When I play games, I try to win. Whether and to what degree one believes I "try" is subject to interpretation. If you ask Katie, I always want to win and I will do whatever it takes to do so. If you ask me, I'm merely playing to the best of my ability and not giving anything up to be nice--no one wants to win because another person went easy on them.
In World of Warcraft, there is no real way to "win" (with the common exception that people who stop playing WoW (as it is commonly refered to) state that they "won" or they "beat WoW." I can't argue with this concept, but that's not what I'm talking about). The game progresses indefinitely, even if you beat the "last boss," which also changes as new expansions are released. Thus, the point is not necessarily to win; it is to enjoy the journey and continue to have fun engaging in various activities peripheral to beating the "last boss."
(It should be noted that it is commonly preached to enjoy the journey on the way to the result. Yet, this concept is not necessarily accepted as applied to video games--if there is no way to "win," what's the point, right? Perhaps the absence of an end point frustrates this concept. If so, I should buy into that, based on my other viewpoints of things with no end point: I didn't learn to drive until I had somewhere to go, and I generally don't take walks if there is no destination. But that's a conversation for another time.)
When I started playing WoW, the endgame raid zone known as Black Temple was either just released or released soon after. BT was supposed to be the "final" raid zone, containing the "last boss" until the next expansion (as it turns out, this wasn't the case, but that's not important either). BT is a Tier 6 raid, meaning that's the quality of loot that drops from enemies contained within, and because loot quality increases based on difficulty, BT was the most difficult raid.
I never set foot in BT. Nor did I see the Tier 5 raids, and my experience with the "high end" Tier 4 raids was limited (lower tier raids were part of the original game and rarely visited; again, not important, except to say that Tier 4 was the "entry level" raid when I started playing). See, because I joined the game at a later stage of the game, I was not well-equipped to see the higher tier stuff--the groups who did that had been together longer and didn't need new players. So, I did what I did, had a lot of fun, acquired new gear, but was never among the "best" or even the "best geared" in my class (which is not necessarily an attainable thing either).
Fast forward to the new expansion: I started playing at the outset of the newest expansion, collected some good gear in Tier 7 content, then through a cooperative agreement with another 10-man guild, collected some great gear in Tier 7.5 content. In fact, my character is very well geared and only missing a handful of pieces that would make him "best geared." Yet, I know and everyone knows that new bosses and raids are on the horizon, and that the current expansion will go until at least Tier 9 or higher. So while I'm on top now, so to speak, that will change swiftly once more difficult raids are available.
Is this a problem? Now that I'm, at the moment, "winning," is it terrible that my "winning" status will no longer apply once new content is available?
I say no, for a number of reasons. First, having great gear, while somewhat telling about what a player has experienced, is in no way determinative of anything more significant. If anything, it means I had the opportunity to be present when the gear happened to drop, and I managed to win the gear ahead of others who might also have used it. In other words, I could have been the most useless player--getting myself and others killed, not doing my job in damaging the boss, etc.--and I still could have "achieved" all this gear by virtue of my schedule and my ability to permit my friends to keep letting me raid with them despite my apparent incompetence. So, just because my gear is great doesn't mean I'm "winning."
Second, I have not really "won" in any sense of the term--though my guild has beat the current "last boss" once, I wasn't there when it happened, and we haven't duplicated the feat since. Plus, with the addition of "hard mode" bosses, the real "last boss" is no longer the most difficult feat in the game.
Finally, winning in this game is not really possible in terms we usually see it--it's about the journey, not the destination. In that sense--enjoying the journey--I have never stopped winning. I am enjoying the journey with friends and other players, meeting new people and sharing new experiences, and generally having a good time while progressing--slowly or rapidly--towards various "ends." I "win" every day, even when I lose.
Thus, though from a gear perspective, I am near the top--the Journey's End, so to speak (which is, funnily enough (or not), the name of the best melee weapon I can equip at the moment), as long as I'm enjoying the journey with good friends and good players, I am always on top. New content only allows us to continue the journey further. Thus, new content means more winning for everyone.