What happens in our careers to move us along from one phase to the next? How do we cope with what is sometimes massive change in our careers – those days that come at us with little warning as well as for those which we've planned for? And what skills, knowledge, and habits come to us along the way? In this chapter, I hope to open the way to define and describe the forces that seem to push (sometimes forcefully) us forward into new stages of our careers. I call those forces TESOL (Teaching English to Speakers of Other Languages) career path rewards and milestones: professional and personal.