International research on the effects of educational regimes on intergenerational mobility suggests that Singapore's education system possesses characteristics that tend to decrease intergenerational mobility. These characteristics include ability-based and school-based streaming, privatization of basic and tertiary education, expansion of tertiary education while increasing fees, and possibly regressive public expenditure on education. These characteristics are motivated by a belief in offering multiple pathways for success, and thereby developing a globally competitive workforce. However, comparisons between Singapore and Finland suggest that greater equity and mobility can be achieved without necessarily compromising students' performance and the nation's economic competitiveness. Given wide income disparity and at best moderate intergenerational mobility in Singapore, evaluations of the mobility effects of the various characteristics of Singapore's education system should be conducted. Priority should be given to rethinking Singapore's educational model. Remedial interventions such as bursaries and peripheral interventions such as the regulation of early education or private tuition have limited effectiveness if the main system reinforces immobility. The lessons in this study for Singapore can also be extended to other countries with differentiated education systems.