1) Are privileged kids at a disadvantage when it comes to learning the lessons of financial independence?

2) Have I romanticized being poor to facilitate my financial goals, and what are the implications of doing this?

“There is no success without hardship”

Sophocles said this. In my case, I've found it to be true. Growing up “ poor” forced me to learn the tenets of hard work, responsibility and resourcefulness - qualities that have helped me find success in my endeavors. My mom had even less money, and she learned those lessons even more thoroughly. To this day, I've never seen anyone more frugal or with more self-control than my mother.

So I grew up believing that wisdom comes with adversity. But thinking in terms of financial independence, what does this mean for those who grow up privileged? It's usually a parent's goal for their children to grow up without financial hardships. Consequently, can those children learn the lessons of personal finance just as powerfully without going through all the tough stuff? Can we be wise without having to endure adversity?

How much can you learn with a safety net?

Of course it's possible for the privileged to learn to be industrious and diligent and all of that, but I feel like the lessons are much different when you have to learn them. Here's a somewhat nerdy example.

In The Dark Knight Rises (spoiler alert) Bruce Wayne must escape his prison by climbing to the top of a deep pit and leaping out of it. He tries this a few times while secured by a rope - his safety net. He's unsuccessful each time. Then, he decides to try the escape without the rope - the motivation is, if he doesn't succeed, he'll fall to his death. Of course, Wayne finally succeeds without the rope. His will to survive leads him to accomplish his goal. He succeeds when there is no other option but to succeed.

I know it's just a movie, but it's also a parable. So I ask myself:  How successful can you be in learning the lessons of value, responsibility, etc., when you'll be totally fine if you don't?

The problems with romanticizing poverty

I plan to have a safety net for my own kids. In fact, I don't plan on having kids until I can afford to have a safety net for them. Does this mean they'll grow up at a disadvantage when it comes to financial independence? Will they have less success because they have less adversity? How do I teach my kids to be financially independent when I plan to give them a financial safety net?

Second, even though I finally have some financial elbowroom and am able to live comfortably, I still have this “impoverished” mind-set. I discussed this a bit when I wrote about not buying a new computer because I didn't feel like I'd suffered enough to afford a new computer. This mind-set has kept me from enjoying the fruits of my financial independence. Exaggerating my poorness has worked in my favor in the past, especially when I needed to save money to pay off my student loans. But these days, it's given me a false sense of insecurity. And why else have I worked so hard for my financial independence if not to feel secure?

Another issue I have with romancing poverty is that it's kind of condescending.