Sh*t my brain says and forgets about

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Farewell, Automattic!

On April 3, 2013, I was sitting in the #devmke Freenode IRC channel talking to other developers in the Milwaukee (Wisconsin, USA) area. I saw a conversation about one of the people working from home and thought, what an incredible place this must be to work! For some reason, I had heard the name Automattic before – and after landing on the homepage, I realized why! It was because of WordPress and specifically signing up for to get an Akismet API key to prevent comment spam. When I saw a Mobile Wrangler job posting, I immediately applied. I got the offer in May and started near the end of July 2013.

Without really exaggerating, working remotely at Automattic has literally saved my life. I’ve learned more about how my mind works, how I approach work, what relationships mean to me, and what value I can bring to an interaction. I’ve learned how to lead like Aaron, embracing my own unique style of seeing the universe and helping inspire others to connect and create outcomes.

Every year (pre-pandemic), every Automattician would get together in one location for a week – called the Grand Meetup. My heart is sad that I won’t be at the next Grand Meetup. That annual event has created some of the fondest memories of my entire life. I’ve become friends with people that I still have yet to actually work with directly. That’s the power of the system there – we value our connections over the work. With those connections, we overlay the work after. I can’t tell you how many times I’ve turned those lunchtime conversations at the GM into conduits to get things done later. Meetups are critical to Automattic’s success.

DJing @ the 2016 GM – photo by clickysteve

Some of the highlights of my time at Automattic was with helping organize several of the Automattic Grand Meetup closing parties. In 2015 it was with the first Automattic band performance and the Jane Doze DJing, 2016 with a coworker and me DJing, and 2017 with MICK DJing. This all came from me plugging my phone into the PA system of the dinner tent in 2014, playing some of my favorite songs. Our favorite Chief of Staff, Rose, noticed everyone enjoying themselves and pinged me to help out in the following years. Little did I know that I would be negotiating performance contracts and coordinating an audio and lighting production crew in the next months. What a rush. Seeing the look on Matt’s (the CEO) face walking into the ballroom before we opened the doors in 2015 was the best payoff ever.

Trying out the photo booth before the 2015 GM

For the last four and a half years I’ve been leading the Woo Mobile product teams, and it has been a joy. I started the team with just one other person and grew it into the group of 30+ people it is today. Mentoring & coaching four leads made me see how I could be a better engineering lead. I also got a chance to develop product management skills, wearing multiple hats. I’m so proud of everyone on the team (and everyone else we’ve worked with!) for getting the product to where it is today. I feel like I am leaving at a high point in my career there. Nine years will have been the longest I’ve ever been at a place before.

Automattic has been a great home for me and has helped me through a lot of bad times and given me a lot of good times. It wasn’t my intention to find a different place to work. I started looking at other companies for inspiration on defining my role better and for seeing where I should aim my career at. The side effect of that research was a little spark of excitement forming to try something different. Life is too short to not take some risks once in a while.

My last day at Automattic was Friday, June 3. I spent the last couple of weeks passing the baton off to a teammate and getting as much as I could out of my head for others. I had 1:1s with my boss, my team leads, and other Automattic employees wanting to say goodbye.

Those two weeks were tremendous in helping me process my exit. I posted my farewell notice, told the team, turned in my hardware, filled out the exit survey, had a final 1:1 with my HR rep, DJed one final Friday jam session, and then attended a farewell Zoom I planned. My team put together a very thoughtful farewell video and organized a couple gifts for me which were amazing. I definitely felt the warm fuzzies and the sense of loss we all were feeling. What a great group of humans! 🥰

I didn’t stick around for my access to get cut in Slack – it was already an emotional day and waiting for that felt unnecessary. I walked away from my last day feeling a bit lonely which is certainly an artifact of not being in an office with other humans.

The departure process at Automattic felt anticlimactic. I’m not sure what else I had expected to happen, honestly. They celebrate new hires, new houses, new partners, and new babies, but don’t really celebrate someone leaving at a company level. My farewell post had a LOT of heartfelt goodbyes and the process of reading and replying to them was cathartic. It helped me recognize my true impact on the company by hearing the stories of how I’ve helped shape the culture there and affected so many lives. That was priceless.

