Telework is a decentralized work arrangement. Although it is a widely studied topic, there still is no single definition of ‘telework’. The empirical verification of research in this area remains a pending subject. In this context, our work determines the influence of lifestyle and cultural traits on the preparedness or ‘willingness’ to telework in Medellín, Colombia. Accordingly, we start by reviewing the available literature. We propose a conceptual model, which subsequently is verified at an empirical level, applying a sequential mixed methodology. In a first phase of this empirical verification, several in-depth interviews with teleworkers and their supervisors or superiors are analysed, using a qualitative approach. Then, in a second phase and based on the previous stage, we verify the incidence of two of the emerging categories with respect to the preparedness for telework. These two categories are lifestyle and cultural traits. The verification process is carried out based on structural equations. The obtained results show that cultural traits have a more significant impact than lifestyle when it comes to determining the willingness to telework. Based on these results, we recommend future telework research in the following areas: background analysis, software and hardware requirements and the effects of telework.