To further understand differential perceptions of work and wellbeing this paper considers the influence of gender and years in current role (YCR). We surveyed 399 secondary school teachers (class teachers n = 185; middle managers n = 175 and senior managers n = 38) from the central belt of Scotland. Sixty-six per cent of middle managers reported work as very stressful and 63% of this group reported a significant change in their wellbeing. No gender differences were observed within this study however aspects of the content (e.g. "workload") and context (e.g. "changing demands") of work presented as significant occupational hazards for class teachers and middle managers with > 10 YCR. Middle managers were the only group concerned with "low staff morale" and we would suggest the consequences of change and a lack of time. On the basis of our findings and, in light of debates centring on teacher wellbeing, quality retention and high quality educational provision, we would argue that these teachers with > 10 YCR, are in need of the physical and emotional space to reflect on and make sense of the changing context of work before they reach a point where their wellbeing is compromised. This space could be created by increasing weekly non-teaching time, restructuring the school day and/or providing sabbaticals that enable teachers to focus exclusively on their professional learning. This would of course incur a financial cost but we would argue that this would be but a small price to pay.