happiness engineer

How to Schedule Your Tasks with Calendar Blocks

As I’ve settled into my work at Automattic as a Happiness Engineer for WordPress.com, which is remote and requires self-discipline and managing my own time well, I’ve tried several different methods of scheduling my tasks and keeping track of my time. I used this method of calendar blocks for several months very successfully. (The past few months I’ve been trying a more digital bullet journal-type method, which I’ll share the details of soon, in case you’re not a calendar person.)

How to Schedule Your Tasks with Calendar Blocks by sarah.blog

Mapping out your day with calendar blocks isn’t anything fancy, but it can definitely get the job done if you’re needing to assign tasks to the hours of your day to stay on top of things.

This quote basically explains why it works:

“When it comes to task completion the major difference between a calendar and a to-do-list is that the calendar accounts for time. You’re forced to work within the constraints of the 24 hours that you have. Not only that, given that there are only 24 hours it also reduces the paradox of choice. This tends to be great for scheduling time for high-level creative output.”

Read more here: Why Calendars are More Effective Than To-do Lists.

So, how does this work for me as a Happiness Engineer?

Here’s a screenshot of a week of my calendar:

How to Schedule Your Tasks with Calendar Blocks by sarah.blog
click to see larger.

I tried to add a bit more detail in the tiny spaces than I normally would for myself, so hopefully it makes pretty good sense to someone who didn’t set it up. Note: Slack is our internal chat communication tool and p2s are our internal blogs where we document a lot of our work. We use these instead of email for most things.

How, when, and why did all of that get on my calendar?

I aim to fill it out a week or two ahead of time (at least in large part), but my official self-imposed rule is that it’s done by Sunday before I kick off the next work week on Monday morning. (I tend to add myself to the live chat schedule for a few weeks at a time, so those hours are usually ready to go quite a bit in advance.)

First I add any recurring blocks, like the team hangout on Wednesday mornings. If I had other groups to meet with, like the Training Guild, this is when I’d add those blocks.

I also add my live chat hours early. Live chat makes up a signifiant portion of my work, so it’s important to get it on there early. I tend to chat during similar blocks each week, so I have them set to repeat weekly and usually only have to do minor edits. If you have something that consistently repeats, consider making the blocks recurring so you don’t have to keep adding the same things week after week and Google handles it for you instead.

Next I block off any commitments I’ve made that are time-specific, like a trial buddy chat, a hangout or learnup I want to attend, or personal appointments (like when I go to the doctor). I add these as I agree to them, but this is when I’d check to make sure they made it on here, because it’s starting to be pretty full and soon there won’t be room.

I add a lunch hour at this point. It’s usually at noon, but shifts around based on the week. My afternoons go way better when I take the break, so whenever it is, I make sure it’s there as many days as I can. I close my computer and watch an episode of a show, read a book, play a game, or go out for lunch somewhere, or exercise, and then come back in an hour refreshed and ready to work.

Then I add Helpshift, which is a small portion of my work and very flexible, so I can squish it in where ever I’ve got the time. Next  I fill in the empty spots with project and dedicated ticket/forum time. I also work on tickets (or forums, if tickets are handled) when I’m in live chat and it’s slow enough to allow that, so these ticket blocks are extra time to really focus there, beyond what I get done while chatting. For project blocks, I add a note about what I’m going to be working on during that time, since I have a few different things I do outside of my usual support work. (See: the Instagram block on Thursday. I used that hour to look for sites to feature on the WordPress.com Instagram account, the create and schedule posts for the week.)

A few extra notes on why I think this has worked well for me: 

  • It’s flexible! I don’t let it feel like an over-scheduled trap. No one is in charge of it except me, so I allow myself to move things around as needed, or to switch gears if I blocked off too much time for a task. This is meant to be a basic layout of how my time will go and removes the time spent each day deciding what to do next. It can change whenever I want, and often does.
  • The blocks for p2s are not only for reading p2s, but also for writing p2 posts. I have many drafts floating around in my Simplenote. I’m trying to make an effort to finish them up and actually post them, so they’ve got official time on the calendar now.
  • I take short breaks throughout the day (every hour or so), but they’re so tiny they’re not on the calendar. Still, don’t forget those just because they’re not shown here! Your eyeballs need a break and your muscles need a stretch.
  • I add Reminders to my calendar for very specific tasks I need to remember to do at a certain time, such as a phone call to make or a domain to check on. They catch my attention, and will also keep following me around if I miss them, instead of disappearing in the past like a random calendar block would.
  • For more detail, I use IDoneThis to track completed tasks. My calendar is the overview and plan, while IDoneThis is the official record of what happened (completed tasks) or what has to happen soon (goals). I drop links to things I wrote, stats, project updates, etc. in there and use that to write my weekly update post each week (where my team shares an overview of what we each did the past week) and make sure to complete specific tasks that I may otherwise have forgotten. (I get the email each morning to remind me of what’s on the to do list there, and then reply to it with completed tasks throughout the day.)

