Episode 145: Will Doubt Cost You Your Retirement or Financial Independence?

Listen here on our website:

Or jump to this episode on your favourite platform:

Watch Now!

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 and book a call here.

Have you ever second-guessed your financial strategy, wondering if you’re making the right moves for long-term wealth?

Doubt is a natural part of financial decision-making, especially as you gain more knowledge and experience. The more you learn about investing, tax strategies, and wealth-building, the more you realize how much you don’t know—which can create hesitation, second-guessing, and even fear of making the wrong move. But what if doubt wasn’t a setback, but rather a sign of growth?

In this episode, we explore how to navigate moments of uncertainty, manage emotional decision-making, and take strategic steps toward financial success—without getting stuck in analysis paralysis. Whether you’re deciding on an investment strategy, considering leveraged insurance, or just trying to make the best use of your retained earnings, we’ll help you reframe doubt into confidence-building action.

What you’ll learn:

• Discover why learning more about money can sometimes increase doubt—and how to turn that into an advantage.
• Learn how experienced investors manage emotions and make confident financial decisions despite uncertainty.
• Get practical steps to take action today, even if you’re not sure it’s the “perfect” move.

Hit play now to learn how to push past doubt, make smart financial decisions, and build wealth with confidence!

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.

Achieving financial independence requires smart planning, especially when it comes to growing your net worth and generating passive income. We explore conservative leverage strategies such as the Smith Maneuver to convert non-tax deductible interest on your primary mortgage to tax deductible interest as well as conservative leveraged life insurance strategies including immediate financing arrangements (IFA). For business owners, navigating the complexities of corporate structures, tax implications, and investment strategies can feel overwhelming. From understanding capital gains rules to leveraging life insurance for wealth optimization, the right approach can transform your financial future. By aligning your strategy with tax-efficient tools, you can unlock the full potential of your business and investments, ensuring sustainable growth and long-term independence.

Transcript:

Jon Orr: All right, let’s, you know what, we’re gonna let our listeners in on the conversation like we have been having and we decided to hit record right now in the middle of the conversation because we thought this is a conversation that I think we need to have on a regular basis, you and me, but also I think, you know, generally many people in their business world, in their life, they need to have these types of conversations which,

which is really around kind of, I guess the way though our conversation was shaping up Kyle was doubt, know, in doubt that we’re on the right path or doubt that we’re doing the right thing or doubt around our current systems of financial gains and compounding growth or just in business, know, like our systems. we often have these conversations where like, we on the

Are we doing the right thing? And then we, and sometimes those emotions creep up and it makes us go, hmm, maybe we need to switch or not, or quit or like abandon everything or like start off from scratch. Like, I think it’s natural that we get these moments as human beings of self doubt or doubt in general. And then, and then sometimes that throws a monkey wrench into the work that you’ve already done and the work that you’re hoping to do.

So in this episode, we kind of want to just continue the conversation you and I were just having around what do do when we have those doubtful moments and what does it mean about what the next step is?

Kyle Pearce: Yeah, yeah. And you and I have these conversations all the time. But also, a lot of them are fairly open because a lot of them are really just podcast episodes, right? Like when we’re sharing what we share out, a lot of times these are conversations that you and I have had or they’re conversations that we’re having with clients, right? So folks reach out and they are either our prospective clients or they are clients.

Ultimately, we’re helping people through some of these most common challenges. And, you know, it’s interesting because what we do as humans most often is we are seeking more knowledge, right? So like you’re listening to this podcast, probably not because you’re like, I’ve got it all figured out, right? If you have it all figured out, and you’re like, I’ve, you know, I’ve arrived, they call it a rival syndrome, right? And Nelson Nash, in his book, Becoming Your Own Banker,

talks about arrival syndrome and that’s one of the key pieces of that book that I think is really important is that you’ll never arrive, like you’ll never know it all and therefore you’re always gonna wanna be seeking more understanding and more knowledge and as you do, there’s two things that happen. First off, you’re trying to help yourself make better decisions in the future but with each new piece of information that you learn, it actually creates a little more doubt.

in your mind and you know you think about that for a second you go wait a second like what are you talking about and the reality is is that as you learn something new you actually start to recognize that like up until that moment you did not know that thing and therefore all the decisions that you made up to that point were maybe ill-informed you know in a way like maybe not to a detriment but you’re you’re literally making choices based on what you know to be true today.

