Confrontation of the shadow is different for everybody, and being closer to it - I realize how much work it is to deal with it. Looking back on these dreams (the dreams in Sleep Comics are from three years ago) I can see the shadow everywhere. Naturally so, since the shadow is just another part of the whole person. Jung: "To take a legitimate parallel from the psychology of the individual, namely the appearance of an impressive shadow figure antagonistically confronting a personal consciousness: this figure does not appear merely because it still exists in the individual, but because it rests on a dynamism whose existence can only be explained in terms of his actual situation, for instance because the shadow is so disagreeable to his ego-consciousness that it has to be repressed into the unconscious. This explanation does not quite meet the case here, because the trickster obviously represents a vanishing level of consciousness which increasingly lacks the power to take express and assert itself. Furthermore, repression would prevent it from vanishing, because repressed contents are the very ones that have the best chance of survival, as we know from the experience that nothing is corrected in the unconscious." Jung, Carl. The Four Archetypes from The Collected Works of C.G. Jung Volume 9, Part I. Princeton: Bollingen, 1959.
This is all so clear once you see how your Shadow plays into your daily life. My small progress has been to take a conscious look at my unconscious behavior and examine when my shadow tips its hat, and there have been specific dreams which help to highlight exactly when my shadow is tipping its hat.
I understand this dream doesn't quite deal with the shadow self, but it has themes that trigger the question of whether the shadow is at work here. My motives for paying the man to take care of a friend in need while I have a good time. Or, the friend who is too drunk and needs assistance could be the critic in me judging my behavior if I ever become too irresponsible, particularly by the shadow's doing.