Career progression; some strive for it, some contemplate it, while others ignore it. Yet it’s an element every new teacher is expected to consider; where do you want to be in one, five or ten years time? What position do you want to hold? How will you get there? All too often, just being a classroom teacher isn’t enough. This chapter explores how the experience of new teachers can change as they progress through the first five years, the potential challenges and benefits along with advice to help with difficult decisions along the progression. This chapter is supported with snippets of insight from a range of teachers, school leaders and university professionals from the world of EduTwitter, including the likes of Adrian Bethune, author of ‘Wellbeing in the Primary ClassroomL A Practical Guide to Teaching Happiness’, Gill Rowland, Senior Lecturer at Canterbury Christ Church University and Andrew Cowley, Deputy Headteacher and author of ‘The Wellbeing Toolkit’.