A Stroll Down Memory Boardwalk

How playing Monopoly with my family taught me about money.

When I learned that most people hated Monopoly, I was shocked. Then I learned how most people played Monopoly, and I was still shocked — that anyone put up with that version of it. Most families have a favorite game. Cranium? Sorry? Taboo? My family had a bookcase full of board games, but Monopoly was the only one that didn’t require a re-read of the instructions every time we played.

That being said, reading the actual instructions probably would have badly confused us.

Here are the Gold Family Rules of Monopoly:

• My brother was the car; my dad was the moneybag (according to the Monopoly Wiki, this piece was added in 1998 and discontinued 2007). I was usually the terrier, but sometimes I switched to the horse and rider when I decided a new token would change my luck. If there had been a “razz approvingly from the sidelines” piece, it would have been the sole property of my mom.
• My brother would combine all his money into one rainbow stack; my dad’s cash would inevitably decay into a multicolored nest of madness. I would separate all my bills out by denomination, line the piles up so they were parallel with the properties, and then neatly tuck the edges under the board to anchor them in place. Last, I would push one of my $500 bills under the board entirely, out of sight and out of mind.
• We never, ever skipped an auction.
• All fines went to the center, to be collected when you triumphantly landed on free parking.
• Most importantly, the deal was king. Swapping money and properties was amateur hour — we dealt in speculation and strategy. If you were about to go bankrupt, you could haggle properties you hadn’t landed on yet. If you were about to bankrupt someone, you could make them an offer they couldn’t refuse. If you wanted to knock the winner out of the race, you could agree to not charge the third player. The limit was your imagination and what another player would accept.
• Paper and pen were mandatory parts of the game. We wrote up short contracts to ensure that other parties would not renege or forget the complicated terms of engagement.

If my memory serves, my brother won about two out of every ten games. My dad won the other eight.

I’m not a particularly good sport now, and I certainly wasn’t back then. I’m competitive: I don’t take losing well, especially not to snotty twin brothers. I’m also not one of those admirable people who keep trying and failing until they succeed. Reflecting on it now, it’s pretty darn surprising that I kept coming back to the Monopoly table.

I think I did because it wasn’t so much about winning — though, let’s be clear, it was about winning — but it was really about those deals. About assessing a situation both from your perspective and your opponent’s, and finding a middle ground that worked for both of you. Every game was a little bit different, a new opportunity to try a different tack.

Which really means that after each game, my dad would explain how he had beaten us, which meant the next game was an opportunity to try again. This all makes it sound really dreary and dry, but it was fun. The games were full of laughter and jokes, boisterous bravado and light-hearted taunts exchanged alongside rainbow bills.

Unsurprisingly enough, this is also a Great Big Metaphor about how my family approaches money.

There’s a lot of things that I believe I took away from these silly Monopoly games: practicing negotiations, recognizing incentives, a grasp of long-term strategy. More than anything, though, it taught me that succeeding meant thinking outside the mint-colored Monopoly box.

I’d argue that creativity is pretty underrated in personal finance. This is probably because most people have a healthy fear of personal finance — I know I’m not alone in viewing it as a tightrope act. You go forward, you go backward, but there certainly isn’t room to go side to side. Creativity means a potential for error, and financial error is a terrifying prospect.

But creativity is important because, if done right, it forces you to let go of social norms. So much of how we spend our money is dictated by how the people around us spend money and how we think the people around us spend money. Letting go of the normal gives you more options.

As a very important caveat: thinking creatively about money is a privilege in and of itself. You have to have money to have multiple options in its spending; you have to have time and a roof over your head and internet access to learn about what those options are. In Monopoly, everyone starts with the same stack of rainbow bills; obviously, that can’t be further from the truth outside the board game.

But growing up in my suburban enclave, where my social circles were cheerfully middle-to-upper-middle class, it was pretty clear that having multiple options in spending did not necessarily mean folks thought much about how they spent their money.

Even outside the Monopoly box, my family always did things just a smidge differently. We were the only family I knew on pay-as-you go cell phone contracts in high school, which meant my classmates were confused and amused by my battered flip phone in the age of the first iPhones. We never had cable, though we got DVDs delivered through Blockbuster before anyone else. My mom took me to thrift stores way, way before the advent of the hipster. I don’t think I even thought about the concept of getting my own car.

