Three Singaporeans have made mid-career moves into the technology industry from very different fields. One had worked as a physician in traditional Chinese medicine before switching careers. Another came from a career in music, while the third had professional experience as a rail engineer. Their decisions came after they had already established working lives, rather than at the start of their careers. Each therefore entered technology with experience and skills gained in another sector. Their accounts broaden the common image of people working in technology beyond those trained in computing or engineering from the outset. They also illustrate the value of retraining and transferrable abilities when workers decide to change direction. The article presents their choices as individual examples of a wider range of routes into Singapore's technology sector.