Introduction: Sleeping difficulties, including insufficient sleep, trouble falling asleep, waking up at night, or sleep that does not leave an individual rested, are increasingly prevalent among adolescents and have negative consequences for their’ health, well-being, and education. It is of utmost importance to research adolescents’ sleep. A range of studies with different methodological perspectives are needed to inform and understand adolescents’ sleep. To date, there are few studies in sleep research that take a qualitative approach. Therefore, it is important to illuminate adolescents’ own experience of sleeping difficulties to acquire broader knowledge and the necessary evidence in order to provide preventive care interventions.

Method: The data were obtained from narrative interviews with 16 adolescents aged 14–15 in a Swedish city and were analyzed using the phenomenological hermeneutic method.

Results: Four themes that illustrate the meaning of adolescents experience of sleeping difficulties emerged: feeling dejected when not falling asleep, experiencing the night as a struggle, searching for better sleep, and being affected the next day. The comprehensive understanding illuminates what being an adolescent with sleeping difficulties means; it is a challenge to go through the night; cope with the next day; and to harbor a panorama of emotions that emerge during the night, such as frustration, annoyance, concern, dejection, sadness, and fear. These emotions arise when the adolescent is unable to unwind and has concerns that grow during the night. The adolescent experience a feeling of being trapped in circumstances, all of which are incompatible with getting a good night’s sleep.

Conclusions: In order to understand adolescents’ sleeping difficulties, a comprehensive understanding of the context in which the adolescents live is needed. Adolescents need to navigate and find balance in relation to circumstances that may affect their sleep and that are often beyond their control, such as norms and values in society, in social media, in school, and in family and friend groups. By genuinely listening to the adolescents’ narratives about their sleeping difficulties and the context in which they interact will parents, professional caregivers, and researchers increase their understanding.