My journey from underachieving student to moderately competent adult [2016]

An older friend told me that a parent wanted to talk to ‘learn about my educational journey’ and ‘understand better what I do now’.  It occurred to me that that’s something that might be worth writing down for others as well. Here goes.

I was born in 1990.


I grew up reading a lot of books of all kinds. My mom would take me to the library every week or so. I would read books about dinosaurs, natural disasters, space, ancient Greeks and Romans and Egyptians and so on. My “I know it’s impossible” dream was to be an astronaut, I think, and I sort of assumed that I would be maybe a scientist of some kind, with the lab coat and cool tools solving puzzles. I loved puzzles. I had a book series called Charlie Brown’s ‘Cyclopedia that I would read over and over again, particularly the Space book. (I think that was Book 8.)


I never had to do any. My parents were moderately well off and could afford a domestic helper. My parent’s logic was this: if I didn’t have to do any chores, I could spend more time studying. I think this was a well-intentioned bad idea. Kids should do chores and develop a sense of responsibility and ownership.

Video games:

My first introduction to video games I think was on the SEGA console. My brothers were playing racing games and fighting games. I played Street Fighter and a bunch of other games like that whenever I had the chance.


At some point I fell in love with computers. I loved the Internet. Around this time I began to develop the vague idea of becoming a computer game developer or a web designer. I persuaded my parents to buy me books about HTML and Javascript. I learned a lot of HTML and a bit of CSS, but I never quite got through Javascript and C++ – it was too complicated for me at the time and I didn’t really see the point. I made some websites on free web hosting services, about my favorite games and jokes and so on.

Primary School:

I went to Opera Estate Primary School, which was where my older brother had gone to. I got into Digimon (but Pokemon not so much). I was into more computer games at this point– Red Alert, Metal Slug. I was still reading books. I would get very good results at school (high 90s, sometimes 100). I would read all of the textbooks entirely before school began, and everything was simple and familiar to me.

I think I was in P3 when I first learned from some classmates about pornography. It seemed really weird and I don’t know what I thought about it.


In 1999 I took a test and did well enough on it to qualify for the Gifted Education Program. To me it didn’t really seem like a big deal, I did well on tests all the time and thought it was just normal for me. I think I assumed everyone else must’ve been the same as me, and if they weren’t doing well maybe they just didn’t feel like it…? I don’t know. Anyway, I think this was a big deal to my parents, particularly my dad, who was very proud and would tell anybody who’d listen about how smart his son was. (I don’t recommend doing this if you’re a parent.)

I enjoyed the GEP. I enjoyed how they challenged us and took us very seriously and treated us intellectually like adults. They’d also tell us things like “you’re the cream of the crop” and “you’re the future leaders of the country”, and it didn’t really occur to me to question that. I developed an unnatural, clueless, naive sort of  self-confidence or arrogance that would take me many years to unlearn. I don’t think I’ve completely unlearned it.


I hated homework. I had never developed any sort of discipline or work ethic. I just wanted to play all the time and I didn’t understand why homework was necessary. It was just about decoding textbooks, which were very boring puzzles as far as I was concerned. In fact it wasn’t puzzling at all– it was just grunt work. I didn’t like it and I’d put it off. It was far more interesting to watch Anime on TV (which had interesting storylines and character development), or to play video games that rewarded you for completing challenges and so on.

I didn’t really have a clear mental model for what sort of career I wanted, or what sort of work or sacrifices I would have to do to get there. I was told that I was the creme de la creme, so surely I would figure it out along the way. I was going to do well whatever I did, so why bother? (Prophecies are bad.)

It’s interesting to look back at my report cards to learn more about what kind of person I was. I was typically attentive and engaged when the teacher was interesting, and I would be quick to participate, raise my hand, and so on. But I was also disruptive, I would crack a lot of jokes, talk to other people, read books under the table, etc.

I don’t think I was mean or nasty to anybody– I always felt really bad whenever I got anybody in trouble, or made a teacher frustrated or upset. I think many teachers have yelled at me over the years. Thinking about it brings back a familiar anxiety and discomfort in my stomach. I don’t blame those teachers for what they did, they were in a difficult place themselves and managing a classroom can’t be easy. But that’s how it is.

I kept spending as much time doing whatever I liked as I could. Sometimes I would get angry and upset with myself and stare at myself in the mirror, angry-crying, demanding that I start focusing on my schoolwork and pull my up grades and stop disappointing my parents and my family and the State (because GEP kids get more resources invested in them, I was brought to special meetings just to be told that) and Be A Good Kid. This would typically last a couple of days, maybe a week. But then it would be back to distractions, video games (my parents would try to keep them away from me but I would find workarounds. Sometimes I’d invent projects and other things and go to friends’ houses to play) and so on.

