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Jill
welcome to the Jill on Money Show. It is Tuesday, May 19th and we are here trying to help you make better and sometimes less bad financial decisions. If you've got a question about anything going on in your financial life, all you need to do is get in touch with us. Go to our website jillonmoney.com click the contact Us button, write us a note, and if you'd like to join us live, check the box. Mark will do everything else while you're on the website. Don't forget to subscribe to our free weekly newsletter. It comes out on Fridays. It will also entitle you to our blog post, so check that out. One other thing, you also should check out Jill on Money Live that is where you have access to quarterly live webinars, the back catalog of those webinars, bonus audio and video content, and it costs you just 45 bucks for the next 12 months. Our next webinar coming up in just a month is on Social Security. We have a Social Security expert who is amazing. In fact, when you guys come in, come onto the program, and you ask really hard Social Security questions, what we do is we contact this expert, Heather Schreiber, because she knows so much about the system. So if you'd like to join us, become a member of Jill on Money Live. If you don't want to make that big commitment, your commitment phobe, then all you need to do is click on the box where you can purchase the single webinar for $15. You don't get to participate live, but you do get the content and it's pretty great. Okay, Today we are talking to Aaron from Seattle. Now, Aaron, here's the thing. I just spoke to our friends at Cairo Radio this morning and the anchor told me you're well over six bucks a gallon right now in gas. So what's the mood in Seattle?
Erin
We sure are that high. It's pretty crazy. So. Yeah, it's tough. It's very tough. I think we're the highest or one of the highest in the country.
Jill
Incredible.
Erin
I am fortunate because last year I switched over to an ev.
Jill
So what timing. You're. You time the market beautifully. Holy smokes. That's great.
Erin
Yeah, I haven't purchased gas since December of 24.
Jill
Oh, my God. Well, that's kind of like Mark, except that his. His reason is because he hasn't driven. Have you filled up your tank yet, Mark, or not? Is it. Have you filled up your tank this year?
Mark
Yeah, no, I just did last weekend. So I'm probably good until, I don't know, the holidays.
Jill
Oh, my God. So, Lindsay, you love your ev. You're all in. Why are you coming to us today? What is it that we can do to help you out?
Erin
So my husband and I got started kind of late ish in our career with our retirement savings. And we are talking about retirement and trying to dial it in so that we know exactly when we can so that we've got the freedom to do that. We have four kids and they're all grown, they're all launched except for the cell bill. And I know you're going to give us grief about that.
Jill
I don't know what it is. It's. That is the last one that remains.
Erin
I know, I know. Mama bear, you know.
Jill
Okay. Four kids that. Congratulations, that's well done.
Erin
Thank you. You know, they're amazing humans and they're all doing their own thing and you know, so we focused on them for quite a while and we were moving a lot with work and that kind of thing and we, we lost sight of the retirement savings. So then we had to kick it into high gear. We've been saving with Earnest and we just like a second opinion, you know, to see if we're in good shape and if there's anything different we should do.
Jill
Okay, so first of all, how old are you and how old is your husband?
Erin
Okay, so I'm 55 and my husband's 59.
Jill
And you're both working full time now and we are.
Erin
I'm in a corporate job and my husband actually owns his own business and it's based in Canada.
Jill
Oh.
Erin
We, but we live in the Pacific Northwest.
Jill
Okay. How much do you earn, Aaron?
Erin
So I'm at about 290, including my bonus.
Jill
Okay. Does he draw a salary or does he get S Corp dividends or like what's the sort of. What does his income look like?
Erin
Yeah, he draws salary. So his is like 400,000 Canadians. So that's approximately like 295 US so we're pretty close.
Jill
That's great. Now that you guys are refocused and looking ahead, tell us how you have accumulated retirement assets. What's going on?
Erin
I started contributing to my 401k through work with Earnest once my eldest son gave me a kick in the butt. And so yeah, it's at 558 and 80% of that is traditional. And then just last year In January of 25, I switched to Roth and there's a company match of 5% dollar for dollar.
Jill
Like every for your. You put five in, they give you a full 5%.
Erin
Yeah.
Jill
Okay, that's great.