And you’re like, well, what else is there? And every time you learn something, every time that you have this epiphany where you go, I never thought of it that way. And it actually impacts your decision making moving forward. It actually creates more doubt that there must be more to know. And this is where investing in particular and growing your wealth and really trying to figure it all out.

gets really tricky because a lot of people would say, hey, listen, ignorance is bliss. know, somebody who doesn’t listen to this podcast and literally just hands over a good chunk of their money every week or every month. And they just, you know, hand it over to somebody to even if it’s charging high fees, you know, we always say like, literally, it’s better to hand money over to the big bank and let them do something with it than do nothing. That’s really important. But here’s the other aspect as you learn more.

and you, shoot, there’s high fees over there. You know, like I don’t wanna do that. So what do you wanna do then instead? I wanna do ETF. So, and then you’ll learn about, shoot, if I put it all in this ETF, then there’s this, there’s that, there’s the next thing. There’s all this complication. And what I think is really important for us to understand and for us to work towards, you can’t just turn it on overnight, is that what you learn and what you know is helping you craft

what is rational and it helps you with rational decision making ideas. But the problem is the emotion. And when you get that doubt, like that’s an emotion, right? When you learn that you don’t know everything, you start to doubt that everything you know today is complete enough to make the right choices. And this is why, John, I’ll tell you only one person that I’ve had a conversation with over these past, would say six months or so,

for example, is 100 % equities with all of their investable capital. Only one person. Everybody else is not. Even though rationally, it would suggest that that would be a good idea over the next 20 years, not over the next five, even not over the next 10. We can’t guarantee any of those things. We still can’t guarantee 20. But historically, this person is making a rational choice. Here’s the challenge, though, is that for most of us, it’s really difficult to just follow the rational choice without emotion creeping in.

Jon Orr: Yeah, yeah. And I think what you said was spot on about when you have more learning. So think about the rational decision making that this person is doing by putting all of their money into the S &P 500 and going, look, statistics say that I am going to be fine in 20 years. So I’ve got to stay true. But then the more learning you do,

Like this is what you were saying, the more learning you do, the more self, like the more doubt creeps in because now you’re going like, when you learn things, you can’t unlearn and you start to go, hmm, what happens if I tinker with that? If I tinker with that, then in this way, I should get better returns. But then I’m like, okay, if I tinker with that, am I gonna get better returns? And all of a sudden it’s like the doubt creeps in and then going, well, maybe I should have stuck with that. Well, but then if I stick with that, I’m not gonna get the better return. Like, I think.

I think there’s a few things here I think play into this. One is that with more experience, doubt in the motion, and the emotion that you experience is really, the emotion you get is actually like your lack of experience shining through, right? Because when, let’s say if you had been investing in the market for already 20 years, then that experience of managing that portfolio,

tells you exactly, it tells your emotions to take a hike because you know exactly what’s gonna happen and how this works and you feel confident because of your experience. Your confidence, your experience pushes the emotional part of you down to be non-existent. It happens with everything, Think about you and I when we first started branching out from our teaching days and being.

you know, public speakers and traveling the world and giving talks around like how to how to teach math this way and becoming educational consultants. Like that sometimes was scary, right? Like it was like, we don’t know like what that looks like to go and speak to hundreds of educators and district leaders around a certain topic. But it’s like, but your experience squashed all those worries away because you knew exactly like you’ve gained all that. So to go like, hey, that situation comes up, I got to handle it.

Like that situation comes up, I’m going to handle it. And it’s because you built a system, you’ve built experience to handle these certs and scenarios. And when we think about our investing portfolios, that’s what that’s what experience brings is that when you have a system, when you have some rules that you’re applying, like if the rule is, every time I get a paycheck, I’m going to put this much in that portfolio, and then I’m going to set and forget.

then that being your system, and if it was working for you and you were saying, I’m gonna stick to that for 20 years, then 20 years down the road, you don’t have any emotional problems anymore. But it’s like education can help creep that in, but then you have to compare that with experience to help squash those emotions. So there’s like that trade off, the, is the, how do I stick out the, like how do I gain that experience?

Jon Orr: so that I can squash the emotion. Like, do I have to wait 20 years to be able to squash it? How do I deal with that emotion now?

