This paper will examine the process of change in an Irish street market by exploring some of the key linkages between ‘agency’ and ‘context’ among a set of veteran street traders. Our discussion centres on the careers of 13 veteran traders (the longest standing of whom began trading in 1979) and, in particular, the challenges they faced in getting established as they began trading in Galway’s street market. Our exploration of ‘agency’ will consider the reasons our traders give for beginning their trading careers and how they negotiated the different challenges they faced at the outset. Many of the challenges the traders faced derived from the ‘resources’ they had at their disposal, and from the ‘opportunities’ and ‘obstacles’ found in the wider ‘context’. Getting started presented the would-be traders with a number of specific challenges. What, firstly, did they take to be the resources, opportunities, and obstacles relevant to becoming a street trader in Galway? How, secondly, did they set about mobilising these resources, exploiting opportunities, and overcoming obstacles? How well did they get on? How do they themselves account for how well (or otherwise) they fared? We also must ask what intended and unintended effects did their trading have for the changing character of the market. With the onset of the Covid-19 coronavirus pandemic what unique challenges did this present and in what way did these experienced traders leverage their agency in the face of such an unprecedent global event to continue to trade.