Creativity includes the elements of questioning, playing, immersion, innovation, risk-taking, being imaginative, and self-determination. Among these seven elements, this chapter focuses on being imaginative. The term ‘being imaginative’ refers to the experience of recalling visual information when children see or touch familiar objects, associating them with objects/ideas or with what they already know. In this chapter, I introduce two drawing activities that enable young children to imagine, namely, as-if drawing and monster trucks. The chapter analyzes these activity details, including the preparation and teaching procedures, work samples, and evaluation methods. In the As-if drawing activity, children are presented with an irregularly shaped line. They are asked what the shape looks like to them and they draw their answers. In the Monster Truck activity, children work in pairs to draw an imaginary object—a monster truck. Children discuss their ideas with their partners, which allows them to be as imaginative as possible. This chapter further introduces methods for training teachers who can practice drawing instruction to provide young children with imaginative experiences. I use the persona/scenario method to create an imaginary child for whom student teachers create lesson plans. Early childhood is an important time for children to use and acquire imagination. The two drawing activities and teacher training methods introduced in this chapter will be effective in enriching children’s imagination in early childhood.