Thanks for the thoughtful response, Horst! Your perspective is much appreciated and I think it'll be helpful for other readers as well.
I understand how you might think that "pursuit of failure" is nonsense and "enterprise undertaken without the intent to succeed" is stupid, but that's exactly my point. Doing nonsensical and stupid things is what makes youth worthwhile, not just for the sake of learning, but also for fun.
Worst case scenario, we may not learn anything from our past failures and mistakes. But, at the very least, it will become a nostalgic story to laugh about in the future, like, "Dude, remember when we did that dumb stuff when we were young?"
Although, yeah, there should be a limit to it. While I still think that pursuing failure is good, I do agree that we shouldn't do it blindly. Some mistakes are more irreversible than others, after all.
Anyway, I guess this writing is now another one of my failures. Your input has encouraged me to reevaluate my word choice and improve my articulation. Thanks for that.