Did Dennis Make A Big Mistake...? 😬

Happy Sunday, and happy November 1st! 

It’s a new week, it’s a new month, and it’s time for a new issue of Money Convos. We had a really busy month, and that means we have a few fun things to share with you - along with some important money tips and reminders. Let’s jump in! 

Here’s what’s up in this copy 🤑🗞 

• Pay off debt or invest your money? 🤔

• Steph’s $35k challenge is coming to an end… 👀

• Dennis was a groomsman… 🤵🏿‍♂️

• …and a runner! 🏃🏿‍♂️💨

• Did you know… ⁉️

Money Convo Of The Month

Should You Pay Off Debt Early or Invest Your Money?

If you’ve been with us for a while now, you’d know that Dennis finished paying off ~$50,000 worth of student loan debt about six years ago. 

He paid off that debt before he ever started investing… But, should he have taken that approach? 

In other words - should you pay off your debt early, or prioritize investing your money in the stock market? 

It’s a good question, and thankfully there is a right answer to it! It’s really just a simple math problem, with a little bit of emotion sprinkled in there. 

First, let’s talk about how expensive debt can be. There’s a cost associated with borrowing money - aka the interest rate you’re required to pay on top of the amount you originally borrowed… And depending on the type of debt you’re talking about, the interest rate can be pretty high! So, the cost of having debt can cause you to effectively lose money (aka you’ll have to put money towards interest, instead of just the original debt you owed).  

On the other hand, investing your money - specifically in the stock market - can allow you to potentially gain money (aka your money can grow beyond the original amount you contributed). When you invest in stocks, your money can go up and down over time; but, over the long-term (historically speaking) we know that the stock market tends to trend upwards. The standard long-term average annual return that we typically hear is ~10%; adjusted for inflation, we’d land on a more conservative ~7% average annual return. 

(It’s also important to note that when it comes to investing in the stock market, the benefit isn’t solely the average return - it’s also about compound interest, or compound growth. The TLDR on compound growth is that you benefit the most from it by starting to invest in the stock market as early as possible). 

Okay, okay, okay - so, debt can be expensive, and investing can be rewarding. So… What should you do first??

Well, it’s all about comparing the cost of debt to how much your money could earn if you invested it (which we said before was between 7-10% over the long-term). 

Here’s how we’d categorize the different types of debt - 

• High Interest Debt - Credit card debt (av. 20%+), Personal loans (av. ~12%), and Car loans (8%+ = high interest) 

• Low Interest Debt - Student loan debt (av. 6.5% or lower), and Home mortgages (interest rates vary) 

Overall, if your debt is considered high interest debt (aka it has an interest rate of 7%+), pay it off as soon as possible. If your debt is considered low interest debt (aka it has an interest rate under 7%), you can pay off the minimum balance while also investing your money at the same time. 

Even more simply put, if your debt costs more than you’re likely to earn by investing in the stock market, pay it off first. 

Wait a second… So, does that mean that Dennis made the wrong decision by paying off his low interest student loan debt before investing? Mathematically, yes - but, that’s where the emotional side of things comes into play. In his case, getting rid of the debt ASAP helped get rid of a dark cloud hanging over his head (and he was still investing aggressively by age 25). 

If you want to hear more on this topic, and see a few examples, check out the video that we’ll be posting on YouTube later today.

$35,000 Or Less Challenge 💰

I’m back with another $35,000 or less challenge update!

Alright, alright, alright… I’m officially here to say that this challenge has not been a ‘success’. I’m putting ‘success’ in quotes because - and you probably know this if you’ve been tapped in with us for a while now - we’re not pro money guilt or money shame. Sometimes expenses come up, priorities change, or you simply just weren’t as disciplined as you originally wanted to be.

Clearly I’m hinting at the fact that I spent more than the amount I needed to hit this month in order to achieve my current challenge goal by the end of 2026. Actually, right now I’m on track to spend a little bit more than I did last year. 

With that being said, I’m very happy that I continued to track my spending this year, and that I continued to share my monthly results here every single month! There’s always next month, and I’ll continue to share my spending as the year winds down. 

So, in October I spent $3,494.85, and here’s how it was split out -

That means that I have $3,525.36 left in my annual total to spend for the next 2 months of 2026. 

I would now need to spend an average of $1,762.68/month for the next 2 months in order to hit my goal (🙃).

