something like that if an opportunity came along and I felt like I wanted to do it. So yeah, so I feel like it is a big step to make, but I think the sooner you do, if you can do it, you kind of owe it to yourself to do it and then don't consider the end of the line. There's still lots of opportunity to work and things you can do. So. Yeah, so I think for me, I felt the sooner I could do it the better. And you can always readjust later if you need to as long as you've done the due diligence of your finances. So if you truly don't need to work again, then you kind of owe it to yourself, I think, to take the opportunity and do it.
A
I'm serious. I think there's more wisdom to what you just said. Even that I'm realizing for the first time in some ways that the way we frame things really matters. And if this is framed as retirement, there's a certain amount of both finality to that that can be very scary. And there's this level of Darren's like, retirement carries this connotation of I'm done, I'm not working hard anymore, I'm retiring and slouching off into this life of nothingness now. But you're pursuing your health like you've never pursued. You're doing These things you've never been. So there's this sense of you can still maintain this life full of vigor and excitement and adventure. It just is different than what life looked like before. So I think that what I'm hearing you say is the way you frame it is really important. I think there's actually a huge amount of wisdom in that, that this isn't final, this is not setting anything in stone and this isn't saying it's the end of the line for you. This is the beginning of a brand new adventure that can be filled with far more joy in structure and community and all the above if you approach it the right way and if you make the commitment to doing it.
B
Yeah, yeah, absolutely. Yeah, yeah. I think, you know, yeah, retirement's a nice shorthand because people understand it when you say it, but like. And it's complicated to be segue well, you know, adding a lot of, you know, qualifiers to things. But yeah, I, I'm like, you know, who knows what, like I say I'm in phase one, who knows what phase two or phase three looks like. And you know, now I'm young enough that I can, you know, I still have other things that I could do. So I feel, you know, while you've got your health, you know, you know, do it and then just, you just figure it out.
A
Yeah. Darren, thank you very much for all this. If, if you could tell the audience any final words, any final words of wisdom of why they should retire earlier. I'm using that word, retire. I know we said just don't use it, but why they should potentially consider leaving their current employers early. Words of wisdom, would you give them?
B
Yeah, yeah, I guess, like I said, I'd probably recommend doing it as soon as you can, but always make sure you're doing a due diligence. And so I guess weigh the pros and cons. There's a practical side of it. If you work longer and you save more money, you're going to be more comfortable versus so you have to find that balance for yourself of how. When I was looking at retiring, I also looked at, you know, moving to lower cost places of living or moving overseas to lower cost places. Like, I looked at kind of all the spectrum of what is available to you. So, yeah, so I think basically it's up to you yourself to like understand your comfort, comfort level when you feel like you can retire. And to me, once you feel confident you could retire in the manner that you feel, you know, financially, that fits your lifestyle, you kind of owe it to yourself to do it. So I would. I would encourage. I would encourage people. Encourage people to do it.
A
Yeah. Well, very good, Darren. Thank you so much. Thank you for joining me on this episode of Retirement Reality. Appreciate you sharing how the last eight months have gone and best of luck for everything ahead.
B
Great.
A
Yeah.
B
Thank you for having me.
Host: James Conole, CFP®
Guest: Darren
Date: November 12, 2025
This episode features Darren, who retired at age 54 after a 30-year career. Host James Conole explores what led Darren to take the leap, the emotional and practical side of early retirement, and how life has changed in the eight months since. The discussion dives into expectations versus reality, the importance of reframing "retirement," managing healthcare and finances pre-Medicare, and finding meaning and joy after leaving work—even without a grand passion.
Darren encourages those considering early retirement to do their homework, weigh comfort against additional saving, and act as soon as it makes sense:
“Once you feel confident you could retire in the manner that fits your lifestyle, you kind of owe it to yourself to do it.” [29:36]
This engaging conversation demystifies early retirement, making it less about chasing a grand passion and more about savoring newfound autonomy, health, and small joys. Darren’s deliberate, considered approach, his willingness to revisit work if desired, and his focus on framing retirement as a beginning—not an end—offer a refreshing, actionable perspective for anyone eyeing “phase one” of their post-career life.