Digitalization is happening in every aspect of our lives, from the social sphere, sports, politics, health and work. With digitalization driving so many changes in the economy, all businesses are equally affected greatly by this new industrial revolution. Larger companies have the advantage of more resources to navigate these changes. However, many small businesses face great challenges to re-invent themselves and digitalize. These SMEs in Singapore are faced with limited resources and financing both internally and with respect to competing with larger organizations and financial institutions. With SMEs making up such a large part of the Singapore economy, not much research has been done on how small businesses are faring on the road to digitalization - what is driving these small businesses to digitalize, the obstacles they face and how these drivers interact with the limitations the small businesses have. Therefore, the gap in our knowledge that the study has identified is that we do not really understand what are the main drivers of digitalization for small businesses in Singapore. Much of the available literature covers large businesses and usually focuses on Western countries. Using the framework of the Technology Acceptance Model (TAM), the Theory of Reasoned Action (TRA) and Theory of Planned Behaviour (TPB) as the foundation, this thesis will adapt and propose a new advanced model to explore what drives the attitudes of small business towards implementation of digital systems in Singapore. The thesis was done on small businesses that operate in various industries. From the data analysis we found that four groups of drivers – Technological change, Government policies, Internal factors and Competitive pressures - were influential in predicting attitudes to digitalization and its usage in small and medium-sized enterprises in Singapore. This study’s findings have implications for the government which should consider several critical drivers identified when it is formulating policies to encourage digitalization in the Singapore economy. Small business owners should take note of the drivers that enable their businesses to digitalize effectively.