Intergenerational transmission of disadvantage remains a problem despite political and educational initiatives. This study explored the role of personality and psychosocial factors in occupational status in a survey of 383 participants (174 males and 209 females) over 39 years from age 16 to 55. Mother’s education, extraversion, and mastery motivation were the best predictors of current socioeconomic status. A focus on education and academic development as the single solution to social immobility has been ineffective. Instead a broader approach which includes realistic lifelong educational opportunities and an education system which enables socioemotional development as well as academic growth is recommended.