Episode 198: Wealth Analysis Paralysis: When Too Many Wealth Options Hold You Back

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Are you doing “all the right things” financially, yet still wondering if it’s enough—or what to do next?

That’s exactly where Victoria, a 40-year-old dentist, finds herself. She’s saving aggressively, investing smartly, and has multiple wealth-building strategies in place—yet she’s stuck in the fog of decision-making. Should she buy another property, expand her business, or simply enjoy what she’s built? If you’ve ever felt paralyzed by options, unsure of whether you’re on track or what your future should really look like, this conversation will hit home. It digs deep into why financial “optimization” isn’t enough unless you first know your true vision for life and retirement.

In this episode, you’ll discover:

• Why defining your lifestyle vision is the missing first step in any wealth plan.
• How to identify your financial “floor” so you can make confident decisions without fear.
• The hidden risks of analysis paralysis—and how to finally move forward with clarity.

Press play now to learn how to align your money moves with the life you truly want.

Resources:

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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.

Smart financial planning is about more than chasing returns—it’s about aligning investment strategies with your life vision. In this case study, we explore how Canadian professionals can use corporate wealth planning, RRSP optimization, and tax-efficient investing to meet long-term financial goals. From real estate investing in Canada to deciding between salary vs dividends, the right mix of financial buckets creates a resilient wealth reservoir that supports both modest lifestyle wealth and ambitious early retirement strategies. With guidance from experienced financial advisors, entrepreneurs can design a clear path to financial independence in Canada, balancing personal vs corporate tax planning, capital gains strategies, and corporation investment strategies. Whether it’s estate planning Canada, legacy planning, or building reliable passive income, the key lies in financial vision setting—knowing not just how to grow wealth, but how to design the lifestyle it makes possible.

Transcript:

Jon Orr: In this episode, we’re gonna talk about Victoria, 40 year old incorporated dentist who, like many professionals, has done a lot of the great moves that we’ve talked about here on the podcast. She’s got all the right structures in place. She’s been doing all the right optimizing moves. She’s built up her corporate savings. She’s got high retained earnings that she’s making appropriate decisions with. She holds a high early cash value whole life policy as her optimizing in her wealth reservoir.

She’s maxing out those personal RSPs and tax-free savings account, even owns a pre-construction condo. But despite all of that, Victoria is still a little stuck. And this is, a lot of our clients get stuck like this and they, she’s wondering, should I invest in another condo? Or could I go to the private lending group? Should I buy another dental practice? Or should I just keep working? Or maybe I’m, I’ve done enough.

Maybe I have enough for retirement or maybe I’m missing something. And you know, what is going to unfold here is this powerful conversations we had with her that reveals, you know, a truth that many of us and many high income professionals like you are facing is that how do we know what we really want to do? And that’s what we’re going to unpack here. So Kyle, let’s get into some of the details. Let’s go to it.

Kyle Pearce: Yeah, you you bring this up. This conversation was a great one. And we dug deep here because it’s a great example where we have an incorporated business owner doing what we call, quote unquote, all the right things, right, is being diversified in the buckets, has been saving a significant amount. You’ll also notice, well, like we even said, like on the personal side, doing your great job, maxing out our SPs, got money into tax free savings accounts. Some might go.

Wait a second, like how does that make any sense? Aren’t you gonna pay a lot of tax to get more money out of the corporation? Well, guess what? She has a spouse that earns a T4 income and it’s fairly significant. So there’s some advantages that sort of come into play when you’re in a position where you have less control with one spouse’s income and more control with the other spouse’s income so that you can kind of move these levers and optimize. And the reality is, is that there’s a lot of amazing things going on, yet, however,

The big question is, like, what do I do next? Am I on the right track? And what should I do as the next step? Because we have some of these tools going on. We have real estate going on, which is great. Primary residence owned, rental property owned, fantastic. We’ve got corporate owned life insurance, which is a financial foundation, a nice cash reservoir, as you mentioned, inside the corporate structure, not leveraged as of yet. And…

Also a lot of money in the markets, right? Through registered accounts and also corporate account as well. And continuing to fund, I believe the policy is getting funded around $70,000 per year of retained earnings into the policy. Now, of course, it’s a flexible policy, which is great, meaning it doesn’t have to go all the way up to 70, can actually go much less, 25 to 30-ish or so on that policy. But with those extra retained earnings, she’s putting them there.

contributing $30,000 $40,000 typically each year in the corporate investment account. That is great as well. And still, based on the income that she’s been pulling personally, is still maximizing those RSPs and again, using spousal income in order to help on the tax-free saving side of things. So the big question a lot of people might be wondering is like, what gives here?

