Catherine Clark: Why do you use terms like happiness and fulfillment when you’re talking about money?
Melissa Leong: I have always viewed – well, I don’t know if I have always viewed – but when I first started writing and creating content about money, I felt a lot more intimidated. I felt like I needed to approach this topic in a way that gave people a lot of information and would empower them with information. But as I was a personal finance reporter for The Financial Post during this time, I quickly realized that money is the story of our lives. If you start to have conversations with people about money and what they’re using money for, it’s essentially to try to find some happiness and peace and health and wellness and all the things in between. So when I talk about money, yes, I want you to be wealthy. I want you to have options. I want you to feel like you are in control. And that’s going to be beyond talking about numbers. It’s going to be talking about happiness, how you view happiness in your life, and how money fits into that.
Jennifer Stewart: Melissa, were you ever bad or avoidant with money? Like, “the problem’s over there, I don’t want to address it, I don’t want to think about it”? Or did you always have this grasp on your financial health?
Melissa Leong: I’m not going to use the word good or bad. I think that financial empowerment, wherever you are in your journey, is exactly what it is – a journey. Money is like a language, and how fluent you are doesn’t even mean that you’re going to be good with it. I can give you all of the financial literacy you can handle; it doesn’t mean you’re going to make the right decisions. So do I always make the right decisions? Hell no. Do I have a complicated relationship with money? Yes, absolutely. And does me trying to have conversations with you, with my colleagues, with the public – does that help actually inform my own behavior with money and cause me to change? Yes, every day.
Catherine Clark: You’re really good about talking about those emotional touchpoints, though, because I think for a lot of people the idea of money is scientific and specific. But what you’re illustrating is that there’s a huge emotional component to some of the financial decisions that we make. How do you make that link and make it make sense for people – especially for women, who may really experience that quite a bit and who may be trying to change that behavior in 2026?
Melissa Leong: This is a great conversation to have as we head into a brand new year because our brains, according to science, love fresh starts. You can choose to have a fresh start when it comes to your new goals for 2026 – your financial goals – at any point. So I encourage everybody: we’re heading into this year, and if by Q2 we have not adhered to these “rules” – I have air quotes, but if you’re listening to a podcast, you can’t see it – these rules that you’ve set for yourself, I would encourage you to have more grace. As we started this conversation, a lot of our money choices are dictated by our emotions, by habits, and by mental shortcuts. So it’s not always what you promise yourself. It’s not always what you know. We’re going to make choices. But what I’d love to chat with you about is how to create some systems and practices that will be in place no matter what is happening on the outside.
Jennifer Stewart: I’m going to follow that one up, and I’m going to be incredibly honest because normally I probably wouldn’t be about this. I’m great with money from a business perspective. Personally, I love shopping, How do you set rules with grace that are realistic, but also recognize that I do derive a bit of joy from that? And it’s not this quick dopamine hit – I really enjoy it.
Melissa Leong: I guess I would ask you, who told you that it’s not something that you should enjoy?
Jennifer Stewart: Society I guess?
Catherine Clark: Jen, I would agree that there’s this sense that if you just like to shop, you’re kind of like a capitalist, and you’re just spending maybe unwisely on things you don’t really need – that kind of thing.
Melissa Leong: I think the reason why I asked is because I love to shop. I mean, it is one of the things that I used to do with my mother – we would spend hours just trying to get a good deal. I don’t even think she wanted the thing; it was the process. There was a lot involved in getting the win.
I love clothes, I love knickknacks, I love home decor – all these things. But, sometimes it’s weird, because you get this message from society that you do need to consume, that you do need to buy something new. “Oh, that thing is old. Look what this person’s doing. They just got something new. You should buy something new.”
We have this culture of fast fashion because there’s this encouragement to always fulfill your needs. I guess the reason why I asked the question is for us to reflect on our own values. If your value is that “I love this, this is what gives me joy,” then it’s really hard to be ourselves in a society where you’re fed a curated algorithm of what other people think should be empowering to you, what other people think should be fulfilling.
At the end of the day, before we spend our money, we should decide what we actually love, what’s important to us, what we value. And if that for you is shopping, then who – I mean, nobody should, should, should tell you otherwise.
Catherine Clark: But unless you’re racking up crazy debt with money you don’t have, right?
Melissa Leong: I mean, if you… I used to love shopping so much. When I was younger, before I had so many commitments with family and everything, and to be honest, my values changed over time. But when I was younger, I used to siphon off an amount of money into a separate, no-fee bank account with a credit or bank card attached to it.
Catherine Clark: Talk to us then about this system, like you were explaining – that you put in place a system that worked for you. You had some money set aside, you understood it was to spend as you saw fit, while the other money you had was covering your bills, etc. So this was your spending “cath,” if you will. What do you recommend in terms of a system for women who may be looking for that fresh start?
Melissa Leong: A fresh start, for me, involves getting a sense of where you are. For example, if you were to say, “I’m going to get healthy. I want to get super strong in 2026,” you would start by figuring out how much you can deadlift at this one point and then check back to see your progress.
Part of that, when it comes to your money, is taking some stock and deciding, “You know what? I’m going to start the year by calculating my net worth. Let’s see where I’m at.” This is just a number – all of your assets minus your liabilities. That number could be negative, but it’s just a number for you to determine whether or not you are going in the right direction, whether you’re building wealth.
Then resolve to put it in your calendar to check in, maybe quarterly, maybe twice a year, just to see how you’re doing. That number is going to go up if you’re saving money or paying down debt.
The other thing is just to do a quick inventory. It doesn’t have to be this big, involved thing where you lay out all of your bank statements. It could just be opening up your bank app and taking a look at where the money is going, and understanding if you are someone who is maybe overwhelmed or maybe in a super happy place, and that emotion is driving a feeling of, “I don’t want to look. I don’t want to look at risk. I just want to stay happy.”
I promise you, if you just open it up and take a look, it will give you a better starting point to make different choices if you want to do that.
For example, savings is a habit. And I think we think, “Oh man, I have to save more money.” Guess what? Human beings – there are 1,000 reasons why you will probably not save money as easily as you hoped going into the rest of the year.
So how about a system you can put into place where you don’t even think about it? This is where you set up an automatic deduction – just a small amount. If that feels overwhelming, pick a nominal amount. You’re not going to notice it. Then put it in your calendar or phone that a month from now, you’re going to revisit it. If you didn’t really notice it, check again three months from now. Bump it up.
If you already have existing savings plans, then go back to them and bump them all up.
Jennifer Stewart: Do you believe in budgeting, or do you think that budgeting is really not helpful at all?
Melissa Leong: I love budgeting. I just think we just call it different things. We set a budget all the time for different things. For example, my son – if he’s going into a store and wants to buy a bunch of stuff, I’ll say, “Hey, here’s your… here’s your spending plan.” That’s also a budget. It’s just figuring out: okay, these are my resources, these are my priorities, how do I align them?
