Teaching is a part of socialization: both in society and for society. In this paper, the focus is on the university level. The responsibility of higher education is significant: a new generation receives the possibility to influence society over many decades. When talking about the quality of education, different factors are important. One aspect which influences teaching and learning is the size of study groups. For example – there are 8.4 students per one academic staff member at the top ten universities, according to the World University Rankings. In Tallinn University, where I have been teaching since 1997, this figure is 27.2. After a quarter of a century of teaching experience, it is reasonable to reflect on the situation and ways of coping. In my classes, there have always been 35 or more students. One way to handle big groups is the optimal use of energy, but optimality depends on developments in society: different times predict specific behaviours and styles of teaching. Here, the research method was a reflective approach to teaching. Teachers’ self-reflection supports education, because the readiness to analyse processes both inside and outside the school increases objectivity. The aim of this article is to analyse long-term experiences of teaching in the context of changing norms: How can one keep both students and teachers as happy as possible when there is no manual on how to deal with post-Soviet and/or other influences in society? This article concludes that, in my case, teaching began through an approach of trial and error. Later, I started to be proactive: my style of teaching changed in parallel with developments in society, and readiness to reflect become a teaching method.