Kyle Pearce: Yeah, and you bring up that it’s an interesting analogy because, know, as as I think about investment and investing, it’s here’s the other aspect is that everyone is uniquely different, right? And we, you know, we learn it in school when we’re young, we’re all different and we’re all unique and we have all these qualities. the reality is like we don’t only like have unique, you know, appearances.

how we think and how we feel and how emotions sort of drive what we do or don’t drive what we do. These are all very, very individual. And in a lot of ways, even if, and I’m a fact finder and we’ve talked about this a number of times, like I love going down the rabbit hole. And part of why I love going down the rabbit hole is because I’m actually not a super trusting person when it comes to just following blind statistics.

like think about this. I have a math degree. I used to teach high school mathematics. I was a high school or I was a math consultant. And even with all of that and my understanding of probability, I used to play poker. We never talked about this, you know, and I used to use, you know, learned about all the different, you know, probabilities and I still the emotional side of playing poker made me go. I don’t like this. And I stopped playing poker because I could not get over.

When I had such a high probability chance of winning a hand and some guy at the other side of the table makes a silly move and it wipes me out of that hand or maybe wipes me out of that tournament, like I really that really hurt me even though probability said they still had a chance. And when they squeezed it out, it was like, man, my emotions like really held me back from being successful there when in reality I knew rationally if I just kept repping, I would win.

Like I would win in the long run. So I think what I hope people are getting from this discussion here is that everybody is different and it’s okay for you to decide and analyze who you are. And this is where people talk about risk tolerance, right? Like the more you know, the more your risk tolerance should on paper go up. But depending on who you are emotionally,

That may not be equivalent across the board. So even though I know a lot about investment, I know a lot about history of the S &P 500, for example. I know a lot about diversification. I don’t have 100 % of my investments, my investing dollars in equities or in ETFs. I have a very low percentage, actually. Why? Because I don’t get emotionally triggered by real estate. I really don’t. And part of that is because I can’t actually see the ticker movie.

Jon Orr: Well, I think also part of that is because you took that step a long time ago, right? And like you took that step a long time ago to get experience on the real estate. So now it doesn’t feel risky to you because you’ve learned, you’ve gained experience, you’ve risk-tolered along the way and that your risk tolerance has gone way up for that asset class because…

because of the learning you’ve done and the experience you’ve gained. So now it’s like when something awry happens, you’re like, hey, that’s no big deal. I’ve gone through something like that before and I know that it will come out again in the end, which means like, if you want to build your risk tolerance, you want to squash your emotions, probably the best course of action for you is to take a step in the direction to gain experience. So if it’s like,

I’ve done all this learning around, you know, investing in certain asset classes or ETFs or risk managing this or risk managing that or buying real estate or, or maybe I’m, you know, I’m getting this pass through structure set up so that I can do this. Like you’re probably best course of action is to take a step forward so that you can gain and start learning and gaining that experience so that your emotions get squashed down the road. Like it’s, one of the only ways I think that you push that emotion down is to have the system that works.

but you only feel like the system works if you’ve worked it and you’ve learned, you’ve learned and gained the experience you needed to make sure that you feel confident, which is like taking that step forward.

Kyle Pearce: Hmm. Yeah, and that’s so bang on. And here’s the other interesting piece is I get this question quite a bit when people email in or we hop on calls and they ask, say, what’s the best option for me to blank? Or what’s the optimal blank? And I’m like, that’s an easy answer. There’s always an answer to it. And I had a call yesterday with a client, and they were asking, should I? They were going to sell a property.

And they were like, should I take that money and pay off part of this primary mortgage and do the Smith maneuver? Or should I take some money and put it back into my tax free savings account? It’s like there’s really easy ways for us to come out with like the number that tells you, yep, this and that based on assumptions, which again, isn’t going to be, but here’s the thing is like, there’s so many other factors, right? So it’s like, how is that going to affect you emotionally? How is

Jon Orr: Right. But that’s not always the best.

Kyle Pearce: you know, what is your your goal? A lot of people align it to goals. And ultimately, for this individual came down to cash flow, they were saying like, I’m in a cash flow crunch right now. And they were thinking of taking this money and putting it on the margin. That’s not going to solve your problem. That isn’t going to solve that problem. It’s not going to be your best move to do what I’m going to suggest to you. Because on paper can show you why all these other things line up. But sounds like the cash flow crunch you’re in is actually causing you stress, which is emotion.

Even though I can rationally tell you this is what you should do over here, here’s what I’m going to suggest based on where you are emotionally. And I think this comes into your actual plan and how you can move forward. So getting that experience is important, but then also being able to go like, here’s who I am and here’s what’s going to make me feel comfortable. We talk about sleeping at night. Like what keeps you up at night is not rational. It’s always emotion.

