RebootSquad is a series of posts based on interviews with engineers, designers, and other digital professionals who have "rebooted" their careers, entering the technology field via nontraditional paths.
A key theme of this blog has been intentional living—not merely floating from day to day, week to week, or year to year; but instead continuously taking stock of where you are, comparing it against where you want to be, and intentionally adjusting your trajectory. Universally adopting this mindset—for both your career and your life—leads to huge positive changes.
Few people I know have done this to greater effect than my friend Keith.
Meet Keith Chirayus
For the past two years, Keith has been a full-stack developer at Expedia in Bellevue, Washington. Quiz him on the various technologies he's worked with, and you'd think he's an industry vet: PHP, MEAN, Python, Ember, and Scala. But those two years make up the sum total of his experience as an engineer. Before that, he was living in Thailand, working in Finance at PwC.
I first met Keith in 2006, in a Japanese class at Montana State University, where he was studying Architecture.
Keith Chirayus: Back then, I wasn't really thinking about my career. Eighteen years old and right out of high school, I was thinking, "I just gotta find something to do." And I liked drawing—liked drawing houses, buildings. And I really liked to snowboard. At the time I had a cousin that was graduating Architecture School at MSU as well, and it was a great program, so that kinda shaped my decisions.
Asking "Why?" and Doing Research
But he didn't stay in the Architecture program.
KC: It was fun, as most things are when you first start them, but the more I got into it, the more I started to ask "Why?" Why am I doing this? Why am I interested in it? And the more you progress in something the harder it gets, and the questions become more prominent. You start to ask more of them. At the end of it, I ended up with more questions than answers. That made me uncomfortable with it, and uncertain about what I wanted to do. That's when I made the switch [to Finance].
This process of asking "Why?" is critical to intentional living. The answers needn't always be profound, but they should be identified and analyzed. And while Finance still wasn't Keith's final destination, the process leading up to his first switch gave him an important tool when making the second.
Oddly Exceptional: You did a lot of research in finding your purpose, did a lot of research in finding out what the different types of engineering were. A lot of this is about self-directed research. Is that something you've always done, or did you learn to do that? That, "I'm going to go find the answer to this thing."
KC: That wasn't a thing I did before, and that's definitely not something you get out of school. When you go to school, you have a set track. "Go read these materials. Go read these books." It doesn't really pique your interests; it's just somebody feeding you information. "These are the things you need to know. These are the things you need to read, practice, do. Get ready for this test." For this, it was like, "I'm interested in this topic. I'm going to pursue it. I'm going to go into research mode and try to find out where there are resources online, or if there's someone I can talk to." It's like an itch, and you have to scratch it. That was something that never happened to me before.
This tool is something he now relies on every day.
OE: How important do you think the ability to do self-directed study is for software development specifically?
KC: Very important. Going into this field, at first I thought that I needed to know everything, and I felt I was lacking that without a Computer Science degree. But you're not going to know everything going in, and even if you've been working at it for a while, you shouldn't feel like you know everything. If you're somewhere and you feel like you don't need to learn anymore, you start stagnating. New things will always come up, and you need to know how to figure it out. That's really important.
OE: How much "learning on the job" happens for you?
KC: Lots! Constant learning. Hopefully it'll stay that way, and I never stop learning.
Taking Action and Rolling With the Punches
It's not enough to ask questions and find answers if you don't do anything with them. After researching software development and his options for breaking in, he ultimately decided on attending a coding bootcamp, and immediately faced setbacks. While an increasingly accepted path into the tech industry today, in 2015 they were still a relatively new thing, and his initial plans broke down.
KC: Bootcamps weren't as big of a thing then.
OE: It was a little more risky.
KC: It was very risky. But I figured it was only three months. At first I was going to go to App Academy in San Francisco. The reason I got interested was that the program was supposed to be three months of intensive Ruby on Rails, and you didn't have to pay tuition in the beginning. Instead, once you graduated, if you got a job you'd pay ten percent of your salary for six months, which was perfect. I wouldn't have to pay until I found a job. I thought, "I'm going to do that." So I spent as much time as I could learning about Ruby, learning how to use the terminal, how to use Notepad and IDEs. I did all the practices I could find, read Learn Ruby the Hard Way, and thought, "Okay, I'm ready." I flew [from Thailand] in March of 2015, and landed in Seattle because that's where my family was. And right before I made the flight to San Francisco, [App Academy] said, "There have been some changes." They weren't going to allow us to live at the bootcamp anymore. I thought, "I can't do that. I can't afford San Francisco rent. Shit."
He instead looked at other bootcamps nearby. At time there were several options, including Code Fellows, General Assembly, and Coding Dojo. They each had their own differences, and in the end he went with Coding Dojo due to its focus on technical breadth.
Keith didn't call this out, but I think it's worth noting: he flew halfway around the world to execute on his plan, and when he got here, it fell through. But rather than quit, he adjusted. His goals and plan didn't change—only the details of its execution. He still wanted to learn these skills, and learn them through a bootcamp.
This is one of the most powerful effects of explicitly stating the higher-level goal. Without them, such setbacks can make it feel like the entire plan is off the tracks. It can feel overwhelming. I recently heard an interesting quote from Amy Yamada, a business mentor based out of Seattle, who in turn heard it from someone else:
There is no such thing as "overwhelmed"—I'm just not prepared or not committed.
Keith was prepared. Keith was committed.
Success and Ongoing Improvement
Keith's bet on a "risky" bootcamp paid off. After graduating he joined Expedia, and (as of September 2017) recently launched his first major product. But this isn't an end—far from it.
KC: I'm starting to be comfortable with what I'm working on. I want to get back into that bootcamp mentality. Now that we've shipped our product, we have some downtime. It's probably a good time for me to pick up a new language, or a new framework—just see what's out there.
Progress and success are cyclical. They feed on themselves. And while, from the outside, Keith's path to this point may have seemed circuitous, each achievement—even in those in seemingly unrelated areas—helped him on his journey toward the next.
In 2005, Steve Jobs gave a commencement speech at Stanford, and spoke to exactly this:
You can't connect the dots looking forward; you can only connect them looking backwards. So you have to trust that the dots will somehow connect in your future. You have to trust in something—your gut, destiny, life, karma, whatever—because believing that the dots will connect down the road will give you the confidence to follow your heart, even when it leads you off the well-worn path, and that will make all the difference.
Nothing is lost, and few decisions are irreversible. It's never too late to make a change.