Episode 192: Canadian Retirement Wealth Without Clarity: The Silent Stress No One Talks About

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What if you reached retirement age with over $2 million in assets—yet still felt anxious and uncertain about your future?

That’s the dilemma Jasmine faced. Despite years of saving, investing, and “doing everything right,” she found herself chasing risky trades and second-guessing her decisions after an unexpected layoff just two years before retirement. Her story highlights a common struggle: financial freedom isn’t just about the math—it’s about clarity, vision, and emotional confidence. Without defining what “enough” really looks like, even wealth can feel shaky.

In this episode, you’ll discover:

• How to create personal guardrails that balance security with growth so you can stop second-guessing.
• Why defining your lifestyle vision matters more than hitting an arbitrary number.
• Practical ways to separate “need-to-have” assets from “nice-to-have” investments, giving you peace of mind while still leaving room to optimize.

Press play now to hear Jasmine’s story and learn how to align your money with your vision—not your fears.

Resources:

• Ready to take a deep dive and learn how to generate personal tax free cash flow from your corporation? Enroll in our FREE masterclass here. 
• Book a Discovery Call with Kyle to review your corporate (or personal) wealth strategy to help you overcome your current struggle and take the next step in your Canadian Wealth Building Journey!
• Discover which phase of wealth creation you are in. Take our quick assessment and you’ll receive a custom wealth-building pathway that matches your phase and learn our CRA compliant tax optimized strategies. Take that assessment here.
• Dig into our Ultimate Investment Book List
• Follow/Connect with us on social media for daily posts and conversations about business, finance, and investment on LinkedIn, Instagram, Facebook [Kyle’s Profile, Our Business Page], TikTok and TwitterX. 
  

Calling All Canadian Incorporated Business Owners & Investors:

Consider reaching out to Kyle if you’ve been…

• …taking a salary with a goal of stuffing RRSPs;
• …investing inside your corporation without a passive income tax minimization strategy;
• …letting a large sum of liquid assets sit in low interest earning savings accounts;
• …investing corporate dollars into GICs, dividend stocks/funds, or other investments attracting cordporate passive income taxes at greater than 50%; or,
• …wondering whether your current corporate wealth management strategy is optimal for your specific situation.

Retirement planning in Canada isn’t just about saving—it’s about building financial freedom through clarity, strategy, and structure. From managing retirement anxiety with emotional finance insights to applying tax-efficient investing and RRSP optimization, Canadian entrepreneurs and families can create a wealth management system that balances personal vs corporate tax planning, salary vs dividends, and corporate wealth planning. By setting clear financial goals and using retirement planning tools such as financial buckets, wealth reservoirs, and investment bucket strategies, you can align your financial vision with a modest lifestyle wealth or early retirement strategy. Whether it’s real estate investing in Canada, developing a capital gains strategy, or choosing between real estate vs renting, wealth building strategies Canada demand diversification, legacy planning Canada, and estate planning Canada. With the right corporate structure optimization and financial systems for entrepreneurs, you can achieve financial independence Canada, protect your future, and pass on lasting wealth through smart corporation investment strategies and business owner tax savings.

Transcript:

Jon Orr: Many Canadians nearing retirement have done all the right things. They’ve saved diligently, built equity in their home, and even explored investing. But despite this, there’s still sometimes some anxious feelings. Why?

because wealth doesn’t just come from the numbers, it comes from clarity and alignment. So today in this episode, we’re gonna be talking about Jasmine, a 60 year old CPA who was laid off just two years before retirement. There’s some anxious things happening right there, but despite over two million in assets, she found herself chasing risky trades and considering complicated strategies, all driven by fear that she hadn’t made it just yet. We’re gonna unpack this story.

to reveal powerful truth. Real financial freedom doesn’t just come from knowing the numbers exactly, it comes from whether your investments match your vision and not your fears. Let’s do this.