Erin
And so I'm maxing that and have been.
Jill
And when you say just want to make double check, you're maxing it with the catch up contribution of being over the age of 50.
Erin
Yes.
Jill
Okay, got you. Good. Great.
Erin
And then I also have an employee stock purchase plan that became available to me a couple of years ago. And so I'm also maxing that you can do up to 15% of your pay. Of course it's capped at 25,000 annually. So I do that and that's done quite well. So I'm really glad I did it as soon as they made it available. I have a Roth IRA and we do backdoor conversions. So I've got 60k in that. My husband has a Roth IRA as well, and he's got 54k in his. We have a couple brokerage accounts, one at 77 and one at 425.
Jill
Wow, it's a lot. And you guys are managing this yourselves?
Erin
Well, the one that's 77, I'm managing myself. The one that's 425, we have an advisor managing it. So the 77 kind of started as my fun money. Like it was much slower and I wanted to see what I could do with it in a really aggressive format. So it's done really well.
Jill
Great. I mean, it's a good time to do it if you're going to be aggressive. The last few years, I guess. Yeah.
Erin
And I got all into AI.
Jill
Oh, boy. Here you go.
Erin
I know, I know. So it's risky. I get it. And I know I'm kind of old to do that, but, you know, it's a smaller percentage of the overall scheme of things.
Jill
Okay, understood. So let's just like backtrack here. So we've got the 401k, the employee stock purchase, the Roth. The Roth. The brokerage. The brokerage. What about your husband's retirement? Is a Canadian that. You have a funny you. He must have that Canadian Retirement System accounts or not.
Erin
So he has. Well, so we both do because I used to work in Canada or before we moved here and became US Citizens. So.
Jill
Okay, wait a. Before we go that. So before we do Canadian assets. So we've got all the retirement accounts. We got the brokerage. Do you have some cash in US domicile banks? How much is in there?
Erin
Yeah, we have 100k in a high yield savings.
Jill
Okay.
Erin
And I also have an HSA with 55.
Jill
Oh, great. But you are US citizens now.
Erin
Yeah.
Jill
Okay, good. I never really include the HSA because I just presume that's all going to get spent, which is great. I mean, it's good to have it. So I don't really look at it too much on the balance sheet, so. And you own a home in the
Erin
U.S. yes, we do.
Jill
What's that worth?
Erin
So the house is worth 2.5.
Jill
Oh, boy. Hello, Seattle. Okay. And is there a mortgage?
Erin
There is. So we've got 417 on that.
Jill
What's the interest rate?
Erin
2.89.
Jill
Oh, my God. You're never leaving. Do you love it?
Erin
I love it.
Jill
Okay, good. That's good. Okay, we got the. All the US assets accounted for now?
Erin
Not quite. We also have a vacation Home.
Jill
Oh, all right.
Erin
Yeah, we. And. And it's appreciated fairly well. So it's probably worth about a million. And we've got 313 and a mortgage on that and 2.9.
Jill
And that's not something you're interested in selling. That's something you want to maintain.
Erin
Yeah. So our thinking was that when we retire, we would sell the primary and get that equity invested to work for us as part of the catch up plan. Okay. And that we'd move into the vacation home for at least two years so that when we sell it, we can avoid gains on it. Yeah.
Jill
Okay, that's good. And obviously there's, you know, $2 million. You will pay some taxes if you were to sell your primary. What. What price did you pay for it? And fluff it up a little bit, presuming that you put some money into it. So give me, like, what you think your cost basis is of the primary house.
Erin
Yeah, like a million.
Jill
Okay.
Erin
Yeah.
Jill
So everyone listening. Don't forget that, you know, when you sell your home and you're married, you can exclude a half a million dollars of gains of whatever your capital gain is. So there'll be some taxes to be paid. But Erin and her husband have money, and they could certainly afford that. So. And, you know, listen, housing prices have gone crazy. This is the downside of it. But it's still worth it, you know, to think about selling. If you are interested in doing that, Erin, would you prefer if money were no object? Would you like to stay where you are?
