I would prefer a society that does not measure everything in dollars and cents ONLY. However, that doesn't mean I don't agree that in most cases, most things should be measured in dollars and cents. Otherwise, how do we quantify them?
If we paid toilet cleaners too much, then fewer people would invest in themselves to pick up more valuable vocational skills since they can get by on the bare minimum of job skills.
With regard to self-worth, most people measure their own self-worth and that of others through accomplishments - salaries, medals, highest computer game score, some sort of ranking. Money is just an easy way to gauge level of professional success across most professions. If we don't use money, then what should we use?
Ideally, I would prefer more people to achieve financial success by age 45, so that they can get out of the rat-race and enjoy a slower pace of life. Smell the roses, travel, or just work part-time. But the fact is, most people make poor decisions with regards to their education, financial and career planning, which ensures that they will be perpetually in need of money. Some others, even after they enjoy career success, continue to work long hours because they see it as a form of validation. I know of very successful hawkers who became millionaires. Yet, they continue to work 15 hours a day as though their lives depended on it.
Singapore is a modern society. It is not a society where only the top few elites earn a lot of money. I earn a lot and have a lot of money, but I can assure you that there are many people out there who earn more than me. This is not some medieval society where there is a very small or non-existent middle class. There is a large middle class and upper middle class of Singaporeans. As long as our needs are mostly met and our wealth kept intact, most of us will vote for PAP.
High competitive system is meant more for people who have poor financial planning and risk losing it all overnight if their income source gets cut off. For people like me, even if my business fails, I will still walk away a rich man because I have made sufficient plans for the rainy day. I would be less rich of course, but still rich.