On the exit survey, Automattic asks “would you consider ever coming back to work at Automattic?”. I answered truthfully:


What’s next? More details to come. 🤫

Ninety days of getting paid to not work

Yesterday began day one of 90 that I’ll be taking as a sabbatical from work.

Every five years at Automattic we’re given an awesome gift of a paid sabbatical – something I’ve never dreamt possible in our current age. The word “sabbatical” is heavily laden with teaching references. Even dictionaries reference education in its definition:

sabbatical | səˈbadək(ə)l |
a period of paid leave granted to a university teacher or other worker for study or travel, traditionally one year for every seven years worked: she’s away on sabbatical | he requested permission to take a sabbatical in Istanbul | he took a three-month sabbatical from his job as CEO of a family business.

What am I planning on doing with this time I have? A whole lot of nothing. Well, not really, but I’m keeping my plans simple.

  • Spend time with the parental units. Learn a bunch of recipes from my mom that I want to know how to make.
  • Get close to riding 100mi in one day on my bicycle.
  • Build something with wood or metal like a chair, shed, etc.
  • Read a bunch.

Ninety days will go by super quick. Here’s to making each day last.

My Two Favorite Logos

Here is a photo of my two favorite logos – the Jetpack logo and the That Conference logo.


Jetpack is a plugin you can install on your WordPress site to give it super powers that sites have but still self-hosted on your own servers.

That Conference is an awesome community tech conference that I’ve blogged about before. I’ve spoken there a number of years and really enjoy the mix of people and personalities it brings. Plus it’s at a waterpark and families are not only welcome but integrated into the conference itself. I’ve seen some pretty smart children giving awesome talks!

The MacBook Pro with the custom Jetpack logo is part of my four year anniversary gift for working at Automattic. We get to pick any one of our product logos or the Automattic logo. Here’s to another four! Thanks, Automattic. 😉

This is what 400 Automatticians in one place looks like from a drone

Watch the drone video below taken at our annual Grand Meetup in Park City, Utah October 2015:

Tater Tots Through Time

Every year at the Automattic Grand Meetup the entire company gets together in one place for a little over a week to work and have fun. Part of that meetup requires everyone to give a four minute flash talk on any subject. This year my coworker Carolyn Sonnek and I decided to team up on our flash talk.

Carolyn and I are Tater Tot experts. EXPERTS. We dug deep and found some interesting facts on Tater Tots and even a conspiracy! Supports (RED).org

I’m proud to say that Automattic / is a supporter of – the foundation started by Bono and Bonny Shriver to help prevent and cure AIDS. recently moved over to VIP hosting and we partnered with them on producing an official (RED) shirt for all Automatticians. This is definitely my favorite piece of Automattic swag :).

Me wearing a t-shirt

The Compression of 400 Teammates

I work for Automattic, a 100% distributed company. We rely upon meetups with our teammates to power the social aspect of our jobs and to work on short-duration high-velocity projects. Every year we also partake in a Grand Meetup where everyone gets together in one place to work and socialize. This year we were back in Park City Utah at the Canyons Resort. Here’s a wrap-up of what I did during the eight days there.


Last year I taught an iOS class to about 10 people. The focus was on the WordPress for iOS application and to get them to become contributors quickly. This year I taught an iOS class again but I shifted from the complex WPiOS app to teaching Swift and how to start an app from scratch. The class ended up having almost 30 students.

The first day we spent most of the day on Swift. The rest of that day and the entire second day focus on Storyboards and Autolayout. I created a demo application prior to the GM which demonstrated a bunch of core concepts including timers, local push notifications, Core Graphics transformations, app lifecycles, storyboards, autolayout, and debugging techniques.


Everyone walked away with enough knowledge about Swift, Xcode, and iOS to get involved in a project or a more complicated tutorial. It was hard coming up with a curriculum that fit the vast range of experience the students had but I felt it worked out well.


I organized two different workshops which were both held at night after dinners. The first workshop dealt with managing your attention at Automattic. The second was a forum/roundtable for all of the mobile developers at Automattic.

