Failing Better was recently installed at the Pierce Street entrance to Trinity College, Dublin. In conducting his research for the work, Rowan Gillespie developed an interest in Trinity College, Dublin’s curious connection to aviation, particularly the flying experiments of George Francis FitzGerald, Professor of Natural and Experimental Physics, in the late nineteenth century. These were mostly unsuccessful but always optimistic which brought to mind the words of Trinity graduate, Samuel Beckett “Fail again, fail better”. Gillespie was drawn to the concept of inspired vision inching towards success through a series of failures. His flying machine is a horse which develops wheels and then propellers, it will never fly just as Professor George Francis FitzGerald’s machine never really flew but he at least dared to try.