From Coding Bootcamp Drop-out to Full-stack Software Developer and Mentor | Outliers

7 min readOct 6, 2022

Welcome to Outliers, where we celebrate the rebels that are shaping emerging tech. We ask developers and engineers how they came into the tech space, what gets them excited, and what cool shit they’re building.

Meet Kat Connolly, a full-stack software developer at Checkfront, a software development company that specializes in building booking software. Her journey into tech took the unconventional route — after studying philosophy and public policy, she worked in government before pivoting to tech. After taking a chance on herself and signing up for a coding bootcamp, she found her place in software development. Today, she manages tech bootcamps and is a true outlier inspiring others to break ground in tech.

What do you do?

I’m a software developer working in full-stack development.

How does your role fit into the overall vision of the company?

As a full-stack software developer for a software development company, I’m right at the heart of what we do. We work a lot with companies that do adventure tourism, but most people wouldn’t know Checkfront directly because companies embed our software on their websites, so the end user doesn’t really see the Checkfront brand while they are using it.

How did you get into tech?

I started university studying philosophy, and by second year realized that this was not what I wanted to do long-term. I graduated in environmental sustainability and international development, with a minor in economics. After that, I did a master’s degree in public policy, and got into politics.

I was working in politics in Toronto and my roommate was a senior software developer. Since a lot of my job was coordinating, he said “I could probably automate your entire job in two weeks.” So I was thinking about where my career was going, because I knew that I didn’t want to have to retrain in my 40s. I was good at my job, but I knew that I was getting tired and it would be hard to compete with someone younger when I might be losing steam. And then I started thinking, well, why not just write the things that are one day going to automate those jobs? So I started to teach myself how to code.

When did you first start coding?

I guess I did some MySpace edits in 2005, but that doesn’t really count! I started coding when I was 26. I did some online courses, went to Reddit, which had lots of practice things that were supposed to be easy, and I sucked. At the time, I also wasn’t sold on the idea yet, so when I couldn’t solve a problem, I would just watch Netflix. I needed the Lighthouse Labs coding bootcamp to commit me to learning.

When did you get started as a developer?

I had crazy imposter syndrome after I graduated from the bootcamp, and I had a job offer to be a developer. But I was just convinced that they were mistaken, so I ended up taking up a job with Lighthouse Labs managing the Calgary campus, because after I graduated from my undergrad, I worked a bit as a career advisor and did recruitment, so I was uniquely qualified.

After I took that ten week coding bootcamp, I didn’t code for almost a year. All my developer friends told me that I was never going to be a developer. I had met the Neo Financial team through Lighthouse Labs, and they kept asking me to interview, but that imposter syndrome was so strong. It wasn’t until they had asked me three times that I finally decided to say yes. I worked at Neo for almost two years, then I freelanced and taught for a bit before joining Checkfront.

What made you want to work at Checkfront?

There were a couple of different companies that I was interviewing with, and I was honestly sold on Checkfront because of the interview process. It was the only company I was interviewing with where it seemed like everyone was actually friends. I had to do a tech challenge, which was me and three senior developers cleaning up some code, and they were joking with each other and it was clear that they actually liked each other. They also have a professional development fund, which I think I’ve probably used more than anyone, and the mentorship program is teaching me a lot.

What’s the most exciting part of what you do?

I love what I do. I’m really excited about coding and development. The thing that appeals to me the most is that I can just keep learning and doing more. If you stop learning, you dry up.

What sets your work apart from similar roles at a non-startup?

Checkfront is 10 years old now, so it’s an older startup, but when I worked at Neo, that was a new startup. With startups, you have a lot more ability to try things out because there’s a lot less red tape. You can do some more interesting stuff, something more innovative, and you can bring in technologies that are newer. The biggest difference is in the creative freedom that you get.

How do you stay up to date with the latest technologies?

I try to build little side projects. The thing with side projects is that if something is too complicated, you’ll get tired of it, so I try to build basic things, like a single page application, and I try to change up what technology I’m building it with, so I’m not building the same thing every time.

How has working at a startup helped you grow as a developer?

When I started at Neo, it was my first job as a developer, and I was still dealing with imposter syndrome, but something that I really valued was that they had the mindset of “we hired people because we thought they were smart, so we’re going to trust those people to make smart decisions.” In my first year as a developer, I was allowed to do a lot of things that probably people working at established companies wouldn’t be allowed to do. There was a lot of diversity in my work — one month I would be entirely front-end, the next I would be entirely back-end. I got to build a lot of really cool, totally different stuff, instead of just going through a training module and being pushed to one section.

Startups are a rocket ship. I do a lot of coaching sessions to help people find where they want to be, and my advice is always that you can have a steady job maintaining code if that’s what you’re looking for. But if you want to wear different hats and push yourself to keep growing and learning more, you’ll be able to do that at a startup. Working at a startup gave a huge jumpstart to my career, which helped a lot because I was a late pivoter and already had careers before this.

What has helped you grow in emerging tech?

Networking. My job with Lighthouse was a community manager role, so I was at a lot of tech events and met a lot of people. When lockdown started, I started writing articles on LinkedIn, then moved over to Medium. I’ve built a community and there’s lots of amazing people to learn from in the tech scene.

What advice would you give your early self about building a career in tech?

I’ve met a lot of students who are going through coding bootcamp and thinking “I don’t think this is possible.” And I see so much of myself in them because I quit. I actually quit bootcamp the first time I tried. I sucked so bad. I cried every day. And I dropped out after a week. And then, thankfully, the Head of Education believed in me and called me, and convinced me to stay on. He’s now actually a very good friend of mine. I gave up on myself a hundred times, like when I didn’t work as a developer for a long time. Every day I tell myself that the imposter syndrome is not going to go away. But I can keep getting better. I know I’m better today than I was a year ago, and a year before that. The imposter syndrome doesn’t fully go away, but as long as I keep pushing myself, it makes it quieter.

What has been the most impactful decision of your career?

Deciding to do it. The pivot was the thing. I made the decision to become a developer three times, actually — when I decided to go into tech, when I decided to do the coding bootcamp again after I first quit, and when I finally decided to work as a developer. I needed to give myself license to be bad at things because otherwise you’ll never start learning to be good at them.

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