The best $50 I ever spent I spent while I was in Elementary school. I can't remember my exact age but I do remember the purchase, the fall out, and exactly how hard I worked for that $50. The first thing that you must understand is that I worked for my money as a child. To earn money I had to read a book (a new one, you couldn't read the same book twice) and do a book report that had both appropriate length and depth for my age. Then I had to sit down with my mother and have the report corrected for spelling and grammar. For every four books I read one had to be a language other than English, and no English books would be paid for until there was a non-english book to fill the void. The going rate was 10 cents a page. Once the amount owed was calculated 40% was deducted for long term savings (my university fund) and 10% was deducted for charity. Needless to say, my money was hard earned.
This was the time when GameBoys were all the rage. All the kids had to have one, so eventually my older brother wanted one as well. Then I wanted one. I remember saving up my money and going with my parents and siblings to the store. We agonized over the choice of which game to buy, as we could only afford one each. Eventually I settled on a game based on the Disney movie Mulan. We all got home and immediately started to play.
I hated it. For the life of me I could not get past the second level, not to mention that every time it took me at least 10 tries to get past the first. It frustrated me to the point of tears. Eventually (in less then 2 weeks) I stopped playing it. I could count on my fingers the number of times I played that game and still have plenty of fingers left over. As soon as I figured out that the game frustrated me instead of giving me enjoyment I felt cheated. I mean, come on, 50 bucks was a big deal back then, do you know how much ice cream I could have bought?
I sat down at the time and tried to figure out why I had bought the game in the first place. I came to a startling conclusion. I wanted one because my big brother wanted one, every one wanted one. It was simply the thing to do. Now that I'm older (and marginally wiser) I think that that $50 was the best I had ever spent. As hard as it was at the time it taught me some very important lessons.
1) I stopped listening to what everybody else was doing (and buying) and did my own thing. This is such a great freedom to have. I don't worry that needle work wasn't what most of my co-workers (mostly male) do in their spare time. It is my spare time and I do what ever I please.
2) I thought seriously about major purchases. After that day I always slept on a purchase before making it. I can safely say that before making a purchase of more the $25 will probably spend a week thinking about it and deciding if it is really what I want to do with my money.
3) I entertain myself on the cheap. Library books are my main entertainment, free shows on the internet, crafts. (Yes crafts can be expensive but the last $75 cross stitch I got took me 8 years to finish, so about 78 cents a month.)
4) I preview what I'm getting. I never buy a movie without watching it first. There are only 3 authors on the planet who's book I will buy before having read it at least 5 times from the local library.
Most people are astounded that over 4 years at university I averaged less then $10 a month on entertainment. The best thing is that I never felt deprived, I honestly enjoyed my spare time and I was seldom board. "Wasting" that $50 in elementary school taught me invaluable lessons about money management, and I am richer for it today.