At the risk of stating the obvious, Monopoly is a game. Specifically, it is a zero-sum game. “Winning” in Monopoly means that everybody else has lost.
In real life, “winning” can mean many things. “Make a decent living” tends to be a common thread in them, but what does a decent living mean? Most of the people who think it means being in the top 1% of the wealth distribution are going to lose. OTOH, people who think it means something more moderate, such as a dwelling that isn’t too cramped, food, decent healthcare, etc. are a lot more likely to get there.
Real life is not a zero-sum game.