Discussions on policy and management initiatives to facilitate individuals throughout working careers take place without sufficient insight into how career paths are changing, how these changes are related to a modernization of life course biographies, and whether this leads to increased labour market transitions. This paper asks how new, flexible labour market patterns can best be analyzed using an empirical, quantitative approach. The data used are from the career module of the Panel Study of Belgian Households (PSBH). This module, completed by almost 4500 respondents consists of retrospective questions tracing lengthy and even entire working life histories. To establish any changes in career patterns over such extended periods of time, we compare two evolving methodologies: Optimal Matching Analysis (OMA) and Latent Class Regression Analysis (LCA). The analyses demonstrate that both methods show promising potential in discerning working life typologies and analyzing sequence trajectories. However, particularities of the methods demonstrate that not all research questions are suitable for each method. The OMA methodology is appropriate when the analysis concentrates on the labour market statuses and is well equipped to make clear and interpretable differentiations if there is relative stability in career paths during the period of observation but not if careers become less stable. Latent Class has the strength of adopting covariates in the clustering allowing for more historically connected types than the other methodology. The clustering is denser and the technique allows for more detailed model fitting controls than OMA. However, when incorporating covariates in a typology, the possibilities of using the typology in later, causal, analyses is somewhat reduced.