From Answers to Questions | Jun '26

For most of my life, I was surrounded by people who valued answers. Good answers got good grades, good schools, good jobs and a stable future. Paradoxically, I’ve grown to become someone who vehemently opposes good answers in favour of intellectual honesty, sometimes to the point of becoming unnecessarily contrarian. For the most part, I think Singaporeans have a kind of self awareness contradictory to what they posit about their environment. Many think our obsessive pragmatism begets a suffocating conformity. This banal view held by locals, outsiders and even myself once, often becomes the “but…” in a long list of praise for the state’s institutionalisation of everyday life. But as I’ve grown and benefitted from the system, I struggle to reduce a complicated reality to such a simple explanation. At its best, pragmatism requires intellectual honesty. It demands a willingness to acknowledge error and abandon convention when it ceases to be useful. While my pragmatic upbringing did not hand me intellectual honesty outright, it did provide a stable foundation from which I could afford to question things. Somewhere along the way, the answers I sought became more questions.

Growing up, I was never what one would typically describe as an obedient kid. My mother constantly reminds me of my irreverence. I tried to always be respectful, but I soon realised I did it out of a practical desire of avoiding the cane rather than out of courtesy. If I had just shown remorse and agreed with my mom whenever I made a mistake, I did not actually have to follow through with anything she said. She was appeased, and I get to keep my ways — it was a beautiful compromise. I sometimes wonder whether the display of remorse was simply the right answer. My parents weren’t necessarily persuaded by me being right, but they definitely were persuaded by me saying the “right” thing. More than a decade later, I still do not change out of my pyjamas nor eat breakfast, and I eventually eliminated the need for pyjamas entirely by only wearing clothes that can be worn both indoors and outdoors.

Recalling the fringes of my memory, 6 year old me sought entertainment in books like “My First Question and Answer Book”. The 500 pages sparked my intense fascination with The Pyramids, F1 cars, airliners, and how adults carefully word a description of intercourse for kids. Soon these books were made obsolete by the iPad. In my hands were 2 instrumental apps that I still use the most to this day: Safari and YouTube. There was something incredibly liberating in having a device that could answer any question I had at any time. I exhausted the tiny 36 tab count limit of iOS 7 in a matter of minutes, and spent my sick days bingeing Richard Hammond’s Engineering Connections. They taught me that just about every question had an answer.

Primary school got me curious about people. I did much of the learning outside the classroom door, where I had been rather assertively invited for asking too many “stupid questions”. Sometimes I learnt something unexpected; oftentimes I just wanted to know the threshold for the amount of nonsense my teachers were willing to tolerate before I became out-standing. People generally don’t have a predefined response to provocation. Some teachers saw right through the sarcasm and snapped immediately, others… well, they surprised me. The uncertainty meant there was always an implicit need to course correct to get the desired reaction. I couldn’t put it in words then, but there was an insatiable pleasure in toying with the tension and accepting the crushing disappointment from going too far. Even now, I punctuate my interactions with tiny provocations to keep the other person on edge. Many years later, people started calling this rage baiting.

Nevertheless, good answers and good grades got me into a “good school”, where my biggest takeaway was that school rarely distinguishes being right from being interested. A rage-baiting tinkerer like me found it difficult to fit into a place more interested in lecturing birds how to fly than accepting that they didn’t learn it through lectures.

I’ll illustrate it with an example of how we were taught to analyse Lord of The Rings in literature class. The book begins with the following line: “When Mr. Bilbo Baggins of Bag End…” Our literature teacher paused, and remarked with a voice lacking entirely of frivolity, “Class, I’d like you all to draw an arrow joining “Bilbo Baggins” and “Bag End”, and annotate with the words “lives in/hails from” to highlight the way Tolkien associates Bilbo with Bag End”.

To not repeat the same mistake, I will not “unpack” this anecdote.

Because school doesn’t care about genuine passion—one can observe in the preference for final exams to continual assessments—I found it to be a system that’s profoundly simple to exploit. I’ll digress a little to tell you why.

First, the system doesn’t expect knowledge retention. You can cram everything in a week, go for finals, forget everything the moment you step out the door, and nobody will question whether your A was deserved. Exams care less about the quality of your learning than the quality of your answers in the moment you’re being tested. Second, an A grade is the ceiling, and there is absolutely no rational reason to build past a ceiling. So the actual skill isn’t studying hard, but accurately gauging how much cramming a subject needs before an exam… And then terminating the revision plan there. Because calibrating this threshold requires trial and error, the primary barrier to adoption is simply tolerating an imperfect start, which unfortunately for many was a non-starter. Once I’d figured out where that threshold sat for each subject, studying became an inconvenience I could schedule around. A couple of years later, it struck me that if I had to go through the motions of school anyway, it felt only rational to profit off of the parts I was good at.

