Striving to rebuke his critics and prove there would be no return to the more controlled society as was the case under his father, Lee Kuan Yew, the new prime minister showed in his first National Day Rally speech that he is his own man and wants to embrace an open and inclusive society, tolerant of diversity.
The new government says it aims to encourage more debate and participation, especially from the younger generation. Lee wants more people in their 30s to become directly involved in the political arena and in recent weeks he has reiterated that the search for a new generation of political leaders is on. "Don't ask what the government is going to do. Get up and do it!" he said on Sunday night.
But Lee will face an uphill battle to attract younger Singaporeans who are notoriously apathetic and shun political debate for fear it may harm their career prospects. The "don't know, don't care" attitude is prevalent, and a local newspaper's quick survey recently highlighted that some didn't even know whom their new prime minister was.
Sunday night, Lee announced some relaxation in freedom of expression. Indoor meetings will no longer need a licence from the police as long as they avoid sensitive issues such as race and religion. This left the door for political meetings to take place within this framework. In another relaxation, people will be able to hold performances and exhibitions at the so-called Speakers' Corner without having to apply for a licence. These relaxations, Lee said, were a signal for Singaporeans to "speak your voice; be heard; take responsibility for your views and opinions."
Political commentator James Gomez, who is co-ordinating a publication project entitled the Singapore Studies Workshop Series at Monash Asia Institute, noted "these announcements (speaker corners and indoor meeting) will mean a few things, only a few things," pointing out that Lee remained silent on freedom of assembly in public places, freedom of association for gay groups and the use of microphones at the Speaker's Corner.
"Many civil society actors in Singapore are cut from the same conservative cloth as the majority of Singaporeans. Hence, to expect civil society to bring about political change in Singapore in view of these simple licensing changes is either to expect too much or to be a tad too naïve," Gomez said, "Why? Because civil society by nature is conservative in Singapore and changes to freedom of expression rules do not go far enough for civil society groups to be bold and effective."
Fear is often put forward as the reason why Singaporeans refuse to participate in the civic and political debate. But some point out that this fear is exaggerated and that Singaporeans mostly exercise self-censorship.
Earlier this year, opposition politician Sylvia Lim noted that the fear of political reprisal was "largely perceptual."
Political observers note that with the government still refusing to give out a list of OB markers (out-of-bound topics the government does not want to be discussed in public), most Singaporeans are unlikely to test the water and push the envelope. Though there have been numerous calls for the OB markers to be defined, most recently by the Remaking Singapore Committee, the government had argued these markers cannot be delineated absolutely as they will shift dynamically according to the circumstance.
"I suppose it is a start (the relaxation), but given Singaporeans' psyches I don't expect people to go overboard and start having a free flow of discussion. The main reason is that people here just don't care. They place much more of a premium on how the society is managed, whether people have jobs, whether they are safe than on freedom of expression," notes Dr Lee Chun Wah, assistant professor at the Nanyang Technology University.
"As long as the government creates jobs, helps people that have been retrenched to retrain, then everything is ok," he adds.
Another tenet of Lee's policies appears an emphasis on better family life. The move is aimed at lifting the baby blues which have fallen hard on the city-state.
Last year, the country's birth rate fell to 37,600, an all time low since its independence and well below the 50,000 needed to sustain the population.
The ailing stork is posing policymakers a real headache and previous financial incentives, like generous tax breaks, have had little impact on the falling birth rate.
This time, the government is aiming for a more rounded "holistic" approach. While promising even more financial incentives - with tax breaks, lower maid levies, infant care subsidies - it is also increasing maternity leave by 4 weeks to 12 weeks (subsidized by the government) and giving parents of children under 7 years old, two days a year off.
Acknowledging that starting a family was an issue about values and not incentives, Lee conceded the package alone would not solve the baby shortage, but he hoped it may help change Singaporean mindsets towards marriage, family and children.
"Lee advocated a certain ideal. He encouraged Singaporean to spend more time with their family, to strike a better balance between family life and work, but I'm not very optimistic it will work out this way," said Dr Lee Chun Wah. He pointed out that while the prime minister announced the working week of civil servants would be reduced to 5 days a week instead of the current 5 and a half days, working hours would not be reduced "This means civil servants could work longer hours during the week," he noted.
Notable deaths of 2014 [PHOTOS]