This article examines the challenges faced and lessons learned while developing the SPEAK Young Women's Vocal Empowerment Curriculum and leading 30 educators through a Professional Development Training on the curriculum in Guatemala in 2019. The guiding question is, "What does it take to train non-teaching artists in the skills needed to lead a curriculum traditionally taught by teaching artists?" This is the first in a series of two articles that examine this guiding question through the lens of a "Voz Empoderada Diplomado," or Vocal Empowerment Certificate Program, led by teaching artists for 30 educators, mentors, and community workers in Guatemala. This first installment introduces the author as a teaching artist, her approach and experience with professional development, the development of the SPEAK Young Women's Vocal Empowerment Curriculum, the design of the training program, and the initial lessons learned.