Singapore: The sheltered nation

So sheltered that it obsoletes the umbrellas ☂️

In Singapore, it rains often and unpredictably. Decades ago, bus stops could be just poles marking routes, with no shelter. I recall dashing off buses without umbrellas, getting drenched even with one. Today, Singapore is seamlessly connected by covered and underground walkways—so extensive that umbrellas can be unnecessary to many.

We can walk for kilometres under cover, through void decks, HDBs, and MRT stations. Even construction sites adapt, constantly shifting temporary shelters to ensure connectivity. The pavements are designed to prevent puddles, and the infrastructure is wheelchair-friendly. Train stations on new lines now have multiple entrances linked to a vast network of sheltered paths, shielding us from rain and the sweltering heat.

The Walk2Ride programme has added 200km of sheltered walkways since 2018, prioritizing commuter convenience within a 400-meter radius of major transport nodes. Singapore’s pedestrian infrastructure is a quiet luxury compared to many countries where sidewalks are cracked, littered, or even unsafe. Beyond physical comfort, these walkways symbolize something deeper.


前人栽树,后人乘凉—one generation plants the trees, another enjoys the shade. These sheltered walkways are more than just infrastructure; they reflect decades of thoughtful planning and resources. They are a reminder of how well the earlier generations built, allowing us to walk comfortably today.

Yet, like many public amenities—exercise corners, playgrounds, clean streets, greenery—these structures blend into the background. We take them for granted, just as we do safety, stability, and opportunity.

This is 身在福中不知福—living in comfort without recognizing it.

Singapore is an exception. Speak to foreigners living here or Singaporeans who have lived abroad—they’ll tell you how different things are elsewhere. Infrastructure, security, governance—these are not guaranteed in many countries.


Yet, with rising standards of living, expectations grow even faster. The Tocqueville effect describes this well: as conditions improve, dissatisfaction can increase. More people feel entitled to more comfort, more benefits, more perfection—without considering what it takes to maintain all this.

This mindset shows up everywhere: complaints over minor inconveniences, outrage over slight inefficiencies, and the assumption that things should always be flawless.

In a major construction project, I once saw a small section (barely 3 meters) uncovered. Instead of letting pedestrians endure a few drops of rain, a worker stood there holding an umbrella for passersby. That moment struck me—we are too pampered.


Singapore’s success is a double-edged sword. Circumstantial advantages—a stable economy, world-class education, and safety—give us a head start, but they can also breed entitlement, complacency, and fragility.

This is what worries me.

Are we raising a generation that knows only comfort but not struggle? If we lose what we have today, can we adapt, rebuild, and persevere?

G. Michael Hopf’s famous cycle explains it well:
Hard times create strong men, strong men create good times, good times create weak men, and weak men create hard times.

We don’t grow when things are easy. Character is built in adversity, not abundance. Without struggle, we may not develop the grit to survive real challenges and the ambition for more progress.

Former minister George Yeo put it succinctly:

“Characters and communities are forged in pathos, not laughter.”


It is tempting to stay sheltered, avoiding discomfort. But how long can we stay protected? When the shelter is gone, will we survive and thrive—or crumble?

We are becoming too soft, too entitled, and too easily dissatisfied. Many Singaporeans unconsciously expect a utopia. They demand more but offer no solutions. They compare and complain, unaware that governing a small island with finite space and resources is an immense challenge. Every job looks easy when you’re not the one doing it.

Ask not what your country can do for you, ask what you can do for your country. – John F. Kennedy


To preserve Singapore’s success, we must reconcile comfort with consciousness:

  • Acknowledge the shade: Recognize that today’s luxuries were built on yesterday’s sacrifices.
  • Embrace discomfort: Let children walk unsheltered sometimes. Let adults endure delays without outrage.
  • Build and sustain: Progress need not be discarded, but it must be stewarded—with humility, not hubris.

The true test of our sheltered walkways isn’t whether they keep us dry, but whether we remember how to walk through rain.