46. When to Downsize: Timing the Real Estate Market vs Timing Your Life

Is the housing market making you second-guess your downsizing plans? You're not alone. Many homeowners—especially in their 50s, 60s, and beyond—are stuck waiting for the “perfect time” to move, only to feel more stuck as life keeps changing around them.

In this episode, we break down the truth about market timing vs. life timing when it comes to downsizing. You’ll learn why waiting for better interest rates or higher prices might not serve you in the long run—and how to tell if your current life stage is actually giving you the green light to move forward.

We share:

• What “timing the market” really means—and why it rarely works
• Real-life examples of families who waited too long (and those who moved at just the right moment)
• How to evaluate your own life readiness beyond just the headlines
• A simple mindset shift that can give you clarity, momentum, and peace of mind

📍Whether you’re actively planning to downsize, exploring your options, or just feeling overwhelmed by the what-ifs, this episode is packed with wisdom, encouragement, and practical next steps.

🎯 Ready to stop second-guessing?
 Schedule a consultation or check out our free downsizing resources at www.downsizingroadmap.com

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Transcript

Jodi Rosko 0:01

Welcome back to another episode of the Downsizing Roadmap Podcast with your hosts Jody Roscoe and Heather Fisher. We're talking about all things downsizing, from our own experiences with clients to guest experts. Let's make downsizing easier, one conversation at a time. Hello, and welcome to Downsizing Roadmap Podcast. Today we're going to talk about timing the market versus timing your life. And sometimes I think people get caught up in like, you know, oh, the market's not quite right, and um and not think I'm ready. This is what needs to happen.

Heather Fisher 0:35

Yeah, I think that people are looking for that crystal ball to know the exact right time, not only in this instance in life, but in so much we wish we had that crystal ball.

Jodi Rosko 0:48

I say that all the time. Gosh, if I had that crystal ball, I'd be a millionaire.

Heather Fisher 0:52

Right, right.

Jodi Rosko 0:53

We would use it for for all of our people. We would use it for good.

Heather Fisher 0:58

All the things. Good, of course.

Jodi Rosko 1:00

Of course. But we don't have it. We don't have it.

Heather Fisher 1:02

We don't have it. I mean, we're both experienced realtors, have been in the real estate market for a long time. Um, but even with all of that experience, we do not have that future look of what the market's gonna look like next week or next year. Um so if the real estate agents out there can't time the market or tell you that perfect time, yeah. Um kind of difficult for someone else to just look at what they're hearing on the news and reading in the paper and and try to time that time the market.

Jodi Rosko 1:39

So we'll give you some good ideas and tips on what that is uh on in this episode. So I'm Jody Roscoe. I'm Heather Fisher. And I I think that what we hear often is um, yeah, I want to move, but I'm but but dot dot dot, right? So I want to move but so it's um, you know, the interest rates aren't aren't either too high, they're too low, you know, what not not they're never too low, but they're too high, that you know, whatever. Um I'm not sure that that the timing is right because the economy may seem a little uncertain or we're not gonna know what's going on in this or that.

Heather Fisher 2:13

It's school hasn't ended, school just started. Right. The holidays are coming. Right. Right. The holidays were just here. Whatever it is. Other things. Home prices are high, right. Interest rates and home prices are the the two biggies that none of us can predict, but are of concern for for all of us for to watch and and do our best.

Jodi Rosko 2:40

So what I can say about that is if you looked at what the price of your house was 10 years ago, you would buy it. Have bought it 10 years ago, right? And so you can't really look at the real estate market or the stock market. I mean, all of the markets are the same, right? Is there going to be a high? Yes. Is there going to be a low? Yes. Is it going to go up it in, you know, from 10 years ago till now? Very likely. You know, if if you look historically over what's happened at the real estate in the real estate market, it has always gone up, but it does not go up in a straight line. And if you could see my arm, because I use my arm all the time as my straight diagonal line up, um, you know, and then my finger is going up and down over my arm, right? And sometimes it's a little bit above that line, and sometimes it's a little bit below that line. Um, but the line is always going up. It the market just doesn't go in a straight line, it kind of zigzags up.