Looking back, selling $10 History notes with a blank “Korean War” section captioned “You studying this? Har Har you funny man” doesn’t seem entirely ethical. But it proves my point. Mirroring Apple’s laser focused marketing, I gave what were unremarkable school notes a carefully defined niche of “psychology based”. While everyone else was selling notes, I was selling the idea of studying smarter. Each copy came with a companion guide explaining how to use the material effectively (and, where necessary, justifying the conspicuous lack of effort in certain sections). Whether any of it qualified as educational psychology was, well, debatable. It was mostly a collection of my own empirically derived views on learning wrapped in corporate sounding jargon. To complete the illusion and attract the attention of status-conscious tuition teachers, I even sprinkled in the Hwa Chong name as a cheap but astonishingly effective marketing trick.

In retrospect, the entire venture reads almost like satire, which makes my sincerity then even more embarrassing. In business, where there is rarely a right answer for anything, I suppose “the end justifies the means” felt like a reasonable one. I was definitely pretty satisfied with the extra change used to buy overpriced spinach soup at the high school canteen.

Convincing someone to buy my idea brings me great fulfilment. Convincing myself to buy someone else’s, however, triggered every alarm bell in my head. The reason should be pretty obvious by now. My suspicion of narratives meant that finance should be an impossibly odd place to end up.

It turns out I wasn’t suspicious enough.

I brought everything I’d learned from business into markets, initially staying out so I could dissect the financial system first. I read Pat Dorsey to learn the mechanics of fundamental analysis. I broke down the philosophies of quirky investors like Howard Marks for second-level thinking. I even ventured into psychology and epistemology through Taleb, trying to learn the art of respecting randomness. The lesson I thought I’d absorbed was simple: if I understood the system well enough, I could find an edge. Just like every time before.

The markets, fraught with randomness, quickly exposed the flaw in that idea. Especially when it is helmed by a world-class comedian like the incumbent US president.

Following Taleb’s advice on capital preservation, I kept most of my capital in fixed income, and used a small portion, around 20%, on asymmetrical bets in technology. I entered gradually and deliberately. Whenever I thought I’d found a good price, it became cheaper still. Out of the blue, the punchline would come, and I would capitulate at the worst possible moment, unable to stomach watching the losses deepen.

I reckoned that the problem was insufficient “discipline”.

By early 2024, I had become increasingly cautious on AI. I believed the market was pricing in more optimism than fundamentals could justify, and later on multiple occasions, wrote about that view on this page. I took increasingly conservative stakes in tech and waited for the correction I was convinced would come.

My discipline earned me exactly what discipline gets you in a market galloping in the other direction: nothing. I spent almost a year watching from the sidelines, waiting for a crash that never arrived.

When tech finally corrected by about 20% across the board, I entered. Then it fell by another 10%.

I was right, and I was wrong.

Yes, the correction I’d been waiting for arrived exactly the way I’d thought. But I was naive to assume that being correct about a thesis and being correctly positioned for it was the same thing. I had unconsciously treated investing as a pursuit of deriving the right answer for corporate value, and success as exploiting this delta between market and intrinsic value. To that end, I was right. I did not overpay for my equity stakes. Yet, market outperformance and making good decisions rely on a deliberate application of several skills. Identifying value, judging timing, controlling risk and tolerating volatility are ones that cannot stand on their own.

For someone obsessed with landing on the unorthodox right answer, it left me unsettled. Every valuation model I’d built was meticulously tuned to price in the unknowns, the “second level thinking”, and spit out a precise number. Those numbers were precise enough to persuade me that I understood something I couldn’t. (which makes no sense in hindsight) That realisation sent me back to Taleb. It turns out I understood the concepts well enough to explain them, but my behaviour told a different story.

As earnings season rolled around, my models needed an overhaul. I kept my habit of stress-testing for unknowns, but accepted that I couldn’t price in every piece of information. I ditched my deterministic “buy” or “sell” framework for probabilistic thinking, and expanded my DCF model into three independent valuations to capture a range of outcomes. For what it’s worth, chasing precision in randomness is self-defeating. A valuation is nothing more than a range of assumptions built on assumptions. Now, these models only supplement my decision on how much confidence a trade deserves, and consequently, how much capital that confidence justifies.

Ironically, becoming a better investor required becoming less obsessed with being right. My trades around earnings season are now executed with the expectation that I may have misunderstood something, and only made when I am convinced I am taking a small, controlled and highly asymmetrical bet. If my thesis survives new information, I add to the position. If reality contradicts it, I re-evaluate. I tested this hypothesis on positions in United Health, Visa and Berkshire over multiple earnings seasons as I diversified away from technology. A significant proportion of bets realised disproportionately large gains that lifted my entire portfolio with relatively small positions.

