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Robert Brokamp (3:47)

After saving for retirement for decades, you'll actually get to a point when you realize, hey, I I could retire soon. I'm in that situation, as is my next guest, fool contributor, Dan Kaplinger. So for this episode, Dan and I are going to have a conversation about how we're approaching the decision about when to retire. Dan, welcome back to Motley fool money.

Dan Kaplinger (4:06)

Hey, thanks for having me, bro. Great to be with you.

Robert Brokamp (4:09)

So we have a lot in common. We're both former financial planners. Both have been associated with the fool for more than 25 years. We're in our mid to late 50s, we have kids in college, and we both are getting to the point where we could retire soon. Though likely I probably should work for a few more years just to be safe. What's your situation and how are you approaching the decision about when you'll actually pull the plug?

Dan Kaplinger (4:29)

Well, bro, I'll tell you. The way I'm approaching the situation is the way that I approach most of my work, which is by overanalyzing and overthinking and going back and forth to try to figure out how to weigh all the factors. Because there's so many factors. There's emotional factors, there's financial factors, there is personal life and personal lifestyle factors, all kinds of stuff. And there's so much uncertainty that it is the thing that I'VE learned here is that whenever I make a final decision, when that day comes, I'm not going to be 100% certain that it's going to work out. It's going to be a jump into the void. And you just kind of have to have the faith that it's going to work out. And that's kind of what I'm trying to build myself up to at this point.

Robert Brokamp (5:17)

From the financial standpoint, how are you analyzing your situation? I know you're a guy who loves spreadsheets. Do you have your own spreadsheet or do you use some online retirement calculators?

Dan Kaplinger (5:26)

Oh, I've got spreadsheets out the wazoo, bro, which should surprise you. Not at all. And I've been tracking them throughout my career. And so I can go back and look at what I've done in the past, how it's gotten me to where I am today, what it is likely to bring me to in the future. And and I feel confident about the projections that I've made, that they're as good as I can make them. But there are still all these unknown unknowns out there that you have to somehow account for. And the way that I've done that is to try to give myself as many additional escape valves, as many, I call them slush funds, almost of kind of extra pockets of money that are dedicated for certain things that like if I need more money in one area, it'll be there. It won't necessarily affect my regular budget. And I try to use spreadsheets to figure out where I'm going to be with my investments and what effect changes in how I invest might have on what my future looks like. I do use some online calculators. The Social Security websites calculator for Social Security has been extremely helpful. In addition, there are some calculators on the Motley fool website that I've used really just to kind of double check my numbers on my spreadsheets and also to try to get some additional insight on kind of what the established financial community would tell me is the right answer. And then I can kind of customize and do my own tweaks to make it more my own because I know what my preferences are. I know where I differ from kind of where the mainstream thinking is. And so making allowances in my own personal financial plan, that I can do. But I still like to know kind of where the baseline is.

Robert Brokamp (7:20)

Yes. And I like retirement calculators and I'm going to list a few in the next segment here. You mentioned that they're both really emotional, maybe psychological issues as well as financial issues. Knowing you as well as I do, I know that you probably could retire right around now. What is preventing you from retiring? Is it the fact that you like what you do? You're not sure what you would do in retirement? Are you nervous about the financial situation right now? Maybe stock valuations? What's preventing you from retiring?

Dan Kaplinger (7:49)

It's a combination of factors, bro. But I'll tell you, I mean, I've been thinking about retiring for a long time now. When I was a younger person early in my career, I'd kind of set age 50 as my target for early retirement. That was at a stage in my career that I wasn't as happy with my work as I have been at the Motley Fool. And so being at the fool kind of took away the urgency for, okay, I got to get out of this rat race as quickly as possible. At the same time, it just so happened that my 50th birthday came right in the middle of COVID And so I had been thinking about it. I had about 2 1/2 million dollars in retirement at that point. And my numbers, like, I'm not that profligate a person. My budget, I think I could have made that work. The health care, early health care before Medicare is always the big factor there. But at that point, like, all the things I wanted to do, I wouldn't have been able to do. And so retiring in the middle of COVID just made no sense whatsoever. Wouldn't have been able to travel, wouldn't have been able to do the things that I really wanted to do. You know, it was just as easy to stay inside and do the same work that I'd been doing for 15 years at that point. Fast forward to now. And I mean, I've really enjoyed the past five years of work. And so, yeah, it's been a great market in that period. I've roughly probably more than doubled my retirement savings in that period. And so from a financial standpoint, like I think any financial planner would say that I'm totally set and that I shouldn't worry. But nevertheless, just as I experienced earlier in my career when I was a financial planner, I was working with people who were at the age that I am now, you never feel like you have enough. You never feel like you have everything set, that you're going to be able to account for every possible contingency, that you're going to be able to deal with whatever the uncertainty of the moment is in current events and politics. And geopolitics in economics, whatever it is. And so I think that holds me back as much as anything, as well as trying to figure out, okay, yeah, I know what I'm going to do the first year of retirement and it's going to be a blast, but am I going to really want to do that? Am I really going to want to travel? Am I really going to want to be away from home for 10 years? And if that's not the case, well, geez, should I just take a one year sabbatical and then just kind of come back to where I am? Those are some of the questions that I'm asking myself at this point.

