This chapter bridges studies on artefact design, creative learning, and mathematics education by exploring a concrete case on a booklet design process adhering to the principles of Creative Pragmatics. The interpretation of the case is based on the first author’s autoethnographic account of her iterative, reflective, collaborative, and creative learning process surrounding the design. The three rounds of user tests gave insights into the further design of the booklet, and more broadly into the design of artefact-mediated creative learning environments in mathematics education and STEM education. Based on this, we recognize the affordance of an artefact as a complex phenomenon; we also reflect on the importance of artefacts in mediating creative learning environments associated with playful learning; and by discussing values of art, we bring inspiration to future mathematics and STEM education.