There are some commonalities among the successful leaders in education technology. They tend to be flexible and a little disrespectful of the status quo. They take risks, but they also know the politics of the situation and know how the game is played. Timing in leadership is as important as the ideas being proposed. One cannot always anticipate the perfect time to introduce or, more important, push an idea. As a result, one of the best attributes of a leader is being lucky; and luck is only what each person makes of it. This is a particularly important and tough time for leaders. Dedicated funding for education technology, particularly at the state level, has declined. Some educational technology departments at both the state and local levels have been decimated by budget cuts. Regional education service centers, which are a major supporter of technology, have also seen cuts. These budget cuts, coupled with the flexibility within the No Child Left Behind Act (NCLB), require even more adaptable and creative leadership to accomplish the successful integration of technology into the classroom.