The paper reveals the phenomenon of jazz music and analyses the expression of vocal jazz in a historical, philosophical, and educational context. The historical origins of jazz are related to a community culture and to the natural and authentic creative process; inner freedom is one of the most significant aspects of jazz music, based on improvisation. The global practice of jazz vocal studies is predominated by a systemic approach that links the physiological, psychological, and mental levels. The study process is not separated from the personality (self) development and the creation of a sensitive and enabling relation culture. The paper presents a reflection on personal practical experience and is based on the data of a presentation Unique Self Search in Vocal Jazz: Jazz Voice + Theatrical Elements: Wider Opportunity for Self-Expression, given in the 2nd International Scientific Jazz Vocal Conference held in the Sibelius Academy (Helsinki, Finland).