This paper argues that the “kindergarten approach to learning” – characterized by a spiraling cycle of Imagine, Create, Play, Share, Reflect, and back to Imagine – is ideally suited to the needs of the 21st century, helping learners develop the creative-thinking skills that are critical to success and satisfaction in today’s society. The paper discusses strategies for designing new technologies that encourage and support kindergarten-style learning, building on the success of traditional kindergarten materials and activities, but extending to learners of all ages, helping them continue to develop as creative thinkers.