A question I get fairly regularly is where my passion for financial management first started.
I’ve given it some thought over the years, and I think the blame, or credit, has to go to Santa Claus.
When we were growing up, my sister Shannon and I lived on a large farmstead with our parents in Lisle, Ontario.
Lisle is a small hamlet in rural Ontario, closer to Lake Huron than Toronto, and when I grew up there, it was mostly farmland. Summers were extraordinary, and winters could be brutal, with average temperatures hovering right around 0°, and near-constant snow cover.
Which meant that when it was nice out, we played outside. And there was a whole lot of outside for us to canvas.
But when it wasn’t so nice out, we were stuck inside. And our parents (and Santa!) were always looking out for new ways to keep us entertained.
The Christmas I was 8 years old, I was given my first Monopoly set.
We were always a gaming family. I remember my parents were very into card games. When we were young, they’d have friends over and everyone would play Rummoli. If you’ve never played — it’s worth looking up the rules and getting a game together, especially if you’re still quarantining with a few bored family members. The game is very entertaining, though it can get intense.
So when my parents introduced me to Monopoly, I took to it immediately. I couldn’t get enough of the game, but Shannon, being younger at 5 years old, didn’t always want to play with me.
For those long winters cooped up inside, I devised a creative way of keeping myself entertained, playing Monopoly — against myself.
I set up three sides of the board as different players, usually the dog, the car, and thimble (my favorite!), and the fourth edge would be set up as the banker.
And then I would try to win with all three of my characters. When it came time to make a property trade, I’d make it make sense for each player to have a positive outcome, rather than, say, unfairly prioritizing the thimble over the car.
It somehow never got confusing for me, keeping track of who had which properties and money. I even played with house rules like using the middle pot to collect cash, which the player could win if they landed on Free Parking.
Back when I was a kid, this was all just a game for me, of course, but when I look back on it, I can see that’s where my love of money first started, and it’s the genesis of my budgeting strategy wherein I use the image of buckets to connote the different areas of spending.
In each of the jobs I’ve had, no matter where I worked, there was always a financial component that I could help my employers or colleagues understand, and my approach was always to level up their existing systems, to make them more sophisticated, or more egalitarian, or just to work better for everyone.
There were some lightbulb moments for me back when I was playing Monopoly as a kid that have carried forward into how I work today. For instance, I always tried to win with each player. But if one of my players happened to get Park Place and Boardwalk, and then they collected the other properties on that side, the expensive green properties, the other two players likely couldn’t win. But cashflow was low for someone who had spent all their money on expensive properties. So they needed people to land on their properties quickly. If that didn’t happen, they could flounder. But if people were landing on the expensive properties and paying money on them consistently, that one property-holder would eventually wind up with everything. And then the other two people would have nothing left. That didn’t happen very often, but when it did, I would be like “Wow, that’s cool, look what I did.” (My very own personal Boardwalk Empire!)
Recently, I’ve taken on some new clients who had personal credit cards that they were using for both business and personal expenses. I find this most often happens with clients who own a sole proprietor business, and it makes sense — folks have to do what they can to get things off the ground at first. But it makes things unwieldy for bookkeeping purposes — think how messy things would get if two of my Monopoly players were working from the same pool of resources. Everything would become too complicated very quickly.
Very quickly, the game would fall apart.
In Monopoly, as in life, it’s easiest to keep everything separate. Since I’m a visual thinker, that metaphor of keeping everything to its proper bucket works for me. If a personal credit card is to be used for a business venture, designate that card and only that card as a business card, so that one is the only one you’d use and the only one you have to update for your books.
My childhood boxed set of Monopoly has long since worn out or been donated — I can’t even remember what happened to it. I don’t own a physical copy anymore, but then I don’t need to. In some ways, I’m still playing; some days my job really does bring me that sense of joy and wonder, like when everything syncs up just so for a client, or they’re able to pay off a large debt after months or years of hard work and commitment.
These days, of course, my satisfaction in these wins runs much deeper, since we’re dealing with real money, and real livelihoods. But the central driving goal has always been the same: trying to achieve a win for everyone playing.8
