When Singapore was simpler and younger, I learnt to swim at a black & white bungalow that had a pool and a caretaker who would do up an excellent English brekkie. I was five and just starting to swim in the big pool when I saw a man who looked familiar doing laps.

I tried to swim up to him but he was too fast. So I got out of the pool, trotted along the side to the end just as the man was surfacing, and smiled down at him. When he swam away, I started off to the other side to do the same.

At this point, the family story is that my father put down his newspaper to go over and stop me.

Otherwise, who knew what the burly security guards who had been eyeing the boy might have done. I was just being friendly, I told my father.

He nodded and explained that even the prime minister needs privacy to just swim and exercise.

We all have our circles (or should have). Places outside the home and office where we feel comfortable. People we are used to, and with whom there is an instinctive, basic trust.

As some circles are more important than others – in power, money or prestige – the idea of an insider becomes especially seductive: someone inside that elite circle, who knows more than the many others outside.

The fact is that “know-who”, and not only know-how, has value. A tightly connected circle can mobilise more quickly. An insider can do much good. At a private dinner, an insider with a good heart can rally guests to cough up donations – without the song and dance of a big charity event. In the corridors of power, a quiet word from a trusted individual can break policy logjams for the public good.

Some insiders, however, abuse their position. Not just through gossip, prejudice or old boys’ networks (you can say “old girls”, but many women object to that term).

Worse, there is the outright illegalities – cronyism, corruption and insider trading.

As President Xi Jinping of China cleans up the circle around former security czar Zhou Yongkang, there is a parallel controversy of Western banks hiring the children of party leaders to gain access to their parents’ power. Corruption, or only guan xi? With insiders, there are always rumours and conspiracy theories.

Consider the Skull & Bones fraternity at Yale University. In contrast to the open and inclusive values of the university at which I once taught, the Bones are highly secretive and selective. Members include pioneers of the CIA, and both George Bushes. Such cabals serve up a cocktail of power and money, intrigue and exclusivity that can be intoxicating, and insiders can get drunk like a frat boy.

Some wish to dismantle such groups. But shut down one group of insiders and another clique would take over that position.

There are, however, ways to improve things. Integrity and transparency help maintain that line between acceptable know-how and venal corruption. Embracing the new creative economy, technology and entrepreneurship also opens the circle to more people, with more varied talents and perspectives.

This can leaven the current circle of insiders – just as in centuries past, a merchant class rose to challenge privileged landowners.

Increasingly, there is no single pyramid with a small, closed circle monopolising the top. Diverse and complex societies are instead like a range of mountains, with different peaks (no reference whatsoever to this magazine and those who read it).

If you are keen to understand insiders (or to irreverently pass off as one), here are three things to try.

First, explore different circles. Invest time to hang out at a hipster joint – say, that new cafe-cum-art gallery at that edgy address. Observe those who visit (yes, eavesdrop), and then engage the owner to find out why the place was started and who the regulars are.

Don’t start your own joint (it’s a slog) but practise understanding what sociologists term “emic” and “etic”. The former describes an insider’s view, from within a culture. The latter is more from an outside perspective, based on how views can be compared to other groups’.

If you can observe and contextualise that hipster vibe, you are halfway to understanding circles quite different from your own (if not, the coffee should be good). Such skills can be helpful in societies and companies where the insider circle is tight and hard to understand.

Second, if you want to try the trendiest brands, beware their souffle-like rise and fall. Superdry at the moment flies under the radar, and its quasi-sporty, faux-vintage look appeals to insiders. But it is now worn by David Beckham, Justin Bieber and Kristen Stewart, and may risk becoming mainstream tomorrow.

So get ready to move onto the next thing.

Or, develop your own style. Perhaps classics, with a twist, or something that those in the know can distinguish straight away, even without any identifying monogram (to name the brand would be self-defeating).  

Third, when something is new and seems worth trying, get to it early or else delay with some disdain. Apply this especially to the newest restaurants – with so many coming and going faddishly, I shouldn’t name the places I avoid.

But one new place to try will soon open at the Fullerton Bay Hotel – The Clifford Pier, offering high-standard Singaporean food with waterside views of the bay. Combining new and historic, comfort food and first-class ambience, this could become the place to bring visitors or gather with members of your own circle.

There’s nothing wrong with being an insider, or aspiring to be one. But bring in a streak of the unconventional. For ideas, try Camus (no, not the brandy; the rebel philosopher), or The Outsider – a classic by Colin Wilson that told the then drab, polite England about the angry young, trying to shake things up from the outside.

An insider is to be envied; a person who’s comfy inside a house, lounging around a well-appointed living room, with all his needs met. But there is a changing world beyond. Insiders are well-advised to open a window to let in fresh air or, better yet, step outside once in a while to take in broader vistas. That can be more than luxury these days.