But... but... I'm only a thirty-something! ;)
Thanks to Joseph Bloch for pointing out Steve's Random Musings on Wargaming and other stuff's post titled "Definition of old School."
It can be summarized as follows:
Old School Wargamers...
1. Enjoy doing their own research on the historical periods they like wargaming in,
2. Understand that the game is just a representation of what happened on the historical battlefield,
3. Are often not tournament players or rules lawyers,
4. Do not mind taking weaker side to see if they can get a different result than what historically happened.
5. Have a "practical, do it yourself, ethos."
6. Behave like gentlemen (or ladies) at the table while enjoying libations and resolving disagreements with a d6.
7. Aren't defined by the games the play or who they've gamed with. It's how they approach the game.
So according to this definition, I am old school as both a wargamer and a roleplayer. Up until now I liked to avoid labeling myself as Old School because I was afraid it'd make me sound... old. But there's a lot of wisdom in Old School, wisdom I've been touting for years since my earliest days as a roleplayer.
My philosophy on gaming is this: Wargaming and Roleplaying aren't really the hobbies themselves, but a product of people enjoying the history and literature that inspired both. Participants will often spend more time in "preparation," doing their research, than actually playing the game--this is especially true in wargaming (all those miniatures to paint!). Thus, they should enjoy these aspects along with playing the games themselves.
Anything else is gaming in a vacuum.
And when you game in vacuum, without outside inspiration, you start eating through any material you can get your hands on--new modules, rules, supplements...the egos of other players. You become dogmatic because of your percieved sense of scarcity, putting the rules first before the game, before the other players. In other words, you become an annoying bore.
I believe people should be well-read in literature and history before taking up either wargaming or roleplaying, or at least have an appreciation for it. Sorry, movies, TV, videogames, and stuff on YouTube don't count. These are but distillations of history and literature. Many of the best movies out their have been inspired by books, which often why those who've read the books will say, "The movie was good, but not as good as the book."
Playing these games can inspire people to read more history and literature. D&D did so for me. I wanted to learn more about the Middle Ages and general history so I could add more versimilitude to my games. The same is true for wargaming. I wanted to read more fantasy and general fiction, and not just the TSR novels (Dragonlance, et al).
But I'm glad my brother waited until I was ten before letting me play D&D. While I hadn't read the "classics" from Appendix N, I was fairly well-read for that age. This gave me a better appreciation for the game itself ("Wait? You mean I get to fight goblins like those in The Hobbit? Awesome!").
I also believe that the relationships you develop at the tabletop are more important than the rules, more important than winning. This is why I've never played in a wargaming tournament. Don't get me wrong, I like to win--but what's the point if my opponent resents me because I quoted a bunch of rules to him? (And someday I will win with the French in HYW!)
If you're reading this, then I'm probably preaching to the choir. Yet I've encounter folks who've describe themselves as "old school" halt games for a half-hour (or more) so they could look up and argue over rules. The d6 method works well in both roleplaying and wargaming (1-3: the argument goes in your favor; 4-6: the argument goes in mine; now let's keep playing).
If, however, I'm not preaching to the choir, then take a look again at the definition of Old School. You might learn something that will make your games a lot less stressful and far more enjoyable, and even young at heart.