That outcome ultimately doesn’t prove the framework right; a few earnings seasons are far too small a sample for that. Yet that experience did compel me to reconsider what I meant by “discipline”. Sometimes, discipline really is genuine risk management. Other times, it’s just a post hoc excuse for standing aside because you’re afraid of being wrong. The hard part is knowing which one is actually driving your investment decision. Staying “disciplined” to avoid a 30% drawdown in tech can be an excellent outcome. Yet an even better one might have been redeploying that capital into another asymmetric opportunity instead of waiting indefinitely for a perfect setup. Being intellectually honest means admitting that I’m just as capable of rationalising fear as anyone else. In that sense, discipline is pragmatism. It is being humble enough to use a bad trade as a feedback loop to make better future decisions.

The older I get, the less I think this essay is really about my mother, school, business or even finance. Each merely surfaces the same tension between being right and sounding right that, until fairly recently, had always been the same transaction. For me, pragmatism and intellectual honesty only truly converged in the markets. Everywhere else, being pragmatic meant finding what a person or a system wanted, and giving it to them. A good enough answer sold with sufficient conviction was the right answer. But markets don’t value that. It doesn’t reward conviction, and has no interest in what I meant to say. Uniquely, being practical and being intellectually honest both required admitting continuously that I might be wrong, and asking, what went wrong?

To their credit, Singapore’s institutions did teach me pragmatism. They taught me to think in incentives and navigate systems, but they never truly pushed me to connect pragmatism and intellectual honesty. Perhaps that was never their role. Institutions rarely impart their most valuable lessons directly. More often, they create conditions under which people can discover those lessons for themselves. In my case, the system worked. Its stable and predictable framework reduced the cost of challenging orthodoxy. Teachers condoned my antics more often than they punished them. The small tests I flunked in the pursuit of optimising my studies did little to affect my final grade. Even my note-selling venture depended on a predictable base of equally kiasu customers. Had those experiments carried heavier consequences, I suspect I would have become much better at justifying caution as “discipline” than at questioning it. Thankfully, the limited cost of being wrong allowed me to experiment, fail, get lucky and connect the dots organically.

I don’t think I’m taking irreverence to America, at least not the trivial kind that my mother spent a decade caning out of me, or the kind that sent me outside the classroom. What I’m bringing with me are the lessons that instinct led me to. Reading a system and finding its incentives are still fundamentally useful skills. My revelation isn’t merely identifying the difference between being right and sounding right; that quickly becomes hypocrisy if I don’t apply it impartially. It’s whether I bother turning that same scrutiny on myself as honestly as I turn it on everyone else. That’s the part I’d like to get better at. After all, suspicion of narratives is easy when the narrative is someone else’s.

I suppose I’ll only know once I have skin in the game. For the longest time, the cost of being wrong was cheap. Fourteen thousand kilometres from home, I’m not sure that’s true anymore.

For now, I am leaving with more questions than when I started. Perhaps that is progress. My goal was never to arrive at a final worldview. It was simply to remain intellectually honest enough to revise it every once in a while. Whether or not that is pragmatic depends on the situation. In the grand scheme of things, I think that matters less than the former.

The Original Foreword, now Afterword

I hate to begin my essays with “It has been a long time since I wrote”. I think it’s lazy and unoriginal, for this blog at least. But truth is, I believe my procrastination has become chronic. I began writing this piece nearing the end of June. It’s currently mid July and I’m still in the midst of it. I can’t be sure whether the weeks spent dwelling on it have improved the clarity of my thoughts and its delivery, or whether it has just devolved into a long drawn rambling of incongruent ideas.

As I inch closer to the next chapter of my life away from Singapore, I want to reflect on my experience growing up here. I want to understand how each period of my life contributed to the values with which I navigate the world around me, and interrogate the complicated relationship between pragmatism and intellectual honesty.

As a new convert to Taleb’s epistemological philosophy, I should preface all this by saying that this retrospective reflection is ultimately a fallible reconstruction from bits and pieces of my memory, which makes it highly susceptible to survivorship bias and narrative fallacy*. Nevertheless, I believe there is some value in introspecting.

*our tendency to fit disconnected facts into overly simplistic, cause-and-effect stories to make sense of the world

On a final note, this piece has taken so long that I genuinely cannot be bothered with correcting some of the idiosyncrasies in my syntax and grammar, insofar as they do not inhibit comprehension.

Glad you read to the end! If you enjoy my rambles, consider dropping a follow!