Self-employment becomes more and more current as an opportunity for realizing a flexible employment in the conditions of limited employers’ demand. In Bulgaria it has a well recognized economic and social significance for maintaining certain levels of employment, as well as a way out of the unemployment. The change of the economic situation in the current crisis, as well as the recognition of the integrated approach to the employment and the implementation of the principles of flexibility and certainty, have imposed a new meaning to popular so far characteristics of the employment. In this connection, the new evaluation of the opportunities for developing the business of the self-employed not just as a transition to employment, but also as a real and profitable area and career development area, becomes necessary. The study namely corrects or refutes past theses, as well as formulates current problems and solutions in favor of the flexibility and certainty in the self-employment and through it.