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I have a really important life topic to talk about today: The game of Monopoly. I have heard the word “monopoly” over and over and over from my eight-year-old son's mouth over the past week. In rhythm like this:
We've been playing the same game of Monopoly for the past week by my children's request. Yesterday, he wiped us all clean of all we had - all the money, all the get out of jail free cards, all our properties, everything. He literally took three other people to the cleaners. I've never played a game of monopoly in my life - and I have played some games of monopoly, especially with two brothers and no TV on weekends with our grandmother in the summer growing up - in which we played to the bitter end, and one person just wiped the table clean. And my eight year old son just did that to us, the entire family, all older (but perhaps not wiser when it comes to monopoly), this week. It was interesting to watch it happen. We're all competitive in our own fun way. He's especially competitive. He loves sports, he loves math. He had the cheapest properties on the board at first, the two brown properties, Baltic Avenue and Mediterranean Avenue, which were right after you pass Go. At the very beginning of the game, he nearly went bankrupt putting four houses and then a hotel on each one. Then after he gained some of his money back, he eventually bought all three of the green properties, Pacific and the other two green properties, on the other side of the board, in the lineup before passing Go. Then he did the exact same thing, bought: one house, two houses, three houses, four houses, and then hotels on each of those. Here he is, sitting with these two fully stocked properties, the brown and green sets, all with hotels, while the rest of us are just playing and scrambling for whatever on the board we can get. He set his in investment, had very little money sitting in front of him, and waited. He passed go, collected his $50 on the Beauty Award or whatever refunds from the Chance or Community Chests, and slowly but surely build his own bank up. Then we started landing on his hotels. It was a clean sweep on his behalf. A thousand monopoly dollar mistake to land on his green hotel on Pacific Avenue. A $450 mistake to land on his Baltic Avenue. He just kept getting richer and richer. And the rest of us… did not. At the beginning of the game, we were all trying to scramble to collect what we could get to keep playing, pass Go. Meanwhile, he's investing. Investing in himself; in himself by way of his properties and the belief in a better future. During that early part of the game, he almost went bankrupt. He had this vision of hotels - again, at eight years old - for his two sets of properties. And found a way to do it, no matter what. I thought about this strategy in a bigger way. While life isn’t a game, this particular game has many things that life also does: rhythm, emotion, strategy. There’s an obvious connection to real estate, and being a landlord in this way, in the right market, can be a very, very good business to be in. If you're in that business, I'm sure that that would be a connection you would see as well. But let's talk about the bigger picture of investing in yourself. That's what I'm trying to envision for myself, for any entrepreneur, for any person who sees the light, for anyone who's starting a new venture, be it going back to school, starting a new venture, whatever the case may be. Should we not invest in ourselves to such a degree with all of our beliefs and hearts and vision and strategy go into it? Such that we are willing to almost go bankrupt doing so, because we know that in the long run, it's going to pay off? How do we set ourselves apart and be different, and make investments that are unique to us and our unique qualities? How do we create that blue ocean in which we have endless potential possibilities and abundance? That clean sweep monopoly board strategy that I learned from my eight-year-old’s natural ability to envision who took us all by surprise in the course of a week. So perhaps the other part of it is the patience to accomplish his vision, too. Maybe some of us would have given up, with the initial low. We did all right, we pursued what we wanted, it didn’t go as planned, them to play a different game. We bought these houses, we bought these hotels, and nobody's landing on our stuff. Nobody likes our stuff. Nobody's reading our stuff. Nobody's investing in us or believing what we believe or understanding our concept. But then he waited. He kept passing go. He kept growing. And he kept asking us:
Do we have the patience to withstand the abundance that we will get if we believe in ourselves and follow the bigger picture here in God's plan? It's an interesting virtue to learn, patience. It’s difficult sometimes. Such an important one, especially for parents, to learn patience. I try my best. Every day is a test. It is challenging. Even just driving down the street, you have to learn: patience is a virtue. That we all could stand to have some more patience. In this particular monopoly game, my little guy knew that if he played long enough, he was going to take us for everything that we had. Kids are so in tune with themselves. It is so fun to watch and learn from them. His investments in the green and brown sections of the board multiplied, by a factor probably only his math mind can understand. He literally took us all for everything that we had at the end. It all started with that initial strategy to investment into himself. I have learned these things, and I'm trying to apply them to my own life and trying to connect the dots:
Also:
Maybe your reward will come in Monopoly bucks. Maybe in some other quantifiable way. But the feeling of abundance by way of purpose and fulfillment, bravery, accomplishment, even adventure, those will come for sure.
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Jackie MorrealeJackie writes from her own experiences and reflections on her journey in seeking wisdom, creativity, spirituality, and life in general. This is "putting thyself out there" at its finest. Archives
August 2026
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Wisdom for Wannabes
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