We analyze the joint life-cycle dynamics of labor market and mental health outcomes. We allow for two-way interactions between work and mental health. We model selection into jobs on a labor market with search frictions, accounting for the level of exposure to stress in each job using data on occupational health contents. We estimate our model on British data from Understanding Society combined with information from O*NET. We estimate the impact of job characteristics on health dynamics and of the effects of health and job stress contents on career choices. We use our model to quantify the effects of job loss or health shocks that propagate over the life cycle through both health and work channels. We also estimate the (large) values workers attach to health, employment or non-stressful jobs. Lastly, we investigate the consequences on health, employment and inequality of trend changes in the distribution of job health contents.