People globally quit their jobs at high rates during the COVID-19 pandemic, yet there is scant research about emotional trajectories surrounding voluntary resignations before or during that era. To explore long-term emotional language patterns before and after quitting a job, we amassed a Reddit sample of people who indicated resigning on a specific day (n = 7,436), each of whom was paired with a comparison user matched on posting history. After excluding people on the basis of low posting frequency and word count, we analyzed 150.3 million words (53.1% from 5,134 target users who indicated quitting) using SALLEE, a dictionary-based syntax-aware tool, and Linguistic Inquiry and Word Count (LIWC) dictionaries. Based on posts in the year before and after quitting, people who had quit their jobs used more sadness and anxiety language than matched comparison users. Lower rates of “I” pronouns and cognitive processing language were associated with less sadness and anxiety surrounding quitting. Emotional trajectories during and before the pandemic were parallel, though pandemic messages were more negative. The results have relevance for strategic self-distancing as a means of regulating negative emotions around major life changes.