When I graduated from college with a degree in East Asian Languages and Culture from the University of Illinois at Urbana-Champaign in 2011 (one year late), I had no idea what I was going to do. To compare with my fellow EALC majors, one had started a restaurant, one got into horseback riding, and another was a brand ambassador. So basically, I was at square one.

A few things from my background contributed to me landing in software, however:

• 🕹 I was a computer enthusiast from a young age, whether that was begging my uncle to start up Commander Keen on his computer, being the first kid on the block with cable internet, or the first with a high end graphics card (all hail the Radeon 9700 Pro). I read MaximumPC to drool over the latest game graphics and that introduced me to Slashdot, where I learned about up and coming startups and also comment karma systems.
• 💻 I picked up Learn HTML in 24 Hours at some point and wrote some basic websites – mostly unordered lists. Then I grew bored. As a result, my websites to this day are still mostly unordered lists and that’s why this website runs on WordPress.
• 🐍 I also picked up a book on learning Python in high school, probably mostly because snakes are cool and installing software had this mythological status. Installing software was fun for the sake of enabling new things. That includes updates to software. I no longer have this fascination, but it’s a nostalgic feeling. Oh, and Python? I did a few simple math problems in the REPL, like 1 + 1, but lost interest. This was the same as my TI-83, but without the graphs! I was almost disgusted at how useless it was. Little did I know. My impression of Python remained, however. Sorry Pythonistas.
• 👨‍🎓 I started my college career at a community college. When I transferred to the University of Illinois at Urbana-Champaign, I tried a semester in a humanities major, actually the one I would end up graduating with, and decided I wanted more of a challenge. I chose Electrical Engineering because I had heard it was the hardest major on campus, and that turned out to be true enough to switch back out of the major after a semester, but not before getting a B in ECE 190, where I would learn how circuits built up to logic boards and how to program in LC-3 assembly and a bit of C. This would actually help my intuition a lot later on. And for what it’s worth, I didn’t consider going into computer science because it was for “smart people.”
• 📚 During a summer break in college after I had broken up with my first girlfriend, I decided I needed some time for my soul to heal. I thought reading some Great Literature™ would be a good way to do that, so I picked up a few books by someone I had heard of. As it turns out, I somehow had a brain fart and mixed up the American essayist David Sedaris with the marketer Seth Godin and ended up reading a lot of marketing books, instead. But by that time I had forgotten why I wanted the books in the first place, so I was happy to read, anyway. This led me to the very repetitive world of business books and, by extension, repetitive business ideas.

Yet, even after all of this, I didn’t really consider making tech a career until after college. I was more interested in get rich quick and 4 Hour Workweek schemes. After graduating from college, I spent a few months chasing these fruitless ideas until I found an article called “How to Build a Web Application from Scratch with No Experience.”

https://twitter.com/briankung/status/780814870392532992

I was excited to build a web application, run a startup, and learn career skills along the way. There was good alignment. Ironically I still haven’t really built any of the web applications I’ve wanted, personally, but it got me looking into Ruby and Ruby on Rails.

At this point, I was definitely 80% interested in startups and 20% interested in programming. But there was some foreshadowing that those ratios might flip. One of the earlier schemes I had come up with was to write books and self publish them. Except that instead of writing, I spent most of the time coming up with a sick website that looked like a literal bookshelf to sell my nonexistent books from. Did the ecommerce work? No, and what the hell is ecommerce? But the website was cool and that’s what mattered.

After some self-study, I got an internship at the Chicago Teachers Pension Fund (CTPF) as an intern. I had a lot of chutzpah, because I was emailing people to ask if I could be an intern even if there were no listings for internships. My go-to line was “I’m not the senior software engineer you’re looking for, but…” and then I’d go into my pitch about how motivated I was. Eventually it worked. Honestly, I wasn’t given a lot of guidance – and in fact there was none to give, since CTPF wasn’t a Rails shop – but I felt like I was on the way, and I’m grateful for the opportunity.

Nearly simultaneously, I found out about a coding bootcamp called Code Academy in Chicago which would eventually rename itself Starter League. I followed a lot of their students, who were highly recommended to write blog posts, and got very hyped up about the entire “code as literacy” movement and bootcamps in general, so I was very excited to apply. They gave me a short window of time to accept and I had to crowdfund around $3000 in order to attend. I have a lot of my friends and family to thank for supporting me, though it would weigh on me later. I hung up my hat at the CTPF and went to attend the bootcamp.

It was less like the bootcamps of today, which are full-time, and more like an paid club, since it was at most something like 6 hours of instruction per week, but I really liked the people and the environment. We operated out of the newly constructed 1871, a coworking space in the Chicago Merchandise Mart. After being one of the star students, mostly because I had done a good amount of self-study beforehand, I realized I was helping people out more than I was being helped. I was also fielding questions from other people in my life and the greater Chicago ecosystem asking about my impressions of the course and I realized…I just couldn’t recommend it.

I get a high off of buying things when they’re on sale – I don’t do it often, but if the discount is large enough, it’s hard for me to resist. It’s part of my immigrant background. I’m used to saving and scrounging, whether that’s hoarding takeout containers and plastic bags, or buying in bulk when there are flash sales on groceries. Code Academy was not a good deal, and I had to come clean about it.

On the other hand, I was really drinking the kool-aid when it came to startup hustle culture. There’s no doubt that that kind of energy and dedication helped me get into the profession, even though I’ve renounced it since then. I was applying everywhere, meeting tons of people, and overall ⚡️ killing it, bro ⚡️.

👉 Fun side story: I showed up to an interview in shorts and flip flops. I also bombed the technical interview, which had a lot of CSS questions, which I shrugged at and said, “I would have to look that up” multiple times. You have to understand, I have almost zero test anxiety, so showing up to interviews half assed is a full ass for me. They very earnestly told me that maybe I should take these things more seriously, wear better clothes, and come more prepared. I very solemnly agreed to their faces and then changed absolutely nothing about myself.

Some of the most fun I had was just hanging out and with the troublemakers Jared Steffes, Agam Patel, and Chris Ingebrigtsen on Matador, an investment advice startup that was all sweat equity, as far as I could tell – I don’t think anyone was being paid a salary. I was technically “working” for Jared, but really the draw was just being part of a gang of jokesters. I got to put it on my resume and build out some image upload functionality. One time I actually needed the money and asked Jared to cut me a check and it looked like he was drawing the money from his arteries. I don’t remember what I needed the money for, but I remember that I was very amused at his pained expression.

Still, I consider my first real step on the path to being a software engineer to be my job at Aggrego, which was a digital “skunkworks” embedded in the Chicago Sun-Times which was funded by a madman. The editorial staff hated us because we were well-funded and an annoying distraction, and the plan of throwing money at the paper until it became a successful digital property didn’t really pan out, but I did meet some great people like Nikola Ranguelov, Erick Arias, Shannon Carey, and Dave Willkomm, who was a great mentor to me.

Aggrego was the most “strict” Agile workplace I’ve been at since, with velocity tracking, team pointing, burndown charts, retrospectives, product managers, visual and UX designers, and more. It was a great learning experience. There were some downsides, like the madman in charge who full-out screamed at someone with the door open while I was pair programming with an intern – and no, that intern did not want to stay with us. I myself was screamed at when I forgot to show up for a midnight deploy. But I also got to feed my friends takeout when the company agreed to host Project Euler Sprint, I got a ridiculously high salary for an entry level job at the time ($75,000 in 2012). I almost bought a house!

And then of course I quit the moment I got bored.†

† …so I could pursue my own startup.