Erin
I love my house. Yeah, like if. If. Or for a while, like. So we were thinking that as soon as I retire, we'd have to sell the house to get the money working for us right away. If there was a way that we didn't have to do that immediately, like maybe stay here for a few more years, that would be awesome. Just, you know, But I. I also understand that that's, you know, the big piece of what we've got.
Jill
When you think about retirement, what are we targeting in terms of your ages?
Erin
Well, we had been thinking 60, and so that was our original plan. And then you have tough days and you go, I can't do this anymore. Yeah.
Jill
You say 56.
Erin
Yeah, exactly. We started, like, looking at different scenarios, and our advisor said that, you know, we could go with my husband at 60, so next year, and then I could do 57. And that would get us, he said, a 98% success rate.
Jill
That Monte Carlo simulation.
Erin
Yeah. Yeah. But I love a second opinion, which is, you know, why I Called you guys.
Jill
What's the Canadian asset level look like?
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What do you got?
Erin
Yeah. Okay, so I have a retirement savings plan there that's got 260Canadian and that's pre tax. And then my husband's got an RSP that's got 802 Canadian. So like 558 ish.
Jill
And also pre tax.
Erin
Pre tax.
Jill
Yep. Okay, got it.
Erin
And. And then we've got about 300,000 in Canadian cash that is just there if my husband needs it for cash flow, you know. But that's. That's our money. So.
Jill
So I mean, the million Canadian is what, 600 something? 650 U.S. is that right?
Erin
Yeah.
Jill
Okay, you ready for the hardest question? I can't believe I'm asking you so late in our conversation, but how much you guys need to. To create an income when you think about retirement?
Erin
So right now we spend about 12,000amonth. And you know, once we sell one of the homes, like the primary home, that brings it knocks it back by like six grand.
Podcast Advertiser
Oh, so that's interesting.
Erin
Yeah, so there's that. But, you know, we also know that we'll want to travel and, you know, we hope to have grandkids one day and be able to do fun stuff with them. So I want to make sure that we're allocating enough. So I think it's good to plan on 12, even if we don't have to spend that much.
Jill
I got you.
Mark
What happens to his business? It just shuts down or does it?
Jill
Good question, mark.
Erin
Well, so he could just dial it back and go slower into retirement, which I think is realistic, what he will do because he's got some really great clients and he wouldn't want to just cut them off. So. Yeah, so he'll probably phase it out.
Jill
And what have. Do either of you have a pension benefit that is associated with any of your previous jobs or current.
Erin
Oh, I wish. No. No.
Jill
Okay.
Erin
No.
Jill
If I were to look at the Canadian assets again, let's just presume he kind of scales back. When you say the. The pre tax assets, could you roll those into the US Assets or not? I don't think you can. I bet you can't. Yeah, we'll liquidate, right?
Erin
Yeah, we'd have to liquidate.
Jill
Yeah. Okay.
Erin
Yeah. But so our financial advisor had recommended that that's what we draw from first, because should we die and still have money there, then it gets taxed at like 50%.
Jill
Oh, yeah. So we want to get rid of that fast.
Erin
Yeah.
Jill
So I think that's Great advice. You will both be. Because you're U.S. citizens, you'll be entitled to Social Security. Yes.
Erin
Yes.
Jill
Okay. Mark, how do you think Erin and her husband are doing? And must they sell the $2 million house, the two and a half million dollar house to get their retirement goals set in stone?
Mark
I think they're doing great. You know, considering that she thinks they got a late start. I mean, they have over $2 million, and that's not even including the real estate, so they're doing great. Do they have to sell that house? I mean, probably. I don't think it has to happen asap, but that's what I was thinking. Eventually it'll be sold and all of your problems will be solved.
