Adopting a qualitative approach to the investigation of high achievement, the authors analyzed how high-achieving women in the Swedish workplace made meaning of positive and negative experiences in their work. The data consisted of interviews with 15 women identified as being high achieving in their respective field, and it was analyzed using grounded theory methodology. The women described five distinct experiences that highlighted both the bright side and the dark side to high work performance: (1) going the extra mile in their work, (2) reaching for career goals, (3) experiencing flow and a love for work, (4) working independently and taking the road less traveled, and (5) having high standards and aiming for perfection. The empirical findings relate to existing research literature on grit, work engagement, flow, and burnout. Implications for employers who want to retain and develop high achievers are discussed. The findings suggest that high-achieving women experience it as personally meaningful to engage in high-performance behavior as long as the benefits experienced outweigh the costs, and they are able to do their work on their own terms.