How a high-school-dropout-turned-farmer ended up kicking butt in the cyber security world: This story looks at the opportunity Dev Degree gave me, the challenges I overcame, and the weaknesses that turned out to be strengths. If you’re thinking about a career in tech, but don’t think you have the stuff for it, this story is for you.

Cailyn stands outside a farm animal enclosure, holding a chicken. She has curly brown hair, glasses, and a happy smile. She is wearing black jeans, and an unbuttoned denim shirt with a white t-shirt underneath.

How I Found Dev Degree

I heard about Dev Degree while I was in a comp-sci for the arts course at Carleton University as a special student. I knew immediately I wanted to be in the program, but before applying I needed to finish high school (yay!) and get the math courses (boo!) required for a Computer Science degree. During this time, I dropped out of my environmental studies degree at Carleton and graduated from the University of Guelph Kemptville Campus with a co-diploma in Horticulture, while also running my own organic farm. My eclectic background and varied experiences led me to Dev Degree, and the varied experiences in Dev Degree kept me interested and allowed me to find and be successful in my career.

Dev Degree wasn’t just a good opportunity for me, it was the only way I would be able to get into the tech world while paying my mortgage and maintaining any semblance of work-life balance. As I mentioned, I had left high school before graduating, and was not what anyone would call “academically motivated”. My whole life I have shifted from passion to passion, throwing my whole self into each one until I found something new. I’ve done everything from blacksmithing to whitewater rafting, and a whole lot in between! When I happened upon software development it was love at first byte (bahaha). I was shocked by how much I enjoyed it, and I wanted to learn more. It was the first time in my life I stayed up into the wee hours doing homework because I was having so much fun. Gross, I know!

Here’s a brief timeline summarizing my Dev Degree journey:

June 2018: Accepted into Dev Degree! After being waitlisted I was lucky enough to snag a spot.
August 2018–April 2019: Training path! I learned CompSci basics, did lots of pair programming and learned about the developer workflow.
May 2019–April 2020: First Placement! I spent a year on the orders team working with Ruby on Rails, and learning a lot about being on a team at Shopify.
May–December 2020: Second Placement! I joined the Infrastructure Security team and fell in love with cyber security and cloud infrastructure.
January–August 2021: Final Placement! Knowing I wanted to go full time on InfraSec, I joined Network Foundations to deepen my infrastructure knowledge and learn more about Shopify’s Network.
September 2021: Graduated Dev Degree! Finished my CompSci degree at Carleton and started at Shopify, on InfraSec, full time.

There’s so much to say about each moment during the program, but in the interest of staying focused I’ll just say that it was an amazing experience and I'm so grateful to have been a part of it.

An Unexpected Destination: How I Discovered Infrastructure Security

When I was learning to code on my own before joining Shopify, I was sure that I would end up working in front-end development. I’m not particularly good at front-end development, and the problems I was solving weren’t lighting me up, but it was all I knew about software development so that was what I aimed for. I never in a million years would have guessed that only a few years later, I'd be working on an Infrastructure Security team and spending my free time contributing to Kubernetes.

Upon joining Dev Degree I was exposed to all parts of the stack, and realized I found back-end development easier and more enjoyable. This influenced my first placement on the orders team, which I enjoyed immensely and learned a lot from. By the end of this experience, I was convinced feature-driven back-end development was for me. If it weren’t for the placement structure of Dev Degree encouraging students to try a variety of disciplines, I likely would have just stuck with back-end Rails positions.

Before my second placement, I had no idea what cyber security was. Thanks to the community in Dev Degree, I heard from a classmate about their experience on the Application Security team. It sounded really interesting, but I was also enjoying my systems and operating systems classes at Carleton. I shared this with the absolutely incredible Dev Degree placement team (that does dating-app-level matching of students with teams and mentors that will be a good fit), and they suggested Infrastructure Security. Even though I had never heard of it, I had a feeling it would be the perfect fit.

It’s really easy to settle and become stagnant. Software is a huge domain, and it can be overwhelming to explore the various parts of it. This was a huge challenge for me when I first started exploring a career in computer science. I was constantly intimidated by the sheer amount there is to learn and it often felt impossible that I’d be good at any of it. I overcame this fear thanks to Dev Degree encouraging students to move around and try new teams. In my opinion, this is one of the most valuable things about Dev Degree. I never would have found my way into such a niche area of computer science if not for the placement team, and being able to hear about the variety of placements other students have done. This broad set of experiences set me up to choose a career that I’m extremely passionate about and would not have discovered otherwise. Software is constantly changing and evolving. My tendency to change passions frequently—something I always saw as a major character flaw—has actually helped me gain the skills to learn fast and adapt to change. So, my advice for finding the right specialization for you is to be open to trying things you might not typically consider, and to not consider it a failure if something isn’t right for you and you want to pivot to something else. If you're interested in learning more about the value of being a generalist I would highly recommend Range by David Epstein, which happens to be one of the many books in Shopify’s book bar!