Jon Orr: I like that bucket.

Kyle Pearce: are aren’t you doing all the things and it really what what we kind of recognized along the way is that you know she’s not exactly clear on what it what what it is that she wants down the road you know so there’s a lot of things on the radar and and really yeah like sometimes we get into where we’re optimizing and

we can always optimize further. Some people do this almost like as a hobby. would consider myself one of those people. I’m always curious, always trying. But the hard part is you’ll never figure out whether you’re on track or not if you’re not sure what the destination is supposed to look like. So for a lot of people listening, you might be like, my gosh, I only wish that I had been doing what this individual has been doing. For others, you’re going,

I’m doing that as well and I feel confident that I’m going to reach my goal. And then there’s probably a big chunk that are somewhere in between going like, yeah, like, is that enough? Like you might be leaning in right now going like, is, that going to be enough? And the challenge really comes down to is like, what does that target look like and sound like? And that’s sort of where we ran into the biggest hurdle with this particular individual.

Jon Orr: Yeah. we’ve talked and talked about, know, we talk, this is our recommendation here, this episode, you know, the lessons we’re trying to give here is solely living in stage one of our financial and wealth planning blueprint and process, which is, know, envisioning the target, you know.

while we’ve talked a lot about like, what is the number target? You know, what is what is the amount that we really need to live on? Like, there’s that part, like we’ve talked about that on different episodes, which she needs to know, like she does need to know, like, what is what is this? So if she is relying on 4 % rule or pulling pulling, you know, a pension or making herself a pension, she can she can figure out what that looks like. However, I want to like talk about like, what is what is like the lifestyle in the work?

Like what does your day to day look like? Like having a snapshot of what it is is acceptable for you and ideal for you is also extremely important because some of these decisions will be made that way. Like for example, like should I buy that business? Like I could buy another business but does that mean I’m now adding more time to my work life and therefore I’ve got another job and I’m now working longer?

to do that and if that’s part of my plan, then great. You’ve got that part figured out. Your time spent, because it’s not a passive source. You’re operating a business and if you want to use that as an investment, sure, but you now have a job or now have work to do and if you’re going, but that’s what I like to do. I envision myself till I’m 80 years old, 75 years old, just being active all the time.

in the businesses, then that makes, that sounds like a great decision for you, but that’s not a great decision if you’re like, no, I’m gonna be the person sitting on the beach earning passive income where I don’t have to do anything. So then it’s like, okay, so maybe the portfolio route is the better move for you to try to like get, you know, structure and optimize these pieces to get more over here and more over here and get these investments rolling over here so that you can safely go, I don’t have to be relied on anywhere, you know, and anybody.

It’s like, I’m okay with doing nothing with my time that’s active. Or you might be like, but actually that the way I envisioned that part of my life is I’m going to be tinkering. I’m going to be buying, I’m going to be selling. I’m going to be trying to like follow the macro environments. I’m going to be trying to position my portfolio. I’m going to be building that asset as my full-time job when I get there. And that’s okay. That’s what I really want to do. It’s like, okay, then that’s great. Basically all pathways are right. You just have to decide what the trade-offs are.

And a lot of times it’s I think when we’re having conversations with business owners, they haven’t clarified what that is. Like is that the way you see your life? Because that can help decide on what asset to buy now or where or what asset class to send your money in because you can optimize all day long. But you could optimize on the wrong things for you. And I think that’s, like I was saying, the number part is easy for us to calculate. It’s you have to get clear on what do you want your actual day to day to really look like?

Kyle Pearce: And this is exactly that. What I would argue is not only for Victoria here in this conversation, but also for many of the people in our community that do reach out to us for calls. And this is kind of what we help you to shape. Because along the way, sometimes we get nervous to sort of state what that will look like. It’s almost like we say, if we say it now, there’s no way out of it later.

