The influence of digital technology on our modern workforce is significant and has been instrumental in the creation of new jobs in new marketplaces to satisfy new needs. Although we may not know the direction of future technological change, what is known is that change will invariably benefit some groups and not others. One group who have not benefited are Māori in Aotearoa New Zealand. With very few Māori employed in the information technology (IT) sector, the benefits to Māori from the increased opportunities are yet to be realized. Historically, Māori have been the subjects of research as end users of technology rather than as technology workers. The dominant narrative being that Māori are underachieving and that Māori will want to participate if they either acquire the technical skills or see the benefits of working in IT for themselves. The aim of this study was to push past this narrative and explore, via the experiences of Māori IT workers, why so few Māori work in IT. At the heart of this research was the question that drove this study: How can Māori IT workers be enabled to thrive in IT? Seeking answers, I traveled throughout Aotearoa New Zealand to kōrero (discuss, converse) with Māori IT workers. A newly developed approach called kaupapa tika was used, where unstructured insider-based interviews were conducted as a co-creation exercise to explore participants’ complex lived experiences. What was uncovered was that while working with IT is fun and exciting, in many cases, working in IT is not.