If you try to fail and succeed, which have you actually done?
Which do you mean?
You try to fail and you manage to fail or,
You try to fail but you actually succeed?
In the first instance you are successful, and in the second case you are an abject failure! 
Isn’t there a town/ village by the name of Conundrum?
Hence the post title! You try to fail and succeed in failing. More a trick of language really!
maoster - I think theres a conundrum somewhere in america but dont know which state.