Category: Blog

I wrote this piece on Medium on how obsessing over data in business might cause us to lose track of what’s really important.

This is a piece I wrote on Medium about designing things to actually solve problems.

It was a big day for us. Even seventeen years later, I can still remember walking up the “Alice in Wonderland”-like corridor, with the pattern of its wooden walls oriented downwards as the floor sloped up, leading us to the stage. Our concert band was about eighty strong, with an unbalanced eight tuba players (three or four would have been more appropriate for a band this size), and I was one of them. We were taking part in the Singapore Youth Festival, a biennial competition for school bands, and were under significant pressure to play well, both because we had spent the last year practicing intensely, but also to live up to the collection of gold medals spanning the past ten years that hung on the wall of our band room.

We took our seats for a moment, but then stood all at once as our conductor walked up to the podium, our instruments gleaming under the stage lights – as a final ritual, we had spent the last night polishing them. He motioned for us to sit, and waved his baton for us to play a “Bb” note, checking our tuning one last time. A “cut”, a short pause, another wave, and we were off. The next fifteen minutes or so were a blur. I vaguely remember thinking we sounded good, although a cornet player missed a high “C” at the very end, souring the performance in our minds.

And just like that, the central point of hundreds of hours of practice vanished – it was time to put away our instruments and take our seats in the auditorium, awaiting our fate. I don’t remember any of the other bands that played that afternoon; we were far to self-absorbed to pay much attention. I remember being caught in between wanting them to announce the results immediately, but also wanting an appropriate amount of suspense before the tension was released. Two years later, with the benefit of experience, and as a better group of musicians, I wouldn’t feel as nervous – I remember walking off the stage fairly confident that we had nailed our performance.

The fifteen minutes or so on stage were the culmination of more than a year of preparation. A few weeks prior, we all had to be fitted for blazers, and get haircuts to make sure we looked presentable on stage. I remember hearing the barber repeat, in broken English: “Don’t worry, I make it neat… neat”, as he buzzed off entire swathes of my friend’s shaggy mop. Another friend walked in the next day nearly bald, and was met with derisive laughter. As it turned out, the barber had asked him “What number?” – referring to the size of the clippers, and our friend, without having any idea what that meant, answered “2”, which is the standard for fresh recruits in the army.

In retrospect, the last year had been ridiculously intense for a group of 13 to 16 year old boys. Our regular schedule consisted of a mix of of full band practice, sectionals, and individual practice, four to five times a week (in the afternoons after school and on Saturdays), for two to three hours. However, in the last three months, we had supplemented that by coming to school at 6:30am to practice for an extra hour before school started, and by staying for a couple of hours past our usual practice time, wrapping up at about 7 to 8pm. During these months, our conductor, who was strict at the best of times, took on a “J.K. Simmons in Whiplash” quality – he once kicked a floor air-conditioning unit, only to arrive at the next practice hobbling, with a cane. We kept quiet about it, though.

To further prepare, we also had band camp. Unlike the “American Pie” variety, where apparently no practice takes place, ours basically consisted of practice from morning to night, in addition to foot drills (we were a “military” band), push-ups, and running (either to build lung capacity, or as punishment for being unruly or playing poorly). Once, we found ourselves running around the rugby field at midnight, doing push-ups whenever our drum major blew a whistle. These had to be done synchronously – a “timer” would yell “down”, and we would yell the count in return. I’ve long forgotten why we were doing this, but still retain the comical (in retrospect) memory of noticing a conspicuous silence from my right, only to realize that our “timer” had passed out, and was lying face down in the dirt.

Back in the auditorium, after the last band had played and shuffled to their seats, the results were announced. My stomach was in knots as I heard a bunch of silver and bronze medals being awarded, and I thought I would throw up as the announcer took their time in drawing out: “Saint Andrew’s School Military Band…Gold”.

To date, this is the only time where I can distinctly remember feeling the slightest out-of-body experience, jumping to my feet and cheering without consciously willing myself to do so.

