I got my first job around the age of 10, when my dad hired me to work on our farm. It was hard work. I irrigated fields in the blazing sun, milked irritable cows in the wee hours of the morning, harvested corn and hay--you name it, I did it.

I say my dad was my employer, but he was also my bank. Instead of paying me on Fridays, he gave me a piece of paper that showed me my balance and savings. He would then scrutinize my purchasing decisions and had the final say on whether I got what I wanted. It bugged the hell out of me, especially by the time I reached my teens.

His intentions were pure. He was trying to teach me how to make smart decisions with my money. When I was in the eighth grade, for example, the top tier of cool footwear was Nike Airs. I desired them with my whole soul, and decided that I was finally going to get serious and demand that my dad fork over the necessary cash.

We went to the shoe store, I showed him the pair I was lusting after, and waited while he studied them and looked at the price tag. "You know," he said, "I saw these exact same shoes at Costco at a third of the price."

So we drove to Costco. And he was absolutely right--they had piles of Nike Airs at an amazing discount. The only problem was that they were all bright, blazing orange. Of course they were cheap. No kid dreams of walking around with pumpkins on his feet.

I ended up buying them anyway, and our unique employee-employer-bank relationship continued until I left for college. It wasn't until I was ensconced in my dorm, a free man at last, that I realized the two fundamental lessons that all those years of penny-pinching had taught me:

1. Experience is the best teacher.

My dad had intended to drill me in the virtues of frugality, but the fact that I never controlled my money meant that I never actually learned to manage it. You learn from making mistakes, and I wasn't allowed to make them.

The second I got out on my own, I was broke constantly. I had to trip and stumble and fall, over and over, to master the basic arts of budgeting and thinking ahead. "Levi, if you buy this expensive CD, you won't have money to pay the phone bill. If you don't have money to pay the phone bill, that means a fine." 

I should have been having these conversations with myself from the second I earned my first dollar, but I was a late bloomer instead. I don't blame my dad for this--most of us screw up on money matters when we leave the nest. But his strict policy held me back just a little further than I would have been otherwise.

If you're a parent, don't be afraid to let your children get out there and experiment with their money. It's better for them to suffer the pains of poor decisions now than later. Be careful to hold them accountable--they have to live with their decisions--but hovering too closely will keep them naive. 

2. Buy the orange shoes.

We're a society of consumers. We're bombarded by day and by night with ads for the latest and best in every good imaginable. We're also a society of narcissists--the pressure to be the handsomest, hottest, prettiest--insert your own adjective--kid in class is crushing.

This applies as much to adults as actual kids. In consequence, the temptation to spend beyond our means is constant. I know a guy who took out a credit card just to buy an enormous flat-screen TV. He was content for about six months, when, lo and behold, a slightly upgraded version of the exact same model was released. He couldn't sleep until he got the upgrade.

My dad may have been tough, and it may have taken years for the main lesson of his toughness to sink in, but sink in it did and it laid a solid foundation of frugality and discipline in the process. 

Whatever you've got your eye on in terms of your next purchase, there's always an orange version of it at some Costco or other somewhere. If you know you can afford the version you want, go for it. If you know you can't, take comfort in the truth that pumpkins are pretty popular at least a couple months a year.