Secondary School:

It was sort of assumed that I’d end up in RI. I didn’t. I got 245 for my PSLE– which is criminally low for a GEP kid, you’re supposed to get 260+. My dad slapped me for it. I would go to Victoria School and I’d go there on probation– meaning if I didn’t do well enough at the end of the year, I’d be kicked out of the GEP. That was exactly what happened. For a brief moment I was given the impression that I would have to repeat Sec 1 in another school, but thankfully my Principal (Ang Pow Chew, good man) allowed me to go to Sec 2.

In VS I was in the IT Club but I didn’t really participate very much. I was excited for a while but eventually got bored and would avoid it. I began to develop an interest in Basketball, and I would research things like “how to get better at basketball”, dribbling techniques, drills, etc. Unfortunately VS didn’t have a basketball team (athletic resources were limited and funnelled into Soccer)  so I was mostly left playing at community centers and such after school. I would go to the gym from time to time but I didn’t know how to do the big things like squats and deadlifts, so I wasted my time doing bicep curls and tricep extensions. (Many years later I’d realize that squats and deadlifts are amazing and that I should’ve been doing them all along.)

I didn’t do great in Sec 2– I was probably in the middle third or maybe bottom half of the cohort. I attributed this to my disinterest in the way we were taught mathematics and science (chemistry and physics). It was just Not Interesting. I didn’t like memorizing things without understanding the rationale behind it. (Many years later I would find math and science utterly beautiful when learning about it from people who were passionate about it. Did you know that a parabola can always be described as an intersection between a plane and a cone? Why doesn’t anybody tell you this in school?)

I decided to pick 7 subjects instead of 8 in sec 3, thinking that I would use the extra time / free periods to do homework and study. Ha. Instead I would end up hanging out with most of the weaker students– smart guys (they did get into VS) but underachieving. We did have a bunch of fun. We’d skip school and go to LAN shops or play pool (I was terrible at pool, still am). On hindsight I think those were some of my favorite things about school, and honestly we could probably cut out a lot of the curriculum and people would still be fine. Just show them a bunch of really good videos by really passionate people in their fields and let them follow their curiosities. At least that’s what I would do for my younger self.

Anyway– I did do some studying in the final months towards my O’s. I got 14 points for my prelims, and assumed that that would mean I would get maybe 10 points for my O ‘s, which would get me into SAJC (which was where I wanted to go, because they had a cool uniform, a cool campus and a good basketball team). I got 14 points again and ended up going to TPJC.


My parents sent me to tuition for my O levels, but I ended up just making a bunch of friends there and didn’t study. Around that time I developed an interest in live music, and wanted to play in a band. I found a couple of bandmates and we started practicing, writing our own songs, doing gigs. I had a lot of fun promoting the band– coming up with the name, coming up with an image, talking to promoters, getting us to play gigs, corresponding with fans on MySpace and so on. It was way more fun and way more REAL than school. I started organizing my own gigs and we even made a bunch of cash from it– I think we made over $1,000 from our first gig, which was pretty good money for JC kid.

Junior College:

I found JC utterly stifling and fake, way worse than secondary school (I still miss and love VS). I picked up smoking. I would typically stay up late every night– I would blog, I think, and talk to friends outside of school– and go to school sleep-deprived like a zombie.

I had to repeat JC 1, which was a kick in the stomach from me. GEP student and now a repeat student. But I rationalized it away as “I didn’t do well because I didn’t study”. I tried to persuade my family that I would do better in Poly, but they would have none of it. So I just trudged along. 2007 was a really bad year for me. I liked some of my teachers, but JC in general felt like a farce and I wish I had never gone. My results weren’t good enough to get into any local Universities (NUS, SMU, NTU).

I used to skip school in my O level year and go to the Esplanade to study and get through overdue homework. I wouldn’t do nearly as much as I had planned to do. I would go to the Esplanade Library and pick out a bunch of Men’s magazines to read. I was particularly a fan of Esquire (and I particularly like Tom Chiarella, great writer). I began to develop the idea that I would work in the media industry some day. I might’ve written a blogpost about that somewhere– “I want to work in the media”.

I used to work at Shangri La Hotel when I was saving money to pay for my band’s CD, and I remember witnessing an media event thinking “I’d want to work in the media”. I’m kinda glad that didn’t play out, because I hear horror stories from friends in the media all the time these days. And at this point I have to say it’s utterly criminal how poorly we prepare kids to have the right sort of expectations about what a career is like, what working life is like.


