There are two kinds of people in this world: those who try to live within their means, and those who see money as a constantly-expanding resource—the ones who try to make more, vs. trying to live within a set amount. I am firmly in the latter group, thanks to over a decade of exposure to entrepreneurship.
I didn’t grow up wanting to be an entrepreneur—my parents were journalists and Nortel executives, and in the 90s the word “startup” wasn’t even part of the lexicon. My dream after graduating from journalism school was to work my way up the corporate ladder, and eventually make six figures and have a corner office.
Then I met Sarah. Sarah Prevette, a serial entrepreneur who plucked me out of my first job at a PR agency to join her startup. Through working for her and observing her entrepreneurial spirit, my vision of success changed from getting that corner office to being my own boss, and I also learned the difference between earning a salary and writing your own wealth story.
Along the way, I also learned the concept of multiple revenue streams—I’m not sure where I first heard it, but the idea is that the key to wealth is building seven revenue streams. So in my twenties, I veered off the corporate salary track and aspired to build an entrepreneurial career with as many diversified revenue streams as possible.
After working for Sarah for many years, I joined a boutique marketing and branding agency and led it for six years. During that time, I slowly inched towards my financial goals—I bought my first property, purchased an investment property in Prince Edward County, started doing paid speaking engagements, and earned company equity through advising and investing in startups. My revenue streams were piling up, and I also had a comfy salary and bonus. Those were the days when spending on a Casa Loma wedding, trips to South Africa and Australia, new clothes, or a fancy dinner out didn’t faze me. My happy purchases back then were travel, dinner/drinks, clothes, and any type of improvement to our new Prince Edward County vacation property, and money was not a stressor in my life.
But then my now-husband Kevin’s uncle passed away suddenly. His uncle had a will but hadn’t discussed funeral plans and burial wishes, and his family was distraught as they tried to figure out what he would have wanted. Kevin, who has always been an ideas guy, was inspired to start a company that helped Canadians create a will and share their end-of-life wishes online, and in 2017 I gave him my blessing to quit his job and pursue the company full-time. Goodbye, one revenue stream (Kevin’s salary).
Fast forward to spring 2019. Kevin still hadn’t taken a salary for his company Willful—it was doing well and growing, but he was re-investing any revenue back into the company. In March 2019 I decided to leave my agency for a new challenge—meaning we went from 1 stable salary to zero. I joined Willful as CEO in April 2019, around the same time we moved to Montreal to participate in a startup accelerator program (all of this about six months after our wedding). Now we were newlyweds and coworkers without salaries, pouring our energy into building wealth by building a successful company.
My attitude towards money changed quite dramatically quite quickly. With no consistent salary coming in, we were funding our lives through a mix of Airbnb rental income on our Prince Edward County property, savings, and my public speaking income. Almost a year later, that’s been enough to sustain us, but our lifestyle had to change along with our bank balance. We have no exotic trips planned this year, I don’t shop for clothes anymore (Kevin would say I don’t need more anyway, and he’s probably right), we eat out less and try to cook more at home (and by cook at home, I mean hastily throw 7 things in the crockpot and hope it turns into something edible), and overall we’re just much more conscious about where we’re spending money. We’re sacrificing now in hopes of a big future gain at Willful, and our time is also spent as differently as our money—we recently moved into a new office and we live and breathe the company because we’re passionate about it and are learning more as entrepreneurs every day.
When looking at my Wellspent transactions and how they made me feel, it was so obvious that we’re in a different phase of our money lives—gone are the days of frivolous shopping sprees, and that’s okay. Most of our purchases in the app are essentials—Shoppers Drug Mart, grocery stores—or bills for our Airbnb rental or our rental condo. Those purchases aren’t sad or happy—they’re neutral. They’re necessary, and in the case of our Airbnb rental, they’re an income source. I’m never, ever going to be a bargain hunter who shops at No Frills or compares flyers—so my caveat is that while we’re more frugal, I’m still me.
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A lot of my other transactions are what I call my sanity transactions, and they received a very big happy face. The LCBO charges for the post-work wine or weekend drinks (anyone who knows me knows I love my wine—so much so that my side business, The County Wine Tours, does wine tours in PEC). The fitness fees, including my Classpass subscription and Barry’s Bootcamp classes, which not only keep me physically healthy, they give me mental clarity and reduce entrepreneurial stress. The meals out, which are now very carefully planned as a way to see friends and have a break from the business. And, occasionally, our housekeeper—it’s a non-essential, but during a crazy work week, coming home to a spotless home makes me feel so much calmer and happy.
Our biggest splurge of late was a trip to visit my dad in Florida. My sister and her boyfriend came with us, and we did the typical Florida things—shopped at Target, ate at American chain restaurants. I saw the Target purchase with the exchange rate and was tempted to hit the “unhappy” icon. Was it money I needed to spend? No. But working in the estate planning business gets you thinking a lot about how important it is to spend time with the people you love, especially as you and your parents get older. That week spend with family is priceless to me, and the Target purchase comes along with that.
I categorized my “happy” purchases in Wellspent as things that save me time, destress me, and that focus on enjoying life outside of Willful when I do take a break. Not all of them would be deemed essentials by personal finance experts, but to me, they’re essential to my mental health as I’m growing a startup. Other than a few parking fees that the app shows I regret, overall my dollars today are pretty wellspent—even if me four years ago would say my spending habits are lame.
At 34, I’ve gone through so many different money phases—the new grad phase where you have no money and rack up credit card debt at clubs; the career growth phase where money becomes less of a constraint and more of something you can play with; and now, the startup phase where I’m back to watching my bank balance but with the promise of building towards the future. Looking back at the ups and downs, it’s clear that the value of money changes over time—my wellspent dollar was different at 25 vs. 35, and it was different as a salaried employee vs. an entrepreneur. What has remained—and will remain—constant is my desire for autonomy, constant change and up-skilling in my career, and the recognition that the key to true wealth is not only diversification but happiness. And while my bank balance may be lower today than two years ago, I’ve never been happier.
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