Jill
Yeah, I mean, I think it's one or the other in some respects that you need a little extra liquidity. So I think there's a few things that can happen here. First of all, if your husband goes. Let's say that your husband's like, okay, starting next year, I go from making 290 in U.S. i'm gonna. Let's, let's talk about U.S. dollars. I'm gonna go from making almost 300, I'm gonna go to 200, and the following year I'm gonna go to 150. And, like, he scales back and you guys can keep living your life and saving and doing what you need to do. And you get to your age 60, I think you reassess whether or not you really need to sell that house, you know, in a timely fashion. I hate to tell you this, because I almost feel like I don't even want you to think. Of course, from a tax perspective, the idea that you could move into the rental and live there for two years is so exciting to me. And, you know, avoiding any taxation. On the other hand, I want you to live where you want to live. And so I'd like to be able to. And again, if you're, if you're, does your advisor think that you must sell the house to make this work at age 60?
Erin
No, but. Well, my, my husband does.
Jill
But when you said that 98% probability of not running out of money with. So everyone, this is a kind of a mathematical analysis that' lot of financial advisors use, and it is kind of cool. So it's a statistical analysis of, you know, what is the likelihood that you're going to achieve your goal. And he's saying holding the house, you have a 98% probability of reaching your goal. Right?
Erin
No, he, he did factor. He would sell the house. Yeah. Okay. Yeah.
Jill
So, I mean, I think that, that, you know, I trust, I always like to trust the numbers. But, you know, also things can happen. Maybe you say to your husband, well, if we really love the house, maybe
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I'd keep working a little longer and
Jill
see if we can figure it out. Or maybe I love that. Or maybe it's like, you know what, we don't really use this vacation home. Let's just sell it. We'll pay whatever taxes do and that's fine. Or I do think there's going to be some way to look at this and maybe you would say, I'd rather hold on to the house and, you know, for a couple of years and work a little longer. I don't know. It really. It's going to depend on like the, the cross section of how you feel and how important it is to stay in this house.
Erin
Yeah, yeah.
Jill
It is a lot of money. It's like, you know, that that's a, it's a lot of equity that's in there and you'll pay some tax on it, but who cares, right?
Erin
So other question. So when we do sell it, should we pay off both mortgages or.
Jill
No, no, no, no. You have to pay. You pay off the current and then you move into your vacation home. Don't pay that off. Absolutely not. I love.
Erin
Sorry about that.
Jill
No, your dog agrees with us. Yes, that's the takeaway. No, don't pay off a 2, don't pay a sub 3% mortgage. We need liquidity. Right. So it's like pay off the house. The, you know, you have that you'll have to pay off the house. Right. The current, the primary $417,000 mortgage. Pay that off, roll the proceeds, after tax proceeds into the brokerage account. You'll now have this, you know, your, your 400. I presume that the broke that the advisor is going to take the lion's share of that. But you know, it's going to be, it's going to be a, a real number that is significant. That added, that's added to your brokerage account. Now, the brokerage account is going to have a million and a half dollars or so. Right. Maybe more. You'll invest that and you'll see how you, how you know, you feel. And I would move into the. If you'd like it. I mean, if you, if you're like, I'm done with all real estate and we just want to rent or one of your kids got married and moved to the east coast, like there's all sorts of things that can happen. And I know there's. So I want there to be, like, optionality for you. You have the most optionality by selling the house. That's. That's what's clear to me.
Erin
Yeah.
Jill
But also, you know, I don't want to be a dream crusher because you guys are in good shape. And frankly, if you said, I wanted to work for 10 more years, you probably could figure out how to hold on to the house, but that might be too long for you.
Erin
Yeah, 10's probably too long. I mean, there's days when I think it needs to be next year twice.
Jill
And I'm hearing that loud and clear, my girl. I know what you mean. There are days you're like, why am I doing this? I've saved all this money, and if I just blew out of the house and got that equity, I'd be in great shape. Right. So I understand that. And I think that if you can let go of the house, you will have many more options. Absolutely.
Erin
Right.
Jill
Absolutely.
Mark
It's almost like year by year.
Jill
Yeah, kind of. I would retest it. I mean, and you're working with an advisor, so I think that's a beautiful thing in that they can really retest the assumptions every year and they can say, okay, this is what happens if you spend 12 grand. Here's what happens when you spend 10 grand. Maybe you'd rather have that. Okay. Maybe, you know, you're saying, I want to spend 12 grand no matter what. Maybe it might make you feel better to know that you could do. You could leave your job in a year when your husband retires, if you're willing to say, we're not going to do 12 grand. We're going to sell the house and we're going to do 9510. Have the company you're working with model different scenarios. A lot of people are in this situation where you have a lot of home equity because the housing market has gone bananas in the last 10 years, and as a result, you build up all these possibilities in the house, but it requires you to sell the house, which can be kind of a big deal for people. I get that. So I want to. I'm acknowledging that. I know it's a big deal, but it would be great to unlock all the potential of having that money and giving you more opportunities.
