The Cardboard Boat Race

Tinolympics

Towards the end of my high school senior year, Cupertino High School hosted the first-ever Tinolympics in our history. Tinolympics is like the Olympics sports game, but at a school-scope instead of international-scope and with some silly twists. One of such silly twists was the cardboard boat race: build a rowboat out of cardboard, row it across the school swimming pool back and forth, don't sink, and the fastest team wins.

I was going to graduate high school soon. For the past few years, I've built several accomplished web projects at CHS and also founded my school's wildly successful TV newscasting program. Before I graduate, I wanted to do one last thing, preferably something that would make me feel proud of my effort, have a good result, and wouldn't be too stressful compared to running a TV newscast program that forbids failing. So I signed myself up to build the Tinolympics cardboard boat for the senior class.

Building the Boat

I watched all the Youtube videos on how others built and raced their cardboard boats, studied all the articles via Google search on how actual boats get designed and built, and then designed and built my boat with every nerve and muscle I can give it, because I know this is the last project I would build in my high school.

The outcome was a cardboard boat that I thought couldn't get any more perfect: its shape was an elegant trapezoid with pointy geometric front and back to reduce drag, and its hull was fully duck-taped with no chance for the boat to sink. I meticulously painted my prized baby with my favorite colors and carefully transported it to CHS on the day of the race.

As I looked at the competition -- a bulky pirate ship, another bulky boat, and a tiny square-shaped boat that I'm pretty sure they assembled last minute -- I was assured that this would be an easy win.

I Failed

The outcome threw me off-guard. The bulky pirate ship sank in half because its length surpassed its structural integrity, the other bulky boat returned last to the edge of the pool, my boat spun in circles before going on the correct course and finishing second place, and that square-shaped boat -- the boat they admitted to have built last minute with no design whatsover --- won the race.

My sense of failure was multiplied by the college admission result released later that day, which I was admitted to none of my target schools. The disappointment was multiplied once again upon hearing that some people, who didn't even code at all in high school, was admitted in Berkeley EECS and CMU CS.

So here I am, with the best design and construction, lost to a square-shaped boat someone else built last minute. Both in Tinolympics and in college admission.

And, Such Is Life...

From all the previous endeavors I did in high school (web projects, Tino News Today, etc.), it seemed that with every additional effort I put in, I won a bit more. Sure, there were challenges, but challenges were eventually overcame by just more effort. It seemed that the output is a linear function of my input. And I was wrong.

I would hear cliche like "take risks in life" and think, oh well, if there's risks then it probably meant you didn't try enough, and if you tried enough, you would have sorted it all out. But no. The cardboard boat race was the first concrete moment in my life when I realized that, there's definitely things that, no matter how much you tried, you just fail. There's no recourse. There's no correction. Some failures would at least give you experience so that next time, you come back stronger, but there's definitely cases like this where there's just not another race. You just fail. End of story.

Risks, in pure math, means probability. But when probability becomes unfolded when the moment of truth comes, it becomes finalized to the binary outcome of success or failure instead of a percentage.

And such is life. Life is not a deterministic function that you would hope it strictly matches what you put in. You would think working harder and smarter means more money, only to see some random Chinese mom making millions more than you by buying houses and just letting them sit there. You would think having more lines on the resume means better internship, only to see someone getting into Anthropic¹ because their daddy networked them in. The outcome of one's life is a blackbox function that combines intelligence, effort, and a word that everybody hears but few appreciates its insane power: luck.

What's luck? Simply put, it's randomness. It's randomness in things you can't control, and the things you can't control overwhelms the things you can control in proportion if the things you do are important.

But a fortunate angle to look at luck is that, because of its random nature, if you don't have luck now, you might have it later; if someone else has luck now, they might lose it or continue to have it.

I later realized that the magic to deal with such a magical concept called luck is somewhat straight-forward. And here's the recipe: try multiple things. Try multiple things sequentially or concurrently if capacity allows. If you fail in all but one wins big, you still win big. If multiple things succeed, even better. Make sure the failures won't completely blow you out though. The things you do should have great upside if it succeeds, but limited downside if it fails. Each thing alone must not be able to bankrupt your money, time, relationships, or morale.

One coin flip is unpredictable. But if you flip it 100 times, it becomes a smooth-looking Bernoulli distribution.

The cost of hedging luck by doing multiple things is clear too: you need to put in more effort. If doing one thing requires so much effort already, then doing 3 things would require 3 times more work. But actually, doing 3 things should cost less effort per thing than only doing one thing. This is because the busier you get, the more experienced you are with time-management, risk-management, and thinking, thus helping you have greater throughput in productivity.

Of course, there are breaking points where beyond that, you get burned out fast, lose focus, and get defeated in everything you are doing. And there must be buffer zone against the expected unexpected, otherwise one random blow will bankrupt your time, momentum, and morale. Hedging luck is a delicate art of juggling what you do.

While painting the cardboard boat in my senior year at CHS, a few stripes and red and blue from the paint brush stained my jeans forever. These stains forever remind me of what a magical word called "luck" can do, and how we might be able to hedge against it.