Automatic Grand Meetup 2016

I recently attended my sixth Grand Meetup, the yearly tradition at Automattic where the entire company gathers together for a week.

This year’s GM is a blur, as usual. I taught a class on user interface design (my first time!), played in the Automatic band, had lots of one-on-one meetings, spent a full day with my entire team, and saw lots of new (and old) friends at some great lunches and dinners.

On Threaded Comment Design

Rian Van Der Merwe has an excellent write up on designing comment threads, comparing Reddit, Facebook, NY Times, and more.

I really dig the explanatory graphic he made to show the different approaches:

We’ve been working on the comment design for’s Reader, and this post falls in line with our thinking. Here’s some of the early concepts we pondered as we built the latest version of Reader:

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Commenting Flow Take 2


Why I tend to work at night.

A while ago, I read an interested post about “why programmers work at night:”

Working on large abstract systems involves fitting the whole thing into your mind – somebody once likened this to constructing a house out of expensive crystal glass and as soon as someone distracts you, it all comes barreling down and shatters into a thousand pieces.

This applies to designers, too. My job as a designer is more than just designing and coding individual screens — I’m usually focused on how this whole “abstract system” (a collection of screens in a varied number of flows) looks from the outside. This takes time. Uninterrupted time.

…programmers work at night because it doesn’t impose a time limit on when you have to stop working…

This is the big reason. Sitting down to work at 10pm gives me about 4 hours of uninterrupted time. Time I can use to fit a complicated system into my brain, and make it better.

Old and Unpublished: The 5 Strangest Things About Having a “Real” Job

I wrote this list over 4 years ago (June 2, 2011), right after I started working at Automattic. I don’t know why I never published it, but here it is:

  1. The paycheck. It’s been a long time since I’ve gotten a regularly scheduled paycheck. Even though I’ve only gotten one paycheck, its still a nice feeling to know another is on the way in a few weeks.
  2. Co-workers. Its been a while since I’ve worked with someone on a regular basis. Its nice to have people around who you can get to know and form friendships.
  3. Asking for help. Having others around to ask for help is so valuable. Google can only go so far.
  4. No clients. I don’t have to be constantly thinking about client reviews, timelines, billing, and other crap.
  5. Vision. As a freelancer, I was often left out of the decision making for the future of the project. Though I’d try to influence my clients, they often ignored my comments. As an employee, my main job is to help create this vision. And then I get to work towards making it a reality.

Automattic Meetup


I was fortunate enough to travel to Budapest, Hungary with the entirety of Automattic. It was amazing to meet everyone face-to-face, finally putting speech and mannerisms together with written words and code.

One of the many highlights of the trip was getting to work with some people I don’t normally interact with — having some of my designs/code launched on was another amazing experience. Keep an eye out for the new post-post page; the screen you see after you publish a post on

My Support Rotation

All new “Automatticians” are required to spend three weeks working as a “Happiness Engineer,” reviewing and answering customer support emails. I wasn’t entirely thrilled with this requirement when I first heard it. But, I figured at the very least it’d be a good way to get to know some other coworkers, and ease my way in to the company.

At the end of this week, I’ll be wrapping up my time as a Happiness Engineer. And while I still have a week left, I feel like I’ve already learned so much about, the people who use, the Happiness team, and Automattic in general.

I’ve learned that I really enjoy helping people. Particularly, I enjoyed writing my replies. Even though I was often typing similar responses, I found myself trying to find the perfect tone and voice. I’ve been really focused on finding the best way to answer a question or provide information so that its easily understood. Its been strangely fun.

I’ve learned “alot” about Automattic, the company. I’ve learned that its a company of very smart people, always willing to help. I’ve learned that I’m free to do what I feel is right, and ask questions when I’m not sure. I’ve learned that even though you’ve never met, or even spoken to someone, it doesn’t mean you can’t “get to know” them. I’ve learned that email isn’t required. I’ve learned how to say “a8c.”

I’ve learned that customer support, no matter what you call it, is hard work. I’ve learned that someones probably written an detailed explanation in the Field Guide. I’ve learned that no matter how nice you are to someone, they can still be mad at you for something you didn’t do. I’ve learned that I’m really slow. I’ve learned to look at the history tab. I’ve learned that the Hapiness team is incredibly tuned-in to the current state of the company, products, teams, and so much more.

I’ve learned “alot” about over the last few weeks. So much so, that I’ve gained a whole new respect for the platform. Its done so much for writers, small business, and anyone looking to create a blog.

Since my initial hesitation, I think my time spent on the Happiness team was well worth it. I think its made my transition with the company much easier, and I’m glad I’m here for another week.

But next week. Next week is when I settle in to the Vault.

The New Job

Just a few days ago, I accepted an offer from Automattic. I’ll be the designer for their (our?) VaultPress product.

Upstate Interactive isn’t going away. Over the next few weeks, I’ll be passing control of the business to Andrea Dominick. Andi started out as an intern a few months ago, and has quickly show that she’s ready to take control!

I’ll write more about the job and what’s happening with UI as we approach my start date.