I’ve been working on this octopus on and off for nearly a year. I like the octopus itself quite a lot, in particular the tentacles feel successful. I like the illustrated look and feel, thanks to the inked outline.

Less well executed is, of course, the water. I want to add bubbles, but I think I made an error early on by not planning them from the outset. Bubbles at this stage will just feel on top, and I’d rather they look properly incorporated. The water itself got a little too muddy in the top as well.

Overall, however, I’m excited to continue and have ordered bigger paper to do it right.


I’ll give them this: clothes are convenient in the cold. We can warm specific parts up with strategic clothing. Upper half, lower half, extremities, all separately or together. Even highly specific, like palms. Just the torso. Ankles only. Around the head, but not covering the head. Clothes are targeted.

But clothes aren’t just functional. They’re deeply linked to our sense of selves and our social construct. They gain us access and deny us entry. They’re a passport and a shorthand. They’re a pass and a target.

Yesterday, I wore some ridiculous dog joggers (as in, they had pictures of dogs all over them) and a shapeless wool t-shirt with an oversized sweatshirt to work. When I go to my office (as opposed from working in my house), I tend to dress in tech casual. That’s what I typically feel the most comfortable wearing when in a professional office building. It’s very different from what I’d have to wear when I worked in a colocated office at my previous job – which was business casual and had very definite (restrictive) Rules.

These days, I could wear pajamas 24/7. The outcome of my work is not dependent on my outerwear. No one I work with cares what I wear to work, as the majority of them don’t see me, day-to-day. Clothing is irrelevant to our work, and it’s irrelevant to the outcome of our work. We don’t need PPE, for example, to perform our work and stay safe (unless working in a public place and wearing a mask), and wearing a particular combination of special clothing doesn’t make our work more or less successful (like it would for a professional athlete).

Many offices that are colocated tend to advocate and emphasize that type of clothing affects the outcome of work.

Does it?

Yesterday about halfway through my day, I realized I’d made a mistake and had worn too casual clothing. Not because there’s some ridiculous building dress code or because I was going to not be able to complete my work (indeed, I was physically very comfortable). But the location and clothing didn’t end up feeling compatible, and it was like hearing a low-pitched whine all day.

Physical comfort in clothing is a high priority for me. I have an autoimmune itch disorder and my skin also will hive due to heat and pressure. So I will wear leggings or Betabrand yoga dress pants week in and week out, very happily. I’m always looking for my next favorite dress. I am pretty happy with my clothes most of the time, and I am able to do the things I need to do when in them (aka, transition from work to parenting seamlessly). It seems like it would follow that the more comfortable the clothing, the more comfortable I am.

Why isn’t this the case?

Clothing acts as a kind of visual resonance or dissonance. There’s clothing that’s accepted and expected on social and economic strata. There’s clothing that represses your sense of self and clothing that enhances your sense of self. Traditionally, all of those things can be in conflict and to optimize for harmony can result in a very narrow range of clothing any person may end up wearing. I’m relieved we’re moving away from this increasingly.

However, I still think it’s important to acknowledge how clothing can be both costume and disguise and naked honesty. Put another way, investment of self in clothing is deeply personal, and means many different things. Power suit. Dress for the job you want. Clothes make the man. Lightskirt. Clothes let you explore identities. Someone who gets the job done, someone who is quirky, someone who is ultra feminine (or ultra masculine), someone who eschews gender entirely. Clothes let you assume identities, becoming a goth or a queen and all the shades in between.

On the face of it, it is truly absurd that anyone would be in danger for what they wear. It is laughable to think that a type of clothing has the power to change the emotional resilience of the person wearing them. But it’s not laughable and it’s not absurd, because people do get beaten to death for wearing something that causes too great a dissonance for the observer. People do feel enormous shame for how they feel in the clothes they are sometimes made to wear, because of their job, or their role in society, or their gender. The reality of our culture (and many around the world) is that clothes cost us something and clothes earn us something. They can be restrictive and destructive, and they can be a nod and a wink to buy entry.

My stupid dog joggers (which I love, I do not think they’re stupid, they have pockets) worn within the parameters of my own life are low stakes. Brushing the floor, low. I lose nothing in terms of status or earning power or anything by wearing them, in any part of my life. No one will take away my children, and I am in no physical danger. Even with that context, I still found myself turned around by wearing them where my habits dictate other clothing.

