This study aims to investigate the factors affecting the difficulties Macau adolescent encounters when making career decisions. Following the grounded theory method, semi-structured in-depth interviews were first conducted, and then interview transcripts were coded and analyzed for establishing a relevant theoretical framework consisting of major emerging themes. The sample of this study includes twelve junior high third year students (5 boys, 7 girls) from three different types of secondary schools in Macau. Results reveal four factors that make career decision-making difficult for adolescents: 1. Personal factors: personality, character, ability, and values 2. Contextual factors: lack of diversity in economic development, limited land for further development, government policy, limitations of local tertiary education opportunities, and lagged effect of secondary schools’ career counseling development. 3. Familial factors: family structure, parent-child communication, and parents’ marital relationship 4. Significant-others factors: domination and reliance on significant others when making career decisions Finally, implications on further research and solutions pertaining to difficulties in career planning during adolescence are discussed. Keywords: Macau junior high students, career decision-making difficulty, grounded theory, career counseling, tertiary education