Degree: Master of Psychotherapy and Spirituality Abstract: This study is an in-depth exploration of one woman's experience of coming into relation with such functions as authenticity, personal and professional agency, and creative expression. As interpreted through a Jungian lens, these functions are associated with masculine energy. The mythical figure of Sisyphus, condemned by the gods to endlessly push a gigantic boulder up the side of a mountain, has been used to symbolize an addictive pattern of perfection and defeat that, with the critical inner voice of the \"never good enough,\" prevents the individual from claiming these traits. As a result of walking through the fire of the research process, the final learning is that by coming into relation with the masculine, in this case with Sisyphus, it is possible to know a wholeness of self that brings one into connectedness with others and with transcendence. Although ideas were drawn from a number of methodologies, including feminist research and narrative inquiry, a heuristic approach defined by Moustakas and Sela-Smith, and deepened by Romanyshyn's understanding of doing research with soul in mind directed the process. With the challenge posed by these authors, the researcher engaged in a concentrated praxis of action and reflection that finally exposed a depth of knowing that established congruence with personal values and academic requirements. The concept of facing and coming into relation with a complex belongs to Jungian thought and it is this framework that has guided the research. Many authors contributed but the most significant insights came through a dynamic interaction with women authors who share the feminist belief that personal experience cannot be separated from the political and it is by understanding the nature of these interwoven threads that one accesses essential truths. The final message is that a fierce and persevering desire to be in relation with masculine energy brings one to the center of experience. By standing at the core, there is the realization that, for a woman, this is the vast diffuse wisdom of the feminine and it is the masculine that gives it concrete form. With this awareness, there is a significant shift for the researcher on both a personal and professional level. To be free of the \"never good enough\" brings an authenticity of connection that alters relations in one's immediate circle and in the counselling room with clients. Furthermore, it is believed that this form of energy ripples outward. To heal oneself is to bring healing to others and hopefully to the planet as a whole.