My Journey as a WordPress.com VIP Intern

For a decade I’ve been building WordPress websites, as both a freelancer and at a digital marketing agency. In that time I had built nearly 200 custom WordPress themes and plugins for just as many sites. I had worked alone (on a small team of marketers, but never with other developers). I was self taught, self driven, and was a guru of my stack, my platform, and a master to the 100 or so sites that were actively hosted with us. I created intricate solutions to complex problems. I knew the clients, I knew the code, I always had a fix and solution to any issue. I saw problems before they occurred. I got paid well enough, was constantly busy, worked remotely, was good friends with the owner, had benefits, bonus’s, flexible hours, and on and on. For a long time, I had a very comfortable and stable life.

However, in early 2018 a sort of perfect storm started brewing:

  • My wife and I started planning our future with more children, a bigger house, more property, a second car, savings, retirement planning, investments, college savings. We needed much more than my current employer could possibly provide.
  • I was growing tired of working alone, I wanted to be in a team. I pushed myself to go outside of my comfort zone to my first WordPress Meetup, and a month later at the next one, I was giving my first ever presentation on Gutenberg.
  • I had begun answering developer questions on Stack Exchange, it became my hobby, my passion. I was enjoying it more than building sites, solving the little problems developers and talking with them was the best part of my work day.
  • The agency I worked for was having some legal turbulence which created some doubts in my long term future there.
  • I was getting into my late 20s, nervous about my growth and skills getting stagnant in the industry. I worried I would be designing and building small business websites for another decade, until I became low hanging fruit replaced by the next generation of WYSIWYG builders.

This combo of factors, mixed with encouragement from employees of Automattic from the Meetups, lead to me looking for new opportunities.

Now, jumping ships may be normal to some people, but this was a big deal for me, I never saw myself anywhere else, doing anything else. I had worked at the same place for 8 years, done the same thing for 10+ years. After three months of internal debate, some interviews at various agencies, and preparing myself, my portfolio, and my resume, I decided to apply to WordPress.com VIP as a Developer. I chose this role as it focused around the maintaining of websites and solving developer problems, which is “my thing“.

After a nerve-wrecking interview, I was turned down and given suggestions to improve some specific areas and re-apply in a years time. I was devastated, but remained motivated. So, like in any good story, I pushed on through adversary and I self-boot-camped my skills, doubled down on learning, gave myself sort of a years course on what to learn and when.

However, to my surprise, a few months later I was approached and made aware of an opening in the VIP Internship program. It was an honour to even be remembered or considered! My wife and I had to weigh the options though: stay at my job where employment and perks were known, or, take a chance on an internship which offered no benefits, no vacation, and would only last 4 – 12 months with no guarantee of employment. At this time, we had a new mortgage, a one year old daughter. A lot to think about. After a day of deliberation, it was clear to us that being part of WordPress.com VIP and Automattic would be the best move for my career, my happiness, and our future.

With a heavy heart I quit my job. Four months in now I know that joining the VIP Internship Mentorship program was the best decision I have ever made in my life.


The first month of the mentorship was a blur. In the first half hour or so of the movie Goodfellas, there’s a scene were Henry walks Karen through the back door of an exclusive club. They go through a maze of loud and exciting rooms and activities, start greeting and exchanging with people, then a table and lamp are brought to them as they approach the performer on stage, giving them the best seat in the house. This is what my first month was like, I felt like Karen. Here I was, accustom to building small business websites, and suddenly I’m greeted by an incredible team, given all these tools and access, then put to work on websites for huge companies. I was so excited and dizzy with all the knowledge I had to take in, all the things I had to sort out and work on. I was a big fish that just left my small pond and found myself in an incredible lake.

I quickly confirmed my suspicion that Automattic / WordPress.com VIP was an amazing place to work. It is truly wonderful how the distributed company works so efficiently and well. The team demonstrated themselves as being the hardest working, most dedicated, passionate, and helpful group of people I’ve ever had the pleasure of working with. Working along side them has been an honour and a privilege. Everyone shares the same unified goals and visions and helps each other to get there as a single entity. I was where I needed to be, where I wanted to be.

After the haze of the first month cleared, my second and third months were, in contrast, hectic, and the most mentally exhausting span of my life. I spent my days both learning best practices, as well as handling website performance issues. I was giving 100% every day, and was totally wiped by 5pm. It was hard, really hard, but I knew this was what I signed up for. This program isn’t a shallow-end of the pool deal. It is a program for those who want to grow, and grow fast. Again, this is a big lake, and you are thrown into it – but in the best possible way.

The learning encompassed many factors, it wasn’t just raw technical info. I’ve learned how to work in a strong team, how to handle big clients, how to use sustainable workflows, communicate more effectively, document properly, and how to provide true white glove service. For the technical side, I learned how to build WordPress sites for maintainability, security, performance, and for scale.

As I hit the fourth month mark, suddenly everything “clicked” and the mayhem slowed down. I was able to keep on top of things, able to filter out irrelevant info. I knew my role, my coworkers, my purpose, how to start charting my own course. I felt more like a part of the team and started acting more like it. I found my footing.


In a short fraction of a year, I can now confidently audit code and point out security and performance concerns (the type of code that I used to write!). I feel the mentorship program has sanded off all of my rough edges, shown me a clear path to being a VIP level Developer, and has overall turned me into a better developer and person. It has upgraded me.

With my first term complete, moving forward I’ve decided to continue my mentorship for another four months. I will be focused on helping new mentees acclimate to the program, while further improving and refining my skills. Once ready, I plan on applying for the VIP Developer role. Working for VIP and Automattic is my dream job, and I can’t wait to call it home and my coworkers family.

Do great things: Apply to VIP or the mentorship program today!


Comments

  1. The application deadline for this time around is just a few days away, so I’m sure you’ll have some potential Automattic mentees reading this post! I’m applying because I have a similar story – I have experience making WordPress sites, themes, and plugins, but I feel there are some gaps, which inevitably happens when you’re self-taught. I was fortunate to have a mentor at my latest (and first ever) web dev job, but all the WordPress stuff I had to figure out on my own.

    The fast pace sounds awesome. I’m thinking it might be similar to immersion in a foreign language, which worked for me very well. Not everyone is able to excel in self-study; others do better, but they may still plateau at some point… A lot of us know that even if you put the time in, you can still be spinning your wheels if you’re studying with no direction. It’s these self-taught folks who really stand to benefit from a structured mentorship opportunity like this. Man. I really hope I land this now. Thanks for the encouraging story dude!

    – Al

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