Kyle Pearce: Yeah, so John, we had this conversation with Jasmine and you know, for those who are listening, we always change names. We always change slight details as well. I had someone call and say on a discovery call and say, are you going to like just openly share all of this information about me? So there are of course small nuances we changed to make sure that people are not identifiable here unless they truly do want to be. So in this particular case, we’re going to talk about Jasmine in this case and

you know, when you are, we’ll call it forced into retirement, or at least retirement for now, like she has here, it really forces you to sort of think about, am I good? And this is one of those challenges that, you know, if you haven’t been thinking about it, and here’s the crazy part, like she’s got over $2 million in assets, and I’m looking at this, she’s doing,

really well, but the problem is, like she’s been doing all the right things, but really skipping over what we call stage one and really thinking about truly what is her vision? What does that entail? And I think a lot of us do this. We’re like, if we just slowly put some money aside, we try to do all the right things, it’ll all work out. And you know what? That may or may not be true.

The reality is though you go, put in my best effort and we’ll see how it goes. And you know, really what we’d like to chat about in this episode is how can we take this scenario and how can we make it less of a guessing game so that we feel confident while we’re working, you feel confident because you know you’re gonna be able to put food on the table this week, next week, next month. But as soon as that job is gone, that career or maybe that business, you hang it up in the business.

or you pass off the keys to the kids or whatever it is that you’re doing now, as soon as that steady flow is gone, it gets very, very scary, very fast, especially if we’ve been using the hope and pray model of just trying to do quote unquote the right things and letting it all play out as if it were just chance.

Jon Orr: Yeah, like, or even just not even having a hope and pray model, just not even thinking about it. And I think, you know, us, business owners, us entrepreneurs, people who are actively building those retirement accounts on their own, they don’t have the predetermined pensions or the predetermined benefits that they’re going to be coming their way where we just know it’s locked in. You’re constantly, like, you’re constantly going like, do I need to tinker? Do I have enough?

These are the worries that come along with the uncertainty of businesses in building, say, these portfolios. And we get to this point where you’re in your accumulation stage and you’re kind of saying, because we talk about that for stage one, it’s like, what is your magic number? What is that retirement number or the fire number? How much do I need? If I’m going to rely on the 4 % rule, how much does the liquid assets, liquid assets meaning

I can convert these assets when it’s time to move from accumulation to withdrawal stages that will fund my lifestyle. And if 4 % is the right number, then I’m constantly going, what’s the right moves to get me there? And how can I make sure I can get there faster or with confidence? And then like Jasmine here, it’s like now I’m there and now I’m still asking that same question.

You know, and it’s probably not because of the 4 % rule itself or just knowing like that I have all of these numbers. I think it comes down to, and this is the part that is really the basis for stage one is knowing what is it that you want your lifestyle to look like and knowing the numbers to help you get there. And I think that’s where the real fear here is. And I think this is the part that we helped her with is trying to just get clear.

You can have anything you want. You just have to say what is it you want? Like do I want this house here? Do I wanna be able to do this? Do I wanna tinker with my own numbers? Do I wanna invest in real estate? Do I wanna, like there’s wants and there’s needs. And sometimes when you cover your needs with the current numbers, it helps you rest at night. It helps you go like, okay, in a worst case scenario, I’m covered because I’ve done that thinking. And then it becomes,

know, gravy on top of that. And I think that’s the real issue here for Jasmine is that we’re not exactly, she’s not exactly sure what it is she wants because if like all options are gonna seem great, it’s just which ones are the ones that are gonna formulate, you know, your foundation.

Kyle Pearce: Well, and you know, a lot of people might be thinking as well, like as you’re listening to this and you say, OK, well, I mean, oh, jeez, she lost her job. She had planned to retire at 62 and had lost this job at 60. However, there is severance. So I think she’s got pay for another year. So she’s essentially, you know, kind of forced and retire a year earlier, but she gets an extra, we’ll call it bonus year of not having to work due to the severance. So.

A lot of people are probably thinking to themselves, like, man, like, I bet I would feel the same way if I was forced to stop working earlier. However, in the reflection, Jasmine said I was financially close to freedom. So she knows that she has enough or feels confident that there’s enough there, but emotionally far from it. And I bet.

