Those who embark on the journey towards transcendence are brave indeed. They strive for purity in a world degradation, they embrace simplicity amongst rampant materialism, and they cultivate selflessness in an atmosphere charged with exploitation. Anyone who goes against the grain in such a bold way will undoubtedly be faced with temptation, doubt, ridicule and moments of weakness. Behind the high ideals and expectations of any religious or spiritual tradition, stands the relatively frail and weak aspirant. Lapses and mistakes are to be expected in the life journey of any human, and spiritualists are no exception. Scriptures are replete with accounts of spiritual aspirants who fell victim to the material appetite. Nobody likes to be a hypocrite, and a gap between the ideal and the real naturally generates feelings of frustration, guilt and regret. This is an interesting phenomenon. Without a sense of guilt or shame one will lack the impetus to improve. They generally gravitate towards a life of justification, where they comfort themselves in their compromised position and accept their weaknesses with no concrete plan to overcome them. On the other hand, an overdose of guilt becomes highly debilitating. It usually leads to depression, hopelessness and an inferiority complex where the aspirant feels powerless to improve. They often end up leading a subdued and isolated life, distancing themselves from people and situations that remind them of their shortcomings. To avoid the two unhealthy extremes of justification and hopelessness, we need to manage a healthy and balanced amount of guilt to create positive change.