How our culture thinks about particular events as linear, normal, and expected does not always fit with the experiences of every learner, particularly underserved urban adult learners. As adult educators in this context, are there ways we might improve or change our pedagogy of instruction by developing a better understanding of transitional life moments for vocational learners. What is the role of alternative approaches to transformative learning for these learners? Specifically, what is the role of alternative approaches learning for underserved adult learners transitioning into a vocational education classroom, after years of disengagement with formal learning institutions with the need to update their technology skills? In this article, we discuss the need to use alternative conceptions of transformative learning to understand vocational learners as they make decisions to participate in vocational education programs. We explore the key issues for adult educators including implications for practice and research.