“My tendency to change passions frequently—something I always saw as a major character flaw—has actually helped me gain the skills to learn fast and adapt to change.”

Why Did Security Stick?

As I mentioned, I’ve had a pattern of shifting passions pretty frequently. So what made this one stick? The cyber security community is a magical place full of wonderful people from a variety of backgrounds (I’m not the exception!). Security roles are not always developer roles, and because of this many of us have varied backgrounds. As soon as I started working in the Trust organization at Shopify, I felt like I was a part of a tight-knit community. This, along with how compelling I found the work, made it a no-brainer to look into joining Infrastructure Security full time. It’s also worth noting that my team is incredible (like really incredible), and that was no small part in helping me to fall in love with Infrastructure Security. But also I think that this is one of the many areas I could have ended up and been very satisfied with my work. I felt similar working on the Network Foundations team in Production Engineering. I don’t know if I’ll be an Infrastructure Security person for my whole career, but I know it’s where I want to be now and that I have a lot more learning and building in the field ahead of me!

From Dev Degree Intern to Full-time Security Engineer

For me the transition to full time was really smooth, and actually felt like a reduction in stress and my overall workload. I have ADHD and dyslexia and have always found school to be fun but challenging, so the consistency of a full-time schedule and reduction in context-switching was a huge load off. Although computer science was easier to stay engaged with than anything I’ve tried in the past, the work itself was demanding and constant. Once I finished my degree I felt like a weight had been lifted, and I had more energy and mental bandwidth to dig into things at work. As a Dev Degree intern, you’re only working with your team 20 to 25 hours a week. This often left me with a bit of FOMO, so being able to be with my team for the entire work week was really nice.

The placement portion of Dev Degree is where all my big learning happened. I was able to work on complex problems and get help from industry experts. If you want to get started in software development the best thing you can do is just that: start. Build something, get your hands dirty, and learn along the way. I found that diving into a problem first and doing research after I had a cursory understanding to be much more effective than just focusing on theory.

I was able to join the team and make an impact right away because I had already onboarded and had a lot of Shopify context to work with. Shopify’s flexible working hours made the adjustment easy, and remote-first means that I can do my laundry and walk my dogs while still being able to have a high impact on my team.

Life After Dev Degree

To be honest, it’s been a doozy! Since graduating, I’ve contributed to and led many impactful projects on my team, given three internal talks about security at Shopify, received a promotion to Senior Infrastructure Engineer, won a contributor award from Kubernetes, been accepted to speak at two conferences (catch my upcoming talk at CloudNativeSecurityCon 2023!), and been accepted into the Kubernetes Open Source Experience program at Shopify. This is more than I expected to be able to accomplish within a year and half of graduating and I couldn’t be more thrilled. Thanks to Dev Degree removing the stress of co-op selection and internship job hunting, I was able to focus on getting varied experiences during my time in the program. This allowed me to better understand the type of work I’m truly passionate about and advance in my career quickly.

I’ve been able to provide a lot of value to my team through the connections I’ve made and the context I’ve gathered while in the Dev Degree program. This, along with the exposure to multiple technologies, languages, and tools used by Shopify, feels like a cheat code to having a high impact fast.

The things that I thought would hold me back in a software career have been some of the most important factors in my success. Notably the variety of experiences I've had and the communication skills I developed along the way. I’m a firm believer that it’s never too late to change careers, and that every person has unique things that they bring to the table. Fortunately this is also Shopify’s stance on the people they hire and it makes for a delightfully diverse company chock full of incredibly skilled individuals.

I hope that my story has been informative, maybe a little inspiring, and most importantly entertaining! If you want to know more about Dev Degree, cyber security, Kubernetes, or Shopify in general please feel free to reach out!

More About Dev Degree

Cailyn is outdoors on a sunny day, smiling, proudly holding up a small radish from her garden. She’s wearing a straw hat and a striped t-shirt.

Cailyn Edwards (she/her) is a Senior Infrastructure Security Engineer at Shopify, where she spends her time paving roads, putting up guardrails, and generally helping to secure the cloud. She’s also an active contributor to Kubernetes SIG-Security/SIG-CLI and 2022 Kubernetes Contributor Award recipient. Her current focus is on network, and Kubernetes multi-tenancy security. Outside of work Cailyn can be found running, playing squash, walking her dogs, or working in the garden. You can find her on GitHub, Twitter, or in Kubernetes Slack as @cailyn_codes.