This last week marked my first year anniversary as a Happiness Engineer with Automattic. Starting this role was a big shift for me professionally and required me to go back to being a beginner again. It’s been a scary and challenging experience in the best way possible, and to say I’m glad I did it is a huge understatement. I can’t imagine not doing it now.

To celebrate, it feels like a list of reflections is due. Here are some thoughts after reflecting for a couple of days on the past year.

Things I’ve learned about myself and my work

• I do well with the structure that’s enforced by my work – I have complete flexibility for setting my schedule but once it’s locked I have to stick to it. I’m basically free to choose any 8 hours of the day when I’m available to work, and I get scheduled to work directly with WordPress users for 6 of those.
• The constraints on my time mean I need to carefully “time-box” my work – I can get lost in an important task to some extent, but there is always a hard limit when I need to transition to something else. Again, I’ve found this is freeing rather than constricting, but it’s taken some getting used to.
• I have almost zero meetings every week, and the ones I do have are great. This is how life should be.
• I’ve rediscovered how much I enjoy teaching others (and the other way around). Teaching is the core of the work that I do, and it’s fantastic to get to do it everyday. I host regular 1:1 and 1:many training sessions on Zoom and they are so gratifying to do.
• I enjoy having a lot of writing and reading to-do at work – there was a lot of (bad) powerpoint in my life before.

Things I’ve learned about working remotely for a fully-distributed company

• It’s amazing!
• Communicating almost exclusively via typing requires you to a) be good at typing (which was something I was not actually very proficient at until last year) and b) master the tactful use of emoticons, not too much and not too little.
• It’d be nice to be out of the house more, but that’s also a pandemic gripe too.
• I’m so lucky I have a partner that keeps the kids out of the office, lucky to have a good space from which to work from (and a door for my office).
• I’ve never met any of my teammates in person but we meet every week on Zoom and I feel like I know them reasonably well.
• In a company where everyone is remote and everyone has different schedules, everyone is committed to working asynchronously and responding (thoughtfully, in writing) when they can, not as soon as they can. It feels much more balanced by default.

Things I’ve learned about working for a smaller company

• Automattic is not that small anymore (~1000 people) but it’s a grain of sand on the beach that was my previous company. There is a bit more of a camaraderie I feel with my colleagues because of this I think.
• There are the same work and company gripes everywhere. Leadership is losing touch with what matters. The product is going in the wrong direction. They are universal laws.

Things I’ve learned about technology

• MacOS is great once you spend some time with it, but so is Windows. You can’t convince me that one is better than the other.
• We use two tools for communication internally at work. One is Slack and the other is P2. Almost everything that happens here can be seen/found by anyone else. Almost no email. There are bad habits or behaviors that can happen with any tool, but the transparency this facilitates is truly great.
• I learn about a new tool or service or bit of tech every week. There is so much more that I have been exposed to in the work that I’m doing now.

Other things I’ve learned (or been reminded of)

• There is always someone who knows more than you do.
• Being a good listener, being curious, and asking good questions will help you solve almost any problem.
• You might not mind wearing your pajamas all day from the day before, but don’t be surprised when your son or daughter says bluntly, “You stink!”.
• One of the things I like to do on our Zoom calls is to draw portraits of my team members on camera. Aside from wanting some drawing practice, it also helps me listen to the meeting and not get distracted by other things on my screen. The series to-date is below.

I think you can probably pick-up on the fact that I’m enjoying myself at work. I’d go even farther and say that I am having the most rewarding experience professionally that I’ve had in at least 10 years. Looking forward to year. 😃