In this thesis I share my journey of building my identity and confidence as a jazz vocalist. A transformational work that has served as a steppingstone for my continuous artistic work as both a vocal jazz soloist and ensemble singer. I started with a broad sense of wanting to examine the differences between solo singing and ensemble singing in jazz. This purpose was turned over, transformed, and changed several times to the very end, when I instead realized that what I truly needed to do, in this text, was to focus on myself and my own artistry. In the beginning of these studies, I had identified specific challenges and areas where I experienced difficulties in my singing and performing. During this work I summarized them in the following categories or areas: my voice, my musicianship, and my mind and mindset. I have been exploring these areas using feedback loops with performative documentation, as well as alternating between writing and reflecting, with the purpose of beginning to clarify my aesthetics and artistic choices and building my identity and self-assurance. This work resulted in my exam concert and the recording of two albums: “Unraveling” as a soloist, and “New Horizon” as an ensemble singer with Stockholm Voices. Besides these artistic results, I have reached a higher level of vocal freedom and control. I have made myself more aware of my aesthetic judgments both as a soloist an ensemble singer, and I feel I have reached a higher level of awareness, expression, and communication as a performer. Furthermore, I developed strategies for dealing with self-doubt and lack of confidence.