Evolution of a Hackathon Hacker

While I enjoy Medium, most of my writing has moved to my personal blog. I’d love to see you there.

This is a personal story. As I write this, I’m halfway through Angelhack 2016 Singapore, watching the room in front of me. I used to love that there was exposed brick on the walls, there were no false ceilings, and beanbags everywhere. I’m not sure why; I just did. I loved to look around at 2 am, watching people code, sleep and repeat.

I still do, just not the same way.

Stage 1: What Ifs and Why Nots

I was picking colleges on the CommonApp when I first heard about hackathons. I was writing my essays from India, on a Skype call with a longtime friend of mine. We were spacing out on three-hour calls as we always do. ‘Hackathons are awesome’, he said. ‘Why?’. ‘The money, what else? I made five grand last semester just smoking my way through these things. It’s fish in a barrel.’

‘Sign me up. Why not?’, I said as I checked the box for Yale-NUS.

So I went to orientation, skipped the second day and signed up for my first one with a fellow freshie I hadn’t known for very long. We signed up as a two-man team, and despite the compulsions of the organizers, we stayed the dynamic duo.

We came in second and won just as much per person as the winning team. I was hooked. It wasn’t the money, it was that we had made something that only a day ago existed merely in our heads. I distinctly remember brainstorming the night before, wondering what we’d build. We were in an alley, looking around at the dirty walls so unlike the rest of Singapore. ‘What happens to Graffiti in this place?’ I wondered aloud. ‘Are you nuts? You can’t graffiti here, you’d get in trouble.’. ‘What if you could, and no one minded? What if you could paint anything you wanted anywhere?’ 24 hours later, WonderWalls was born.

Hackathons for me were the playground of the What Ifs. You could go in with any idea and actually find out if it meant something to someone else, instead of languishing in your head like every other thought you meant to write down. You could explore possibilities, get criticized, see people use it, and travel ahead to the point where it was real. All it cost you was a weekend. In that first hackathon we built a prototype that worked well as a Random Number Generator. A crash was a zero, a success was a one. This was before the age of AR and VR, before Electron or Heroku or Firebase, when JavaScript was still in diapers. Yet I got up on the stage, opened up our phone and pointed at the ceiling to show the words ‘Welcome to Startathon’ written in rough letters. I was 36 hours in with no sleep, but I could make out a faint ‘ooh’ from the crowd, and I knew I’d be doing this for a while.

We didn’t sleep after we got home like we said we would; we watched two movies back to back and talked for hours. I skipped class the next day, and hung my lanyard on my door handle before unwillingly crashing on my bed.

The next year and a half went by and I signed up for every hackathon I noticed. Team-mates came and went, themes and APIs flashed by, but the setup was always familiar: find something original and build, leave if you can’t. We placed in every single one, and I found myself thinking of ideas every idle moment I had. I caught myself looking for ideas every time I hated doing something. This was the golden age. I traded my weekends and ideas for dark circles, junk food and oh-so-appreciated money.

Stage 2 — Ad infinitum

Infinite loops are interesting to me. Every computer has one on some level; it’s what drives the system, keeps it alive. We used to joke that an Artificial Intelligence would optimize itself and its environment away until all that was left were infinite loops. Yet I liked infinite loops in my code as much as I liked being in a rut, and it was in the first semester of my second year that I realized I was in one. I still had ideas I considered original; I just never used them anymore. I had internalized the act of winning. It was never the idea that won, it was the pitch. Looking back, the ideas I was least proud of were the ones that placed the highest. I didn’t like the scene anymore. The long night of coding became an effort to decrypt and pander to the sensitivities of the judging panel. I wasn’t alone; this was around the time I started seeing the familiar faces disappear, replaced by a new wave of hackers. Meanwhile the pile of lanyards on my door kept getting bigger and bigger.

Perhaps I had graduated, maybe it was time to move on. I didn’t want to. I liked what I did, and I was addicted. I was in deep enough that we held private hack nights at our Hackerspace where we ordered in pizza and coded through the night, a new project each weekend. Original ideas only.

This was good, yet I missed the smell of hackers in the night. The pitches, the pure joy, the success and the defeat fueled by exhaustion. When you’re mentally drained and exhausted, it’s not easy to bullshit. It makes for a sweeter-smelling room than most.

So I went back, but things were different.

Stage 3 — Hello

From the other side, it was a different matter. I had been turning down requests to organize hackathons for a while, pleading out for the reason that I wanted to compete. This time, I couldn’t think of a good one, which is how the same friend and I ended up organizing hackathon after hackathon, working with new hackers. We were helping them find things we had seen through keyboards covered in blood (okay not that dramatic, maybe just Red bull).

There is a limit to a hackathon, something you realize after you’ve built up an irreverence through years of bullshit and eurekas and pissed off teammates and cheques cashed. It’s not the altar of creative energy I’d naively seen it to be, and it wasn’t the jaded bazaar of APIs I gave up hope in. Somewhere in the middle, it was still something.

Stage 4 — DIY

We’re still naive. I’m still naive. We think we can fix hackathons, do them our way. I know, I know. Probably not. We’re the guys in the stadium that look at a missed penalty and think we could’ve done better. The way I see it, we’ll be either a little successful, or a little less whiny. How could we lose?