Let’s get (un)comfortable!

#Bloganuary day 3: write about leaving your comfort zone.

A few months ago, I wrote this short post about starting a new job. I wrote very little on the subject at the time. In hindsight, I think this is because even though I was very excited, this is one of the scariest things I’ve done in a long time.

I worked for Pinger for 15 years. Over those years, I became many things, including subject matter expert on product history and product quality, the go-person for questions on just about anything, a manager/director, a leader, a cheerleader for my team and colleagues, a friend, and much, much more than that.

When I left my previous job for Pinger, I was nervous about working for a Silicon Valley start-up. Starting as employee number 10 and the only quality engineer was a bit daunting. However, it was a fantastic opportunity and my current job at the time completely sucked.

This time around, I was leaving a job that I loved. My team was like a family. I established the department, defined the roles and best practices, hired all the people. I knew all the company lore and legends, knew the in-jokes, and always felt at home. In short, it was comfortable.

If I loved it so much, why leave? Why even interview for another job? It all started with the pandemic and a small layoff within the company. While I knew I was safe, many others weren’t. And even though I felt confident that the company would come out OK post-pandemic, this was a moment of reflection.

After so many years, was I still learning? Was I growing and becoming the best me that I can be? Or was I too comfortable or even complacent? I didn’t have clear answers to these questions, but I knew something needed to change.

I came across an exciting job opportunity for a role at Blizzard. The job was a global VP role, and I didn’t write a cover letter or update my resume when I applied. No surprise that they immediately said no. I am very thankful for that. Since then, I’ve learned what a terrible, misogynistic place it is.

If something DID happen, and I needed to find a new job, was I prepared? This experience told me that no, I was not. I needed to update my resume, and I needed some practice interviews. Pinger hired me as an individual contributor, and I had never had an interview for a manager- or director-level position.

Hope for the best, prepare for the worst, right?

All in all, I think I applied for about 12 jobs, and I had only a few interviews. Even though this was all just for practice, I applied almost exclusively to jobs I thought I would actually want.

During this time, I also went through a very stressful period at Pinger. I won’t go into details. The individual I had issues with no longer works there either. However, it’s hard to stay at a job you love when you feel undermined and devalued by someone, especially a person in a position of power.

As I thought more about my career and my career growth, I realized that I was in a very comfortable, complacent place. (The last time you left your comfort zone? This blog post! I feel very exposed writing this.)

I knew there were still things to learn and ways to grow; I wasn’t sure I was getting those at Pinger. But when I thought about leaving, it was very scary, and I would tell myself that I’d quickly be discovered as a fraud at any other job. Hello, imposter syndrome!

Pinger did an amazing job transitioning from a mainly in the office culture to everyone’s at home indefinitely. However, the already meeting-heavy culture meant I was spending 4 to 10 hours per day on Zoom, at least four days a week.

How would I grow or change the system if I was sitting in all these meetings all day, every day?

At the same time, I read this book, Think Again, by Adam Grant. Grant talks a lot about identity, and one thing I realized was that Pinger had, for better or worse, become part of my identity, and that scared me as much as, if not more than leaving did.

Our identities are open systems, and so are our lives. We don’t have to stay tethered to old images of where we want to go or who we want to be. The simpliest way to start rethinking our options is to question what we do daily.

– Think Again by Adam Grant

And now, the part you’ve all been waiting for: Brie decides to take a new job.

I could (and should) write a whole post about the interview process at Automattic. For now, I’ll only say that it’s not for the unserious. There’s a real-time commitment, not just an hour or two for some zoom interviews. There are actually zero zoom interviews!

The job at Automattic, Head of Quality Engineering for WordPress.com was very appealing to me. The Automattic culture, creed, async, and just everything about the company resonated with me.

During my first interview (on Slack, by text), I found out that the team I’d be leading consisted of 3 people. Wow, this was going to be a step down from Pinger, where I had a team of 11 in the US, and around 13+ contractors and growing. I almost didn’t continue when they asked me to do a second interview.

The point of all this was to get experience with interviews though, right? Not to find a new job. So I said yes to the second interview. And then I said yes to the paid trial. A project that you’re expected to spend 30-40 hours on, at your own pace.

It amazes me the stories we tell ourselves to stay in that comfort zone. I wanted this job. A LOT. But, should I not get that offer, it was way easier to tell myself that this was still practice. That I didn’t want it. It was a step-down. That I’d never leave Pinger, I was happy there. Negative self-talk is a real thing, and it can be really damaging. I’m so glad that I saw mine for what it was, and ignored it.

When you stay in your comfort zone, you’re not growing. (I wanted to put a really cool illustration here, that will have to wait for a follow-up post). I was stagnating at Pinger, even though I enjoyed working with my team so very much. And if I’m being really honest, I was bored and unhappy, because I was in these mindless meetings all the time.

During my trial with Automattic, I tried to convince myself I didn’t want it, wouldn’t get it. As I was working on the project though, I really enjoyed it, and I saw how big this opportunity is. It may be a small team today, but they are hiring someone to grow the team, and that’s something I know how to do and really love doing.

When I got the Slack message that Automattic wanted to offer me the job, I was over the moon. And that told me all I needed to know. I’d found a new (work) home, and hopefully, it wouldn’t be quite as “comfortable” as the last.

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