First week at Automattic

On May 19, 2025, I started a brand new chapter in my life—I joined Automattic! 🎉
(If you haven’t heard of Automattic, it’s the company behind WordPress.com, Tumblr, Pocket Casts, and a bunch of other great tools that support the open web.)

There were a lot of reasons I was drawn to this company, but the biggest ones were:

  • Its strong support for open source
  • A culture rooted in humility and helping one another
  • A deep commitment to diversity
  • And of course—remote work!

Working remotely has already allowed me to spend more time on my workouts, hang out with my dogs, and enjoy little everyday moments with my partner. 🐶❤️

My first week here was amazing. At Automattic, everyone starts with a two-week support rotation, where you dive into helping users directly. It’s a way to get familiar with our products, values, and the folks who use them—and honestly, I loved it.

This post is a little retroactive (I’m now wrapping up my second weekend), but when I think back, the strongest feeling that comes to mind is warmth. Everyone has been so kind and incredibly supportive.

I never once felt uncomfortable asking for help. In fact, I was actively encouraged to ask questions—by HR, my onboarding buddies, and honestly, just about everyone. I received so many cozy “hello!” and “welcome to a8c” messages (a8c = Automattic) that I felt inspired to sketch something about it. Here it is:

Week 1 (19-25 May 2025) illustration. It shows my character and 2 dogs waving hello (or howdy - the preferred hello at a8c).

I also did a few color comps for the sketch because I wanted it to be a bit more polished since I planned on adding it as the “feature image” of my introduction post at Automattic. This post is visible to everyone within the company!

Color comps for week 1 sketch

I’ll probably write a more detailed post about the first couple of weeks soon—there’s a lot I could share—but for now, I want to talk about the why behind this post (and the sketch that comes with it).


A Little Weekly Sketching Project

Toward the end of 2023, I realized how much I love making art—and I’ve been trying to get better at it since then. But there’s a catch: I second-guess myself a lot. Like, to the point where I don’t share anything I make because I’m too worried it’s not “good enough.” 🥲

It’s okay to keep some sketches to myself. But when the main reason I don’t share is shame, that’s not doing my confidence—or my growth—any favors.

So, here’s what I’m going to do:
Every week, I’ll draw one simple sketch. I’ll give myself a strict time limit of 1 hour, just to lower the stakes and keep perfectionism at bay. I’ve also designed a little character that I plan to feature regularly (at least in the beginning), and each sketch will be a small summary of my week—at work or otherwise.

Now that I’ve joined Automattic, my love for blogging has also been rekindled. So these posts will pair a quick weekly reflection with a sketch. I might also share them on my Instagram stories (we’ll see how brave I’m feeling 😅).

If you like the idea, feel free to join me! I’d love the company. ♥️

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