Charon is the ferryman of the dead. According to Greek mythology, the old Charon helps the dead souls to cross the river (Acheron or Styx) to the underworld. The Greeks and Romans would put a coin (obol) in the mouth of a dead person in order to pay Charon, otherwise they would have to wait 100 years at the river untill Charon would help them at last.
Charon was an old man with a hooked nose, grey skin, an unclean beard and foul clothes. His eyes were described as 'hollow furnaces on fire'. His name means 'fierce brightness'. In his hand he had a large pole with which he would push the boat forward.
To approach this from a psychoanalytical point of view, I think that Charon is some kind of Shadow side. He is the connection between the realm of the living and the realm of the dead, thus the connection between the conscious and the unconscious. We know from many stories that the Ego, the hero, the individual, needs to go to the underworld to die. There is one part of him that won't die (the Self, the potential) and so the hero resurrects. Going to the underworld, that is, exploring your unconscious, your inner darkness, is a crucial part of Self development, of the process of individuation. Charon, your Shadow, will help you with this ordeal, BUT you will have to pay him. You will have to make sacrifices in order to transform yourself for the better. You will have to look him straight into his fiery eyes which will show you the painful truth of yourself. If you won't do that, you will roam near the river for 100 years, that is, you will be stuck on the verge of death, and you won't be able to transform. You will be plagued with a life near the underworld, without getting any benefit from it. That is, anxiety, depression, addiction etc.
Make sure that you won't live a dreary life at the river of the underworld. Be brave, pay that coin and go into the underworld. Let the old you die and be reborn as the better version of you.
