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This paper examines the experience of work stress and its psychological consequences among Singapore's life insurance agents in the context of the institutional arrangements of the life insurance industry. Results showed that our insurance agents generally experienced a low level of work stress, probably due to the cushioning effects of a supportive work environment of the industry. The most stress was found to be derived from work demands, and the least stress from interpersonal relationships at the workplace. Work demands were also found to contribute to the overall experience of work stress. However, such stress did not deter them from having a satisfactory work life nor did it result in mental ill-health. Rather, job satisfaction and mental health were associated with emotional strains caused by professionalism. The professional expectation for working independently may predispose the agents to self-isolation and loneliness while trying to hide their weaknesses and keep their problems to themselves. These feelings were aggravated by the generally low level of acceptance of the insurance profession by Singapore society.