A Day in the Life of a WordPress.com Happiness Engineer

This post is part of a series describing what Automatticians do on a daily basis. You can read more posts like this by following the tag #a8cday on WordPress.com and Twitter.

Hi! I’m Tish, and I work as a Happiness Engineer at WordPress.com.

I get asked a lot what it means to work from home, on a remote team where my coworkers live all over the world. So today I’m giving you an inside look into my day and schedule.

My days rarely look the same, because I love the variety. I’ve structured my Mondays to be my “long day” since I tend to get a lot of work done, so I work from 9am – 7pm.

This is what my Monday looks like:

sleep7am: My alarm goes off, but my alarm knows that I only set an alarm for this time because I hope that one morning I’ll wake up and be a mythical creature called a “morning person”. Groan. Nope, still not a morning person. I turn off the alarm and go back to sleep for another hour and a half.

8:30am: I begrudgingly get out of bed and get “dressed for work”. Today I’m wearing my favorite sweat pants and my WordPress shirt. I grab a banana for breakfast and since I’m not a coffee person, a glass of water. It’s 8:40am and I decide still too early to “go to work” so I go back to bed for another 15 minutes. I mostly make a mental list of everything I need to do. Then I get out my phone and check Slack, to see if any pings came through. I read through any backscroll that happened the night before.

Working from the couch

8:55am: I’m officially out of bed. I have a live chat shift starting at 9am, but I’m not quite ready to go sit at my desk. So I take my laptop and sit on the couch, under a blanket. I also check my team’s p2 and spend a few minutes reading through posts and comments. I open the p2 posts I’d like to comment on/keep an eye on the discussion in a new window and then using my FAVORITE browser extension in the world called Tab Snooze, I set those windows to close and open in a few hours. This is my version of organizing my window tabs in a To Do List.

9am – 11:30am: I start live chatting. I signed up to live chat for 2.5hrs this morning, helping the users of WordPress.com. It’s pretty busy for a Monday morning. Within an hour into my shift, I notice things start to slow down. So I start answering tickets (emails) that came in, between replying to live chats that pop up. Mostly I’m helping users with their domains, one person needs help setting up their theme, another person has a question about CSS. All pretty normal questions for a Monday.

A tricky chat pops up that I’m having a hard time figuring out, so I send a Slack ping to a teammate and ask for help. I immediately get several replies, which help me get to the bottom of the issue. I honestly don’t know what I’d do without my super helpful coworkers. I get a reply to the user I’m live chatting with right away and we resolve the issue fairly quickly. They’re super kind and thank me, if only they knew the magic behind live chat was teamwork.

Working while out and about

11:30am: My live chat shift is over, so I log out and say Bye to my team. I get dressed into clothes I can wear outside and leave my apartment. I bring my laptop, since I plan on working while out and about.

I work for an hour and a half at the restaurant I had lunch at. The food is good and they have fairly decent wifi.  I try to work outside of the house at least once a week, either at my coworking space or a coffee shop/restaurant around town. I spend my time replying to tickets that came in. Then the p2 posts that I set to open later via Tab Snooze pops up, so I finish reading p2 posts and leave a comment or two. When I first started working at Automattic, I had a hard time commenting and being active in p2 posts, since I’m naturally very shy. I still have a hard time with it, but I regularly set aside time to participate and by picking out posts first thing in the morning that I’m interested in, this helps me be active here.

While I work, I keep Slack open, checking it for ongoing conversations or calls for help. This time I notice a trial asking for help with a live chat, I jump in and immediately reply. Helping them troubleshoot the issue. Within a minute or two, they seem to have a good handle on the issue, so I check all the other Slack channels I’m in, reading the backscroll, which mostly consists of troubleshooting, witty batter, and generally just Automatticians helping each other. While I scan through the conversations, it hits me how amazing this all is. Most of my coworker’s avatars look familiar to me, I see them on a daily basis in Slack. I’ve met most of my coworkers at least once, but it’s been around 4-5 months since the last time I saw them (at the Grand Meetup). The way they type is so familiar to me, it’s like I can almost hear their voice. Some avatars are newer, I haven’t met them in person before but I see them often around Slack and while I can’t hear their voice in my head, I already feel like I know them. And then finally there are some avatars, I’ve never seen before- they may be a Trial or Support Rotation, so they’re brand new. I do my best to keep an eye out for them and their calls for help. But whether new or not, no matter location (some of my coworkers live in another country or are half way across the world from where I sit here in Southern California), we work as a close unit troubleshooting issues. It really is amazing to work on a team like this.

Working from the patio

1:30pm: I head back to my apartment since I have a live chat shift starting at 2pm. It’s a beautiful day outside, so I decide to work outside on my patio. I answer a few tickets and then jump back into live chat.

By 3pm, it’s starting to get a bit colder (it’s been raining a lot lately), so I head back inside and for the first time all day, I work from my desk. Even though I’ve been hard at work all day, I officially feel “at work” now that I’m sitting at my desk. Funny how where you sit impacts your mindset like that.

Live chat slowed down a lot, since we’re well covered… so I let my teammates know that I’m switching to tickets. I still keep live chat open, but mark myself as “away”. I check in every 15 minutes or so to see if it’s picked up. Which it hasn’t, so I stay in tickets. I do my best to go wherever I’m needed most.

