In the fast-paced and bustling city of Hong Kong, making ends meet is always the top priority of labourers who live from entrepot period to the industrial city period to the international financial hub period. An artistic career choice is often discouraged as the structure of the profession does not secure a regular monthly paycheck, unlike the popular business-related jobs in the city. Over the years, public participation in arts and institutional resources has gradually increased, allowing artists to pursue their desire to work with arts and stabilise financial security simultaneously. These resources also offer educational opportunities to young artists in the field to further explore the endless possibilities of Hong Kong art, and inspire artists-to-be. We included nine artists in our timeline project, categorised according to their active years and separated into three periods. Including Period 1: Artists with multi-professions from the year 1950 to 1970, which features Lui Shou-kwan (1919-1975), Ha Bik Chuen (1925-2009), and Gaylord Chan (1925-2020). Period 2: Artists in art-related business, featuring Lul Chun Kwong (b.1956), Oscar Ho Hong Kay (b.1956), and Ellen Pau (b.1961). Period 3: Full-time Artists, including Luke Ching Chin Wai (b.1972), Chow Chun Fai (b.1980) and Kong Chun Hei (b. 1987). By assembling biographical records of artists and creating separate timelines for each artist that mark the changes in their occupations, artistic activities, and institutional support they received in their careers, we see parallels and intersections between our selected artists and observe the shifting landscape and art ecosystem in Hong Kong over the years that influenced the generations of artists.