With the constant influx of new art (paintings, films, books, etc.) being produced at a rapidly-increasing rate in our Post-Post-Modern age, it’s becoming incredibly hard to stay abreast of our culture. This problem is multiplied a thousand-fold for digital content, to the point where an earnest desire to “stay current” requires such an immense time commitment that it borders on futility.
Furthermore, it’s undeniable that the individual works of art themselves are collateral damage in the mad rush to see all of them. One simply cannot give each piece of art the observation and analysis it deserves if the time allowed doesn’t at least appear to be unlimited. Take movie critics as a prime example: their jobs are based around getting you information on new movies, so you can compare and decide which one you’d like to go see. This requires a) that they see every movie they can (otherwise how would they be objective?), and b) that they do it as fast as possible (so they can deliver reviews for movies you haven’t seen). Like an assembly line, they churn out half-baked judgements, without slowing down to appreciate each film fully. It’s ironic, then, that so many people value critics’ opinions over all others.

"Video games will never be high art. I know this because I'm a CRITIC."
This situation is also easily seen in public education. Students are crammed with multitudes of assignments, instructed to read this or that, flung back and forth between eight different subjects, and at the end (and only at the end!) are expected to retain any of it. Many a superintendent is probably proud to proclaim that all students in the school read “Hamlet” by their Junior year, and perhaps they do. But how many of those students took the time to examine it? To ponder the interwoven meanings? Just like with films, it’s tragically typical for viewers to look and still not see.
Time-based media necessarily falls into this trap, since there’s an obvious way to determine when one has “finished” it. There’s a definite beginning and end, and once you get to the end, there’s a feeling of accomplishment, even if you didn’t understand a bit of it. Static media, like paintings, resist this pull a little more, but it’s still easy to say “I saw the Mona Lisa,” and leave it at that. The act of viewing is equivalent to the act of completion, because the piece never changes.
What, then, of media that doesn’t have a set time limit? That is dynamic and ever-changing? How do we mark a video game as “Completed”, when a definition for completing it doesn’t derive naturally out of the medium itself? Why, it’s simple! We impose arbitrary, artificial boundaries. We give players a score, we give them levels, we give them mission objectives, and we give them title and ending screens.
Above all, though, we tell them when they’ve won or lost the game. For the act of “winning” has become the driving force for players, the goal they shoot for, after which they know they’re allowed to stop playing. Finally, they can mark this game off the list, and move on to quickly beat the next one. And the next one. And in catering to this rushed playstyle, we cripple our own games. We set constraints for victory conditions, and make them reasonable enough for players to actually attain them. Because nobody wants to play a game in which they always lose. Players just want games to make them feel good, to give them something at which they can easily succeed.
Have we forgotten that “winning” is not intrinsic to the medium of video games? That games don’t have to be winnable, or even fun? They don’t even have to let you play.
Can we accept games without a way to quantify progress? Where the experience of playing is of itself the point? There are so many reasons that could exist for playing a video game, but all we can think of is getting to the end.