In Ireland, youth work is delivered largely in marginalised communities and through non-formal and informal learning methods. Youth workers operate in small isolated organisations without many of the resources and structures to improve practice that is afforded to larger formal educational establishments. Fundamental to youth work practice is the ability to identify and construct learning experiences for young people in non-traditional learning environments. It is therefore necessary for youth workers to develop a clear understanding of their own learning capacity in order to facilitate learning experiences for young people. In the course of this research, I attempted to use technology to enhance and support the awareness among youth workers of their own learning capacity by creating a digital video artifact that explores the concept – learning-to-learn. This study presents my understanding of the learning-to-learn competence as, I sought to improve my practice as a youth service manager and youth work trainer. This study was conducted using an action research approach. I designed and evaluated the digital media artifact – “Lenny’s Quest” in collaboration with staff and trainer colleagues in the course of two cycles of action research, and my research was critiqued and validated throughout this process.