Older adults face many challenges in the workplace, one being the advancement of technologies both in hardware and software development. The purpose of the study was to understand the learned experiences of older adults integrating advanced technologies into their critical decision-making work experience because of training. Literature claimed a degradation of cognate abilities as a person ages. However, literature also showed that older adults can learn like their younger counterparts. The answer then for older adults and their ability to learn advanced and changing technologies must lie deeper than just the loss of cognitive abilities as one ages. The research question for the study was, "What is the experience of older pilots in training who are transitioning to technically advanced aircraft?” The study employed grounded theory using seven participants answering guided interview questions. The population was pilots who fly for a volunteer organization within the state of New York. Out of a population of 52 pilots, seven participated whose ages were between 40-80 years and went through transition training from basic aircraft cockpits to computerized G1000 models. Data analysis began with guided interview questions along with coding and memoing. The first stage of analysis was the initial coding process, then focus coding, axial coding, and finally theoretical coding. Theoretical coding generated a theory, which pointed to self-efficacy. Self-efficacy along with self-regulated personal learning were motivators for the optimum outcome of reaching goals regardless of age.