This article introduces the reader to the pragmatic perspective of measurement that goes beyond the traditional view of measurement as assigning numbers (Stevens, 1958). The educator has to consider the measurement process and the assumptions (theoretical and psychometric) that he or she has regarding that process in order for the measurement to be valid and actionable. In addition, measurement should shift from focusing on normally distributed continuous variables to the use of measures such as ordinals and nominal that allow us to address other phenomena of interest such as levels of progression and improvement. Finally, an example is presented with the pragmatic measurement of 21st century skills.