This is not your father's Singapore where people doing work like technician can afford 5room.flats, drive car and start a family. Things have changed Singapore is a globaliaed city now with a population of 6 million. Singaporeans' unrealistic expectations given the current context is a major source of problems.
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6 million people. Obviously unlike in the past where people keep upgrading to bigger flats, it is no longer possible given how crowded we have become. Consider yourself luckly just to have your own place and you should be happy with that.
Not everyone who needs a car can get one now. Things have changed. You learn to take the public transport carry your newborn stroller and all up the bus. Teach your elderly parents to balance themselves and not fall down on the bus. There are only so many COEs allowed each year no matter how badly you need it. Learn to adjust to the new reality.
This is not the Singapore of your father's time. If you want that go somewhere else..Singapore is an ultra competitive society. It competes at all levels from the time you enter primary school to your working life. As if the competition is not intense enough, they will import foreigners to make sure you are on your toes all the time. Please don't be relaxed like your father's time. Things have changed it is different.
People complain that it is too expensive to raise children in Singapore. Why complain when you make the wrong choice to start a family. The other day I was at the hawker center where I saw a father tell his son not to order western food but to eat chicken rice instead because western food is to expensive. You want to be "that father" who cannot deliver to what your kid wants?
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You have to remember that Singapore is a Globaliaed City with access to global talent. You kid yourself that no one in whole of China or whole of India can take your place here easily. You still have some value serving in NS and being readied to die defending Singapore - learn to appreciate this.
The earlier you reframe your mind and thinking the better it is for you as you accept the nrew reality and move on. You can't change the unchangeable. Once you set your expectations of life in Singapore to the correct realistic level many of your problems will be solved.
I, being poor, have only my dreams; I have spread my dreams under your feet; Tread softly because you tread on my dreams.