When in reality, it’s more or less, it’s going to be a moving target, but at least you should have a target in mind of what that could look like. And of course you can modify as you go. But at the end of the day, if you’re going, listen, this is an incorporated dentist who owns a dental practice. And it’s like, you really have to do a little bit of soul searching before you say, should I open up another dental office? She knows she can do it successfully. She’s done it. Do you enjoy it? Right? And if the answer is yes,

seems like a fairly logical next step in terms of investing. But if you’re saying, actually don’t like it, or I would actually only like it for maybe 10 years, and then maybe I’ll sell it. These are the things we have to get clear on. Because then there was a discussion where it was like, should I buy more real estate? Maybe in Florida. And then it was like, maybe it might be for me to use sometimes, but then also use it as an investment. There’s a lot of things that we could do. And the beautiful part,

And the hard part is that all of them could be correct for you, but they could all lead to different, very different places. And we have to be really clear. We meet some people that are like, I’m thinking of one client in particular and, this, this client, John, might be able to guess who this person is, but this person was like, they literally put money in.

and they dollar cost average into their policy. And then when the market goes down by more than 20%, they borrow against the policy, dump it into the market and they just shut their eyes. Like they don’t actually care about what happens to the market and they just go and that’s great. I could not do that. Like you know me, John, like that’s not me. Is it right for them? It’s perfect for them, right? Because they don’t have any of that emotion. They don’t have any of that.

you know, concerns, stress, worry, and it’s, it’s a great move for them. They don’t invest in real estate like we do quite a bit. They don’t do, they don’t want to open up another business, right? They want to be more passive and neither one is right or wrong. And ironically, I think in my opinion, the thing that is a better fit for you to help you get to your goal is probably going to lead to the greatest overall return over the longest period of time as well.

Whereas I think what holds us back is you go, which one’s gonna be the better investment? Should I do, should then mention private lending? Should I do just indexing into the market? Like all of these things are gonna lead to different potential results. But here’s the thing, if I index into the market and then I pull it all out when the market’s down 20%, that’s gonna be a really bad move, right? And the same is true if I want to invest into a new business, but I’m not willing to put the time and effort and energy into it.

in order to make it successful. So I have to get really clear here. And then once we know that, we also have to figure out like about how much, like what do I want my lifestyle to look like? And I like to add this keyword as a bare minimum. I don’t want your lofty goal. I want you to think about like, what would make me feel comfortable and confident in retirement? And that for a lot of people is usually what a pension does, right? They go,

The pension’s going to be my baseline. That used to be you and I, John, when we were working in the education sector. Now we use our corporate wealth reservoir, our whole life policies to represent that portion. That doesn’t limit me from all of the other upside we can have by investing the difference, investing the rest, or even borrowing against that policy and putting it into investments so that in my mind, I know I’ve checked off my base case.

and there’s still a huge opportunity for upside, that allows us to think a whole lot more clearly on what we want our financial freedom years to actually look like and sound like. And therefore, which paths should we take in order to get some of that extra upside that we’re looking at in terms of risk on assets?

Jon Orr: Yeah, that’s the benefit of knowing the number, you know, in your base case scenario of knowing like what is the, if I’m using 4 % rule as my pension, like what is that number that I need to accumulate to? And therefore, if you hit that number, or if you’re on track to hit that number with your current investing strategies, then knowing that when that should occur, it’s like it gives you the freedom to start crafting like what else do I, like when I now can do these other things.

Like what do I want my lifestyle to look like? Because what happens is like knowing that that number is there, like this is what pensioners do, right? Like I know that’s like, well, have you thought about what you’re gonna do with your time as a pensioner? Like screw that, I’m gonna sit my ass. You know, like this is what our teachers used to tell us. The teachers that we work with, right? Is they say like, it doesn’t matter what I do. Like I’m gonna do nothing for like six months and then you’re gonna, I’ll figure it out then because I have this floor to build off of. In a way, that’s what your number helps you do.

