This paper documents an analytical autoethnographic approach to the development of a digital storytelling (DST) app for enhancing young adults’ employability prospects. Development is rooted in the classical DST approach proposed by StoryCenter Founding Director Joe Lambert. Blending theoretical consideration and empirical user testing (individual user observations and a co-creation workshops), we affirm the value of DST – and classical DST especially – for facilitating critical self-reflection and self-branding. By structuring discussion using Lambert’s seven steps of classical DST, we highlight how particular design decisions have promoted enjoyable and effective storytelling, recognizing both user preference and empirically demonstrated usage. This paper is the result of a positive interdisciplinary academic-industrial partnership.