This is just a hunch I have based on this conversation. There’s so many conversations we have where we all struggle with this, where that emotional side is the biggest issue here. So even if she went to 62 and she like picked this number, right? A lot of times we pick a number, we go, I want to retire by blank age. That part’s the easy part, because you’re like, okay, I’m gonna set this number. But what we don’t set is how much we actually are gonna need.

how much we actually want, right? Those are two different things too, right? So I might need one number and then I might want another number. And we often don’t say what that is. So we’re like, I wanna retire by this number. We set this arbitrary goal based on age, just like she has. I’m gonna guess that if she kept working to 62, she’d probably be in the same spot, maybe not financially, cause she continues to put money away.

But emotionally, she feels the same way because now this time has come and you go, do I have enough? Like we’re asking the question just two years later and we’re not exactly sure because ultimately at the end of the day, we haven’t set a clear target for ourselves to say, this is what I’m really after and this is what I wanna have. And I think sometimes we don’t do this because we don’t wanna set a ceiling on it.

You know, you don’t want to say like, all I want is this much money. But I doesn’t mean that you’re not allowed to have more, right? Like if you beat that target, that’s a bonus. But like nobody wants to set the ceiling on it, because it’s like, I would like to have an endless supply of money. But the reality is, is that, you know, it’s really in order for it to control your actions so that you actually can be very strategic in what it is you’re going to do financially.

you really have to start doing some of this thinking to at least create what we call guardrails, right? Those minimum numbers and then maybe like more of your ideal number. And of course there’s never a maximum number, right? Like you always would take more, but you just wanna know what these guardrails look like and sound like so you can figure out like if I keep doing what I’m doing now, what’s that gonna look like for me? And do I need to make any adjustments now?

Jon Orr: Yeah, and I think she’s her main, one of the main barriers here, and this is what’s causing her anxiety around this, is really just this kind of constant pull, push and pull and tug between chasing higher returns, but also going like, when do I get peace? Because it’s like, when you’re constantly thinking about that, and it’s like, could,

chase higher returns, but that might mean I’m not in passive mode. I’m not kind of retired, and therefore it’s like, well, what do I do with my time? And she’s in this constant battle between like, I need to tinker, I need to tinker, I need to tinker, but I also, I wanna retire, but I don’t wanna retire because maybe I don’t know what to do with my retirement time. And all of these pieces kind of play into our emotional state when we’re retired, and thinking about what do I do with all my time if I…

If I’ve been in the finance world for most of my career, that’s what I was doing. So now do I stop tinkering? Do I stop chasing returns? There’s that battle right there. I think that’s the part that she’s gonna need to decide. She has to decide, what does that lifestyle look like when you’re retired? What is bringing you happiness? Because if you are truly going, I’m just after enough money.

so that I don’t have to think about or tinker or do anything, then just decide, do I have enough now to do that? If not, continually contribute. Now keep tinkering because you’re not there yet. But the other part about the happiness is maybe she’s really happy to tinker. Like maybe it makes her happy to like figure out should I downsize my home or should I go into student rentals or should I?

buy a Caribbean legacy property for my kids and figure out how to manipulate that and get a good deal on that or maybe I should do private lending with my RRSPs or like these parts, like right before we hit recording I was reading some of these things that she’s tinkering with, these things that she’s like, I could do all this stuff. And I said to you, said, Kyle, this is like what you’re going to be like because the difference between you and me, exactly, it’s like the tinkering makes,

Kyle Pearce: Yeah. Because I’m like it now. Yeah

Jon Orr: like gives you joy. You’re not, you constantly are trying to figure out what’s the best deal here. Where do I optimize these decisions? And that actually I think brings you a lot of joy to try to figure out strategy. And that’s where this podcast came from is tinkering and then figuring, let’s share some of these strategies. And if that brings her joy, then just accept it. Just go, that’s what I wanna do because it’s gonna bring me joy to figure out how to downsize my home or maybe I need to

incorporate so that I can, you know, sell that home to the corporate, like all these moves. And when we talk about our third stage, which is optimization, if you just find joy living in the optimization stage, then just own it. But if it’s not, if it’s like, that’s a means to an end, then figuring out the number makes a lot of like, really needs to she needs to really double down and going like, I do vision envision doing something where I don’t

even think about my finances and if I wanna not think about my finances, then we just need to satisfy how much is enough to pay my bills and pad me for security, pad my lifestyle, maybe set up this over here, the structure over here for my heirs when the time is right. Like having that in place gives you all that freedom. But I think her real battle is I think she’s a tinkerer and she loves it and she’s just not owning it.