Anyway. So I didn’t get into any of the universities, and it was time for NS. I was determined to make the most of my NS experience– I was hoping to chiong sua and become an officer. But I was given a temporary PES E status because they suspected I had Marfan’s Syndrome (for being very tall and skinny). So I couldn’t go to BMT straightaway– I became a storeman instead. I decided to use the free time to read and learn as much as I could, and threw myself into books about business and self-improvement and philosophy and everything else I was interested in. I built a community of friends (some from the music scene, some from friends-of-friends, Facebook was becoming a thing by now). I built a Facebook community. I started blogging regularly.


At some point I had written a blogpost about Singapore that got a bunch of comments, and that made me happy and excited (to get a bunch of comments) so I did more of that, and developed a bit of a reputation and a following. I decided that that was going to be my beachhead into my new life– that I was going to become some sort of blogger/writer type person. I figured that if I did it well enough for long enough, I’d get some interesting opportunities that I wouldn’t be able to imagine yet.

(I think some of this thinking might’ve been from some of the books I read, but I can’t quite pinpoint it to a single thing. The Internet always seemed like a magical land of opportunity to me, and I didn’t understand why other people didn’t see it that way.)

I decided that I was going to re-take my A’s as a private candidate, and document that process, and become a tutor for underachieving smart kids.

Eventually I actually got invited to the Istana to chat with the PM. The post I wrote about that got a lot of attention, and I got a bunch of invitations and job offers. This convinced me that I didn’t need to force myself to worry so much about the A’s– so I pretty much stopped studying and just kept blogging. (I did only slightly better than the previous time, I think, but with an entirely new subject and no teachers.)


I was planning to become an SIA flight steward, thinking I would make money and then blog in my downtime. But that didn’t work out. I went out for coffee with a couple of people who asked me, and one of them was the co-founder of a software company.  He asked me to manage their blog and social media efforts, which I agreed to mainly because I needed the money.

Turns out that I really loved the team and the working environment, and I’m still there 3-4 years later. I’ve developed my marketing and writing chops, and even manage other writers now. I’ve had several job offers since, but I’ve turned all of them down because I like where I am too much. (I wish I could clone myself. I suppose the next best thing I could do is train other people to do what I do– it’s really not that hard, it’s just applied common sense.)

So I’m in a pretty good place now, career-wise. I make a pretty decent amount of money, and I have the luxury of turning down job offers. My skillset is something that’s quite in demand, so I don’t really need to care about the economy or job prospects or whatever. There are several people who’d love to hire me tomorrow if I quit, which is something I honestly always believed would happen someday as long as I kept doing what I was doing. In the early days people would tell me that I was stupid, delusional, small-minded, didn’t understand how the world worked, idealistic, blah blah blah.

But at the end of the day it’s simple economics, isn’t it? If you can do something that people are willing to pay for, then you’re not going to go hungry. If you have design skills, writing skills, or best of all, if you can code, then you’re never going to go hungry. It might take a while to get good enough that people notice you and seek you out, but it works.


Anyway so I’m guessing the reason my friend asked me about this is because a parent has a child who’s similar to me– really unhappy with school. What would I say to a person like that, or to their parents?

I guess the first thing I would say is– if you’re not happy in school, you’re probably not going to be happy working in the sort of job that school prepares you for. You’re not going to do well in the civil service, I think. So you shouldn’t try to force that, because then you’d probably be miserable and life is too short to be miserable at the thing you spend most of your time on.

Secondly– I wish I had spent MORE time pursuing my random little interests, not less. I wish I had also learned to code, and draw, and do design. Because those are very valuable skills in demand in the modern web age. Startups are a big thing now, and they’re not going to go away. People are constantly looking to build the next Facebook, and there’s a lot of money looking to invest in those things. What that means is that there are many young new companies willing to take risks on hungry young people who’re willing to learn.

That said, I did get lucky, the first person I seriously talked to turned out to be the real deal. There are a bunch of scammers and bullshitters who’ll try to get you to work for next to nothing. That’s why you should develop your bullshit detector as early as you can. You can increase your own luck by developing a body of work that you put in the public domain. The more work you do, and the more you put yourself out there, the more chances you

The worst thing about my life is that I never developed much discipline or work ethic. I don’t mean that in an exaggerated sense. I can foresee myself saying that on my deathbed, and that’s an outcome I’m desperately trying to avoid. The problem with smart, bullshit-sensitive kids is that they won’t develop discipline just because you tell them to. You have to pick something that THEY WANT TO DO, and then show them how discipline helps them achieve THAT. I think Randy Pausch’s Last Lecture covers all of this beautifully, so I’d refer you to that.

Life is really hard, but it doesn’t always have to be miserable. It can get better. Good luck.

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