Heather Fisher 3:33

Yes. Yeah.

Jodi Rosko 3:35

And so um whatever choice you're making, I mean, if you're living in a house that you've lived in for 30 years or 20 years or 40 years, um, you know, you've made you made that decision, and that decision has paid off. And so whatever that decision, next decision is, if you live there long enough, it will likely pay off. And even if you don't, um, and it's it's e even or not, you're already ahead, right? You're already ahead from where you started.

Heather Fisher 4:02

Yeah, I was gonna say the same thing that um oftentimes in conversation, people are pinpointed on one of the factors instead of the whole math problem. Have you gained equity in the house that you're in? Have you lived there and used it? And did it serve its purpose? And that was just the cost of having a place to live and gaining some money. Have you uh, you know, just gotten that full picture? Does the math and the timing work on all of it together instead of narrowing in on one of the factors that might not be feeling like the perfect time?

Jodi Rosko 4:44

And we joke as realtors, we say the best time to buy a house was 10 years ago, and the next best time is today, right? Because 10 years from now, you're gonna be like, man, I wish I would have made that move, you know, whatever that is. And so, and even if you're not moving into, you know, a next house, maybe you're gonna, you know, rent or or move into a community or do something different. Um, but if you but if you're moving from one house to the next house, um it's in in the long haul, it's not gonna be a bad time. And if you're just selling your current house, we still have all the equity that we've gained. We've gained a huge amount of equ of equity in our houses in the last five years, and that's all still in there for you to to realize when you sell.

Heather Fisher 5:24

Yeah, so many people, you know, they're waiting for something that may never be perfect. They're waiting for perfect, but there won't be a perfect. Um you know, and so more importantly, what makes your personal situation the right timing? Correct. Much more important to look at than the timing of the market.

Jodi Rosko 5:47

And I think sometimes when we hear these these reasons, because um it's not just downsizing people who give us these reasons. Um, but I think that's fear talking, right? Um and they're afraid they're either gonna make a mistake, it's a big purchase, you know, it's a big sale, they're either gonna make a mistake, or they're not sure what's gonna come next, and they're feeling uneasy about what's coming next. And so then there's all the reasons which I might say if you're really gonna be honest with yourself, maybe excuses of reasons why you can't, you know, you can't do this. There's too much competition for the buyers. I can't get a house I want. There's, you know, whatever it is, it it may be, and and that may be true, but there are people who are getting houses. And if you hire uh an experienced realtor who knows how to handle the market, um, they will help you navigate whatever that looks like. If you're in Dayton, please reach out to us. If you're not, reach out to us anyways, downsizingroadmap.com. We can connect you with an experienced agent that can give you that that um expertise. And um so whatever's happening in the market, um, does that make it challenging potentially? Um, but that doesn't make it impossible. And if it's your right time and you know it's your right time, then that all can be handled.

Heather Fisher 7:04

Yeah, and exactly that is why we're able to sell your home at any time of year and you know, any year, homes will sell because there are timing things in life that cause buyers and sellers at all times. Um, you know, so those if everybody was waiting, nothing would be happening. Um, you know, the the fact that people are going based on their life events and their life timing is what keeps the market moving at all times.

Jodi Rosko 7:39

Yeah. I mean, and the thing is even the experts can't, you know, they they don't see what's happening. They all told us that the market was gonna crash during COVID, and we all know what happened, it just soared, right? Um, and so in the last few years we've gained like 24%, you know. Other areas have gained even more. It you know, it's it is local, real estate is local. But um, you know, sales prices have risen uh dramatically in the last few years, and at the beginning of COVID, they were saying, you know, that was gonna be terrible for the real estate market and all the. So even the experts don't always have, you know, uh the right answers on that stuff. So um don't we're what we're saying in essence is don't don't wait to m to really look at what the m or you know for the market to do something. And when you're looking at your house if buying and selling, if you're selling, it's high right now, like we have gained all that equity, so it's a great time to sell. Um if you're buying, uh it's also a good time to sell because of what might happen in the future. But uh we're we're looking at uh inventory is probably not gonna change a lot uh um coming in the future because um we just have too many uh buyers and not enough sellers. And uh that may change sometime in the future for whatever reasons, but economically we're not seeing that change because um what happened the last time when when the when the housing market uh did actually crash, there were no building of houses. For five or six years, there were no new builds of houses because the lenders wouldn't lend to builders and people weren't buying, and it was um there was just a whole huge time bracket where not many houses were built.