Kyle Pearce: Yeah. And you know what? I got a sense that clearly very creative, because everything you just said as options were options that she had brought up on this call, right? So she’s been thinking, she’s doing all of these things. And yes, very much like me in that regard. The one thing that

And I’m trying to become better at this. So again, everything we talk about on this podcast, it doesn’t mean both you and I are like experts in every one of these stages for ourselves. We know how to talk about them, but sometimes putting them in place for yourself can be very, very challenging. And I actually find talking about these things on the podcast very helpful for myself and my own planning process. Because what I found very helpful for me and maybe helpful for this individual, for Jasmine, is

to actually look at your assets that you’re planning to utilize for your financial freedom number. Why I say that is I don’t include my primary residence in that number. Exactly, it’s like some people are like the plan has always been that I wanna downsize and I’m gonna use some of that money for my retirement. Awesome, like there’s no rule around that. Just make sure you know what you’re signing up for. Again, get that target going.

Jon Orr: Right, that’s what I call liquid assets.

Kyle Pearce: For me, I don’t include my primary residence. I’m looking at everything else. And I look at that and I go, if I can accurately set up what I call those guardrails. And if I say like, what’s the minimum I want? The minimum number, I wanna be more conservative and I wanna be more closer to guaranteed. Now I say more closer to guaranteed, cause I’m not necessarily gonna take all of those funds and put them in an annuity for example.

But I do wanna make sure that it’s more solid, it’s less unpredictable for the lower part of that rail, right? So I go, okay, I wanna make sure that no matter what, I’m at least hitting this sort of like, what’s gonna make me feel comfortable and successful? Now for me, that was always like recreating a teacher’s pension since I came out of that industry. was like, I want that as my minimum. Then I look at all the other,

portion of my net worth and I go, okay, with these, can use and do my tinkering, right? Now with tinkering, we don’t want it to be, you know, just random, you know, we want to make sure it’s all about optimization, we want to make sure it’s calculated and that it’s clear. But this might be a strategy that’s helpful for Jasmine and others who are listening who are maybe struggling with this idea, right? Because like, it’s hard not to want to chase a higher return. It is hard because

Everybody wants to feel like, I, you know, I learned something. I’m smarter than, you know, the average investor out there or whatever it is, whatever reason that you want to go chasing. However, we don’t want to chase and lose money or do things, you know, just because now we’re gambling, but at least if we sort of separate it and we get that like minimum and we make sure the minimum is like sort of like solid foundational, we can then look to all of the rest.

and you can stay 100 % equities with the rest. know, like that allowed, that gives you the freedom, the permission to go, I’m 100 % equities over here. Why? The data says it. I want it. I’m okay with the volatility. It doesn’t affect that lower guardrail I was talking about. If I go through a market downturn, not if, but when we go through the next market downturn, if I want to do student rentals, like use that bucket, you know, because guess what?

Sometimes students aren’t always very nice, you know, and things go wrong, right? With rental properties or owning properties in foreign territories. All of those things are definitely possible here, but to me, it’s all about for this individual, it’s getting clear on what it is that you really want and then figuring out what are those two numbers and instead of just the one, because if you put it all into one bucket, sometimes it feels like it’s an all in or an all out. Like I gotta be a hundred percent conservative.

or I gotta be 100 % risky, and you definitely don’t need to do that. You can find a middle ground, and here’s the crazy part, John, each and every year as you get older, you might change your approach a little bit. As long as it’s calculated and as long as it’s based on actual numbers and goals and setting these goals and monitoring these goals, I think you’re going to get closer and closer to that place you wanna be and probably, I’m gonna guess, be. what you had planned for, especially if we’re being conservative in our projections.

