That’s what I wear to work every day and I wouldn’t change it for the world.
A year ago I finished up my “trial” with Automattic where I performed contract work for 6 weeks as I learned the role, exhibited my work habits, and showed my value. I was passed along to our CEO Matt Mullenweg for one final chat during the hiring process. Our chat lasted a few hours and at the end I found myself with a job offer. The next morning I put in my 2 weeks notice with Atomic and was on my way to no-pants-land once again (except I wear pajama pants every day, actually).
See, I had worked for Geek Squad Online Support for a few years towards the end of my college career. The job was alright but I found the remote experience pretty boring even though Anthony was (and still is) working from home as well. Geek Squad Agents that work for Online Support rarely met each other in person, I think I’ve met a total of 3 Covert Agents. I wasn’t too excited about this environment long-term which is why I left for a “big girl job” shortly after graduating.
For a while, I enjoyed socializing with co-workers again and having company outings. But after about a year of working in an office setting, I realized it just doesn’t truly fit my needs. I detest driving to work and having to take a 1 hour lunch. I’d rather spend my time more wisely which I can do from home. Just by cutting out the commute I save 1.5 hours per day – a whopping 7.5 hours per week! I also feel more efficient working from home and I have the added benefit of socializing with co-workers with all different interests and from all different locations and walks of life. Plus, I get to spend more time with Anthony and my pets by working from home!
If you haven’t heard, Automattic is a “distributed” company. What does distributed mean exactly? It means that we have employees across the world in all different countries working at all hours. Essentially we’re 24/7 due to our geographic distribution, and it makes for one heck of a workplace.
Because Automattic is distributed, we place an emphasis on meeting co-workers and socializing. Once a year all 500+ employees year meet up (in Whistler, BC last year and this coming year) and work together for a week on projects, attend classes, and more. There are endless fun activities to participate in such as zip lining, gondola rides, biking, photography, escape rooms, and more! There’s also no shortage of food (including specialized meals for those with different diets) and also alcohol.
Aside from our yearly “Grand Meetup” we also meet up at least once per year with our individual teams. My team is Athens and this last year we met up in Washington, D.C. I primarily planned this meetup for myself and 8 team members. We rented 3 rowhouses near H Street and throughout the week we had a great time with team building exercises including a Strengths Finder adaptation of D&D, a food tour, a tour of the DC mall, a free day, loads of delicious restaurants, and more.
Meetups are great but they’re only a few times a year at most… how about something more local? You got it! Local “Automatticians” often meet up when time permits. For example, when I lived in the Dallas area the “Dallasmatticians” met up every 2-3 months at local coffee shops or co-working spaces to catch up, get some food, and do a mild bit of work in each other’s presence.

Since moving to the Richmond, VA area a week ago, it seems there’s only one other Automattician within an hour’s driving distance. That’s somewhat of a bummer but I think I may join the Automatticians in Washington, D.C. for their Christmas/Holiday/End-of-the-Year meal since they’re only a short train ride away.
You may be able to tell that I love the social aspect of this company. I’ve never felt alone or secluded since becoming a part of Automattic and I don’t think I ever could with all of the ways that we connect with others and encourage communication and relationships. I think this is something a lot of “remote” jobs could improve upon (wink wink, nudge nudge Geek Squad Online Support).
So what is it that I do on a daily basis? Well, it depends on several factors but here’s a general idea of how a day in the life of a “Happiness Engineer” looks… at least for me… sometimes.
Monday through Friday:
- Wake up around 8:30ish, potty the dogs
- Eat Breakfast – always paired with chocolate soymilk
- Catch up on relevant P2 posts
- Catch up on relevant Slack messages
- Have a 1:1 with my team lead (Cesar) – but only if it’s Monday
- Feed the dogs
- Live chat with users on WordPress.com through our HappyChat software – usually billing inquiries, tech support for websites, etc.
- Break for lunch for about 2 hours – sometimes I’ll run out to Jason’s Deli or another restaurant to pick up lunch
- Potty the dogs
- Every other Monday – have a meeting with my “mastermind” group consisting of Livio and Trevor where we chat about things we’re working on, hurdles we’re overcoming, and just life in general usually
- Chat again for 3 more hours with users on WordPress.com
- Wrap up my work day and usually do some chores around the house or spend time with my pets (including pottying them once more)
- Head out for dinner because we’ve both been home all day and haven’t hardly been out of the house if at all
- Catch up on some TV
- Remind Anthony to feed the dogs
- Potty the dogs
- Go to sleep
Saturdays and Sundays are quite bit more relaxed. I usually complete some asynchronous work for our users which consists of responding to email using the Kayako software. It’s similar to the work that I do via live chat only I can manage my time a little with a bit more flexibility. I also do this in the evenings and other spare time during the week.
It’s taken me a while to manufacture this schedule but I’m pretty happy with it. At no point during the day am I sitting at my desk for more than a few hours and usually I can find time throughout the day to run errands or work on personal tasks such as running a pet to the vet or making calls. Other Happiness Engineers lay out their days completely different, but that’s the great part about working from home and with such great flexibility.
Maybe you’re reading this lengthy run-on post about how much I love the job that I’m celebrating an “Auotmattiversary” for today and you’re thinking “that sounds pretty sweet”. If so, you should check out Sandy’s post “So You Want to be a Happiness Engineer, Huh?“. He’s a fellow Happiness Engineer and published this post a few weeks ago and I think it’s a great read as I often write about how much I love my job but not as much about what it takes to be an Automattician or a Happiness Engineer in particular. Check it out and if you decide to apply and need a recommendation let me know!
As for me, I’ll continue unpacking my house while working and awaiting for my new motorized standing desk (thank you Automattic!) to arrive. Once we’re all settled into out house here in North Chesterfield, it’ll be time for me to head to Whistler once again. 🙂
3 responses to “Pajama Pants”
Congrats on your one year anni at Automattic Carissa!
LikeLike
Thanks Hieu! Hope you’re doing well 😀
LikeLike
[…] but I feel like we were able to go and do more during this trip than we were able to do during our trip to Washington D.C. last […]
LikeLike