Recent literature on education and work well recognises the 'crowding-out perspective' of how higher education expansion impacts the labour market experience of young people with different educational levels. However, the relationship between the labour market experience and young people's self-reported happiness remains less well understood. This paper examines whether a 'crowding out' effect occurs amongst post-secondary degree-holders on the self-reported happiness of young people (aged 16-34) amidst increasing difficulties during their school-to-work transition. Drawing on a city-wide online survey in a leading global city, Hong Kong, statistical analysis shows that contrary to the mainstream 'crowding out perspective', self-reported happiness is lower amongst young people with high rather than low educational attainment. However, in the absence of a 'happiness premium' of educational attainment, young people in Hong Kong with secondary degrees or below are much more sensitive to adverse labour market experiences, such as unemployment, high job pressure and long working hours. No similar moderating effect of educational attainment is found on the relationship between the self-reported happiness of young people and regular work shifts. The implications of these findings on the 'crowding out perspective' for youth development policy within East Asia and Hong Kong productivist welfare paradigm are discussed.