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.
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.
PROFESSOR LAN LUH LUH, NATIONAL UNIVERSITY OF SINGAPORE
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."
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.
DR GILLIAN KOH, senior research fellow at the Institute of Policy Studies
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.
FOCUS ON FAMILIES
Babies and newlyweds already receive special treatment this Golden Jubilee year. Those born in 2015 get a bundle of gifts and a commemorative birth certificate. Couples marrying this year also get an SG50 touch on their marriage certificates.
These, say observers, drive home the message that Singapore's population is still in need of an urgent boost, and the Government will continue to encourage - with incentives, bonuses or special commemorative trinkets - efforts to raise birth rates here.
Of Singapore's three prime ministers, PM Lee has so far been the staunchest champion of more babies. He first raised the subject in his maiden rally in 2004.
He did so again in 2008, where he unveiled a slew of measures to encourage Singaporeans to have more babies and spent over half an hour playing family planner.
And in 2012, he outlined measures being studied to encourage parenthood, including giving couples with young children higher priority for Housing Board flats, and allowing dads to take paternity leave.
Some expect the Baby Bonus scheme, which helps families defray the costs of raising children, to get another boost.
It was last enhanced in 2013. Cash gifts for the first and second child rose from $4,000 to $6,000, and from $6,000 to $8,000 for the third and fourth child.
Beyond dollars and cents, some hope for more measures to ease parents' present concerns. MP Ang Hin Kee, for one, suggests improving childcare options by training and certifying nannies, or by expanding workplace childcare facilities.
Another consideration for the Government is making changes to leave. Currently, working mothers are entitled to 16 weeks paid maternity leave, of which working fathers are eligible to share just one week.
The introduction of paternity leave was a significant step, says Dr Kang Soon-Hock, head of the social science core in SIM University, as it recognises fathers' role in bringing up children too.
Institute of Policy Studies research fellow Christopher Gee says the Government could help couples strike a balance when it comes to childcare, by introducing a more flexible shared parental leave arrangement. This could involve allowing fathers to take on half the 16 weeks of paid maternity leave their wives are entitled to.
Ms Anita Fam of Families for Life says instead of more monetary incentives, there should be more practical solutions for young couples, to support their housing and infant and childcare needs.
The Government is trying to boost population growth by managing immigration, promoting active ageing and encouraging marriage and parenthood, PM Lee said in a speech earlier this year
"But the Government cannot solve these problems just by policies, because it requires all of us to change our norms, our culture, to become a more family-friendly country," he said.
Sociologist Tan Ern Ser agrees: "At the end of the day, what is necessary is to ensure there is a less stressful and more comfortable and secure future for our children."
Dr Tan Khay Boon, senior lecturer at SIM Global Education, says the most significant improvement has been the delinking of the prices of new Build-To-Order flats from resale market prices, and bigger discounts for new flat buyers.
"This can be seen as a policy to facilitate the creation of families to address the low population growth issue in Singapore," he adds.
But other areas could do with a boost.
Ms Lee Bee Wah, who heads the Government Parliamentary Committee for National Development and Environment, has a laundry list of hopes when it comes to housing.
For one thing, she would like to see some adjustments to income ceilings for Housing Board flats. The National Development Ministry in 2011 raised income ceilings by $2,000. A similar quantum, she says, would be helpful this time around.
And married couples who want flats in estates where their parents live should get more help still, says Ms Lee. The Government should also help those living in rental flats who, if gainfully employed, would like to buy over the flat, she adds.
"Public housing has played a key role in our society and we will continue to help Singaporeans move on to home ownership, leaving no one behind," she says.
This year's rally is likely to be one with heart, building on PM Lee's new direction. In recent years, he has shifted the speech away from hard numbers charting Singapore's economic growth, focusing instead on broad directions of policy shifts to to uplift people's lives. In 2013, PM Lee announced MediShield Life and the Pioneer Generation Package. In 2014 came the Silver Support Scheme.
Dr Norshahril says: "If we look at the trend for the last two National Day Rallys, the government is sincere in wanting to help the needy. In the past, the concept of a welfare state was definitely a 'no' for the PAP, but I think there is a paradigm shift in the Government's attitude, particularly under Lee Hsien Loong.
"I still think we will not move into the European model of welfarism, but will incorporate some aspects of it… I think the Government is balancing 'self-help' and welfarism, but tilting towards the former. For me, this is ideal."
The Government's shift to the left now comes out most clearly during the National Day Rally, and this is likely to continue.
"I think we just started…. I suspect there will be more of such policies to eventually create a social security network in lieu of a welfare programme. This is something that is unavoidable," says Dr Singh.
"As a well-off state... it is politically difficult not to go down this path. Hence, I think you are going to see more and more of these 'left' policies but they will be calibrated gradually."
Finally, tonight's rally is a time for Mr Lee to bring together the achievements of his government and to highlight in particular the progress made since the last general election in May 2011. That is what veteran Ang Mo Kio GRC MP Inderjit Singh will be listening out for, ahead of the coming polls which is on the minds of both politicians and voters alike.
"It will be good for the Prime Minister to share the results and impact the measures announced have had on the lives of Singaporeans, and also, when the full impact is expected. It will be good to get the expectations aligned," he said.