And that’s it. (Ha!)

If you’ve struggled with managing your time or always seem to miss a task, give this method a try. It goes beyond the standard to do list, by making the space in your day to actually complete the task, which can be really helpful.

automattic, happiness engineer

A Day in the Life of a Happiness Engineer

I work at Automattic as a Happiness Engineer for WordPress.com. I’ve shared some details on what that’s like before (see here), but never a whole day play-by-play… until now! My day, as it happened on Wednesday, February 22, follows.

Note: The organization and demands of the job have changed quite a lot since I wrote this post, so it is no longer an accurate depiction of how a day would necessarily go. When I find a post with a good, current example, I’ll add a link here to update.

A Day in the Life of a Happiness Engineer by sarah.blog

7:30am – This is when my husband says goodbye and heads to work, so I start thinking I should probably get up too. I rest a while longer, then grab my phone and check Slack to catch up on my team’s channel plus a few others, and see what happened on Twitter overnight. I’m still not quite ready to get up, so I read a few chapters of a historical romance novel I’m in the middle of in the Kindle app. (Book: A Duchess in Name, The Grantham Girls #1 by by Amanda Weaver.)

8:50am – I jump out of bed and get dressed in real-ish clothes so I’m video-worthy, then I finger comb my hair, brush my teeth, grab a big ol’ cup of homemade cold brew iced coffee and a piece of toast, then wedge myself into the corner of the couch in my living room with my laptop propped on a cushion.

9:00am – It’s time for my team’s weekly video hangout. The ice breaker this week is about songs or playlists we use while working on tickets. My answer is very un-musical (except that one episode), because I tend to keep Buffy the Vampire Slayer on a loop while I work. I’ve seen it so many times that I can tune it out when needed, but I never tire of it so it’s nice to look up and see my old favorites anytime I want. When I do listen to music while I work it tends to be movie scores so words don’t distract me, although sometimes I can manage some catchy pop tunes while I live chat.

We use Zoom for our hangout, so we can see each other (in a Brady Bunch-style grid) and chat about a bunch of things, like helping another team cover their workload while they’re away for their upcoming meetup, a new feature recently added to WordPress.com we’ll need to check out so we’re able to support it well, and so on. We also had a special guest this week (our lead’s lead) so we grilled him asked him a bunch of very nice questions.

10:00am – A roofer swings by my house to give me an estimate on some work I need done. When he remembers I work from home, he asks what I do and when I mention WordPress, he lights up and tells me how much he loves it. He shares how he’d never imagined he could handle making his own website, and previously had to pay someone every time he wanted them to update the content, then a friend told him to use WordPress and the rest is history. I basically feel like a hero once he’s done talking about how great it is and how he’s glad I help people with their sites.

10:15am – I open my logbook (a personal p2 I keep in my bookmarks bar) and see what I’ve got planned for the day. P2 theme lets you post from the frontend of your site, rather than in the dash, so it’s nice for this type of work. (You can use the theme for your own logbook if you want!)

In my logbook, I make one post per day and it always includes a checklist that I refer to throughout the day. I also publish a monthly post that I keep pinned to the top with an overview of my month that includes any travel I have planned, time-specific appointments, project goals/deadlines, expense report reminders, and so on. It’s basically a very simple digital bullet journal.

Here’s February’s to do list:

my work logbook's monthly to do

And here’s February 22’s post (screenshot taken the following day):

my work logbook's daily to do for February 22

If I can’t get to everything one day, I make sure to carry things over into the next day’s post so it’s on my list again. I also reply to the post and leave comments throughout the day if I need to save reminders for myself, store URLs to tickets I want to check in on later, notes for bug reports, and so on.

I started this logbook back in October and it’s worked out really well. It helps me keep things all in one place more, rather than having notes in different apps and a mysterious in-my-head to do list. Plus checking boxes is fun.

10:20am – I usually live chat in the mornings for a few hours, but it was well-staffed when I went to schedule myself last week, so I’m on tickets (emails) this morning instead. First I check my replies and I’ve got one that gives me another boost:

“This is EXACTLY the help I needed to get going! THANK YOU for your assistance!”

