I have nothing against Singapore, but that's kind of the whole point of free speech -- the ability to discuss all ideas that can alter society.
I suppose a society where those in charge are all benevolent could get by without it for a long time, but eventually I would expect a disconnect between the perceptions of the government and the needs of the people that can scarcely be solved with free speech, but almost certainly not without it.
Since I'm just reasoning aboit generalizations, I'll ask, how does Singapore work around this problem?
Things are changing there slowly. They do technically censor their Internet (it's illegal to view porn, but if you stumble on it without downloading it, that's legal...or something). I think they gave up on their porn filter years ago. Their level of censorship is way below the level of the UK!
With all that said, the nation is highly progressive in other areas. All the trains are fully automated, no drivers. They can run 24/7. Cars are exceedingly expensive. A permit for buying a car is done on a bidding system and the Certificate of Entitlement (COE) can run between $50k ~ $70k (that's not including the cost of the car or registration). This keeps pollution, smog and emissions down to a minimum. (The COEs are only good for 10 years. A used 5 year extension costs the same as a new car COE, so most ditch their cars after 10 years. It does create an insane amount of consumerism/waste though .. Singapore is the largest car exporter in the world).
I suggest visiting and spending two weeks there. The Adler Lunary Hostel is reall nice and central. It's a really interesting place.
I'm having a hard time articulating my point but I think what I mean is that even as a megacity Singapore can feel somewhat small or shallow, compared to a city like Hong Kong for instance.
In "Nineteen-Eightyfour", there are very few discontents. Everybody else is thrilled by chocolate rations being increased or foaming at the mouth during the hate sessions. The whole point of impoverishing language and thought after all is to make people unable to even see the condition they're in, which comes after they ceased to be able to talk about it.
Since totalitarianism is about the extinguishing of humans as humans (beings that act and are unpredictable, instead of mere cogs which react predictably), there is really nothing to write about the core of it, which is basically necrotic tissue. The only remaining thoughts and actions (that deserve those titles) occur outside or at the fringe of it. Which is why the book is about the exception, people who are still persons, and their process of getting broken. Everybody else either got already broken, or was born broken. They don't need to be killed because they don't live to begin with.
This is not directed at you or Singapore, if anything I feel it applies more to the West, but just as a general thought: Just because you feel happy and safe doesn't have to mean you don't live in a dystopia, it might just mean you're not enough of a threat to it to have it uncloak for you, or that you are even are aligned with it's pathology, either by chance or by having been groomed. We should judge societies and people by how they treat the vulnerable and innocent, not how they treat us, is what I'm trying to say. Again, this is a general thought, I don't know jack about Singapore.
Village -> Urban location -> Metropolitan City.
Those unhappy in well developed Metropolitan cities are usually due to government policies, political trends, CoL, etc. They are likely to move across the country or to an entirely different developed nation (US, EU, etc).
Some return on seeing how policies are stacked against migrants, many endure to see the same cycle go on – They move for better education, kids move out for college, etc.
Humans are inherently migratory, meaningless borders keep us stuck at a particular place.
Based on my reading of some books from Lee Kuan Yew, the reason he did not allow total free media and speech was that he was very much concerned about the stability of the nation, and as such a small country, Singapore really can't afford any civil conflicts (it had suffered one before https://en.wikipedia.org/wiki/1969_race_riots_of_Singapore and recently https://en.wikipedia.org/wiki/2013_Little_India_riot)
Besides that, some of the "free speech" online are actually either falsified or in very explicit languages specifically targeted at raising culture hatred, and hatred towards foreign immigrants. They are not targeted at solving problems
Somehow, the reason that keeps people leaving Singapore is not the lack of free speech, but something else. Most of my foreign friends from University had left Singapore, either to US or China. For them, the biggest problem seems to be high living cost, no space for personal development and no job satisfaction. How to retain these talents may be a bigger issue here