In between tickets and chats, I chat with my coworkers in Slack. The day is starting to wind down for most of my coworkers that live on the east coast of North America. The Slack chatter starts to slow down a bit during this part of the day.

My Desk

4pm: my live chat shift is now over. I have dinner plans with family members tonight, so I decide to take a 10 minute break and relocate to a family members house.

4:30pm: I’m part of a group of Happiness Engineers that have been testing a new type of a support with new users, so I have 30 minute screen-share call with one of our users that has the Business upgrade. It’s like a phone call, only they can see my screen as well. It was super productive and we talked through items like designing their site and search engine optimization.

5pm: As soon as I’m out of my screen share call, I jump back into live chat for my final shift of the day where I work until 7pm.

When I jump back into live chat, I note some of the new avatars appearing in Slack, it’s my coworkers coming online that live in Asia-Pacific/Australia. While I only have a few hours left online, their day is just starting. It’s kinda amazing how no matter what part of the world we’re in, we continue to work together like a cohesive unit.

I’m mostly helping users to get started with their sites, another user wants to embed a video on their site I help walk them through each step. Then another user pops up and needs help with Twitter Cards. I know we integrate with Twitter and I feel like we already have Twitter Cards integration built-in, but I can’t remember. I do a quick search through our internal documentation for Twitter Cards, and I still can’t find what I’m looking for. So I do a quick Google search. Something pops up on Twitter’s documentation, ah ha! WordPress.com already has this built in. Great news! I let the user know and I make a note for myself since we should probably add this to our internal documentation. So I set this tab to pop up later (using Tab Snooze) in a few days, since I won’t have time to write that up now. I keep chatting with our users all the way to the end of my shift.

7pm: I log out of live chat and then have dinner (pizza!) with some of my family members.

by 11pm, I’m back home and I go to bed. Then I remember I forgot to post my weekly update to my team’s p2 (which we try to have posted on Mondays) so I post it from my phone and then go to sleep.

Two for one deal: Tuesday’s schedule!

Also a bonus, just to give you an idea on the variety between my days I’m going to give you a look inside my Tuesdays as well!

Tuesdays are in stark contrast to my Mondays, in that they’re my “short day” (I only work 5hrs) and I don’t do any live chatting. Tuesdays are also the day that I have my team call and my 1:1 with my team lead. It’s really the only time I “see” my coworkers (via video chat) all week, so it’s my favorite day of the week.

mornings7am: Alarm goes off. I check to see if I’m a morning person yet, I’m not. So I go back to sleep.

8am: I realize that I have my team chat today, which requires an actual outfit. So I begrudgingly get out of bed and have breakfast, shower, and wear normal clothes. Since I actually like my team, I don’t want them to have to experience “Morning Tish” aka grumpy-messy hair Tish.

9am: I start work, today I go straight for my desk. This morning, I’m sitting in on a presentation via Zoom that is specifically on a Diversity and Inclusion topic. Today, it was on viewing the company from a non-North American point of view. A good portion of the company doesn’t live in North America, so I found the presentation completely fascinating and took notes of tips that I plan on implementing when communicating with coworkers that are not in North America (example: not using my own time zone when scheduling rather communicating in UTC timezone).

10am: My calendar alerts me that I have a live chat shift? I panic for a moment, and double check the schedule and found my calendar was wrong. So I shift to answering tickets. Then I check my team’s p2, I catch up on comments and read through my teammate’s weekly updates. I love hearing about what they’re working on.

excited11am: Team call!! I’m not even exaggerating, this is a highlight of my week. The Happiness division is rather large (with over 100 Happiness Engineers) so we’re broken into smallIer teams. My team Sparta, consistents of 8 HEs that live mostly in the western half of North America, so we’re all roughly around the same timezone. This means we’re usually online at the same time. I really do adore my teammates and getting to work with them on a daily basis is amazing. We all log onto our Zoom call and spend 15 minutes just chatting (we somehow got on the subject of cleaning coffee machines). Then we discuss any agenda items we submitted for the call. We discuss goals, weekend coverage and shift around a bit to make sure we’ve got it covered for the upcoming weekend, we figure out who is taking time off in the upcoming months and generally just plan ahead. The conversation flows easily and it was a super productive call! We run a few minutes over an hour and end by 12:05pm.

12:05pm: I take a 10 minute break and go for a walk to go pick up my mail. It’s not far, but I take my time and enjoy being outside for a few minutes.

12:15pm: I’m back at my desk and I start going through my notes and to do list, figuring out my schedule for the upcoming weeks. Then I research a tricky ticket I’ve been trying to figure out, and reply to that user.

1pm: 1:1 call. This is a call I have scheduled with my team lead, Jeremey. He is awesome btw! We chat about upcoming goals, my travel plans (I leave in a few days for Europe) and I bounced a few ideas off of him. It was a great chat and I love that we have a weekly call scheduled. Definitely, helps keep me on track.

1:30pm: I have 30 minutes left for work today so I start writing a p2 post idea that came up with Jeremey in my 1:1 call.

2pm: I log off and call it a day!

Now that I’m no longer working, I spend my day running errands.


So there you have it! That’s what several of my days look like. If you’re interested more in how I schedule myself as a Happiness Engineer that focuses on live chat, read this.

Interested in Automattic? Apply already! 😉