The study aims to explain the mechanisms of entrepreneurs’ goal realisation in the work and family domains. It contributes to the understanding of the role of positive and negative goal-related affect and positive orientation in personal goal realisation. A multilevel perspective is applied, as goal realisation varies not only between but also within individuals. The participants in the study were 246 entrepreneurs; each of them had started and owned a business and was either married or had a stable partner. Three scales assessing three components of positive orientation (self-esteem, life satisfaction, and optimism) and the Personal Projects Analysis method were used. Each of the entrepreneurs rated five personal goals related to work and five goals related to family life on dimensions measuring goal realisation and goal-related affect. The results of multilevel structural equation modeling show that positive goal-related affect and positive orientation are positively related, whereas negative affect is negatively related to personal goal realisation in entrepreneurs at the individual and goal levels. The relation of positive affect to family-related (but not to work-related) goal realisation can be further strengthened by positive orientation, both at the individual level and at the goal level.