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Taking a Shortcut: Christine Cha


Welcome back to Taking a Shortcut, a series where we interview members of the Shortcut staff. The order in which we interview people may appear to be random, but it's based on science: our Director of Content recently traveled five years into the future, looked at the order in which we had interviewed our colleagues up to that point, made a list, and then brought that list back in time for us to follow when scheduling the interviews.

These interviews are meant to provide a glimpse into what it's like to work at a remote first company, while also exploring the topics of table tennis, pizza, and insult generators. For this week's edition, we spoke with Christine.

How long have you been at Shortcut?  

I started last June or July, I think. I’m closing in on a year soon.

Do you live in NY or do you work remotely?

I live in Queens, but I usually work from home. One of the reasons why I looked at Shortcut for a job was because it was remote.

What were you up to before coming here? 

I was at a startup called Jetty. That's how I found out about Shortcut, actually. We started using it as our project management software and I really liked it. When I left, I checked out the Shortcut careers page and now – here I am. Before that, I was at Squarespace, which was my first engineering job. I went to school for fine arts and dropped out after two years, so I don’t have a college degree. I’ve been an engineer now for five years-ish.

That's very cool that you were at Squarespace, because I was the fourth employee at Weebly. I think of it as a lesser Squarespace.

Actually before Squarespace, with some time in between, I worked at Wix. But I didn’t quite make the rounds to Weebly. I was only at Wix for a year on the marketing team and I was at Squarespace for two and a half years.

What prompted you to make the change from marketing to software engineering?
It was very roundabout. I quit the marketing job, and I wanted to go out on my own. I had been a freelance graphic designer for a while, designing anything from posters to websites to album art. I wanted to start my own design agency, so I left to do that. I started working with clients and ended up doing more web-related things than I had done before.

I quickly realized I didn’t know anything about websites or how they work. I just knew how they should look. I was like, "Okay, you know what? I'm just going to learn a little bit about how colors change and how things are laid out because I don't understand any of this stuff." I wanted to know what happened to my designs after they got sent off to the magic website factory. I meant to just poke around with some HTML and CSS, but I fell into the abyss of programming. Now I'm here.

What was it about software engineering that you enjoyed so much?
Well, for me, software development – or programming – just feels like solving puzzles. I'm a huge puzzle fan. I am a big New York Times crossworder. Crossword player? What do you call it?

A participant?
Hmm, how about – I'm a New York Times crossword enthusiast. I’ve done it for a while. I love puzzles, word games, and just games in general. I like learning languages as well.

Programming is like all of those things combined. You're learning a language and solving riddles. Plus, there's the whole visual element, which, coming from a design and art background, I really enjoyed. I couldn't stop once I started.

I started with like really dumb simple apps. The first interactive thing I made was an insult generator. Literally one button on the website and when you pressed it, it would generate some pseudo-random insult at you. I just built a bunch of things like that, and slowly they got more complicated. And eventually, useful.

I mean, an insult generator could be useful depending on the situation. If your arch-nemesis is standing across from you and you don't know quite how to respond to them, a random insult generator would really be helpful.

How do you feel like your art background helps with your engineering work? 

Drawing is all about figuring out the relationships between two things, two points, two objects, two colors, whatever it is. To me, I come at it very analytically. I don't think of visual art as a free-form emotional activity. To me, it’s very logical and technical. It's very similar to the way that I like to program.

One thing that’s cool is that when you don’t have a traditional programming background, you often don't have a predefined way of solving a problem.

If you went to school for computer science, you might approach a problem and say, "Oh, I've seen this before. I've heard about this before, I've read about it somewhere." Your mind may have already started leading you to the “correct” solution. But in reality, there's no correct solution. If you don’t know anything, you might come up with 10 different solutions instead, and learn way more from it. I didn’t start out knowing the “right” ways to do anything.

What else are you up to besides programming and puzzles and art? 

Before the pandemic, I mostly spent my free time playing table tennis. I have a mini table at home but it’s not the same.

How long have you been into table tennis?

I think it’s been almost four years now since I picked up a racket. I started playing when I was at Squarespace because we had a room dedicated to it. I’d go down and play with a few coworkers during lunch sometimes. Then pretty soon, I’d go play before lunch, maybe play a little after lunch, maybe get an afternoon game in, and then even stay after work and play.

At first I was so bad – I could not hit the ball, and if I did, I would run away from the next one because I was scared it would hit me. I think that's what drew me in so much because I was like, "First of all, how can someone be so bad at something? Second of all, if I put in just a little time, I'm going to be so much better because I can't get worse than this." That's where it started.

My obsession really blew up when I found this place called Spin, on 23rd Street. It's a bar, but completely dedicated to ping pong, with some real players. I started taking lessons there, and playing – well, losing – every week at the casual tournaments. I met a whole table tennis community. I met my boyfriend there who also plays table tennis. Since then, we've been traveling and playing internationally, doing training camps, competing locally, and going to see professional tournaments. It's become my whole life.

Wow. What’s your favorite type of pizza? 

I'm not a big pizza person.

But if you had to choose? 

Probably a meat slice, either pepperoni or… yes, pepperoni.

Why do you like working from home? 

One thing that I really like about working remotely is the communication. I believe that working remotely forces people to be more communicative, more articulate and provide more documentation, and that makes a lot of things easier on so many different levels.

I also find that people manage their time more responsibly when they're remote because when you're in an office, you have this social pressure to pretend like you're working. Even when you don't feel productive or say you go for a long walk or something, you have to be back because you don't want to be away from your desk for too long.

If you're not feeling productive, take a break, take a nap, take three hours out of your day to go do something else and come back later. It's so much better for your long term productivity than just sitting at your desk and pretending like you're working.

It also forces everyone to be more respectful of different work styles. Not everyone works the same hours as you, or in the same way as you. You learn to be more flexible.

What’s something you’ve learned from working at Shortcut? 

One thing that I've definitely learned from my co-workers is proactive communication. Reaching out before things even become a problem.

I've been really impressed with my co-workers at Shortcut. I've had a handful of cases where someone preemptively reaches out and says, "Thank you for doing something." Or I've had someone reach out after a meeting and say, "Hey, I'm sorry, I feel like I interrupted you. Let me know what I can do better." I've had people schedule calls with me to talk through something that maybe would never have been an issue, but just because it might have been, they reached out to talk about it.

I think that's been a really great thing to learn and observe. No one should be alone in a situation, worrying, "I don't know if I said the wrong thing. I don't know if I did this correctly. Maybe what I did bothered this person." Just reach out and talk to them about it.

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