This study (i) provides a comprehensive analysis of the determinants of educational and occupational aspirations of teenagers; (ii) analyses the link between aspirations and achievements, and (iii) explores the effects of unmet aspirations on life satisfaction. Using the British 1958 NCDS cohort data that follow individuals nearly 60 years since birth, we show that aspirations are largely influenced by parents’ socioeconomic status and by parents’ own aspirations for their children. Next, we show that aspirations correlate with achievements, over and above socioeconomic background and ability, suggesting that aspirations are a driver of achievements. Finally, when achievements in early adulthood fail to reach the level of aspirations set at a young age, people report a lower level of subjective well-being. This negative effect from falling behind own aspirations is more pronounced among male adults, but it disappears in later adulthood. By age 50, exceeding one’s childhood aspirations positively affects life satisfaction.