Jon Orr: Well, I’m gonna add three, you know, three zones, three buckets. Like you’ve got your, in a way, and this is gonna align with our four stage process for our wealth planning because, you know, stage one is about vision, you know, clarity, what is it that we want it to look like? What we’re talking about here is a big, you know, a big piece of what Jasmine needs to kind of get clear on it and try to make. does this five years look like, 10 years look like? But then the second part here,

is kind of what you’re talking about with like, let’s section off, like have a growth, a growth kind of assets where I get to tinker. But then over here is like, this covers everything. And what I mean by is it covers everything. Basically you’re saying it’s gonna cover, it covers my like lifestyle forever. It’s like that pot is my draining pot and it’s gonna be there forever. But part of that too is go, where’s the wealth reservoir?

You know, like that’s that part too. It’s like maybe that’s included in there. I would like to see it a little bit not included in there because of that, if I’m gonna continually withdraw, let’s say it’s all in a nice mix of asset or asset classes, say on the stock market, between bonds and equities. And it’s like, all of a sudden, that’s where you’re pulling this money, this livable, this expense money from. I’d like to see where does that wealth reservoir look like. One year, two years of expenses.

Ready to go. Now it doesn’t mean that money is sitting there in cash. It means that that money is like for us. We’ve got that in our whole life policies, ready to like get a policy loan in an emergency or we’ve got access to capital. Maybe that’s your HELOC right now. and you’ve got that access to one to two years of expenses if you needed it. It could also act as your wedge. Like what you were saying is all of sudden it’s a down year and you’re not gonna wanna pull from.

this maybe you’re gonna pull from your wedge sources, which could be your HELOC, but it also could be to say like for us that those whole life policy loans, so that we have that. Like I’d like to see that for her as well, because that can help have a lot of peace of mind to say like the tinkering I do over on the third side allows me to kind of be flexible. know my full plan is covered with the middle section.

but I’ve got this safety net over here in case I need to like dip in over there or hey, maybe something comes up and I’ve got, because of my tinkering, I need a little bit more access to capital. Like I like to see three of those buckets for her so that she has a lot more flexibility in allowing her to do, when she does get clear, allowing her to do all the things that I think she really wants to do.

Kyle Pearce: Yeah, I think that’s a great idea. And the beautiful part is, is that there’s no rules here. That’s the good and the bad of all of this, right? It’s like, it’s not one rule that works for everyone. And here’s the crazy part. And the part that I think holds people back is sometimes we stop because of analysis paralysis. And we think like, well, I don’t want to like write it down on paper that I’m going to do X, Y, or Z because now I’m held to it. Well, hold yourself accountable to it until there’s a reason to change it.

Right? So it’s like, yourself accountable, but you’re allowed to change it, you’re allowed to go, hmm, I didn’t think about this, or I didn’t think about that. But it does need to be well thought through. And again, this is all stage one planning, which I would argue is one of the biggest gaps that we see with folks that do reach out, you know, like we have the 30,000 foot view, which is like financial freedom and optionally working and all of these things. But we haven’t

quite defined what does that really look like and sound like for us? And it’s a really, really hard one to answer. And I would argue that it might take an entire lifetime to get more and more clear on it. But the more work we do, the better off we’re gonna be. So John, let’s chat here a little bit about the scorecard. So first off, I’m gonna argue stage one, which is true, which is true for most people that we chat with, designing your vision for freedom.

I would say that we now have a start to this process, right? So we’re gonna say that there’s a lot of work to be done here around really trying to figure out that emotional side is going to stay there until you get more clear that it’s the unknown that your body is sort of like fight or flight on you right now, right? Like it’s going like, I don’t know if I’m okay, if I’m protected, if I’m, will I be able to have enough money in order to do the things I want to do?

Why? Because I don’t know what those things are. So a lot of work to be done here in stage one. John, how about stage two?