Robert Brokamp (10:26)

Foolish colleague I had lunch with recently, he did leave the fool. And at the time he said, I'm not sure I'm retiring or not. I'm just going to just see what happens. And sure enough, within a year he was bored. He's at another job and he said to his wife, you know what, I probably just needed a sabbatical, just needed a break, which many people out there might be in that situation. They enjoy their job, they're not ready to retire, but they're burnt out and they would like to take a break. The studies on whether retirement is good for us is very mixed. Many studies have found that folks who retire sooner actually die sooner or experience accelerated levels of cognitive decline, physical decline, higher rates of loneliness, higher rates of depression. So certainly a big part of it is deciding how you're going to spend your time and who you're going to spend it with. What are you thinking in those terms? Like what should people be doing as they approach retirement to prepare for how they're going to spend all that time, how every day is a Saturday, as they say.

Dan Kaplinger (11:25)

So I think that probably the best thing that people can do is to work with the people that they know, talk with the people that they know, either who are in that situation or who are preparing the same way that you are looking to prepare. Talk to people who've recently retired, ask them what are they doing and how's it been and has it been as good as they expected it to be? What are the things that are better? What are the things that aren't quite as what they expected? What are some of the things that if they had it to do over again, they would change maybe. And you know, how are they dealing with the process? I think that it's important to build that network in advance, both outside of work and at work. I think people that you work with, I mean, I know Bro, I'm often guilty of this. People will leave the fool, and, like, I don't do as good a job as I should keeping in touch with them. Like, maybe LinkedIn tells me to wish them a happy birthday, and then that's just kind of me feeling, oh, geez, I probably haven't talked to this person for a year. Doing that is important because it does two things. One is it gives you that perspective outside of that bubble of your own work. But two is that it gives you kind of a window into what your future might look like after you decide to make the leap. And you knowing who those people are, knowing who your friends and contacts are, you can draw some conclusions from what they tell you. Some of it's like, oh, boy, I'm just like, that person. And I thought that you would really love that. And it turns out you don't. Well, gee, maybe I need to rethink that for myself.

Robert Brokamp (13:05)

Or.

Dan Kaplinger (13:06)

Yeah, you always want to do this totally different thing. I had no interest in that. And so, you know, you can kind of draw your own conclusions from that. But I think that's the most important thing, is talking to people, both the people that are around you now and the people who are doing the things that you might want to do some period of time down the road so that you get an advance view of what that life looks like. And you can kind of make course corrections now to guide you towards the better parts of that and steer you away, maybe, from some of the pitfalls that they fell into.

Robert Brokamp (13:43)

One thing that's changed with my own retirement planning is that I used to think I would work well into my 60s, because I just love my job and I love the Motley Fool. I'm very fortunate that way. But as I've gotten older, I've seen more and more people, frankly, either die too soon or experience health issues such that they won't be able to pursue most of their retirement dreams because they're no longer in the healthy enough to do it. And then there's the other aspect of whether I will still have a job another 10, 15 years from now because of AI. I'm primarily a writer and podcaster, and if there's something that AI can do, it's right. So I have been planning on an earlier retirement than I had previously planned. I may not retire early, but I think that's the prudent decision. In fact, studies show that people, on average, retire three years sooner than they thought, often because of an unplanned retirement.

Dan Kaplinger (14:36)

Yeah, and I'll tell You, bro, I kind of had a head start on you on this because unlike you, you're a full employee. I'm a full independent contractor. I work on a one year contract. And I'll tell you, I took that seriously from day one. It was kind of like everybody would tell you, oh, don't worry, they'll renew you, they'll renew you. But lawyer brain in me was like, hey, this is a one year contract. End of that year, like anything goes. And so I always kind of planned it that way so that if something did happen that I'd be ready. And as the years have gone by, I kind of laugh at myself every time I have that thought because it's like, you know, well, really? But just like you point out, bro, there are real threats to what we do and our industry is changing quite a bit. And so having that kind of contingency plan I think is is vital, not just if it happens, but also to kind of give you the security and the confidence to get you through your daily life if it doesn't happen. Because then you can just kind of like push that to the side. You don't have to stress out about it as much. Sure it's going to be a stressor maybe, but you still can have the confidence that yeah, if that happens, I'll be okay. And meanwhile, I'm okay now too and I can figure out where I want to go from here. That's just hugely important for your well being. And in these kind of challenging times where it was a lot of uncertainty. It's not just us, bro. All kinds of occupations out there, there's not as much hiring. You may know it from your kids. I know that my daughter's running through this. Those entry level positions. A lot of the people our age who are like partners at law firms and stuff, they're looking at the future and they're kind of like, you know, maybe we don't need to hire as many young people because the AI can do all the grunt work that the young folks did. I think that's short sighted, but it is reality right now. And so all kinds of factors going on right now that's hard to consider, that just makes shoring up your financial plan even more valuable to you, both for your financial well being and just for your peace of mind.

