This chapter reports on a Continuous Professional Development (CPD) trek into the urban and rural terrains of Pakistan (Raza, N. A. (September–October, 2017). Pakistan Diaries. IATEFL Voices, Issue 258, pp 6–7. ISSN 2412–6578). It documents the journey of professional development undertaken by a group of English language teaching professionals who were all at the time resident in the United Arab Emirates. The chapter also highlights how effective collaboration can positively impact teacher development beyond geographical borders, the need for mid-career teachers to step forward and initiate the professional development of teachers in under-resourced contexts which can become a vehicle for their own CPD in innovative ways, and the legitimacy of outreach CPD as a service to the profession.