I didn’t know it then, but that cycle of events, lasting just over a year, would have a profound impact on my life. It was the first time my 13-year-old self saw the point of preparing for a goal way out in the future (remember that a year was about 8% of my entire life at that point). I’m sure it was the same for many people in my year, too. What we learned, however, was deeper than just “working hard”. Instead, we formed a culture that many of us still try to live up to today, for better or worse. By being punished for someone else’s mistakes, we learned that nothing was “Somebody Else’s Problem”; under the constant reminder that our actions had consequences for the reputation of those who came before and after, leaving the band “in a better state than you found it” became like mantra. There are many of us who might have been put on different paths in life if not for this shared experience.

Of course, that sense of perfectionism and elitism came with a price, at least, for me personally – a general sense of constant self-loathing, an attitude of “do it well, or don’t do it at all”, and a strong preference for “my kind of people”.

For the longest time, while learning to play the guitar, I refused to play anything by my hero Stevie Ray Vaughn in front of anyone else, because I felt like I would be doing a disservice to the music. Even today, I can still feel in a gnawing in my stomach when I, or other musicians are “off”, and the back of my head is still filled with snarky quips that I would never say, like “This isn’t music, this is just noise”, or “Let’s try that again – this time, correctly.”

Outside of music, I spent many years ashamed of being less than perfect at anything. It took me a long time to realize the most simple, blatantly obvious thing: That before you’re good at something, you’re going to be bad at it. It also took me too long to realize that you don’t have to set out to finish everything you start – that some things don’t have a pot of gold at the end of the rainbow, and you only realize halfway; that there’s nothing wrong in giving up.

Despite the anxiety and despair that these flaws have occasionally caused, I wouldn’t trade them for the world, for they have afforded me a life I would not otherwise have had. Besides, it’s far easier to lower your standards when needed than to try to conjure them up after a lifetime of absence.

 

 

A couple of weeks ago, I took some time off work to reflect on what I was trying to accomplish in my life. It very quickly dawned on me that I had basically “ghosted” through the last year.

Ghosting

When I was in college, there were a group of (other) snobby nerds who would refer to everyone else who didn’t explicitly have a strong sense of purpose as “ghosts” – floating around without any real direction. Although I didn’t share the same level of derision or contempt, I definitely shared the same pressure to make life meaningful. And throughout the last year, I’d definitely been remiss in acting upon that pressure.

The Point of Everything

Over the last ten years, I’ve discovered that I’m basically happiest doing things for one (or, hopefully more) of three reasons:

1. I’m producing something that people use
2. I’m working with people who share my values
3. I’m learning something new

And over the last year, while I had lived a life someone my age is supposed to live (e.g., moved into my own place, bought shares in EA, the most evil gaming company in the world, etc.), I also didn’t spend enough time actually living.

To be clear, this is not some crisis. Plenty of people go through their entire lives without worrying about how they spend their time. I’m pretty sure most of my ancestors were more concerned with putting food on the table than making sure their lives were filled with some higher-order purpose.

But it bugs me, because I am the product of good luck. My family in Singapore is upper-middle class, and throughout my life, there were countless occasions where my laziness or ignorance would have sent a less fortunate person down a much darker path. When I joke about how someone with only 4 ‘O’ level passes also has a Ph.D from one of the top programs in my field, the subtext is that I got a second chance that many people in my position would not have had.

So, to quote Michael Lewis’s speech here, I “owe a debt to the unlucky”, and I’ll admit I don’t know how to fully repay it. I think part of it is not having Machiavellian goals like “be more rich, famous, and powerful than everyone else”, and I think another part of that debt is to responsibly wield whatever influence I have over the world. Most of all, however, I think paying off that debt means living the life that hypothetical less fortunate person would have wanted to live, and not squandering it by floating around until I randomly die one day.

I’ll keep working on it.

I can barely remember the most beautiful thing I’ve seen in my life. I was 15 or 16, and my family and I were in Japan. My dad’s company had paid to send his entire office on a trip to Tokyo, Osaka, and the places in between.

I don’t recall exactly where in Japan we were at the time, other than squeezed into a passenger van. As it sped down a large, man-made dam, going blindingly fast while barely making a dent through the landscape, I looked to my right and saw a little village nestled on the outskirts of a forest. Then, to my left, I saw the sea. And as my attention vacillated between the left and right windows, we drove into a tunnel, carved through a mountain.