Robert Brokamp (16:48)

Since you keep bringing up lawyerly stuff. I just want to point out to the audience that Dan is a former attorney. So besides being a former financial planner, which is why I often say Dan is just about the most knowledgeable guy at The Motley Fool. Anyone who is thinking about retiring early, certainly before age 65, when they get Medicare, they have questions about health care. For me personally, I don't think it'll be an issue because my wife got a PhD at age 52 and has begun a whole new career as a professor, and she has every interest in sticking with that for at least another decade. I always like to bring up her as an example because she was someone who changed careers later in life and has found something really enjoyable. So even if I retire, she'll keep working. I'll get health care through her. What about you? What are you thinking in terms of health care?

Dan Kaplinger (17:36)

So I've been milking off my wife's job in the public sector as the town librarian here in the little town that I live in throughout my career, because as a contractor, I get paid for my work, but the benefits, I don't get the same benefits that an employee does. So that's a factor. My wife is a few years younger than I am, and, you know, we talk about these plans, and it's kind of like, well, do you want to travel with me? And the answer is sometimes yes, but probably not as much as I want to. And so at least for now, she's comfortable with the idea of kind of, even if I were to go to a full retirement, she'd be comfortable working and continuing to do the health insurance stuff. You know, that's another one of those uncertainties, though, that comes up because right now, if we retired, I live in Massachusetts. We have the Obamacare coverage. And even before Obamacare was around, the state had its own health care exchange. And so that's an option for us, but it's a really expensive option. The coverage under her job is a lot more affordable. And so that's a big question that comes up is sort of like, okay, if I stop doing what I'm doing, like, do I want to go full retirement or do I maybe want to do something else, like get another job that might. I don't have to worry about the financial aspect of it as much. I don't have to maximize my salary anymore. But just getting something for those benefits might actually be the most important part, because it's a natural thing. The healthcare expenses tend to go up. This is kind of the most vulnerable time in my late 50s and early 60s, before I'm eligible for Medicare. That's the biggest threat to my financial situation is an unexpected health situation.

Robert Brokamp (19:29)

Right. So that's an important consideration for anyone who does want to retire early. Check in to how much it would cost to get insurance through the Affordable Care act or some other source because it's pretty darn expensive. All right, Dan, prediction time. If you're forced to give a date right now, in what year do you think you'll actually retire?

Dan Kaplinger (19:47)

Well, boy, I hesitate to say retire because I kind of feel like I'm almost like one of that friend that you were mentioning before where it's more like it's going to be a transition more than a retirement. And so, you know, I really hope that I'm spending my time doing something whether it's paid work, whether it's volunteering, whether it's something that makes a difference, need to make a difference somehow. But I will tell you this. There is a natural transition point coming up this year in 2026. It's my 20th fooliversary as a contractor is May 31, 2026. And so, you know, I'm kind of looking at that date and trying to figure out, okay, is that when I do a transition and what does that transition look like? Is it just kind of a phase in, is it cutting back on some of the stuff that I do? Is it a clean break? Still trying to figure that out. But I'll definitely keep you posted for sure. You'll be the first to know, bro.

Robert Brokamp (20:43)

Thanks, Dan. In my situation, I have two kids in college, so I'm definitely not going to retire before then. I would say at the earliest, probably by 2030, 2031 for me, but I'll play it by year end like you. I would be very surprised if I go cold turkey. I'll probably do some sort of a part time situation and freelance. Maybe prepare taxes and tax season, something like that. It's just something to keep me busy. Well, Dan, this has been a great conversation. Thanks for stopping by. You bet.

Dan Kaplinger (21:12)

Great talking with you.

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Robert Brokamp (21:46)

It'S time to get it done. Fools of this week, I encourage you to analyze your own retirement plan and to see if you're on track to retire when and how you want. There are plenty of free calculators out there, but some are much better than others. My favorite comes from Calc xml. Just do an online search for the Calc XML Comprehensive Retirement Planning Module. They offer a few retirement calculators so you'll know you found the one. I like if the last three numbers in the URL are 606. There are also some high quality tools that will cost you a bit of money, but I think it's a worthwhile investment. Three to consider are Maxify, that's M A X I F I Projection Lab, and Bolden, that's B O L D I N. And I should disclose that Motley Fool Ventures, a sister company of the Motley fool, has an investment in Bolden. And that, my foolish friends, is the show. Thanks so much for listening. And thanks to Bart Shannon, the engineer for the episode. As always, people on the program may have interest in the stocks they talk about, and the Motley fool may have formal recommendations for or against. So don't buy or sell stocks based solely on what you hear. All personal finance content follows Motley fool editorial standards and is not approved by advertisers. Advertisements are sponsored content and provided for informational purposes only. See our full advertising disclosure. Please check out our show Notes. I'm Robert Brokamp. Full on everybody.