It’s like your FU money, right? So it’s like, I’ve got this floor and now I can start going, what do I wanna do with my life? Like what do I want that to look like knowing that I’ve hit the floor, I’ve built the floor? Because now it doesn’t matter. So now it means like, because I could just quit everything and I could do whatever I want at that point. Like she doesn’t have that yet. Like she hasn’t done that part to create that so that it doesn’t matter what these moves look like. Now it’s like, now the moves become personal choices on what.

way you want to spend your time because you’ve already built your floor. And what you were saying before reminded me of like, like just thinking about like the different types of risk, you know, like when you’re trying to decide that, like let’s say you have your floor, now you’re trying to decide where do I want my, do I want to be all investments wise? Do I want to, you know, keep operating this business? It’s like you’ve got the market risk that you have to worry about. You have got effort risk and you’ve got planning risk. It’s like all of these things include these three aspects.

planning, like obviously market risk is like your return risk. It looks like, yep, okay, I could go down that route and I get this type of return or I could have risk this return. But I think we don’t often think about the other two. We don’t think about like, like, what’s the planning risk here? Like, like I could send all day analyzing this thing. Like we could spend all day trying to figure out what we really want to do. But it’s like, there is a time limit there. There’s a risk to your time going, I’ve been, I’ve been doing analysis paralysis for an

for a long time and I still don’t come up with anything and that’s risk. You’ve wasted or not wasted, but I mean you’ve burned hours trying to figure out a good move.

Kyle Pearce: Well, you said all day. Typically, it’s not an all day event. It’s like months and sometimes for many years, right? That they’re not actually acting because they’re just trying to figure out what the perfect play is. But you’re never going to get there because you’re not actually clear what that goal is. it’s so interesting because when you look at the statistics around those people who do have pensions. So again, right away.

pensions do not produce a great return on investment. You’ve got typically a dollar coming in from the employee and a dollar coming in from the employer, all right? Government, whatever it is. So it feels like the return is decent, but it’s actually not great. It’s basically being managed much like insurance manages an annuity or how they deal with high early cash value life insurance. Very, very similar.

which is why we sort of started there for our foundational asset. And the reality is, is the vast majority of pensioners wouldn’t give up that certainty. And this is the toughest part. When you don’t have the pension, the pension told you what the base case is gonna be and you accept it. Here, you get to choose the base and nobody wants to choose a base that’s like.

low because they want to, you know, they want the upside. Like nobody wants to give up the upside. If there’s what you’re telling me, I could do better than that. Like I’m going to, I’m going to go for the, for the, you know, for the, for the roof here. The problem with doing that by not setting that base is that it makes it very difficult for you to make moves with confidence. And I’m not talking to those people who are there sitting there going, listen, all of my money is going straight into a hundred percent equity ETFs cause they’re all in or

there like I met a gentleman recently who’s like 90 % of his assets are in Bitcoin because he believes and I’m like, honestly, I believe in Bitcoin too. But my god, you are my hero. Like how cool is that? And I I’m hopeful that it all works out great. I could not I could not do that.

Jon Orr: That’s harsh. Yeah, that’s hard.

Kyle Pearce: you know, but people that are really confident with the strategy typically aren’t listening to a podcast like this. They’re like, no, this is how it’s going to be. I’m clear and I know exactly what I’m going to do. And it’s fantastic. So if you’re sitting there thinking about this and going like, I feel like I’m doing the things, but I still don’t know what that looks like or sounds like. Like that’s where the planning really comes into play. Right. And oftentimes it really just comes to

trying to divide things up a little bit and we talk again, that base case is like, let’s get that down. And that we want to make sure that happens for sure. You know, like there’s like no way that we’re not going to have that. And then the reality is, is that typically that’s going to leave you a significant amount of your portfolio available or your net worth available to put into other growth assets, which is only going to make things better. Meaning there’s lots of upside there for you and there’s lots of opportunity. And then later,

you’ll have that that challenge of now what you know like now what do I want to do with these things do I want to build up my financial floor which is what a lot of people do as they get closer to that financial freedom age they start to recognize listen if I just start pulling from my floor and my floor can last the rest of my life at this amount that I’m going to be in really good shape it makes the rest like so so much more easy to stomach when

markets downturn when an investment maybe goes bad because that can happen too. You want to go down the private lending path, guess what? That can completely eliminate your financial floor if you get too heavily invested into a risky asset where a deal could go bad, right? So these pieces I think are really clear, but before we can get there, we have to zoom out a little bit, try our best to try to figure out like, what does that look like on a base case?

And then maybe there’s like a more, we’ll call it, you know, a bit of like a moonshot goal that you have that you want to work towards. And then we try to craft the plan and to ensure that, hey, based on what you’re doing right now, could I get there just by doing what I’m doing without doing any more active work in this investment business that I’m in or

Can I literally just continue along and feel pretty confident? If I get inspired to open a new office, great. Or if I get inspired to buy a rental property, awesome. But I don’t have to.