Heather Fisher 9:26

Yeah, and that gap has not been made up.

Jodi Rosko 9:29

We're realizing the gap. It did we didn't feel it right away, but now we are definitely feeling it. And that gap can't hasn't been made up.

Heather Fisher 9:37

Yeah.

Jodi Rosko 9:37

Even with the new build starts that we've had in the last few years. So um so that cr has created supply and demand issues, right? So um not enough houses for the number of people that we need.

Heather Fisher 9:49

Yeah, there's several factors pushing on that. Um you have millennials that are jumping into, you know, cur their careers and and able to buy their first their first home, you know, have that income to try to do that earlier. There's just more people in the market on that end as the that big group of millennials are jumping in. And then we have, you know, all of us getting older, but we're living longer, we're staying in our homes longer, and so that inventory is not flipping back down, you know, in that circle quite as quickly, um, you know, along with that gap in building new houses. We just have more people that are in the housing market, um, and it's tight.

Jodi Rosko 10:39

Right. And then we have companies, we have big REITs, big real estate investment companies that are buying up homes as rental homes. And so they are buying a lot of the starter homes, the kind of less expensive homes, because that's where they can make a better profit margin. And so we're, you know, h home buyers are competing against big companies, corporations that are buying up houses as rentals. So there it used to be that the interest rate really, really affected the the um buyer, whether it was a buyer's market or a seller's market. And it does affect it, but there are so many other pressures against, you know, what's going on there too. And for new builds, you know, part of part of why there aren't as many new builds, you used to be able to choose between a new build house and uh you know an existing property. And they were, you know, so maybe a little bit higher in price, but you could definitely comparable um in price. They are not comparable in price anymore, um, especially in the first-time home buyer ta you know bracket of pricing, because um the costs of all of the um the materials had got has gone up so much since COVID. So inflation um in the marketplace means you know windows and doors and m all of that stuff is so much more expensive. Inflation in your house translates to equity, right? So it can be a good and bad thing, right? So um when the government's trying to s you know slow down that inflation, we're also, you know, nar we're also leveling off um the home prices, right, because that they're not you know going up quite as high. So but all of the all of the in equity that the inflation caused is still in your houses right now.

Heather Fisher 12:28

Yeah, I think one big takeaway, and and Jody said it before on other episodes, and and we've talked about it, but with that pr this pressure on the inventory that we have, the best time to get started downsizing, and by started I mean handling the obstacles in front of a move, your stuff, your plans, your financial paperwork, all of that. The best time to do that is early so that when those limited options, when the something great comes along, that is the perfect opportunity, you are ready because you've done the other steps. It is higher pressure on you if you want or need to make a quick move into another house. Um, you know, not a community. There's plenty um to choose from of senior living communities. But if you're looking for something in the housing market, be ready because when it comes up, you need to be able to move quickly or it will be gone.

Jodi Rosko 13:34

Yeah. And I we definitely do not, at least here in our area, have enough um single-story ranch home, you know, that are downsizing homes that people are looking for.

Heather Fisher 13:46

Um in a downsizing price point, which people, you know, would love to in a many instances downsize that that payment or the the cost of the home along with the size. Right. And the new construction does not do that.

Jodi Rosko 14:04

That is something that's a different mindset change too to think about is that it it did used to be. You're gonna take your big house and you know, you're gonna trade it for a smaller house that's gonna be less money. Well, this time you might just trade it for another for a similar priced house that is right sizing, right? You're just changing it into, you know, a ranch with maybe a basement or maybe just no basement, maybe just a ranch or a condo or whatever that looks like, but it may not be a whole lot less money than your big house, and sometimes that's hard to wrap your mind around that the space should, you know, cost more, and sometimes it just doesn't, especially if the one you're buying is newer, more updated.

