The aim of this exploratory research is to identify how working from home and the consequent social isolation interfered in teachers’ work and students’ learning and to identify the challenges, difficulties, advantages, opportunities, demands, trends, implications, outlooks, lessons, directions, and feelings of students and teachers in the teaching processes during the COVID-19 pandemic period. To reach its aim, the authors of this paper developed searches and scientific databases and they also sent an email questionnaire to Rio de Janeiro city schools. The descriptive analyses were made by descriptive statistics (proportions, rates, minimum, maximum, mean, median, standard deviation, coefficient of variation—CV). The results show that working from home and the consequent social isolation interfered in the students’ and teachers’ feelings and sensations and highlight the words “frustration”, “hope”, and “strangeness”. From the sample, 96.4% of the teachers affirmed that working from home and the social isolation interfered in their work and 97.4% of the teachers affirmed that working from home and the consequent social isolation interfered in the students’ learning. This research is the starting point to boost discussions on the subjects of COVID-19, working from home, social isolation, and education. This paper will support researchers in the development of future studies related to the subjects.