This article contributes to literature on the sociology of sleep by exploring the sleeping practices and subjective sleep experiences of two social groups: shift workers and students. It draws on data, collected in the UK from 25 semi‐structured interviews, to discuss the complex ways in which working patterns and social activities impact upon experiences and expectations of sleep in our wired awake world. The data show that, typically, sleep is valued and considered to be important for health, general wellbeing, appearance and physical and cognitive functioning. However, sleep time is often cut back on in favour of work demands and social activities. While shift workers described their efforts to fit in an adequate amount of sleep per 24‐hour period, for students, the adoption of a flexible sleep routine was thought to be favourable for maintaining a work–social life balance. Collectively, respondents reported using a wide range of strategies, techniques, technologies and practices to encourage, overcome or delay sleep(iness) and boost, promote or enhance wakefulness/alertness at socially desirable times. The analysis demonstrates how social context impacts not only on how we come to think about sleep and understand it, but also how we manage or self‐regulate our sleeping patterns.