Most of the time that I'm writing on this blog, I'm relaying to you the daily process I go through of reaffirming in my mind that there is no way I could send my kids to school. Because believe me, if I could somehow justify it in my head, I'd do it in a second.

Last week we hung out in Florida with people who have a lot of money. I did a lot of watching, and (when the weather warmed up enough to take off our winter coats,) I found myself on a deck chair next to a talkative mom, and I chatted.

I talked to a mom who sends her kids to private school where they have five hours of homework a night, and so much homework in the summer that kids can't go to camp. And she was telling me that she's starting to think all the homework is just to cater to the parents' insecurities about their kids being special enough.

That sounded true to me. And I almost wanted to be her friend. At least long enough to see if I thought her kids were really learning anything remarkable.

Part of my pool reading was New York Magazine. It's my favorite magazine in the whole world. This week there's an interview with someone who helps kids get into elite schools. This is a huge business in NYC, and I need to tell you that the final crushing blow for me deciding that I couldn't raise kids in NYC was when I wrote a check for $10,000 to a consultant to get my kid into preschool.

So anyway, here's what the consultant in New York Magazine had to say about parents who are nuts about their kids' education: "Most people go where their parents went. And their parents went to good schools. Or they know the board of trustees. I have a lot of kids who are hooked up. Really hooked up. It's outrageous! The rule of thumb for themost part: The more money a parent has, the less intense they are. They know their kid will be okay."

I want to project this onto my kid: You will be okay.

The big difference between rich kids and regular kids is a sense that they really will be okay. Yes, wealth can be damaging—I have had friends with trust funds that killed their initiative — but generally speaking, teaching your kids that they will be okay just being who they are seems like a good thing to me. And people who don't do that are projecting fear onto their kids.

The Conrad hotel and resort group  advertises with the slogan: The luxury of being yourself.

That is a luxury. It's a luxury to hear your parents tell you that you can choose what to learn because you have good judgment. It's a luxury to have all day to play and explore and be a kid instead of go to a classroom and be taught to follow orders.

When I was a child, people would read Robert Louis Stevenson's poems to me. He describes a childhood where he is free to explore—trees and people and books—and a governess that follows him around making sure he learns some manners and doesn't hurt himself. That seems like the perfect model for childhood education, and it's something only secure parents can do. It requires so much faith in the child's innate ability to succeed as an adult.

Today this isn't the purview of only the rich. But it seems scary to take the leap that kids who do not have friends on the board of trustees at Yale or Harvard can also be fine if the parents relax about schooling and  believe in their kids.