This paper attempts to engage the field in a discussion about what mathematics is needed for students to engage in society, especially with an increase in technology and digitalization. In this respect, mathematics holds a special place in STEM as machines do most of the calculations that students are taught in K-12. We raise questions about what mathematical proficiency means in today's world and what shifts need to be made in both content and pedagogy to prepare students for 21st Century Skills and mathematical reasoning.