This paper seeks to explore the process, challenges and journey of setting up counselling within a boys’ public school setting, as an independent practitioner. It looks at the structure and way in which the service was set up and what had to be changed and adapted as time went on. The school had a strong reputation for pastoral care but had come to recognise that there were some issues that it was neither possible nor appropriate for school staff to deal with. So, whilst the school could and did provide containment for many of its pupils, there were those who got lost or were outside of the culture. This seemed to get reflected in my own experience. Setting up counselling in a school is not straightforward, and like the process of therapy itself, it takes time and is not a linear process. Although the service grew steadily, there were factors that led to my finally resigning from the post – I also got lost in the system. There is also a comparison with setting up a service under the auspices of an organisation at the same time.