Prime Minister Lee Hsien Loong worries about the Singapore identity in 50 years' time.
Will people still want to be Singaporean? Will they be proud to be one? Will they believe the country has a future?
What will strengthen their sense of national identity and the character of this nation and society?
Those were questions he posed in his Ho Rih Hwa lecture at the end of June and is likely to take up again tonight as he takes to the stage at ITE College Central for his 12th National Day Rally speech.
This SG50 Rally is an apt platform to reflect on the founding principles of Singapore's success, and to rally the nation to unite for the road ahead.
And since this is election season, there's also no running away from the expectation of yet more goodies from the government store.
In his National Day Message earlier this month, Mr Lee spoke of the Old Guard ministers and the Pioneer generation - "the lions and the lion-hearted" - and how they had turned the "moment of anguish" at Separation into "a lifetime of determination to forge a path for this island nation".
Tonight, he is likely to further develop that theme but perhaps placing the emphasis this time on how Singaporeans can and must display that same determination in forging a future for themselves and for this nation they call home.
National University of Singapore(NUS) professor Lan Luh Luh expects Mr Lee to take stock of the areas in which Singapore has excelled, where it has stumbled, and how it overcame its challenges.
If done right, she says: "It can be an encouraging speech as well as a timely reminder that we did not arrive where we are today on pure luck or organically. We are where we are by the sheer determination and deliberate actions taken by our people, led by our previous three generations of leaders."
Coming in the midst of election season, and with Parliament expected to be dissolved within days of the rally, tonight's speech is also a golden opportunity for Mr Lee to remind Singaporeans of the key role the People's Action Party (PAP) government has played in leading Singapore to its present success.
Dr Gillian Koh, senior research fellow at the Institute of Policy Studies, says: "Since a general election is in the offing too, he may emphasise the broad themes of government action over these past four years as well as the governance values that have guided the PAP as a national movement through these 50 years."
These include "the PAP's commitment to social inclusion and social mobility; to policies to enable a broad band of Singaporeans to do better than what their starting points in life would suggest".
Dr Koh also predicts that the rally will include "an appeal to Singaporeans to continue to take that long view of what government should be about, to recognise that the things that matter to Singaporeans are being attended to, be it making the essentials in life affordable or the population issue".
Some expect Mr Lee to make mention of Mr Lee Kuan Yew, whose death in March this year galvanised Singaporeans to express deep gratitude to their founding prime minister and an emotional commitment to this country that impressed even observers abroad.
That national week of mourning bears the hallmarks of a formative event for younger generations of Singaporeans and the forging of their national identity.
Analysts are divided as to the extent to which handouts and financial support will be dispensed to sweeten the ground ahead of the polls.
Political science academic Bilveer Singh expects giveaways as tonight's rally is a time for the Prime Minister and his government to "demonstrate their political appreciation to Singaporeans".
"The country has been on a left-of-centre paradigm, giving goodies to most people to assist them. Add to that SG50.
"Now add the election factor and I will not be surprised if it will be blockbuster season as the Government wants to show 'We are good, these are your benefits. We have led well, and this is the evidence. Now keep us at the helm and more will be on the way," he says.
Others like Singapore Management University law don Eugene Tan caution that such handouts may be counter-productive.
"There is no guarantee that voters will vote for the ruling PAP on account of the handouts, giveaways and bonuses", he says, adding: "It might even be seen as crass."
But in previous speeches, the Prime Minister signalled his grave concern over population trends and spoke at length about encouraging family formation. MPs and family advocates are hopeful more measures will be announced to do so.