Actually, its not only about boastfulness or hot air.

I really don't understand why they are so proud about having failed to attain a degree or get into a reputable (i.e. not a private education provider) tertiary institution.

Why do they talk about their low educational attainment like as though it is a point of pride? "I come from SIM and I have 5 NUS graduates working under me and I make $15,000 a month!"

Good education is a wonderful thing to have. Getting a chance to learn in a reputable and stimulating environment like our local universities is a wonderful thing to have. In America and Europe, almost everybody goes to college, whether they are actually aiming for a high flying career /well paying job or not. It is part of their culture to do higher education, and not merely for a piece of paper.

It is always said that Singapore is a "Confucian society" and there's great emphasis on learning and being knowledgable and cultured. But I don't see it here.

How is it a point of pride to have failed to get into a good university (regardless of how much I'm earning now). If anything, I would be very sad that I missed a great opportunity and 4 years of university life in a real academic setting. These are good life experiences that cannot be easily enjoyed at other stages of your life, when you have family and other financial commitments.

Now don't get me wrong. I don't despise people of low education. Many of our parents' generation didn't have much schooling and they worked hard and did well in life. There are also many young Singaporeans who simply cannot not afford to go for university and I never despise them for that.

But SIM students obviously have the money to pay for expensive private tuition fees to get their degree. So its a matter of discipline that they did not get to a real full-fledged university. If I were them, I would be more regretful that I passed up a chance to study at a real university, rather than smug that I earn well in spite of not having studied in a good university.