When I was preparing for my O levels as a secondary school student in Singapore, our teachers liked to joke (it was more of a warning, actually) that the acronym for the Institute of Technical Education (ITE), Singapore’s public vocational institute, belied a more sinister meaning.

They liked to say that ITE stood for “It’s The End”. You see, back in the day (maybe it’s still prevalent now), the best method to get school kids to pull up their socks and bury their heads deep in textbooks, was to nurture this deep lingering fear inside their impressionable, young minds.

The fear is that if they do not make the grade, they would have to go to a school (a.k.a ITE) reserved for the losers, the punks, the delinquents — people who would never make it in life ; people who were earmarked to be subservient to those who memorised their equations, trimmed their hair neatly and paid attention in class.

Sure, if you read the papers, you would see the occasional report of some person who turned over a new leaf and took their exams under the dim light of a prison classroom at the age when their peers would already be climbing the career ladder. These stories were inspirational, sure, but they were obviously not aspirational.

And it is not that teachers are fear-mongers by nature. The students, the teachers — they are all part of the same system. It is a pressure-cooker, whipping up a broth of KPIs, grades, extra-curriculum points, all of which formed the ingredients of standardised success.

That long science fiction story you spent weeks writing? “Sorry, it falls outside our word count, and the descriptions are too abstract. You get an F. Write a simple story about how you went shopping with your mom and walked away with some moral lesson instead.”

“Your essay on General Eisenhower’s retreat from the Philippines during World War 2 contained details not found the textbook, therefore you get marks deducted for that.”

“Why are you playing Starcraft in your spare time? Those games are frivolous, go play chess (nothing against chess, by the way) so you can join the school club.”

Experimentation is very much anathema to the Singapore education machinery. There are only two outcomes when you try to fit people of all shapes into square holes: one, people out of shape will go through hell to be moulded into a square; and two, people who refuse will not make it through and drop out.

The problem with this scenario

Dropping out of school would not have been such a stressful situation if parents and general society did not put such a premium on graduating. In Asia, particularly in developed countries like South Korea, Japan and Singapore, people go to great lengths to uphold and save ‘face’ — an individual’s personal image and honour.

It is not uncommon for parents in Singapore to compare grade scores and extra-curriculum achievements of their children among their relatives or friends — in a not-so-subtle way to one up one another.

The tuition industry is also booming in Singapore, generating over S$1 billion (US$730 million) in revenue last year. Singaporean parents put their kids into this 18-year marathon so they can get to the best universities and get the best white-collar jobs in a swanky corner office overlooking the business district (who would then settle down and have kids and rinse and repeat).

Few people in Singapore want to risk falling short of the Singaporean aspiration. Few people want to step out of the comfort zone — and this is growing to become a big problem.

The digital economy doesn’t like how Singaporeans think

Readers of our site will no doubt immediately recognise how this would become a problem, as Singapore strives to become a tech innovation hub.

The very word ‘innovate’, according to the Cambridge English dictionary, means “to introduce changes and new ideas”.

To introduce new ideas, you need to experiment, and to experiment, you need to entertain the strong possibility that you will stumble and fall along the way; and you will need the tenacity to pick yourself up and try again.

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In Dan Senor and Saul Singer’s book,  Start-up Nation, published nearly 10 years ago, they wrote: “Singapore’s leaders have failed to keep up in a world that puts a high premium on a trio of attributes historically alien to Singapore’s culture: initiative, risk-taking, agility.”

“Singaporeans are specifically instructed on how to be polite, how to be less contentious and noisy…Singapore’s problem is culture-bound,” they added.

Earlier this year,  Joel Ko, a Managing Partner of Marvelstone Group and CEO of its VC firm Marvelstone Ventures, told e27 that failure is an essential criterion by which he evaluates founders.

Yet, despite the endless stream of entrepreneurs, panel discussions, TEDtalks, expounding on the importance of trying, failing and trying again, Singaporeans still shudder at the word ‘failure’.

Indeed, last year, a report showed that only 14.1 per cent of Singapore businesses were willing to embrace innovation (which, as I have just mentioned, includes failure).

So it was little surprise when I saw the Economist Intelligence Unit’s damning report put Singapore 14th out of 45th when it came to how confident businesses were in the Lion City digital transformation readiness. In terms of innovation and entrepreneurship, it fared even worse, at 21st.

“In corporate society in Singapore, failure is not in the dictionary,” said David Burns, Telstra’s group managing director of international and global services, which commissioned the survey.

The Singapore government is doing an excellent job in providing the necessary funds to drive new technologies; in fact, out of most countries in the APAC, it is probably doing the best job in terms of drawing up initiatives, attracting foreign companies and talent, and providing monetary and policy support to make the city the shining rock star of the tech world.

But there are more nuanced and fundamental changes that need to be enacted if Singapore wants to move forward into the digital era. Roots that go decades back need to be uprooted; it requires a total upheaval of the Singaporean mentality.

Singapore needs to learn to embrace scrappiness, it needs to welcome outliers. It needs to learn how to tolerate a bit of lawlessness if it wants to be ready for the new era of disruptive and innovative industries.

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