It puts into perspective the bravery of someone who dons a garment that is fully outside their socially acceptable parameter in order to align more perfectly with their sense of self. It’s astonishing.

It’s interesting, because it’s easy to say “ah well a perfect world is one where clothes have no meaning at all, then.” But I don’t know that’s the case. I think it matters when someone joins a social group through clothing (for them, intrinsically). There is a frisson of joy in moonlighting in some other space, whether it’s Halloween or getting gussied up for a fancy evening out (which is about my extent of moonlighting through clothing). In looking and feeling your best, or your funniest, or your silliest. We have big barriers for many people who would live happier lives in other clothes, and those I think we should continue to work to remove. But I think it would be nice to preserve the relief and delight in stepping into those clothes. In belonging.

Also to take a fairly sharp left for a moment, I think if you go to the Met Gala you should go in costume. Be cute another time. Wear that traditional tux the next day to dinner. It is literally a costume ball, and I’m disappointed in every single person who won’t go in theme. The end.

Earbud tip recommendation

I have been on the hunt for earbud tips that are small enough for my tiny ear canals for as long as there have been earbuds.

The problem with large earbud tips (all earbud tips are “large” to me) is that they won’t seat properly. My AirPod Pros extend straight out of my ears, with a gap of about a centimeter between the stem of the AirPod and my face. Over the course of any given session, they tend to slide out of my ears. So I’m constantly re-seating them, which risks turning them off accidentally (annoying in a call, at best) and hitting the mic, etc.

I’ve tried several memory foam tips that are sized “small” in the hope that a combination of them being technically small and also moldable foam would make them work. Alas. This has not been my experience. Every month or so, I’ve started a dive into finding an extra small tip that works with AirPod Pros (not all tips do) and found myself putting off making a decision because it just feels like a low priority. Many recommendations I found online weren’t actually for extra-small tips, or they didn’t work with Pros.

Finally, in a Reddit thread, I found a recommendation for an extra-small tip that works with AirPod Pros, and I figured I’d just bite the bullet and buy them without diving in any further.

I ended up buying the AZLA SednaEarfit XELASTEC tips in SS for AirPod Pro. They fit the standard AirPod Pro oval connection without any adaptor necessary, and measure about 10.4mm across (according to the literature). They’re (obviously) small, so they fit into the case while charging, which was a worry I had about some of the flanged options out there.

These fit really nicely. They actually make the AirPods feel less obtrusive/heavy (heavy isn’t quite the right word), which makes sense since the larger tips were simply not fitting into my ear canal properly. They feel more secure, and forgettable while in — I don’t feel pressure against the walls of my ear canal where the tip fits. This isn’t even something I had pinpointed as a problem, but it’s very noticeable now the problem is gone. They also “hug” my ear and the stem of the AirPod actually touches my face, which tells me that they seat more deeply than larger tips (again, makes sense). I don’t know if they come in other colors, but the black works great with the custom paint on my AirPods!

Also, in my experience, they need to click twice to be fully connected. Don’t do what I did and rush through connecting them, or you might end up with a very small tip nestled in your ear, sans AirPod. Everything turned out fine, don’t worry.

Hey Mom…?

If you’ve ever wanted to listen to the things Grant says, instead of occasionally reading them, then boy have I got news for you! We’ve started a tiny podcast, which will drop episodes infrequently (or maybe frequently; he loves recording) for your listening pleasure! Expect episodes shorter than 10 minutes, and mostly nonsense.

In this episode, Grant told me he wanted to tell me a joke, so we paused for a minute so I could start recording. He was very interested in the phone screen. And, this is how all our conversations go.

Listen to our first (and so far, only) episode below!

Halloween costumes Hey Mom

Grant talks costumes while he works on a drawing.
  1. Halloween costumes
  2. Chickens are chickens

First day of school

The twins are starting fourth grade, and Grant is starting kindergarten! All their bags are packed, they’re ready to go. They’re standing there, trying not to sneeze.

I can’t wait to hear how their first days went. Henry and Eleanor have lockers this year! Grant was wondering how they’ll account for quiet time (he noticed that there were no cots or mats in the kindergarten room), and thinks they’ll have the kids put their heads down on their desks. We will have to wait to find out!

