This chapter discusses the life courses of women in their sixties and above. Therefore, it analyses the unusual life trajectories of four professional women who have accomplished outstanding careers at a time in which there were virtually no professional women. The results of this analysis are based on intractions and interviews with seven women in their sixties, one in her seventies, one in her eighties, and two in their nineties. The combination of the four generations reflects the similarities among these women's experiences while growing up and establishing a career. Their upbringings were marked by two postwar periods and, regardless of when they entered the job market, they were outliers in their workplace. The more social, economic, symbolic, and cultural capital we have, the more choices we will have, but it does not mean that the more choices we have the more content we will be.