There is remarkable convergence in perceptions of working in space – the work is highly scheduled, intensive, and interdependent. These perceptions are clear from interviews, diaries, and other accounts of those who have lived and worked in space. In designing work in space, it is important to consider the overall flow of work from one task to another. There are switching costs and flow advantages to be gained by designing work schedules so that tasks are grouped and sequenced in ways that are more natural for astronauts. In this chapter, we summarize five factors that affect how work is experienced and the ease with which astronauts can transition from one task to another: task characteristics, social relations, technology affordances, individual differences, and situational constraints. The first three factors affect work engagement and can be used to design work schedules. We report on perceptions of these factors in ISS astronauts and analog crews. Lastly, we conclude by describing a computer model of task switching, CREST, that we developed to assist with generating recommendations for designing astronaut schedules that minimize switch costs and maximize flow advantages. Taken together, these interventions provide promising directions for improving the experience of working in space.