We all go through bad times, but only the resilient ones bounce back. Resilience, as a key concept of positive psychology, is the process by which individuals adapt in a positive way during or after stressful situations that involve adversity or risk. Resilience is therefore an essential skill for both adolescents and the ageing adults to master the art of living well in their uncertain future. Although existing literature has empirically demonstrated that the skills of resilience can be reliably taught, the prevailing school systems focus more on preparing students to excel academically rather than promoting the skill of wellbeing. This paper capitalizes the feasibility of resilience training through a structured program that facilitates exchange between two different generations (aged under 20 and aged over 50). The project took place in 20 secondary schools, serving 300 students and 100 senior participants between 2017 and 2019. Paired sample t-tests were conducted to assess the individual changes. Among the senior participants, significant positive changes were found in the measures of purpose in life (t(83) = 2.37, p = .020), attitude towards youth (t(83) = 2.78, p = .007), and accommodation (t(28) = 2.63, p = .014). Among the students, significant positive changes were found in psychological constructs, namely, positive outlook (t(166) = 5.00, p<.001), resilience (t(166) = 6.13, p<.001), self-concept clarity (t(166) = 1.98, p=.049). The study provides insights to educators and elderly carers who care to nurture an adaptive workforce of the future with the skills it takes to face challenges beyond our anticipation.