I’ve mentioned before on this blog that I’ve been dealing with ADHD for some time – mainly since starting at Automattic. Over the past 2 1/2 years I’ve amassed knowledge and tools that can be applied to everyone working here, not just those with ADHD. We had a great discussion and discovered that we all have our own unique challenges with our work habits.

The mobile roundtable was also a success. When I first started at Automattic all of the mobile developers lived on one team. After about 6-8 months it was decided that we split the team up and embed mobile devs on product teams. This completely made sense and it has been a success since. The one thing that I miss from “those days” was a tight connection between all of us. We still try to hang out in the same Slack rooms but it is hard for new hires to get connected in the same way. The roundtable gave us a chance to talk about things that affect all of us and to make sure we all see faces with the names.

Outside Activities

Part of the Grand Meetup is set aside for doing activities with your teammates. This year I organized a guided bicycle tour around Park City. I did this last year but with only seven of us – this year it ended up being around 60 people over four time slots.

As Automattic grows we have to accommodate more people in these planned activities. I knew going in that it was going to be a challenge to coordinate people signing up internally and getting those details to the shop to allocate bikes. I started communicating about a month prior with the shop and ended up working directly with the manager/owner. Each planned activity had to accommodate up to 80 people in order for it to be on the master schedule. 80 was going to be a stretch with the shop, but they said they could do it.

Of those 60 people I think we ended up with 50 that attended. I made sure everyone got an Automattic “Poetry in Motion” fitness shirt if they desired one and worked with our activity planner to get boxed lunches arranged. It was a lot of wrangling but I actually had fun doing it. Nearly everyone who went said they had a great time and couldn’t wait until next year.

Flash Talk

Every Grand Meetup you’re expected to give up to a four minute talk on any subject. One of my coworkers, Carolyn Sonnek, and I decided to do a group talk on tater tots. I think you can see a theme here.

The talk ended up covering the history of Tater Tots and then uncovered a grand conspiracy surrounding them. When the videos become available I’ll make sure to post it here. 🙂

It ended up being super hilarious and a lot of fun to work with Carolyn on.

The Party

My coworker Rebecca Collins and I planned most of the closing party the last night of the Grand Meetup. It started out with the idea that we’d shuffle a playlist on a set of speakers. Then a couple weeks out it ended up that the two of us were to get some talent in and make the night AWESOME. So, we made it awesome.


The evening started off with a number of our fellow Automatticians forming a band which was organized by Carly Stambaugh. The music was great and it was surreal seeing your coworkers showing their rockstar nature. It was EPIC.

After the band finished their set the special guest came on, The Jane Doze. They rocked the Kokopelli Ballroom until midnight with dance music that made everyone get up and party. Between the lighting, decor, photo booth, glowy paraphernalia (sticks, rings, bracelets), and custom cocktails it was a sight to see and hear. It took a lot of effort from everyone involved in the planning but it was a clear success. As soon as Rebecca and I saw the looks on people’s faces it was obvious we pulled it off. 🙂


Coming back from a Grand Meetup means a depression sets in. Another Automattician, Maria Scarpello, posted on the realness of the post-GM blues calling it decompression. She alluded to it being very similar to the decompression that happens after attending events like Burning Man. It’s nice having a name for the condition and knowing you’re not the only one.

This year, for some reason, I didn’t feel (or haven’t yet felt) the decompression. I very much felt energized after coming back home to kick ass at what I do. I seriously miss my coworkers and know that most of them I won’t see until next year. I’ll get to see the people on my team sooner, of course, but being around the group as a whole is a ways away again.

Next Year

I really can’t wait for next year’s Grand Meetup. The effort I put into it this year was totally worth it.

And PS if you want to be there for the next Grand Meetup, Automattic is hiring!

2014 Automattic Grand Meetup

At Automattic we all are a distributed workforce – we all work from all over the world.  Every few months we meet up with our teammates and work on projects designed to be started and finished within the week.  Once a year the entire company gets together in one place and we affectionally dub it the “Grand Meetup” (abbreviated GM).  This year, we all met up in Park City, Utah USA at the Grand Summit Canyons Resort.