The day before I’d walked through setting up a theme in detail and answered several questions about configuring this person’s site. When I look at it now, I see he’s done it all and his site is looking great. This is exactly the kind of thing that makes me happy to do this work.

I work on tickets in batches for almost two hours from my couch corner. I tend to claim a handful, work through them, then pop over to Slack to see what’s going on and say hi to my team, before grabbing more and going again.

12:oopm – I post a photo to the WordPress.com Instagram account. I started running the account a little over a year ago when I noticed we had one but it had no photos on it and wrote up a proposal about how I thought we should use it. I got the green light and have been handling it ever since. I share content from WordPress.com sites, and really enjoy searching the Reader to find new-to-me bloggers and websites to feature. I try to share a mix of food, quotes, DIY projects, travel photos, art, journal pages, style bloggers, books, and anything else that catches my eye.

Posting this photo right now is really simple, since everything is ready to go. I plan posts on Trello, which has a nice iPhone app, so I open it up, copy the caption and hashtags, save the image, and head over to Instagram to share. While I’m there, I also check for spam to delete, comments that need replies, and mentions to like.

12:15pm – Lunch time! Today I have salad and chicken tenders waiting, plus yesterday’s episode of The Mindy Project. I eat and laugh a bunch, which makes for a really nice break. I run and unload the dishwasher so my husband will load it as he cooks dinner tonight. This is pretty much the only chore I can manage during the day. When I try to do laundry, I end up starting one load in the morning and forgetting about it until around 5:30. ¯\_(ツ)_/¯

1:00pm – I write captions for a few videos I recently helped record for a video series I’ve been a part of making for over a year now. We record short videos with coworkers about what it’s like working at Automattic, what their application process was like, their favorite things and the most surprising things about the work, and more. The playlist for the series is on YouTube here. If you’re curious about applying for a job with us, I recommend checking out the videos. You’ll see how great the people are, and they’ll give you the nudge you need to apply. 😉

1:15pm – I do a 15-minute stretch/yoga routine in my living room to loosen up a bit and help with some lingering shoulder pain I’ve had lately.

1:30pm – I read p2s (our internal blogs) to keep up with everything going on around Automattic. My work email is used almost exclusively for post notifications, since we tend to communicate over p2s and in Slack instead. I especially pay attention to any updates around a project I’m working on right now (but it’s a secret so I can’t share any details about what it is yet). Shhhhh!

2:00-4:30pm – Chat time! I’ve scheduled myself for live chat during this block of time, so I settle in at my desk and hop into chat. I do 15 chats during this time, which means it wasn’t very busy/had plenty of staff on. I tend to stick to up to three chats at a time as my maximum. I can do more, but I feel like quality starts to decline and it drains me quicker, so I’d rather get through three really well then accept some more. When I have some slow times, I grab tickets to work on while I wait for a new chat.

4:30pm – After chat, I troubleshoot an issue I couldn’t figure out while chatting and email the user an update, as promised. I check and clear my ticket replies again one last time before I sign off for the day. I chat in Slack for a few minutes, skim my notifications for anything I need to know right now, then say bye to my team. I publish tomorrow’s logbook post with my checklist for things to do the next day.

5:15pm – I close my laptop. My husband is home, so that’s my cue to stop. We’ve got to head out to look at appliances for our upcoming kitchen renovation.

My days vary in length and work, and I’m starting a rotation in mobile app support soon, so I’ll do another post like this to better show the variety a bit. Beyond how my days vary, every Happiness Engineer works differently, on various projects, and in their own way, so these #a8cday posts are a great chance to get a look at that.

Interested in working with us and finding your way through the chaos too? We’re hiring! 

automattic, career

Top Tips for Working Remotely

Sarah Blackstock's Top Tips for Working Remotely

If you work remotely or have considered it, you’ve most likely seen lots of advice about how to do it successfully, including how you should dress like you’re going into an office or have a whole room dedicated for your office space. And you know what? I don’t agree.

I’ve worked remotely successfully for over two years now (currently: at Automattic for WordPress.com), and the secret is: Do what works best for you. Try lots of variations until you get the right combination, and then be willing to change it up once those things aren’t working as well for you anymore.