Heather Fisher 14:45

Yeah.

Jodi Rosko 14:46

You know, you may you may be looking at something that's similar, but it's still okay because you're just it's basically you're taking, you know, your your equity and you're putting it from one place to another place and letting it continue to be there and grow, right? And so that's like moving it from one bank account to another bank account. And so you just have to decide what what feels good and what is going to, you know, make your life easier and what kind of place you want to be in. And if you're just taking that going from one place to the next place, you still have it in the safe, you know, place that you're investing it.

Heather Fisher 15:21

Yeah, if you're just looking at the math on square footage, you might be uncomfortable with what that looks like, but if you're factoring in the safety and the security and the ease of daily living, that you are gaining that whole package as well worth every dollar, um, you know, just to transfer that from something that's not working for you to something that makes your life just so much easier. And future planning.

Jodi Rosko 15:48

And I think another thing that we get a lot as a fear or a question is, you know, what if the market goes down? Because if you're listening to the news, um, no matter where you're getting it, the news is never gonna be good. It's always gonna be, you know, these bad things are happening and this bad thing is coming next. And, you know, that's I feel like where the news thrives in, you know, making us fearful of what might be coming next. And so if for if by chance, you know, we do have a downturn in the housing market, um whatever level you are at will be equal, right? So if you bought high and sold high, or you bought low and sold low, it's it's going to be the same. It's going to be a rare uh occasion when you are on that exact precipice of I want the best of both worlds. You know, you you bought low and you sold high. Um and that is, you know, some very very rare little magical unicorn time, you know, pace and time that that that will happen. But mostly what happens is the prices equal out, right? So if you're buying high, you're also selling high. If you're buying low, you're also selling low. And so um, as much as we would want to time out that you know, I think that happens more in stocks than it does in housing. Housing doesn't move quite as quickly usually. Sometimes there can be, you know, some quick moves, but usually not. Um and so again, like you're you're it's really usually going to even out.

Heather Fisher 17:19

Yeah. Yeah. You're waiting for the one to go down and you waited all that time, and then you know, interest rates went down, but now all the buyers that were also waiting came out of the woodwork. So competition is even tighter on everything and prices go up. Prices go way up and you didn't gain anything except you didn't have that time in your new home, making life easier.

Jodi Rosko 17:46

And, you know, we've definitely had people who you know missed their market where to to where they they now the house that they wanted is out of their range, right?

Heather Fisher 17:55

And so I mean, personally, I, you know, sold a house in 2020, but before everything skyrocketed from COVID, it was you know early in that. So I sold at, you know, a price that I had gained equity because I'd been there a long time, but I missed, you know, I still get the the email updates on the old address and you know, cringe at like, oh my gosh, if I would have waited a year or two as prices skyrocketed, you know, that would have been, you know, a wonderful bonus, but it didn't fit my timeline of what I needed. Um, you know, and we just built and had to shift that timeline because building prices changed and you know, all of that, but I wouldn't change the end result. Um, you know, over time we're ahead because we met every timeline we wanted to, and we're where we need to be for our family situation and our plans for the future. Um, so you just don't know. I was thrilled when I sold my house in 2020, like, oh my gosh, I got the all this equity from what the price I had bought it at, you know, 20 years before, I was thrilled. You can't look back and be like, oh, if I would have waited, if I would have waited, you just don't know. It the opposite could have happened with COVID too. Right. Um, you know, where I would have lost out, and you just cannot predict that.

Jodi Rosko 19:25

Correct. So um, so what's more important then is to really focus instead of like what's going on in the market, um, what's more important is to focus on what's the timing of your life and what's happening in your life, and are you actually ready to make that move because that's gonna make a big impact on the quality of your life, right?

Heather Fisher 19:49

Yeah.

