I was looking for that one defining item of news that best sums up Singapore's 50 years as an independent nation, and there it was in the first week of the New Year.
"Pinnacle@Duxton flat sold for $900,000", The Straits Times reported last Saturday.
It was the first transaction from this ground-breaking public housing development, making the news one month after it became eligible for the resale market.
The owner, who had paid $340,000 for the flat in 2004, walked away with around half a million dollars in profit.
But this wasn't just another property deal, of which there are plenty, and lots of people have made much more in the real estate booms of the past five decades.
This was public housing, and it was the Pinnacle, with its distinctive architecture soaring 50 floors in the heart of the city, built specifically to showcase the country's housing achievements.
And located in the founding prime minister's Tanjong Pagar constituency, no less.
You couldn't find a better icon to highlight how much the country has progressed in the past 50 years. And now, as if to put the icing on the birthday cake in a jubilee year, the market was valuing a flat there at close to a million bucks.
Happy 50th, Singapore?
As an indicator of what a valuable piece of real estate the country has become, and how much confidence people have in its future, celebrations are certainly in order.
But - and at the risk of spoiling this birthday party - the transaction also raises many other questions that trouble many people at this stage in Singapore's development.
Should public housing even in the resale market be so expensively priced?
Should it change hands so easily, profiting the seller so handsomely in such a short period, and at the same time condemning the buyer to possibly a lifetime of debt?
Is it a source of pride to have Singaporeans living in million-dollar homes?
Or does it say much about the sort of society it has become where everything, including your home, is measured mainly in dollar terms?
Asset appreciation was a key national goal for much of Singapore's modern history and nowhere was this pursued more vigorously than in housing. It seemed then like a no-brainer and a sure-fire way to a better, wealthier future.
But as home prices went through the roof, especially after the 2008 financial crisis, the question is whether it's such a good idea to have ever-rising property values.
If everyone lives in million-dollar homes, does it mean we are all better off?
If not, what should housing policy try to achieve?
Can it continue to provide for the majority but in a way that strengthens the idea of what home means?
As Singapore celebrates its 50th anniversary, these and other questions are beginning to surface, not just in housing, but in many other areas.
One that has recently made the rounds concerns the economy.
As growth slowed to just 2.8 per cent last year, amid declining productivity levels and a tight labour market, there is growing concern over the health of the economy.
If the trend continues, there is worry that Singapore companies will lose their competitiveness, resulting in business closures and job losses.
Has the Government's restructuring exercise, now in its fifth year, aggravated the problem, and are changes needed in the way it is carried out?
More important, are the present difficulties temporary and a result of weaknesses in the global economy or are they structural, requiring fundamental changes in economic direction and policies?
After almost 50 years of economic success founded on being open to foreign multinational corporations, is the old formula still relevant or does it need a major overhaul?
These are tough questions, but even harder ones are to be found on the political front.
Most have to do with how the ruling party adapts and changes in response to a more demanding electorate that believes a stronger Opposition presence is good for the country.
Questions are being asked about the People's Action Party's longevity and how long its dominance will last.
How can Singapore make this political transition in a stable and secure way that does not undermine the well-being of its people?
Some worry that too many of these questions - including those on immigration, health care, welfare, retirement and transport - are cropping up at the same time even as the country celebrates its half centenary.
Is it a sign that things are falling apart?
If you read some of the online postings, you might think so, that the end is nigh, and it's all the Government's fault.
That is, of course, far-fetched.
In fact, it would be most unusual if, after 50 years, the same policies remain unchanged and the population continues to be unquestioning and subdued.
Singapore isn't a stagnant nation.
Policies and strategies need to change as circumstances alter and new needs and demands arise.
A maturing society is one that is able to question the way things are, even if it has achieved much, and ask: Can it be done in a better, fairer, more inclusive and progressive way?
A more confident and developed people want to explore different ways to improve their lives and be actively involved in the process.
The angst and unease that seem prevalent today and which might appear overwhelming at times are part of this healthy transition that Singapore is undergoing.
Far better to be in this state than to be inert, unconcerned and afraid.
Fifty is a good time to be asking questions.
My hope in this jubilee year is that arising out of all these discussions, a better society will emerge, one that has been shaped by the common experience of dealing with these challenges.
It is a prospect worth celebrating.
Happy 50th and Happy New Year.