In the past 25 years, the advancements in media and technologies were breath-taking; in a handful of years, we came from the first home computers to omnipresent and omnifunctional smart phones. Equally, the requirements of economy changed dramatically and along with that the demands on society and the individual job holders. For educational systems, such a rapidly changing world raises massive challenges: the way our children learn, their learning trajectories, and above all what they learn is changing equally fast. Facing the pace of technological and societal changes and demands, we cannot predict what knowledge will be required in the future. Thus, schooling and educational systems must increasingly focus on the so-called 21st century skills and they need to turn towards a strong, competence-oriented education. What it takes is considering teaching skills and competencies as ways of thinking, working, living, and as tools for working in connected, media-rich worlds. Thus, concepts such as creative, smart, personalized, focused, and lifelong are key characteristics of future education. Consequently, much more than today, future learning must be a highly individual process, right in contrast to today’s one-size-fits-all frontal classroom education. Such demands, in turn, are challenging teachers and teacher education. Highly individualized teaching means deeply understanding each and every learner and finding appropriate educational measures. It is clear that in order to realize such kind of teaching, smart technologies based on sound psycho-pedagogical theoretical foundations are required to support teachers in assessing and understanding the learners, their needs, preferences, strengths and weaknesses, possible misconceptions, and their goals and visions.