While teaching challenges have been shown to affect teacher performance in multiple ways, little is known about the transformations occurring in language teachers' perceptions of challenges over time. Hence, this study purported to analyze EFL teachers' current and retrospective perceptions of challenges associated with language teaching tasks. Quantitative data were collected utilizing a questionnaire and processed through Friedman’s ANOVA and a Wilcoxon Signed Ranks Test. A within-subjects comparison revealed a statistically significant difference between current and retrospective perceptions of challenges with a large effect size on all language teaching tasks included in the questionnaire, indicating that experience was a causing variable contributing to transformations in teachers' perceptions of task difficulty. The principal shifts in the participants' views were documented on such tasks as student engagement with language material, effective instruction for all learners, personalizing teaching, and planning and managing instruction. The teaching experience played a less decisive role in the case of teaching speaking, student motivation, teaching vocabulary, teaching reading, student assessment, and knowing students. Notably, the areas persisting as very challenging regardless of experience were teaching speaking, motivating learners, teaching writing, and listening. The study's findings hold implications for initial teacher preparation and development, highlighting areas calling for more attention. The paper presents the results of a rather small-scale investigation tackling only a few of the multiple areas of language teaching which potentially challenge language teachers. Likewise, due to a small research sample (n=208) and its limitation to the context of Ukraine, this study does not claim the generalizability of its findings. Nevertheless, the findings reveal in highlighting the tasks posing a substantial challenge to EFL teachers both at the outset of their career and following years spent in it.
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