Job satisfaction among paid employees has been found to correlate positively with employee commitment and retention and, subsequently, organizational productivity and effectiveness. From a human development perspective, work satisfaction is also crucial to happiness and overall wellbeing. Within a broader overarching study of Quality of Life (QoL), the authors did an evaluation of work satisfaction as experienced by both entrepreneurs and paid employees in Trinidad and Tobago. By contrasting the experiences of individuals engaged in these types of employment, we uncovered some insightful workplace trends and gained a deeper understanding of the needs of paid employees. Several scales were developed, using an inductive approach, to capture determinants of current QoL, factors which influenced choice of work, current work challenges, and future concerns for the individuals sampled. Information from some of these scales was incorporated, via a series of statistically validated steps, into a multivariate index which could be used to measure QoL, not just among the general population of Trinidad and Tobago but, arguably, worldwide. One of the key scales used to develop the index is a 22-item 'Job/Activity Satisfaction' measure, which captured information from 415 respondents engaged in the different types of employment, along four (4) key dimensions: 'Respect and Recognition,' 'Job/Market Stability,' 'Workload and Stress,' and 'Self-Efficacy.' This paper summarizes some of the salient results from the scale and from its corresponding index. Our findings revealed that both entrepreneurs and wage earners in Trinidad and Tobago were far more satisfied with those aspects of work over which they had sovereignty than with those controlled by their employers (for paid workers) or by market conditions (for entrepreneurs). Those areas of low satisfaction in the work environment could be targeted for improvement by employers seeking to improve labour conditions. Differences in satisfaction levels between entrepreneurs and paid employees were observed in several areas. Entrepreneurs reported greater levels of work satisfaction overall than did paid employees. Further, while only 30% of entrepreneurs signalled their intent to transition from entrepreneurship to alternative employment (full-time or part-time paid employment), a disproportionately large percentage of paid employees (76%) aspired to full-time or part-time entrepreneurship. Some of this may be due to a willingness to trade the stability of a guaranteed pay check for autonomy and versatility, two qualities which, although almost synonymous with self-employment, could be introduced by creative employers into the work environment. Sex, age and ethnicity were also found to be significant main predictors of work satisfaction. The combined (interactive) effects of sex, ethnicity, and employment type on satisfaction also proved interesting, highlighting where there are gaps between self-and wage-employed workers for men and for women of different ethnicities. These outcomes suggest a need for more robust, evidence-based industrial relations policies and possible areas for focussed attention by employers in Trinidad and Tobago which can help to improve employee satisfaction and, ultimately, organizational performance.