This paper examines the complex experiences of full-time employed adults trying to climb the career ladder in their company by making use of company tuition assistance to earn their first college degree. Guided by Savickas' (2005) career construction theory, emphasizing the personal agency and meaning-making within career development, we conducted phenomenological interviews with a purposive sample of eight men and women from six different companies using company tuition assistance while working full-time. Participants held complex feelings toward dual roles of work and school including feeling overwhelmed and delayed in their progress as well as experiencing positive synergy between school and work roles. Workplace features such as flexible scheduling and having an encouraging supervisor facilitated progress. Implications for understanding and supporting the career development of full-time employed adults are discussed. (Contains 2 tables.)