In this article I consider the digital lives of a number of young teachers. Some are confident, competent movers in digital worlds, some are not. I wonder why, and look back at the teachers' digital histories to see whether ways in which they learned about digital worlds affects their lives now. I identify three different routes to learning about digital worlds, and describe these with representative stories. Two are serious solitary journeys, one self-taught the other school-taught. Most teachers in these groups use digital technologies for work and for the business of life. The third route is playful social. Teachers in this group have experienced learning about digital worlds with fellow enthusiasts and in playful contexts. These teachers use digital technologies for pleasure as well as the business of life and work. I argue that it is important that young teachers and student teachers be given time on courses to think about and discuss their own digital literacy histories.