Jon Orr: Mm hmm. Yep. So a stage two is kind of what I was just touching on with his establishing a wealth reservoir. And, you know, we we talked about that that could be your emergency fund. It’s your opportunity fund. And currently, this is where I’d like to see her do a little bit more digging a little bit more structuring but

you know, making sure that we have that, whether it’s accessing your HELOC, I know that she’s doing, you know, she’s considering a little bit of that with saying I have some home equity that I might be able to say move towards achieving one of my goals, which might be owning a place in the Caribbean that could be used for rentals or could be used for our lifestyle. I’d like to see her kind of get a little bit more structure of what it is that she’s looking at right there. And I think my recommendation, however, though,

is to not let that be too complex if it prevents the happiness that you’re trying to actually strive for. If you like tinkering, if you like, this is where it dips into stage three, which I’ll let you comment on, which is optimizations. If you like the optimizations thing, then finding the right reservoir can be joyful for you because it gives you a lot of value and a sense of I did this right thing.

I’d like to see that that set up of the wealth reservoir before, you know, tinkering after that.

Kyle Pearce: I love it. love it. Yeah. And into stage three, which again is connected, as you said, nice little segue. When we think about it, whether it’s two buckets, whether it’s three buckets, like John’s talking about, what we want to avoid is tinkering with it all. Okay, like tinkering with it all is not a good move, even if you got lucky and pick the right tinkering thing to do. Right. And but let’s be real, there’s some work to be done. And if you don’t fully understand exactly what it is you’re going to do because

Here’s the thing, it’s not tinkering if you fully understand it, if you fully are confident in it and you know exactly what that system, that process looks like, it’s not tinkering, right? It’s like, it’s just, this is the move we’re gonna make and here’s what I’m predicting is gonna happen and I fully understand these risks and here’s how I’m gonna mitigate those risks. You wanna make sure that you’re not utilizing everything and.

pushing all the chips into the center of the table when you’re trying to take something on, especially right at retirement time. How many times do we get people that are optimizing? They wanna optimize using the Smith maneuver right at retirement time. We get it all the time. Well, Smith maneuver is like a long-term play. So can you do it at retirement? 100%, but not with 100 % of your assets, right? So we wanna make sure that we’re being very strategic here.

We’re not demoting the idea of tinkering or trying new things, but just make sure that you do it gradually and over time to build confidence. And as you build confidence and build expertise, you are reducing risk because risk is the unknown. So the less unknown you have, the better off you’re gonna be, the more certain things become and the less risky, the less gamble like these types of moves are.

Jon Orr: Stage four is our legacy in a state strategy and she’s starting to think about this. was conversations in our discussions about legacy, leaving value for her children. So she’s already thinking about that. Now the part about structuring what that looks like is kind of like, I’m gonna kind of like say hold off for now on this because she’s got some.

digging to do with stage one and then optimizing stage three here for sure. But she could be utilizing a little bit more of that permanent life insurance policy that could be the wealth reservoir to actually plan for how to pass on assets at say a tax advantage level. So we’ll leave that for her as a next step once stage one, two and three are kind of a little bit more optimized.

Kyle Pearce: Hey, listen, this is a common situation. I’m sure there’s a lot of people listening that are going like, you know what, I kind of feel like that, even if you’re 10 years from retirement, or maybe it is at retirement time, or maybe you are retired and you’ve been like asking yourself like, you know, am I spending the right amount? Am I not spending the right amount? What should I do? Am I doing the right thing? There’s a lot of that uncertainty going on. So stage one is so critical, so important. If you wanna find out,

more about what you can do to get a hold of your own personal or corporate financial situation, you should head on over to our assessment page over at canadianwellsecrets.com forward slash pathways. And you can take our short assessment so that you can go through the four stages and get some of the things you’re doing well and some of the areas you might want to focus on next. And of course, if you believe it’s time for you to hop on for a discovery call.

you should head on over to Canadian wealth secrets.com forward slash discovery. And we’ll chat on a conversation and who knows maybe you’ll be our next Jasmine on one of these upcoming episodes.

Jon Orr: Just reminder, content you heard here today is for informational purposes only. You should not consider any such information or the material as legal tax investment or financial advice. Kyle Pearce is a licensed life and accident and sickness insurance agent and the president of corporate wealth management here at Canadian Wealth Secrets.

Canadian Wealth Secrets is an informative podcast that digs into the intricacies of building a robust portfolio, maximizing dividend returns, the nuances of real estate investment, and the complexities of business finance, while offering expert advice on wealth management, navigating capital gains tax, and understanding the role of financial institutions in personal finance.

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