This paper analyses the development of the Chilean labour market over the last 20 years from a legislative and empirical perspective, and shows how despite consistent economic growth and employment generation, employment conditions present a mixed performance. This highlights the need to look at employment conditions as important indicators of labour market development. The data we present shows which individual and job characteristics most impact a worker's capability to generate income and to maintain him or herself employed. The paper concludes that apart from individual characteristics associated to human capital, the job characteristics that most impact these capacities are a conditions associated with the occupational status of workers, particularly their type of contact. We find that having an open-ended contract is the most important factor that contributes to a worker's employment capabilities. The paper concludes by analysing the implications of our findings for labour policy in Chile.