“My first experience of buyer’s remorse has guided my spending ever since”

Who are your financial heroes?

My financial heroes are those fighting for investors’ rights across Canada. The recent nationwide ban on unfair mutual fund fees, such as deferred sales charges, represents a decade-long effort by groups including FAIR Canada and is a huge win for Canadians.

How do you like to spend your free time?

I spend my free time walking. Walking isn’t just about exercise, it’s a fantastic way to find solitude and disconnect from technology. I also do my best writing in my head while walking.

If money were no object, what would you be doing?

I would be doing the exact same thing I’m doing right now. I live off the grid in the middle of a forest and write about money, do radio and TV interviews in my studio, and publish The Cash and Kerry Podcast. You might also find me driving an orange tractor.

What’s your earliest memory about money?

I was around five years old when my father gave me his pennies because they were heavy and made a mess of his wallet. After collecting about 100 of them, I also discovered they were heavy and made a mess of my wallet. I learned bills are easier to spend than coins, and the form of currency can impact our spending habits.

Today, it’s even easier to spend with digital wallets, especially online. As a financial journalist, I lean towards behavioural science to help people build checks and balances to overcome impulsive FOMO spending. Thankfully, pennies are now extinct.

What’s the first thing you remember buying with your own money?

The first thing I bought with my own money was a pink yo-yo. I regretted it right away because my hands were too small to make it fly. This was my first foray into buyer’s remorse, and that terrible feeling has guided my spending behaviour ever since.

What was your first job?

My first job was babysitting the neighbour’s kids every Tuesday and Thursday after school. My first paycheque was an actual cheque for $25, and I was disappointed instantly—my name was misspelled, and asking for a new cheque was a pain.

I also delivered the Pennysaver to 190 houses every week. My newspaper bag was big, and the pay was tiny. I stuck with it because I was determined to save enough to buy a Walkman.

What was the biggest money lesson you learned as an adult?

I graduated university during a recession, so my financial viewpoint was that money had to be protected at all costs. With the fear of losing my savings, I invested in several GICs with interest rates of around 6%—not the worst rate, but if I had a redo, I’d put my money into a mix of equities. I had time on my side.

I paid off my $17,000 student loan in six months, though, so living as a debt-free new grad helped me save the money to put into GICs in the first place. Despite my very low risk tolerance early on, growing a nest egg in my 20s was a smart move. Compounding cash is better than not compounding cash.

What’s the best money advice you’ve ever received?

The best financial advice is to have diversified income. Tying your income to one employer is a recipe for disaster if you’re pink-slipped.

As a sole proprietor, I receive income from many sources. The upshot is I have flexibility and can part ways if a client gives me grief. Choosing how to spend your time and who you work with is the biggest life hack few people talk about.

What’s the worst money advice you’ve ever received?

I can’t think of any bad advice. I try to surround myself with people who are much smarter than me, and I’m better for it.

Would you rather receive a large sum of money all at once or a smaller amount regularly?

I would be happy and grateful for either sum. Windfalls are fun but often squandered, while smaller amounts require patience and diligence. I’d set up an automated transfer and not view either scenario as “fun” or “free” money. Money is money—it’s fungible.

What do you think is the most underrated financial advice, tip or strategy?

Get a proper will and power of attorney drafted by an estate lawyer. We’re all going to die, so get the paperwork done right.

What is the biggest misconception people have about growing money?

We’re all human and prone to doing stupid stuff with money. Behavioural science has shown we’re irrational people, and knowing something—anything—about the psychology of money can help us understand why we’re doomed to make poor financial decisions time and time again. A little behavioural knowledge can help build strategies to overcome common mistakes.

What does the word “value” mean to you?

To me, “value” means spending time with the people I love and care about. No one says, “I wish I had more stuff” when they die. We want more time. I spend my money on experiences, not stuff.

What’s the first major purchase you made as an adult?

My first major purchase was a second-hand lilac-coloured Subaru Justy. It had four-wheel drive and a manual transmission. While small and humble, the Justy was the perfect car for getting around Toronto in the winter, and I often passed luxury cars stuck in the snow.

The purchase that took the most time for me to buy into was a one-way ticket to British Columbia. I put a lot of thought into the move from Ontario. It’s a fantastic learning experience to live outside your home province.

What’s your take on debt?

Ideally, you want to pay off your debt. What’s more to say?

What was your most recent splurge?

I bought myself a professional coffee machine capable of freshly grinding a multitude of specialty coffees. I should now be able to save millions of dollars by making my coffee at home.

What is the last money-related book you read?

Katy Milkman’s How to Change is fantastic. I loved it so much I got the audio version—she’s an incredible narrator, plus I could walk while I listened. I love her scientific research, evidence-based strategies and insight into the human condition.

What is something you always have in your wallet?

I always carry a spare dose of antidepressants. I live in British Columbia, so I never know if I’m going to be evacuated due to forest fires, floods or avalanches. Having a spare stash is ideal because I suspect losing my house in a wildfire would be depressing.

What is your favourite possession?

My favourite possession is a second-hand Victoria Beckham dress. I wear the darn thing for most television appearances because I hate thinking about what to put on.

What’s your next money goal?

I’d like to pay for my groceries without crying.

Quick money questions

Rent or own?

The pandemic changed everything. The cost of living is more costly with rising interest rates—then there’s shrinkflation, insane inflation, stagnant wages and increased food costs. Do the math, and live where you can afford for now. Nothing stays the same, so housing choices can change, and you can move up or out as the markets shift.

Buy or lease?

My 2005 Smartcar has sat without a roof for eight months thanks to supply-chain shortages. I’ve decided cars are not in my wheelhouse.

Save or invest?

You need to save to invest, so do both.

Budget or not?

I hate budgets, but I still budget.

Read more My MoneySense profiles:

• Mixed Up Money’s Alyssa Davies on striving for CoastFIRE, the value of time, and more
• MYNC franchise founder Nathalie Smith on turning a passion project into her full-time job
• “Dragons’ Den” tech titan Michele Romanow on taking risks, betting on yourself
• Tennis star Vasek Popisil on seizing investment opportunities and living without regrets
• How dating expert Damona Hoffman handles her relationship with money

About MoneySense Editors

MoneySense editors and journalists work closely with leading personal finance experts in Canada. Since 1999, our award-winning magazine has helped Canadians navigate money matters.

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