When you picture Italy, what comes to mind? Pasta, pizza, tomato sauce. And yet, Michelangelo, one of the most famous Italians who ever lived, never tasted tomato sauce. Not once. Tomatoes didn't even arrive in Europe until after Columbus crossed the Atlantic. And that fact has always fascinated me because it shows how easily we assume things have always been this way.
When something is everywhere in the culture, we stop questioning it. It just feels like the way things are. But most of the world we live inside is shockingly new. The 40-hour work week started in the 1920s. Retirement as a stage of life is a post-World War II invention. And the idea that adulthood is supposed to follow a fixed sequence of school, career, and retirement is surprisingly recent. The story many of us measure ourselves against is barely older than our grandparents' generation. And yet, we treat it like it's carved into the structure of reality.
We beat ourselves up for not measuring up to it. We feel guilty for changing direction after investing so much time. Or for wanting something different than what everyone else around us appears to want. But when something becomes culturally embedded, we stop seeing it as a choice. It just feels like reality, like the tomato in Italy. So embedded in the culture that we can't imagine the culture without it.
But here's where this got interesting for me. The other day I was walking along coastal California. It was a beautiful morning. The sun was shining. And ocean breeze. I'm walking past these homes along the hillside. And they're massive. $3 million, $4 million, $5 million. And I felt something I didn't expect. Jealousy, which is interesting because I spent a lot of time talking about breaking free from the system, about designing your own life, about questioning the stories we inherit.
And yet, clearly, the system is still inside me. Because the moment I see those homes, there's a part of my brain that starts doing the math. Who's winning? Who's ahead? Where do I rank? And that made me stop for a second. Because maybe the scoreboard is just another tomato. Something that showed up recently in our culture. But became so embedded that we mistake it for human nature.
Maybe humans didn't always measure themselves this way. Maybe what's actually permanent across human history is something else entirely. Curiosity, play, the need to belong, the urge to build something meaningful. Those have been around as long as we have. So the real question isn't just whether the system is flawed. The deeper question is how much of it we've absorbed without even realizing it.
How much of your life is something you consciously chose? And how much of it is just another tomato? Something inherited so completely, you stopped noticing it was a choice. And here's the question I've been sitting with today. When you say you want freedom from the system, do you actually want freedom? Or do you just want to win the game and then leave it? And honestly, I'm not always sure which one is driving me.
