How to Monopoly
The first time I played the game, I was seven.
The game wasn’t new—its box corners were worn, the lid barely clinging on, a hand-me-down from my cousin. But it felt like a treasure to me. Little did I know then that this game would become more than just a pastime—it would become a mirror, reflecting lessons on competition, relationships, and the art of knowing when something is complete.
Recently, while in Melbourne for the Australian Open, I stumbled across Monopoly Dreams, a physical tribute and museum of sorts dedicated to one of the most popular games of all time. As I wandered through its halls, surrounded by oversized dice and glowing property cards, my eyes widened in a way they hadn’t in years. Suddenly, I was back in that world—the wheeling, dealing, scheming world of my childhood.
I didn’t just love Monopoly as a kid—I lived for it.
I forced my sister, cousins, and friends to play endlessly. I wasn’t playing for fun; I was playing to win. I studied patterns, perfected strategies, and approached every game with surgical precision as well as a ten-year-old could.
Secure the blue or orange properties first. Negotiate deals as quickly as possible. Always keep cash on hand. My property empire always rose, and I always won. And I loved winning—until, one day, my streak came at a cost.
My younger sister, tired of endless defeat, declared a one-person rebellion. She made it her mission to convince everyone we played with that the game wasn’t fun anymore because I always won. And she succeeded. Slowly but surely, nobody wanted to play with me anymore. Just like that, my Monopoly career ended.
Standing in Monopoly Dreams nearly thirty years later, surrounded by pieces of a game that once defined my childhood, I was flooded with nostalgia. But what surprised me wasn’t the intensity of the memory; it was the absence of desire.
I didn’t want to play again. I didn’t want to gather friends for a rematch or feel the thrill of victory. I simply smiled, remembering the joy the game brought me, and felt no need to drag my past forward into my present.
It is rare to feel so deeply about something and not want more of it. So many things in life we cling to, expecting them to evolve with us or remain relevant forever. Childhood passions, relationships, milestones—they often carry an unspoken expectation that they should follow us, as if their absence in the present is somehow a loss. But with Monopoly, I felt none of that. It was a chapter that had done its work, a story that didn’t need to continue.
The game taught me lessons I carry to this day. Strategy, negotiation, the balance of risk and reward—it all began on that worn-out board. It shaped how I think, how I make decisions, how I navigate the complexities of winning and losing. But like a book whose ending you already know, it doesn’t need to be revisited to be appreciated. Monopoly exists as a perfectly preserved memory, complete in itself, untouched by the passage of time.
Walking out of Monopoly Dreams, I realized that not every part of my past is meant to travel with me. Some things are beautiful precisely because they stay where they belong—in the past. They enriched me, they shaped me, and then they stepped aside, making room for what’s next.
The dice have been rolled, the properties bought and sold, and the game, in its own way, is gloriously complete. And in that completion, I’ve found a different kind of victory—not the thrill of winning, but the quiet satisfaction of knowing when to let go.
And that is how I learned to Monopoly.
Click here for a short highlight reel from my nostalgic tour of Monopoly Dreams in Melbourne, Australia.
