This paper seeks to study work-related and geographical conditions under which innovativeness is stimulated through the analysis of individual and regional data dating from just prior to the smartphone age. As a result, by using the ISSP 2005 Work Orientations Survey, we are able to examine the role of work flexibility, among other work-related conditions, in a relatively more traditional context that mostly excludes modern, smartphone-driven, remote-working practices. Our study confirms that individual freedom in the work place, flexible work hours, job security, living in suburban areas, low stress, private business activity, and the ability to take free time off work are important drivers of innovation. In particular, through a spatial econometric model, we identified an optimum level for weekly work time of about 36 h, which is supported by our findings from tree-based ensemble models. The originality of the present study is particularly due to its examination of innovative output rather than general productivity through the integration of person-level data on individual work conditions, in addition to its novel methodological approach which combines machine learning and spatial econometric findings.