According to research across various countries, the mental health and psychosocial well-being of the youth have been deeply impacted by the COVID-19 pandemic. Hence, it is imperative to address the rising problems and develop resources for future preparedness. Applying insights from their previous mixed methods research, the authors integrate a coaching framework within a qualitative approach to design an intervention to support young participants. This research had three aims: firstly, to explore the experiences of the youth affected by the extended pandemic restrictions; secondly, to utilise coaching to help participants explore their coping strategies; and thirdly, to synthesise the lessons learnt for future applications. Purposive sampling was utilised to invite participants from the target group of 21–35 years. Participation was voluntary and the ethical practices of research followed. Sixteen participants joined the in-depth interviews and research sessions from May to June 2021. These participants included seven Indians and nine Thai young adults. Thematic analyses of data revealed that while the participants experienced both challenges and stresses, they also reported strategies of adjustment to the extended pandemic restrictions. The emerging themes were consolidated and discussed within the theoretical frameworks of coping and resilience. The participants’ feedback on coaching confirmed its usefulness as an intervention in a challenging context. The implications of these findings are discussed to rethink the paradigms to support the psychosocial well-being of the youth dealing with challenges for future preparedness.