Objectives: This study identified perceived employability trajectories and their associations with sleeping difficulties and depressive symptoms over time. Methods: The sample was part of the Swedish Longitudinal Survey on Health from 2008 to 2014 (n=4,583). Results: Two stable trajectories (high and low perceived employability over time) and three trajectories with changes (increasing, decreasing, and V-shaped perceived employability over time) were identified. Workers with stable low perceived employability reported more sleeping difficulties and depressive symptoms than those who perceived high or increasing employability. Conclusion: Perceived employability is a rather stable personal resource, which is associated with well-being over time. However, changes in perceived employability do not seem to be echoed in well-being, at least not as immediately as theoretically expected.