To develop second-grade students' confidence and ease, this author presents examples of learning tasks (Number of the Day, Word Problem Solving, and Modeling New Mathematical Ideas) that align with Common Core State Standards for Mathematics and that build mathematical fluency to promote students' creative expression of mathematical ideas. Students become mathematically fluent thinkers when they have many occasions to make sense of problems and apply their understandings toward increasingly sophisticated problems. Such tasks as number of the day, word problems, and modeling new mathematical ideas can be scaled to continually challenge students' thinking and create the space to develop accuracy, flexibility, and efficiency. Matney concludes that students who understand both the structure of mathematics and the meanings of its representations would emerge from classrooms with the quality of creative expression and the ability to construct new associations and meanings with mathematics as they endeavor to solve the many problems and tasks encountered in our world.