This chapter presents three empirical studies on disabled individuals who use their disability strategically as they navigate the labour market. In our first case, we reveal that disabled employees in France reflect on factors on societal, organizational, and individual levels. More specifically, they determine whether the quota system can be used to their own advantage, decreasing their precarious position in the labour market. In the second case study, we draw on 257 qualitative surveys with individuals with mental health conditions in a variety of countries and outline how these individuals make their career choices. More specifically, we show how they self-select into sectors in which the characteristics related to their mental illness can be turned into an advantage. The third case presented highlights that disabled individuals use social comparison based on the characteristics of their disability when determining how they compare with other disabled workers. When they feel their disability characteristics are less stigmatizing than that of others, they tend to use this strategically, enhancing their own employability, securing less precarious employment. Through these three cases, we show the inequalities that exist within the population of disabled workers. More specifically, individuals with a disability in countries with less constraining disability legislation and individuals whose disability is more stigmatizing in nature are more likely to end up in employment that is characterized by low wages, few career development opportunities, little autonomy, and unstable or hazardous working conditions. Practical implications and avenues for future research are provided.