Actually the crux of this is that Singapore despite its perceived unfairness and all, is an pretty elite environment for the best and the more capable and unfortunately they are not quite there to make it much less remain here.
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They want to take off, but they cannot do it fully. They are also not good enough to find well-paying jobs to commensurate with their skills and experience there.
We all know how good LKY & his cronies are They of course deserve the world class salaries which they voted themselves.
If you look at the "successful" in Spore many have used their connections. Not everyone has a network of "connections" to make it in Spore.
Sometimes its about value. & not affordability. Many Sporeans /ex-Sporeans are buying properties overseas because of better value. Why pay a premium for a lower quality of life in Spore?
Years ago I met an office boy who was living a humble life in Spore. He was satisfied with a simple motorcycle. He was using his $$$ to invest in Malaysian properties. While all the executives was busy being stressed out, he was sitting in the corner relaxing He was ahead of the curve with his idea of investing in value.