1. Introduction Transition from education to working life is a significant event from the viewpoint of both the individual and society. Entering the labour market is conceived as a rite of passage decisive of a person's entire labour market career. Transition can also be seen as a complex social phenomenon, which can be the origin of several social problems. High incidence of unemployment among young people and the inability of many school leavers to find suitable employment point to the necessity of studying the labour market transition in post-socialist Estonia. Although the issue of the entry process in the Estonian context has to a certain extent already been addressed by some authors (such as Berde et al. 1999), the recently available new data-set makes it possible to explore this subject matter from a new perspective. The aim of this paper is to analyse the entry process in post-socialist Estonia, to asses the impact of various micro-level characteristics on the success of labour market integration and to describe its developments at the backdrop of the changing social context. Additionally, the results are compared with the outcomes of similar studies from other European countries. The empirical part of the study is based on the Estonian Labour Force Survey 2002 ad-hoc module on school-to-work transition. The rest of the paper proceeds as follows. In the first section an overview of the basic theoretical approaches to labour market transition and the summary of most relevant empirical results are given, also the context of the transition is analysed and hypotheses are formed. The description of the data-set and research methods follows. The results of the empirical analysis are presented in the third part, followed by the final section, which sums up the results and draws the conclusions. 2. Theoretical background 2.1. The nature of labour market transition The sociological concept of school-to-work transition is of recent origin (Ryan 2001:34). For earlier generations integration to working life was characterised as swift and uneventful, while for today's youth labour market entry is marked with growing complexity and diversity. For many school leavers it is a period of remarkable uncertainty and change, which can affect their entire labour market career (Shavit et al. 1990:53). While the conceptualisation of school-to-work transition as a period starting with leaving the educational system and ending with obtaining employment is, due to its relatively unambiguous nature, a commonplace in many studies concentrating on labour market entry (e.g. Sanders and Becker 1994), it is by no means theoretically unproblematic. Some young people begin their labour market careers before officially leaving the educational system, whereas others return to full-time education after a shorter or longer spell of full-time employment. Even when the departure from the educational system is permanent, it is not always followed by smooth integration to working life. Young people are characterised by a greater propensity to change jobs and are found in temporal and part-time employment more than the rest of the employed population. School-to-work transition can thus be called a process of labour market accommodation, without sharp beginning and end markers (Wolbers 2001:2). The success of labour market integration is most commonly measured by the school leavers' propensity to avoid unemployment and mismatching jobs, but also by the duration and the relative social ranking of the first job. Factors affecting the results of labour market transition can be divided into a period effect (time- varying aspects of the social and economic environment), institutional factors (nation- specific aspects of educational system and labour market settings) and individual characteristics. The latter can further be subdivided to ascribed characteristics (e.g. gender and ethnicity) and achievement effects (e. …