Employment and work are identified as a critical area that has been impacted by advancement of ICT and is currently passing through significant changes. Hence, the Bright ICT agenda calls for researchers to focus their effort on this area that is not only in need of better understanding but also holds potential better future for many around the globe. Influenced by the widespread connectivity to the Internet and the rise of digital platforms, new ways of working such as crowdworking is rising encouraging government and International agencies to consider it an alternative route for employment that could extend employment opportunities beyond national geography and regional barriers. This qualitative study responds to Bright ICT call by exploring the lived experience of crowdworkers and how they plan and develop their future. It aims to answer the question of how crowdworkers experience this type of employment and whether they can develop their skills and organize their future? The study identifies four categories of crowdworkers and shows their practices in developing and progressing their crowdworking experience. We conceptualise these practices as a career development path and identify four career progression stages. Implications for research and practice are discussed.