I’m kind of amazed I remember these details, because they’re so petulantly small. But when you’re a high school student — a middle class suburban high school student, to be specific — letting go of the social norm is hard. I begrudgingly accepted that we always did things that my friends’ parents didn’t do, though I never really understood why. Spending differently to save money is a pretty abstract concept when you’re only responsible for paying for movie tickets and eating out with friends. At that point, spending money meant going out; saving money meant not going out. I wasn’t sure why all this meant I still didn’t have an iPhone.

Things began to make more sense when we approached college. When the time came, my parents informed us that they had a set amount of money in our college funds. It was a more-than-generous amount—far, far more money than I now make in a year—but it wouldn’t cover even three semesters’ full tuition at a private or out-of-state university. (And yes, that was a painful sentence to write.) At this point, my siblings and I had a full ride at the University of New Mexico. If we wanted to go to a school that wasn’t UNM, we either had to find the scholarships to cover the difference or take out the loans. If we went to UNM, we would get the money for Abstract Long-Term Adult Other Things, like buying a car or the down payment of a house. My parents’ money was also a scholarship, by the way: if our grades dipped below the merit scholarship standard, that money was no longer ours.

I’ve talked to numerous people about how their parents addressed the question of college tuition, and I’ve never heard of it being presented the way my parents did — even the fact that my parents told me a specific dollar amount is rather unusual. I’ve certainly never heard of familial money being linked to GPA. My parents were, again, more than generous, but made it clear that this was a two-sided deal. We weren’t entitled to all their money, and we weren’t entitled to any of their money if we didn’t take college seriously.

Ultimately, they set the terms, gave us a number of options, and let us choose. It wasn’t the social norm, perhaps, but it worked: I got scholarships to cover the difference, and my brother elected to go to UNM. He’ll get his college funds when he wants to buy a house.

Things began to make even more sense when I finished college. I still remember one of the first times it really clicked into place, when I had accepted a job on the other side of the country. The question then became how to get my car from the Pacific Northwest to the Southeast. Would my dad fly up and help me drive across the country? Would a friend drive with me to my parents in the Southwest, and then fly back to Portland?

A couple days into this debate, my dad called me.

“Why don’t you ship the car?” he asked.

Per usual, my instinctive reaction to one of my dad’s propositions was confusion mixed with disdain.

“Can you do that?” I asked. No one I knew had ever had their car shipped.

“Yes,” he said patiently.

“Why would you do that?” I asked. Road trips were an important part of the American Dream!

“First, because it’s cheaper. Second, do you really want to be in the car at least eight hours a day for five days?”

I thought about it. I did not. I shipped the car.

And yes, weirdly enough, I did get judged for this decision: my friends responded exactly the way I had when my dad had proposed the shipping. It can be difficult to buck the social norm when you’re a young adult. But I had paid to ship the car with my money — the one of the largest transactions of my young life at that point, in fact — and it’s pretty easy to weather disdain and confusion when you saved several hundred dollars and didn’t have to spend a workweek in a car to boot.

Money was never really taboo at my house, but it wasn’t something we discussed in great detail. Now that I’m grown and managing my own finances, it’s become the new Monopoly.

Not that we take our financial futures lightly. It’s something we share, and that there’s more than a bit of competition involved. I send my parents pictures of my new shiny household finance binder. My dad emails me new credit card deals; I crow when my credit score is (briefly) higher than his. My mom texts me the best scores at her local thrift store, and I do the same.

We are incredibly fortunate, to be able to treat money as a challenge rather than an obstacle. I am incredibly fortunate that my financial situation is a topic of conversation without consternation. At the same time, I’m very aware that this can always change: it’s important to talk about money when the getting is good, so you can talk about money when the getting is bad.

On our most recent family vacation, we found ourselves playing Monopoly again in a hotel room in Durango. It was a new set, so there was no moneybag piece to be found; my dad had to settle for the top hat.

I don’t remember if I tucked that $500 under the board, but I do remember that I spent it. And, for the first time in anyone’s memory, I won.

Maya Gold researches, writes, and pets neighborhood cats in DC. Follow her on Twitter.

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