Seeing a homeless person in a dream is an objective first step in exploring your own lack of fulfillment. A beggar or vagabond is a character that can portray a lack of self esteem or the ways that you kid yourself into believing you are happy. You may be going through some type of routine and not acknowledging your lack of fulfillment. The appearance of this character and how you relate to them allows you to explore your own sense of homelessness or the idea that you are not grounded. Sometimes this type of character will appear like the Fool or Trickster that trips you up in your inconsistencies. Often they will pester you as a way of making you look back at yourself honestly.