If you try to fail and you succeed, what have you accomplished?
This question reminds me about the liar paradox often discussed in Ancient Greece.
In my opinion, there are two possible contexts related to this question: You try to fail, and you succeed at failing. So in this sense, you have achieved success through failure. The other context is that you try to fail, and you fail to do so meaning you have succeeded. However, overall, you have achieved failure through success.