This is a WOW post, but I expect all the non WOW people will be able to understand it.
Two days ago I joined a raid to kill the weekly quest boss Sartharion. Now with the expansion as old as it is this is about the most trivial thing you can imagine, in fact this 'raid boss' has been soloed by one very determined player. As such taking a 10 man raid to beat Sartharion on easymode is quite the trivial task. I ended up joining a group that wanted to do the hardmode version instead. I figured I would join them just for some added challenge.
We wiped. Then we wiped again. And again. And then we tried again... and wiped. Then 5 of the people who were part of the group running the show all left. Then the raidleader says to the remaining people: "Sorry guys, my guild doesn't normally wipe. I will get them back and we will just do easymode." I get to wondering at this and check out his guild and the people in it. He is right that his guild doesn't wipe much since they don't do anything that could pose even the most pathetic challenge. They are a group of people who simply do all the most trivial repetitive tasks over and over making sure to avoid anything that might require skill or practice.
Here is the thing: Wiping is great. I rarely have so much fun playing a game as when pulling a new boss for the first time to find out what heinous sorts of things he will do to kill us all. That sense of progress, of getting a phase down that previously was a mess and slowly pushing deeper and deeper into a challenging encounter is wonderful. Something deep inside me just roars with rage and fury when we die; screaming to the rooftops that next time it will not be me facedown on the floor but rather my enemy. There is a tremendous sense of satisfaction in defeating something that you have failed for long hours at and I can hardly imagine wanting to play a game without that.
The thing about victory is that the reward is proportional to the risk, effort and suffering required to achieve it. I don't get a ton of satisfaction from beating up hamsters, nor is a fake Olympic gold medal of any value. I don't mind investing some time into fairly trivial tasks to prepare for a challenging one, and you need to feel that way to enjoy WOW. That said, when the entirety of your play time is doing things that are trivial and pose no risk of losing so that you can become more powerful and do more things that are trivial I don't understand the appeal.
When you can't possibly lose then you also cannot win.