I do hope that overseas Singaporeans stop giving people the impression that Singapore is a dictatorship/totalitarian/authoritarian/despotic state.
What prompted me to write this post is that some of my schoolmates from USA thought that Singapore isn't a democracy - they were genuinely surprised to hear from me that Singapore holds elections at all. When I asked them, "What gave you the impression that Singapore is not a democracy?" The response: "Even the other Singaporeans whom I've talked to don't seem to think that Singapore is a democracy."
I find it rather curious why some people from the US get the impression from Singaporeans that Singapore is some sort of an outright dictatorship. It is a matter of fact that Singapore is a democracy. Leaders are chosen by elections. Leaders are accountable to the people. Citizens have civil rights. What is left as a matter of opinion is the extent to which the above three are true, and whether that means that Singapore is "truly" a democracy.
I cannot generalize this to all overseas Singaporeans, of course, but from the ~5 Singaporeans whom I have encountered describing Singapore to Americans, I get the impression that they tend to be too eager to state why Singapore is not "truly" a democracy, but forget to mention that Singapore is a democracy in the first place. While another Singaporean will understand that Singapore isn't run by Mussolini/Hilter/Mao, someone who hasn't heard much about Singapore might have a different idea in mind when one says, "Well, we don't exactly have free speech, we are known for really strict laws, and the ruling party has been ruling since independence."
Why do we (the ~5 people we have met and admittedly, myself initially) so spontaneously speak of how Singapore isn't "exactly" a democracy before we even state that it is one? My guess is that Singaporeans are used to talking about Singapore-style democracy in the context where they are arguing about the finer points with other Singaporeans, who are well aware of and are used to all the rights that they have in Singapore. The largely pro-government mainstream media wouldn't hesitate to remind us that the government is accountable to the people. The rulers wouldn't hesitate to remind us that they are, after all, chosen by the people fair and square. The truth is not entirely that. Given these information as the basis to agree upon or to critique, New media and coffee-shop talks balance out the dominant influences of public opinion with a primarily anti-government stance to arrive at something that is more accurate.
The effect of this context of pro-government media is that when discussing Singapore politics, a Singaporean subconsciously assumes that the listener already knows some big things about Singapore. We are already used to doing all kinds of things with few state-enforced consequences, the things that we cannot do without consequences are particularly salient. We pretty much take our rights for granted. As such, we are used to talking about the rights we don't have and how elections aren't exactly fair, rather than the rights we do have.
This works fine in Singapore, because everyone lives here and has some intuitive idea of how "oppressed" we are. But when someone who is used to thinking of and talking about Singapore politics this way will be misleading to people who haven't heard much of Singapore. Without the preconception of all the things you can do in Singapore, it gives a rather negative and inaccurate impression.
I cannot prescribe what one should say to others about Singapore. After all, what I say is also mostly my own opinions. But I do hope that when Singaporeans talk to other people about Singapore politics, do consider that people might assume the worst if you only state what is not good.
PS: Another observation is that Malaysians tend to give a more positive portrayal of Singapore than Singaporeans themselves do. Maybe we can learn from them to produce a more balanced "pitch" about Singapore politics.