Increasing digitisation of engineering and social practices has altered the relationship between formal schooling and development of expertise for professional engineering work. What does the development of expertise look like when knowledge is generated and shared at an accelerated pace due to shifts in technology? In this paper, I present case studies of two early career software engineers. Using methodological insights from digital ethnography, I trace their professional journeys over two decades. I empirically demonstrate how the development of engineering expertise is a continuous and perpetual endeavour and engineers learn throughout their lives (lifelong) and across all the different spaces they inhabit at any given time (lifewide). I argue for extending engineering work practices research and research in engineering education more broadly to take larger timescales of learning into account to build a comprehensive understanding of engineering expertise development.