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Mr O'Brien said he had had a wonderful leadership journey at Kavanagh College and enjoyed fantastic support from staff, pupils and the parent community.
However, after nine years at the Dunedin Catholic secondary school, and almost 20 years as a principal, he felt it was time for new horizons.
He does not have any "definite plans" for the future at this time, and said another principalship was unlikely because "it would be hard to top Kavanagh".
By signalling his intentions now, Mr O’Brien hoped it would provide certainty going forward and allow a decent amount of time for the board of trustees to find a successor.