This article builds on the Empirical Monte Carlo simulation approach to study the estimation of Timing-of-Events (ToE) models. We exploit rich Swedish data of unemployed job seekers with information on participation in a training program to simulate placebo treatment durations. We first use these simulations to examine which covariates are key confounders to be included in dynamic selection models for training participation. The joint inclusion of specific short-term employment history indicators (notably, the share of time spent in employment), together with baseline socio-economic characteristics, regional and inflow timing information, is important to deal with selection bias. Next, we omit subsets of explanatory variables and estimate ToE models with discrete distributions for the ensuing systematic unobserved heterogeneity. In many cases, the ToE approach provides accurate effect estimates, especially if time-varying variation in the unemployment rate of the local labor market is taken into account. However, assuming too many or too few support points for unobserved heterogeneity may lead to large biases. Information criteria, in particular those penalizing parameter abundance, are useful to select the number of support points. A comparison with other duration models shows that a Stratified Cox model performs well with abundant multiple spells but less well when multiple spells are uncommon. The standard Cox regression model performs poorly in all configurations as it is unable to account for unobserved heterogeneity.
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