We do a lot of things at the GM.  Primarily the GM is meant to be a restorative time to emotionally connect with our peers.  This comes in the form of group lunches and dinners, flash talks, recreational outings, and just sitting on couches talking over a coffee or beer.  Since we don’t often get to see each other (especially those of us who don’t directly work together) this is a chance to establish the inner voice we have that represents someone’s online persona.  When we see each other online after a GM, we can emote better because everyone has gotten to know our personalities.

We also are required to pick one of three things to do for real work during the GM: work on a project (to be assigned), work on your day to day project if you need face-to-face time, or participate in a learn-up group (teaching or learning).  I ended up choosing to teach a class on iOS development to seven other coworkers.  It was fantastic.  Almost everyone submitted a pull request to WordPress-iOS by the end of the class.

I didn’t take a ton of photos at the meetup but here are some of my favorite:

Tokyo Mobile Meetup January 2014

In January 2014, the Mobile Team at Automattic met in Tokyo Japan for our quarterly face to face meetup. Here are some of the pictures I took from the meetup. It was a great experience and I would definitely go back to Japan!

Working at Automattic

Some people have asked me what it’s like working for Automattic.  Every employee of Automattic has a different perspective on what it means to work here.  Here are a few things I feel are important to me.

Work Wherever, Whenever

Automattic is a completely distributed company.  We have a headquarters in San Francisco, CA USA but only a small percentage of us work out that office.  Most of us work from home, some of us work on the road, others work from a coworking space.  Sometimes it’s nice being able to change your location once in a while – I pretty much like working from my home office.  I like working a regular day, usually 7am – 4pm my local time and I fit some sort of exercise routine in there half way through.  We have flexibility to make our own hours and take the time off we need to.  We’re adults and we’re treated as such.

Equipment for your Job

First thing asked of any employee starting is to order their computer.  You’re allowed to order the equipment you need for your job – usually a Mac laptop and a large display.  You’re also given a budget amount for your home office furniture – desk, chair, lighting, monitor arms, etc.  I got a really nice standing desk from UpDesk and a Herman Miller Aeron chair.  I love standing during the day!

Your Team

Everyone at Automattic is on a primary team, sometimes on a secondary one as well.  We work virtually using IRC, Skype, and private blogs to communicate.  Sometimes we even do a Google Hangout when we want to see face to face:

Group Hangout

The Automattic Mobile team Hangout this past week


One every 3-4 months you meet up with your team in real life.  In January our team met up in Tokyo, Japan.  We spent seven days coworking and having fun at night.  It’s a team-building exercise as well as a chance to get some high-velocity work accomplished.  It’s a great way to recharge your team dynamic and to meet the new people!  Once a year Automattic hosts a Grand Meetup when we all converge in a single place.  We like to create special teams for the GM and either ship new real features within that week or do code training teams.  It’s a great way to meet people outside of your normal team and fun to boot!


It takes the right person to work at Automattic.  You have to be a self-starter and have the ability to stay focused on your work.  I’ve discovered more about myself than I thought I would almost immediately and working here has made me a better person.  Every position, regardless of it being technical or not, goes through a multistep process for hiring.  Matt Mullenweg, the founder and CEO, reviews every application submitted to Automattic.  If an application passes his muster, it’s forwarded onto the team or teams responsible for hiring.  The hiring lead reviews the application and scheduled a text-based Skype chat to see if they’d be a good fit for the position and company.  One or more people from the destination team may be involved, too.  If that goes well, the applicant is directed to complete a pre-trial project.  This small unit of work will show the applicant’s domain knowledge and ability to communicate.  After the pretrial work, if the team agrees to move forward, the applicant enters into a trial period.  You are paid to work on a part time basis with your team on a real piece of work.  This is your chance to integrate with Automattic and immerse yourself in the culture.  Take it all in – the process is a trial for Automattic to hire you and also a trial to see if you’re going to like working here.  If the trial is a success for both sides, then Matt makes the final call on hiring.

It’s not the fastest hiring process, but it’s definitely the most straightforward and transparent hiring process I’ve ever been involved in.  It takes about a year, so I’m told, to get a real grasp on all of the moving parts at Automattic.  I’m still learning every day and continue to work on how I want to accomplish my work every day.  It’s a lot of fun and rewarding!


We’re Hiring!

We’re always looking for more people to join Automattic.  Take a look at the open positions and apply if you see something you’re interested in!

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