In this artistic project, I search for pathways to vocal improvisation in solo and duo formats and in bigger constellations. The research question is: What characterizes approaches to free vocal improvisation, and what obstacles are there in the making? I have searched in the literature and interacted with four singers, with whom I have explored improvisation in duo format, and interviews about their approaches to improvisation. Ways to move forward include ideas such as doing it repeatedly and doing exercises in developing courage, expressions, relaxation, energy, pulse, and rhythm, all with a non-judgmental attitude. Both the singers and literature identify fear and self-judgment as obstacles to free improvisation. The rapport also includes exercises collected from world experts to use in the process.