Jodi Rosko 19:50

So what what are you what is it that you are looking for? You know, make yourself a list. Is it is it less stairs? Is it less maintenance? Do you want to move out of the area? You want to live closer to your family? Um, do you wanna s you know split that into sometimes I you know I want to two places, right? I want a beach house, you know, beach condo, and I want to, you know, stay close to the family half the year or whatever that looks like. Um, you know, stop paying heat and electricity and dusting rooms that we don't use and you know, all of that. Stop mowing the lawn and weeding the thousand garden beds you thought was such a great idea when you put them in and loved loved that, but now it's you know, it's time for that to go.

Heather Fisher 20:32

Yeah, absolutely. Um, you know, common turning points where people start thinking about downsizing, regardless of what the market's doing. Um, sometimes a health scare, sometimes the loss of a spouse or your partner, um, your kids have moved to a different location and settled and you want to be closer, um, or you just have that fatigue on upkeep of the home. Um, but these start going into more of the critical I want to do this now, especially the loss of a spouse or a health scare. Um, so you can really, when you're timing things, you can be ready much sooner than that and start that thought process. Um, so you're not waiting for these things.

Jodi Rosko 21:20

Yeah, and you you don't want to be making choices out of crisis. And so some of that pops up. You get a health scare, you're fine until you aren't, right? And then you're like, whoa, hold on. And so, you know, you're like, okay, now we need to make some different different choices. Um, but some of it you might be able to see coming. And so if that's where you're at, um, make those choices sooner rather than later.

Heather Fisher 21:42

Yeah, absolutely. Make that plan and be dreamy about it.

Jodi Rosko 21:46

So here's a thought if the market just stayed exactly as it was for five years, so you weren't you knew for sure that that's what was happening and you aren't gonna get anything different, um, would you want to move? You know, ask yourself a question. Question like that. If you are you actually waiting for the market or is there a different underlying hurdle that you need to figure out?

Heather Fisher 22:11

Yeah. I think it gives an easy um excuse to delay decisions. Um, but that final answer is never gonna come as to when will interest rates be at their lowest. I don't know if they went down, is that the lowest, or do you wait more? When will housing prices come down? If they dip a little, are they gonna dip a lot or are they gonna go right back up? We just don't know.

Jodi Rosko 22:37

And and the market is whether it's the stock market or the housing market, um, time inside the market is, you know, th there's a quote, time in the market beats timing the market, right? So it's just the consistency of being there. It's just the compounding interest or compounding equity, you know, whatever that looks like. The so being in it is better than being out of it. And so Yeah.

Heather Fisher 23:02

I think what you said m earlier about the news too, about being just kind of a dramatic doomsday sometimes and and being, you know, national news a lot of the times that might not be specific to your area, that this is one of those categories that information can really help you a bit with that timing. Um, make sure that you're not saying you're timing it to the market, well, I'm waiting because they said interest rates are coming down, or I'm waiting for this market factor, unless you're talking to a local professional, a local real estate agent, a local loan officer that can really give you sound advice that maybe waiting a month or two or waiting a s a short time might be in your benefit for various reasons, or you know, just explaining the information to you because the news is never going to be that that source.

Jodi Rosko 24:05

No, they're always gonna be making it sound terrible. Um so here are here's like some examples of of people, right? We've got the waiter, the one who's just they're waiting. They're gonna wait until rates drop. And um maybe you wait a a couple years before that happens, but what could happen in those couple years, right? Um maybe home maintenance costs go up, maybe you have to put a roof on in, you know, two years later, or maybe um, you know, the HVAC goes out. I hate to say any of those things to happen, but you know, houses need maintenance, and maybe some big things end up being, you know, happening in those couple years. Yeah.

Heather Fisher 24:46

You know, maybe the neighborhood changes, or maybe um monthly costs of upkeep, uh hiring people to do things you can't do anymore.

Jodi Rosko 24:58

All of that factors. Yeah. So what and what are so what are you uh what cost, what is the actual cost of waiting um versus you know, an a point or two on the interest rate? Yeah. Um the lifetimer, right? The single retiree who chooses to move closer to family um but but is waiting, waiting to do that. So what are you missing? What are you missing there? Are you missing watching your grandkids grow up?

