The future of work is widely debated in terms of skills shortages, disappearing or emerging jobs, ongoing automation through artificial intelligence (AI), and what might happen if we do not have to work due to increased substitution of human with machine labor. Our goal is not to rehash these debates, but to reflect on them in terms of information technology (IT) work in particular. The purpose of thinking about the future is not to predict with precision or certainty what will happen. Rather the purpose is to sensitize us toward choosing pathways and taking actions that increase the probability of the futures we would prefer and decrease the probability of future states we would like to avoid. This paper considers a number of trends and reflects upon them from the dual, potentially conflicting perspectives of IT worker and of society. We close with our thoughts on convergence of both trends and impact, and potential implications.