If you want to see us ‘compare’ our spending for October, keep an eye on our Instagram page this week!

How Much It Cost To Be A Groomsman 🤵🏿‍♂️

You might remember that a few years ago we shared how much it cost Steph to be a bridesmaid. Now, we get to share the other side - aka how much it cost me to be a groomsman!

My friend from high school got married last month, and I was so happy to be a part of his - and his now wife’s - big day. Steph and I are good friends with them both, so it was really special to see them get married and be there for them! 

Now, when it came to the costs associated with being a groomsman, there were really only three expense categories - my wedding day outfit, a few Ubers to wedding events, and the bachelor party trip.

I ended up spending just over $1,500 - for comparison, Steph spent about $2,300 to be a bridesmaid a few years ago. 

Overall, I’m so happy that I was able to be there to celebrate my friends, and Steph and I had a great time! If you want to see more behind-the-scenes, check out this video.

I’m Ran My First Race 🏆

A few months ago, I did something that I really didn’t think I would ever do…

…I signed up for a race. 

Here’s the thing - signing up for a race really isn’t a crazy big deal or anything. It’s just that I hadn’t ran (outside of playing basketball) in about 13 years. I was also 30 years old (this was before my 31st birthday came around), and I’d been laughing along for years at all of the classic ‘people turn 30 and all of a sudden start running’ memes. 

Turns out, I was going to be one of those people. The reason I signed up was because my brother and Steph’s brother had been talking about doing a race for years, and I thought it would be a fun thing to do together, the three of us. 

It’s also important to note that I’m pretty competitive, and the brothers are still in their 20s and run a lot more often than I do. So, I had to start training ASAP. 

The first step was buying a pair of running shoes. Like I mentioned, I hadn’t ran in years when I signed up to do this race, so I didn’t own any outdoor running or gym shoes. I ended up going to the Running Room and after spending about an hour trying on different options, I bought a pair of Asics Nova Blast 6’s for $214.69. 

The next step was training. I would’ve loved to have started earlier, but by the time I was ready to jump in, I only had about a month to prepare - but I took it seriously. I made a training plan with the Strava app, and I trained three times per week. 

Finally, it was time for the actual race. I paid the $88.27 race fee back when I signed up, so all I had to do was pick up my bib the day before the race, and show up on race day itself. 

We ran the Toronto Waterfront 5k race, and it was a really great experience. We had a really fun morning pre- and post-race with the family (including our cheer squad, aka Steph & my mom!), and I actually really liked the race itself. 

I ended up running it in 24:52, which I was happy with… but now I also know my time to beat for the next race. 

If you want to see some more behind-the-scenes, check out this video.

Did You Know? 🤔

Did you know… that most people don’t have a will? 

Will = a legal document that says what you want done with your things after you die (things = assets, like your property and/or your money); it’s part of the estate planning process. 

Estate Planning = the overall term for what’s going to happen to your estate when you die (estate = everything a person owns).

Having a will makes sure that your loved ones are prepared if something unexpected happens - it’s basically a guide that you create that says exactly what you want done, and saves the people in your life from potential complications and stress. 

If you don’t have a will, then the government decides - based on a preset formula - what happens to your estate and your children (if you have them). 

TLDR - a will is a document that says what you want done with your things after you die, and if you have one, it can save your loved ones time and hopefully take away any extra stress.

It sounds simple enough, right? The thing is, if you do a quick search for how many people have a will, the numbers are shockingly low. 

• In Canada - *60% of people don’t have a will 

• In the United States - *68% of people don’t have a will

Why? From our understanding, it’s because making a will can be time consuming, expensive, and unfortunately there isn’t enough education around why a will is important. 

Education wise, hopefully resources like this are a helpful starting point! But how do you actually make a will? 

Traditionally, you had to go to a lawyer. It’s fairly straightforward - you have to make an appointment, go to the appointment and spend time working on the will with a lawyer, and you also pay for the lawyer's time. 

Here’s some background on the average cost to draft a will in Canada:

• Simple Will - $624 (for a basic will with no extra clauses)

• Complex Will - $2,242 (for a will with personalized clauses) 

If you only need to create a simple will, then you also have the option of making your own will online. It’s legal to do so, and can save you a lot of time and money. Make sure you use a reputable service - for example, Willful in Canada.

If you want to hear more about this topic - and learn some tips about how you can make your own will - check out this video.