conundrum

/kə-ˈnən-drəm/

origin unknown

noun

  1. an intricate and difficult problem

  2. a question or problem having only a conjectural answer

  3. a riddle whose answer is or involves a pun (as in "Why didn't the lost hikers starve in the desert? Because of the sand which is there.")

He is faced with the conundrum of trying to find a job without having experience.

… the political conundrums involved, particularly the problem of how the richer areas … can be made to subsidize the poorer.