Erin
Yeah, yeah. And I get that. And I'm going to be okay with it. I just. I. I like the idea of a ramp.
Jill
Okay. Me too. I like an off ramp myself. I'm in your. I'm totally where you are, which is. I like the idea of knowing I can dial back and be like, oh, okay, here's a glide path to get to where I want to go doesn't mean it to be so sudden. And I think that that will be especially for your husband. If you own your own business, you know how hard it is. You know, everybody who has ever owned a business knows it's hard. And you want to give yourself a way to kind of gently land without, you know, coming down, you know, popping down from the sky from, you know, 10,000ft straight to the Runway. I hate to use a. A an airplane analogy with someone from the great state of Washington where Boeing has had so many problems, but that said, we want a nice, smooth landing, and I think you guys can do it. And I think that you know where the next moves come from. I presume because you have all these assets all over the place that you have done your estate planning, is that correct?
Erin
We have.
Jill
Fabulous. And how much is your advisor Canadian, or is your advisor US Based?
Erin
He's US and he specializes in cases like ours. You know, where you've moved and you've got assets in both countries.
Jill
You are in very good shape for someone who got a late start. Aaron, you and your husband, you should pat yourselves on the back. Go have a little champagne or wine or go out and hike and don't enjoy your electric vehicle. And know that you have a lot of options ahead of you. So we wish you the best of luck, and we're so delighted that you got in touch with us today. Hey, are you like Erin and her husband? Do you have a ton of equity in your house, but you're kind of worried about unleashing it and selling? And where would you go next and how would you do that? And how do you create a glide path and how do you get where you want to go? Get in touch with us. Go to jillonmoney.com, click the contact us button, write us a note. And don't forget, if you want to join us on the air live, check the box. It is so much better when you come on live. It really is. Don't forget to subscribe to the free weekly newsletter, which comes out on Fridays. You can subscribe to this show and all of our shows on the Odysee app or wherever you find your favorite podcast. Please, if you would not mind, do something nice for someone else today. Change your work, change your wealth, change your life. Thank you for listening and we'll talk to you tomorrow.
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Host: Jill Schlesinger, CFP®
Episode Date: May 19, 2026
In this episode, Jill Schlesinger answers a listener call from Erin in Seattle. Erin and her husband are approaching retirement after a late start on savings and want a second opinion on their readiness. The episode focuses on retirement planning strategy, juggling U.S. and Canadian assets, home equity, and the emotional and financial calculations that go into major life decisions like selling your home. Jill uses her signature, jargon-free style to uncover actionable insights and reassure listeners facing similar questions.
[03:35–05:30]
[05:30–09:23]
[12:29–14:55]
[15:22–19:05]
[16:15–17:11]
[19:35–24:13]
[23:58–24:05]
On a late start:
“We lost sight of the retirement savings. So then we had to kick it into high gear.” – Erin, 05:02
On home equity as a retirement asset:
“I trust, I always like to trust the numbers. But, you know, also things can happen…How important it is to stay in this house?” – Jill, 18:49
On the trade-off:
“You have the most optionality by selling the house. That’s what’s clear to me. But also, I don’t want to be a dream crusher because you guys are in good shape.” – Jill, 21:14
On gradual transitions:
“I like the idea of knowing I can dial back and be like, oh, okay, here’s a glide path to get to where I want to go. Doesn’t mean it has to be so sudden.” – Jill, 23:01
On success:
“You are in very good shape for someone who got a late start. Erin, you and your husband, you should pat yourselves on the back.” – Jill, 24:13
For listeners with similar situations or questions, Jill recommends reaching out for a personalized review and subscribing to the show and newsletter for ongoing guidance.