John Bayley's association with Wellington began in 1877 when he was appointed head of the Wellington National (Boys) School on Constitution Hill. Conditions at the institution appear to have been far from ideal and, in his annual report to the Inspector of Schools, Bayley was quick to draw attention to the problems of overcrowding and the generally inadequate fabric of the buildings he, his fellow teachers and pupils were forced to work in. Despite the obvious drawbacks of having to educate children in an environment that, Bayley declared, would 'answer admirably to the purpose of a prison', the Constitution Hill School eventually reaped the rewards of his meticulous eye for detail and good discipline to achieve results that won respect and admiration throughout the district. Seemingly, this was not enough for the ambitious schoolmaster, who tendered his resignation to Wellington School Board in January 1880 to open a new foundation all of his own.