From Selling Beer to Software Engineer

Caitlyn Greffly
5 min readJan 10, 2020

This is a story about how less than a year ago I decided I didn’t want to be doing what I was doing anymore, and how I immediately changed my situation. As with most situations on the decline, I could both see it coming for a while and had a breaking point in which I knew the time had come.

For seven years I had built a career in the beer industry. I was simultaneously proud of the position I had reached and confused as to how I ended up in sales, which I didn’t particularly like or feel good at. I was burnt out from the travel to the point of not even enjoying the fancy hotels I was staying at or the sushi I ate on the company card. Although I met some of my favorite people in the industry, there was also a surplus of masculinity and functional alcoholism that ended up feeling like a frat house I had lived in for too long.

The moment I decided to turn my career on its head came in February 2019 while sitting across from my least favorite bro at the company at a slot machine in Las Vegas. He told me that to be successful I was going to need to pump my chest and be more arrogant, something I had grown used to hearing. I realized that what he was ultimately saying what that I needed to be more like him. At that moment I knew I needed to get out.

Over the next week, I spent every free moment of time and brain space I had researching new careers. I made color coordinated spreadsheets of my skills, my likes, my dislikes and took tests on which career path suited my personality. To be honest, this is my strong suit. I had little idea of what career I was going to move into, but I knew I was going to be organized as hell figuring it out.

It took about a week for me to decide on Data Science. I wasted no time applying for a Data Science bootcamp only to be swiftly rejected for not knowing any coding basics.

“Coding?! Why would I need to know that! I don’t know anything about coding. I think that’s just for nerdy boys who play computer games, right?”

My inner stereotyping was, I would learn, not uncommon amongst non-tech industry folk. The field is, after all, 75% male. Yet I started googling. What even is coding? How do you learn it? What kind of jobs do people who code end up with?

Considering my low-level of knowledge when I started googling, I made the decision to throw $9000 at a coding bootcamp alarmingly fast. I am actually surprised more people in my life didn’t tell me to calm the fuck down and take a breath. But they likely knew me well enough to know that the train had left the station and I was on a mission.

I spent the first two weeks of bootcamp in a complete honeymoon phase. I was elated when I first saw “Hello World” appear in my browser window, and proudly showed off what was probably the simplest, ugliest website of all time — Sally Student’s Resume Page.

Then reality hit. AKA JavaScript. My first impression of JavaScript was that it was math that was wrong. x = x + 1 was mathematically impossible and I was there to let my mentor know that someone had seriously messed up. I spent the next month confused, disgruntled, and exhausted from trying to continue working my full-time job while secretly learning a ridiculously challenging skill on the side. I decided that it was physically impossible to get my Harry Potter Quiz App to move from one question to another and had a good cry about it in the Safeway parking lot.

I needed an outlet for my frustrations, my complaints, and my triumphs. I ended up at a Women Who Code meetup and was shocked to immediately feel supported and cared for by the Portland tech community. I found people to share stories and make coding puns with and gathered intel on the cool companies in town that would hire bootcampers. It was there that I found out about the ACT-W conference (Advancing the Careers of Technical Women), and quickly bought a ticket.

The ACT-W was a conference centered around boosting each other up. From mentors reviewing resumes to panels about how to land your first job to free professional headshots, it felt like there were hundreds of people there with the sole purpose of helping me succeed. It was like nothing I had ever experienced in the world of sales, where there is always a hint of every man for himself.

From there I continued to put myself out into the community, and the community continued to go above and beyond to support me. I was often surprised by the generosity of more senior tech folks because they, in fact, did not owe me anything. Why would they take time out of their day to show me the ropes? Buy me lunch, introduce me to AWS, explain computer science fundamentals to me on the dashboard of their Tesla (really happened), and tell me how sprint review worked. WHY?! Turns out, there’s just a lot of really good humans out there.

This all helped to make me feel like that rash decision I had made to throw $9000 at my computer had been a sound one after all. But it wasn’t until I started my first job, just seven months after making Sally Student’s Resume, that I knew for sure that I had chosen wisely. I immediately felt supported and valued, despite having no idea what was going on. I had a real work-life balance for what felt like the first time since college (minus the job where I was Santa’s helper at the mall — great hours there) and I had more energy than I’d had in years.

I know too many adults in various fields at various ages that are unhappy at work. I know how that feeling can suck the life out of you and make you feel like a person you’re not so proud to be. I am so grateful that we live in a time when there are programs to help you completely change your situation for way less time and money than going back to college. A time when it’s not only normal but valued to change careers and bring a different perspective. And while I don’t get to see people’s faces light up when I tell them I sell beer for a living anymore, I get the fun of telling them how I went from doing that to being an Associate Software Engineer in less than a year.

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Caitlyn Greffly

Navigating the life of a Software Engineer post Coding Bootcamp