Heather Fisher 25:23

Missing simplicity in your daily life so that you have that time with the grandkids.

Jodi Rosko 25:29

Yeah. Yeah. I mean, are you spending your days doing upkeep and not, you know, enjoying the family time that you could be having? So some of it isn't money, some of it's not tangible things. Yeah. Um, what else could you be missing?

Heather Fisher 25:42

Yeah, absolutely. Um, how about the analyzer? Uh they ran the numbers, they would pay more in interest, but they, you know, could gain that better lifestyle sooner, um, but they decided that it wasn't quite you know, wasn't quite worth it emotionally, and they're just pr you know, paralysis by analysis, and they're just constantly running numbers and not really ever just jumping in and choosing the life they want and realizing that there's always, you know, a financial cost to that and just being okay with it. Right, you know, I like this life better. I'm gonna go live it. Live it. Right, absolutely.

Jodi Rosko 26:28

Not waiting to live it. Because uh just like we don't have the crystal ball about the market, we don't have the crystal ball about the time we have in our, you know, here. And so um spending that time in your best possible way um is what you should do. So back to getting dreamy, we're gonna tell you over and over again, because I really feel like it's a step that people miss the most. What is it you want? And then how is that gonna fit into the the decisions that you're making about timing?

Heather Fisher 26:56

Yeah, absolutely. Um just reframing your decision, um, you know, what would be better about your daily life if you moved sooner? What is the cost emotionally, physically, financially of staying where you are? What trade-offs are you already living with by waiting? And just really comparing that to that dream. And here's the reality, how do I move to that dream that I want?

Jodi Rosko 27:26

Because I think like as we get as we because we're ha pe creatures of habit and we stop seeing really what's happening, um, we get to a place where we are living sometimes we see people who are living in situations that are just really not good. And they aren't seeing it. They aren't seeing it. They can't go upstairs anymore, they can't get to their bedroom, they're sleeping on the sofa now. You know, they're, you know, doing things that they're just uh they're giving themselves outs for for it um and not even realizing it because they are living it. So they're too close to it, is what I guess what I'm trying to say.

Heather Fisher 28:04

Yeah, it happens slowly. Yeah. And then it's drastic, but it happens so slowly you don't realize Yeah, and then they're like, it's fine that I you know what?

Jodi Rosko 28:15

But so if that's you, figure out what's holding you back. We have lots of episodes on all kinds of things. Reach out to us if you really have questions, but you know, figure out what's holding you back um if you're really in a situation that's not working for you and you can't figure out how to move forward.

Heather Fisher 28:31

Yeah. So um, you know, guide to decision making on this topic. Um, is your current home still the best fit for your needs? Um, do you feel physically and mentally able to manage a move if you started now? Um honestly, that yes is gonna get weaker and weaker the more that time goes by for all of us. Um, you know, just moving myself, it's exhausting. Right. And it is. So the earlier you do it, the easier.

Jodi Rosko 29:02

And there are move managers. Reach out to us if you have if you have a need for that. If you feel like there's just no way that I can make that happen. We have people who can help.

Heather Fisher 29:10

Yeah. Do you have clear goals about what you want in your next home? That's that dream. Um, have you talked to the right people, agents, and advisors about your market options, your your family included in that? Um, and are you making decisions based on fear or hype, or have you been able to tune out that noise and just make that decision based on what is best for you, your family, and your situation?

Jodi Rosko 29:38

Yeah. So if you have come to the realization that it's time, yeah, um, and you're not gonna continue to worry about whether the market is you're timing the market properly, but it's time for you, please reach out to us. Um downsizingroadmap.com. We can connect you with a great agent that can give you great advice about your market and what needs to happen to get you moving into the next into the next phase.

Heather Fisher 30:04

Yeah, we're excited to help you and we will talk to you again next time. Thanks for joining us on the Downsizing Roadmap Podcast. If you found this episode helpful, be sure to subscribe, leave us a review, and share it with someone who might need a little downsizing inspiration. Have questions or ideas for future episodes, reach out to us on our website, www.downsizingroadmap.com. Until next time, let's keep simplifying and moving forward.