Jon Orr: Yeah, and this is one of the things that we pointed out with her is that she, of that wonder, that worry is like, am I already, maybe I already have a floor and I just don’t know it. And that was one of the issues. It’s like, you don’t know what your numbers look like yet. Like you don’t know exactly, it’s not even like, I knowing what your floor is. She, in a case, didn’t know what the rate of returns on her investments looked like. She didn’t know if she was involved, you know.

the choices she made and say those registered accounts were the right choices. So she had to do some digging and some homework there because it’s possible that projecting with her already existing assets, she did have her floor made. And I think my secret sauce here is that from the discussions specifically is that without that goal, right? I think two goals here is like without those two goals, like everything feels uncertain. So the one goal is what is the floor number?

Like let’s get a number, like let’s know what my like pension looks like. Like can I safely withdraw this much every year for the rest of my life and let’s play around with that. help our clients every day with those types of numbers. But the second is, what is the lifestyle goal? Like what do I want that time to look like? If I am retiring at 50, what do I want 50 to 80 to look like? Like what am I gonna be doing? Like how do I see myself?

in that time, because that can help shape what you do now and what choices you make now. And we can help make those choices with you when we establish that. And I think that’s a really important, that’s my secret sauce. You gotta know those two things so that you can use your wealth reservoir correctly, you know? And you can strategize and optimize in stage three. And you can plan for legacy in stage four. Like we gotta start with stage one. And a lot of times you do it in like,

middle order, you’re like, let me tinker and let me grab these tools, but I haven’t really clarified yet. So those are my two secret sauces here today.

Kyle Pearce: I love it. I love it. Yeah. And I would say, you know, my big takeaway is also understanding what is happening and what does that look like for you right now. So an example was I had asked, you know, what kind of returns are you getting from your RSP, for example, has an advisor that’s managing that again, you’ll hear us on the podcast. Like we’re actually like a lot of people are like, no, don’t ever pay a management fee or no, never, you know, this or that I’m actually

I think that there’s a fit for everyone. Everyone has a fit. Some people are good to do it themselves. Other people, like, it can be a train wreck if they do it themselves and they make big, big mistakes. Trust me, that 1 % MER, whatever it is that you’re looking to save is gonna look like a great deal, right? If they can hold you from yourself from doing something silly. So I just wanna know, like, how is that going? know, and she…

didn’t know, like she didn’t know what that was like, but yet we’re talking about private lending. We’re talking about all of these other things. And I’m going like, maybe that advisor is like able to get you like returns that are similar or better than private lending. Like maybe that’s happening and you just aren’t aware of it, right? And if they are that, that to me seems a whole lot safer than trying to get into private lending and maybe, you know, having to relearn all about this asset class and making sure we’re comfortable. So again,

Know where you’re at, understand what continuing to do that process. John, you’ll have to fill me in. I can’t remember. Is it Dan Heath who said your current system is perfectly designed to get you the results you’re getting? So what results are you getting right now? Like we got to know what is happening right now in order to see what we can anticipate later if we just keep going like that. like maybe, just maybe, we are on track to well exceed what

we are looking for, or maybe we’re way behind. And the only way we’re going to know it is getting clear on what that looks like and getting clear on what it is we’re doing now and projecting that out.

Jon Orr: If you want to get your grade on your four stages of a healthy financial plan, you can head on over to CanadianWellSecrets.com, four slash pathways. Fill out our quick assessment there and you’ll get our customized report that gives you a grade per stage and some next steps to strengthen each of those stages. And if you are looking for specific recommendations, specific discussions with us and our team.

head on over to CanadianWheelSecrets.com forward slash discovery and we’ll hop on a call and walk through those four stages with you and help think about tinkering on those structures and optimizing a plan for you. So that was CanadianWheelSecrets.com forward slash discovery.

Kyle Pearce: All right, Canadian Well Secrets seekers, we will see you in the next episode. And just as a reminder, this is not investment advice. It’s for entertainment purposes only. This content should not be considered investment, financial, accounting, tax, legal, or any other type of advice. And I myself, Kyle Pearce, am a licensed life and accident and sickness insurance agent with Canadian Well Secrets Incorporated.

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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