Here are my top tips for how to work from home:

  1. Wear whatever you want! Take advantage of not having to go into an office and dress however you’re most comfortable while working. Do you need the structure of a business casual outfit to get in the right mindset? Fine. But if you don’t? Get cozy! My loungewear and sweatpants collection has expanded vastly over the past two years. When they became my work wardrobe, I wanted lots of cute options!
  2. Work from home or anywhere. Just remember to leave your house! I’m 100% fine with being on my own a lot of the time, so I don’t get that stir crazy feeling from staying home unless I stay in for quite a long stretch. If that happens, I make a Target run, out among the people, and I’m all set. If you need more time out than that, find a café or coffee shop and spend a workday there. I’m not big on official coworking spaces (too much networking and distraction), but I love a few hours at a table with coffee, snacks, and prime people watching at the local café. I also meetup with my local coworkers about once a month, so if you’ve got any nearby, plan a coworking session with them!
  3. Don’t sit at a desk all day every day unless you really want to. So many remote working tips include needing a dedicated work space. I have a desk, but do I spend all day there? Nope. Some days I spend no time at all at my desk. I let my tasks for the day and mood determine where I’ll be. I’ve worked from my couch, the dining table, standing next to a shelf holding my computer, the back porch on a sunny day, and even bundled up in bed. If you’re not home alone while working, a room you can work in with the door closed is a big plus, but don’t lock yourself in there every day unless you must. I like to change up what I’m looking at, so I tend to move around my house throughout the day.
  4. Take advantage of your very short commute. Instead of just working more because your commute was about 10 seconds, make time to take care of yourself throughout the day. You can have fantastic breakfasts and lunches, if you want. I like to spend my lunch break totally away from my computer doing yoga, watching an episode of a show I’m into, or reading for a while. Whatever I do, the point is to reset my brain for an afternoon of work, so it shouldn’t include working while I eat.
  5. Remember to take breaks. When you’re home, especially if you’re working from a particularly cozy spot, it can be easy to skip the breaks and work through several hours. But your eyeballs need to look away from the computer screen and your body needs a stretch, so make time for those too! You could take a quick walk around the block, workout, or do absolutely nothing for two minutes. I have a whole post of self-care ideas you can use for ideas on how to spend your breaks.

Basically, do what works! Don’t feel obligated to follow all the advice you see out there (including in this post!) unless it truly works best for you. Mix it up and find your favorites!

about sarah, automattic, happiness engineer

Thanks for the memories, Timehop.

Thanks to Timehop, I realized a year ago today is when I had my Matt Chat, which wrapped up my Happiness Engineer trial at Automattic, and led to the job I currently have and love.

My tweet from when I got the first Slack ping from Matt and the chat began:


And then about six hours later when it was done and I’d landed the job:


I spent the rest of the day (and the next few days, if I’m honest) in a haze of excitement. After yesterday’s blahs, this was a perfect reminder of something that has gone (and is going!) great in my life, so thanks, Timehop. I appreciate your perfect timing. This day last year changed my life in an amazing way and I’m glad to remember it.

I’ll celebrate the official one year anniversary of my first day on the job later this month. I marked six months very happily here. <3

automattic, technology & web

WordPress.com on Instagram

Quote from WordPress.com Instagram

I recently started a side project at work. We had an Instagram account but weren’t using it, so I wrote up a proposal with content ideas and Instagram best practices and… ta-da!

I’m sharing standout WordPress.com content there now, like quotes from pieces on Discover, beautiful photos from blogs, and screenshots of great looking websites. Follow: @wordpressdotcom.

Sidenote: Add this to the list of why I love working at Automattic. It’s a real do-ocracy. If you see something that needs working on and want to be the one to do it, you can go for it and I love that.

automattic, happiness engineer

Team Nails & Cookies

Mani/pedi team bonding

For our last full day together at our team meetup, we had time blocked for pausing on the work stuff & doing something fun, so we went for manicures and pedicures. We basically took over the salon and it was a great chance to chat & relax. Once we got back to the house, we baked cookies!

chocolate chip cookie pile

❤️ Team Hedwig!

automattic, happiness engineer

The Shared House Comfort Zone


When sharing a house with your work team for a week, things tend to get really casual very quickly. Our time together has basically been the live-action version of our team’s Slack channel, with #underweargate thrown in for good measure. If you usually work remotely, I highly recommend finding a way to hang out with your team like this (especially if your only other chance is at a much larger company-wide meetup).

(In response to the tip about removing EXIF data from a photo before sexting it to anyone.)

Tomorrow we’re learning about Google Apps integration at WordPress.com to just about finish up the learning/working portion of our week, hitting up the nail salon for mani/pedi bonding time, then baking cookies! 😀