Right? Like if you’re staying up at night, that’s emotion right there. And I guess what I’m hoping you get out of this conversation here is that it’s okay to not have the perfect wealth planning strategy that is rational. I think what you want to have is you want to have the most optimized wealth planning scenario for you emotionally, because that’s going to be how you know that you’re going to be able to follow through with it.

You’re to be able to sleep at night and you’re going to be able to reach the goals that you’re after, regardless of what somebody else might be doing, because the rational move is to do X, Y or Z.

Jon Orr: Right, and then pair that, right? Like pair that, and this is the comfort part too, is to pair that with every step forward. You’re going to gain that understanding, you’re going to gain that knowledge, you’re going to gain that experience just to like change that, you know, your core emotional response. So like what keeps you up at night now won’t keep you up at night 10 years down the road, right? So like,

knowing that that’s gonna happen as long as you take the step, right? And get onto the pathways to start working towards your goals, then 10 years down the road, those things won’t matter anymore to you. They will be less risky, just like your real estate is less risky to you now than it was a long time ago. It’s like, as long as, like just, you’re saying like the biggest thing you wanna take away today is it’s okay that, you know, you’re not.

fully optimizing your pathway forward right now rationally because you know there’s motions in check, but know that those motions will change with time and experience so that, right, you’re gonna scale up, right? Like you’re gonna scale up.

Kyle Pearce: So I’m picturing there’s like a scale or like a spectrum, right? Exactly, which I think if we go all the way back to like, you know, first principles and you think about this and it’s like, why do people say start small? And it really has a lot to do with this as well. you know, I think one thing here that I hope that the Canadian wealth seekers can sort of take with them is that whatever step in the process you’re in now, as long as you’re taking that next step, it doesn’t have to be the leap, so to speak, right? It’s the taking the next step exactly.

Jon Orr: Right. The final step. I think we all think it’s the final step. We gotta take the final step. Like I gotta get the right move now and then I’ll never have to worry about it again. That’s not how it works.

Kyle Pearce: Yeah. So a couple examples that come to mind right now is things we don’t want to do. It’s like, hey, Kyle, listen, I want to start doing the Smith maneuver, which is the best ETF for me to do with the lowest fees? It’s like, don’t care. Just get started. You can change that later. I want to get my first rental property. I’ve got a few I’m considering. And they’re all positive cash flow. It’s like, you know what?

If they’re all positive, you know, you’re in a good place. You’ve done some, you know what? That one might be a little better than that one, but guess what? That one might have a roof cave in on you next week. You don’t really know. So get started, do the process. Hey, Kyle, I was really thinking about using a leveraged insurance strategy. I have, you know, $250,000 of retained earnings every single year, and I want to do that, and I want to do it today. Well, guess what? We could do that, but guess what? For vast majority of people.

you should probably start a little smaller so that you get your feet. Well, you get comfortable with it. We can always scale that up later. So these are things that, you know, as you’re listening here today, it’s like you’re listening to this podcast to get better, but also start making yourself more experienced by starting today, starting smaller and

I’m telling you as time passes, like John, look at like what episode is this that we’re recording? I have no idea. 150 something I think it is that we’re recording today. It’s like just get started. That’s how we started this podcast. That’s how we started our wealth building journey. And that’s our message here to you is get started or take that next step, which is like getting started again in your journey today. And if there’s anything we can do to help you out,

Of course, reach out to us over at CanadianWealthSecrets.com forward slash discovery. On that page, we’re gonna ask you some questions, help you decide what phase you’re in in the wealth building journey. So you can take that next step. And of course, if you’re an incorporated business owner, you can reach out and you can opt into our free masterclass, which is at CanadianWealthSecrets.com forward slash masterclass.

We’ve had, John, I don’t know what the count is. It’s over 300 business owners that have been through this thing since we started it. And it just was released at the end of December, 2024. We’re recording this in March, just a couple of months. And we’ve had hundreds of incorporated business owners through it, lots of positivity around it. And of course, give us some feedback if you have any. We’d love to keep improving it and making it better for the next business owner that follows through.

Jon Orr: Take care, Canadian Wheel Seekers. Just as reminder, the content you heard here today is for informational purposes only. You not construe any information as legal tax investment.

Kyle Pearce: Kyle is an insured life and accident and sickness insurance agent in Ontario and in many other provinces around the country. And I’m part of the corporate advisors and Pan Corp team as the VP of corporate wealth management. That means I can help you with your planning and your insurance and leveraged insurance needs. We’ll chat soon.

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.

OPTIMIZE YOUR FINANCIAL FUTURE