To be clear, I don’t think this actually happened. It’s been more than fifteen years, and our memories are fragile things. I’ve bombarded Google with all manner of queries, and the most convincing hint I’ve gotten is that we were probably on the Alpine Route, and that the dike in question was the Kurobe dam – Japan’s tallest. But there isn’t a village, and the body of water to the left isn’t the sea:

By 柑橘類 (talk) – Own work, CC BY-SA 3.0, Link

My memory hasn’t so much faded as it has been (at least partially) fabricated. It’s the same funny feeling I get when I step into my the apartment my maternal grandparents used to live in. Growing up, I would walk there every day after school and spend hours playing and getting fed while waiting for my parents to come home from work. Stepping inside today, it feels “too small”, like I’m Gulliver in Lilliput. Somehow, my brain doesn’t seem to want to learn the new, subjective size of everything, and insists overlaying my perspective with my 6-year-old self’s vision.

As I’ve gotten older, and I’ve started to worry about my memory. Well, maybe worry is the wrong word, but its transience has long since dawned upon me. On one hand, I seem to remember lots of irrelevant things, and I still have a 10-digit span working memory. But the ever expanding black hole of things I’ve forgotten always seems to loom in the shadows. Most of all, however, I wonder how many of my memories are real, and how much of the present I’ll remember. Although most of us believe we can recall the “good old days” with certainty, research suggests that we’re more often confident rather than correct.

That said, the realization that everyone’s memory is transient has made me happier: I keep hearing about how you shouldn’t be afraid to embarrass yourself, because nobody will remember it – not even you. I never understood that. I’d always remembered every time and place that I’d misplaced my dignity.

But not lately. Lately, those memories seem far away, like someone yelling at me from behind a closed door. Maybe I’ve gotten old enough to see that it’s all like the Kurobe dam: Stuff happens, and everyone thinks they’ll remember, but when they see you again, it’s you who gets to decide if the artificial lake they remember was actually the sea.

As I start my journey into my thirties, I thought it would be a good time to take stock and think about who I want to be when I “grow up”. The first ten years of my life were pleasant but largely forgettable, the next ten were painful and tragic, and the last ten were some of the most productive in my life. It’s clear in hindsight that whether I chose to listen or not (mostly not), for the last thirty years, there were always pressures nudging me in all directions.

Things are different now: Partly because I’ve been itinerant for long enough, but also because I’ve traveled far enough off the beaten path with enough success, those external pressures have largely diminished. On a day to day basis, I don’t really feel the influence of others anymore – more than ever, it feels like I am the captain of my soul.

I don’t think that’s a good thing. At least, not necessarily.

I’m not an arbiter of morality, nor an expert on how to live a fulfilling life. I don’t think the voice inside my head has my long-term interests in mind, at least not always, or often, even. Left to do “whatever I want”, I doubt I’ll be satisfied at the decisions I make ten years from now, or beyond.

So, I’ve been thinking about who’s judgement to use. I mean this differently from “people who I care about or trust” – those groups of people might overlap, but people who love us have the disadvantage of inevitably lowering their standards, for instance. It’s just a human thing.

In my mind, I’ve started to form a “committee”, sort of like the one you have to form when writing and defending a dissertation, except in this case the “dissertation” is your life. Their approval matters, but for objective (or pseudo-objective) reasons, not because you want them to like you. It’s a cheesy metaphor, but only I and everyone who reads this will ever know about it, and I think it’ll be a helpful though exercise in the future.

In case anyone was wondering, here are some examples of who’s on my “committee”, as well as the values that I think they represent and hold:

1. People I served in the Republic of Singapore Navy with – These were the people who oversaw my transition out of my rough teens. Ten years on, we always catch up whenever I’m back in Singapore. More than any other group of people, I feel like the person that they want me to be comes the closest to the version of myself that I’m happiest with.
2. Former research assistants – They’re responsible for some of my happiest times in grad school. They remind me of how I want to lead and mentor others, and how leadership is about building the relationship that remains after the power dynamic is no longer present. That so many of them are my friends now is something I’m really grateful for.
3. Former professors – Somewhat less sappy, there are a selection of professors throughout my academic career whose expectations I’ve tried to live up to, and whose version of intellectualism is one that I believe in.
4. Relatives – Yeah, don’t go to prison and bring shame upon my family.