Explanatory style is based on how one explains good and bad events according to three dimensions: personalization, permanence, and pervasiveness. With an optimistic explanatory style, good events are explained as personal, permanent, and pervasive, whereas bad events are explained as external, temporary, and specific. For counsellors, an optimistic explanatory style creates positive expectancy judgments about the possibilities and opportunities for successful client outcomes. In this research study, we explored the explanatory styles expressed in 400 events (200 good events and 200 bad events) extracted from 38,013 writing samples of first year and final year graduate level counsellors in training. Across the three optimism dimensions and within good and bad events, there was one occurrence of a positive relationship between counsellor training time and the amount of expressed optimism. The implications of this study include the need to cultivate optimistic explanatory styles of counsellors in training and practicing counsellors.