Language & Puzzles

The Language Lover’s Puzzle Book by Alex Bellos

I very rarely recommend books. I am a shamelessly indiscriminate reader, and I am also sort of weirdly possessive about what I read, so I don’t make recommendations often. They’re either going to be too juvenile or too crass or the wrong brow (too highbrow or too lowbrow), or SOMETHING. They’re not going to fit, somehow. I’m not a book-person matchmaker! I accept that! I went to the beach for a week and I read six books (I would actually recommend three of them: The Song of Achilles, Circe, and Gone Girl), but I don’t need to really advocate for any of them. Of the six, one was truly garbage, just very badly written and not well reasoned and meh from soup to nuts. Two more were … fine. The three I’d recommend have been recommended extensively elsewhere, by people who are better at it than I am. Go read those recommendations!

But I’ve found myself actually trying to get people to read this book, The Language Lover’s Puzzle Book, by Alex Bellos. I’ve been compelled to talk to people about it. Actively! This is very unlike me! Every couple years, there’s a book that I try to force people to read, and good news everyone, this time it’s this book.

It’s a fun book. I like puzzles, and that surely plays a role. It’s also deeply educational, in a pretty tantalizing way. If you like trivia, and also being sort of forced to deduce the trivia you’re learning, then this is the book for you. The below video is actually from the book (so, fair warning). The person in the video is Alex Bellos, if that isn’t clear early on.

I’ve learned some very interesting little tidbits, like European number counting systems that aren’t base 10 (you know who you are), and a number system that was alpha-syllabic. Exciting!

The puzzles are set up with a lot of context, and then the answer section is also pretty informative. You can tell the author is really excited about the content, and there are a lot of very nerdy/dry jokes. When I describe this book to people, the universal reaction is “… oh.” And this is accompanied by a general desire to shuffle backwards, and a fervent wish that I change the subject at this point. But I don’t! I really want people to engage with this book! Sorry in advance! (no I’m not, you should read it!)

Becoming Happiness

A little over a year ago, I took on a new role at Automattic: leading the Happiness Experience (HappEx) team. This team is responsible for overseeing the Happiness experience from before someone applies to Automattic, through their last day as a Happiness Engineer. We started out roughly divided into two halves: Happiness Experience and Happiness Hiring. Over time, we’ve grown a bit to include Happiness Onboarding, Leadership Development, and we’re moving with purpose towards Happiness Growth.

This role is very fulfilling for me. I have learned absolute mountains about hiring for this role that I’ve lead for a long time (Happiness Engineer), and I’ve taken a lot of agency to work with my team’s stakeholders to be proactive about improving the Happiness experience at a fundamental level. Fortunately, everyone at Automattic, including my main “external” partner in this work (the lead of the Happiness organization, Andrew Spittle), has the exact same goals. We may have slightly different interpretations and theories about how to move forward successfully, but starting on the same page is a wonderful advantage, and makes work truly energizing and fun every day. Additionally, my team balances taking our work to heart with a healthy dose of whimsy. We hold each other accountable, we deliver when we say we will, and we communicate clearly, kindly, and consistently.

Hiring and Onboarding

Soon after moving into this role, we were mandated to hire at least 25 new HEs as ASAP as possible. We managed to hire 33 new HEs before the end of the year (some started in 2021). Late in 2020, we also recognized that if we were going to keep going at the pace we were, we were going to make some changes. We didn’t want to maintain the pace we had been going at, either, but actually increase it. We wanted to hire nearly seven times as many Happiness Engineers in 2021 as in 2020. That meant a radical change in nearly everything we do. We decided to tear our entire process apart and rebuild it from the ground up. We did this in tandem with running our old process, so we didn’t lose any time.

In November 2020, we identified that the biggest thing we needed to change was the length of our (paid) trial. The old trial was four to five weeks long. During that time, candidates would get hastily trained in all aspects of being an HE, then perform the work. We’d give feedback, they’d have a trial buddy and a trial lead, and we’d just see how it went. We decided to cut it to a three week trial, max. We also changed what we look for in the trial, and how we introduce people to the work. The trial is designed specifically to have two key components: the candidate gets to try out the work and decide if it’s right for them; we get to evaluate the candidate’s skillset. Keeping that in mind, we changed the trial to be much more strictly segmented. Week one involves some broad training about being a Happiness Engineer at Automattic, then some shadowing sessions, and a chance to ask plenty of questions. Week two involves some specific training in tickets, some paired ticket time, some solo ticketing, and a troubleshooting project. Week three includes specific training in chat, some paired chat time, and solo live chat with customers. Another key decision we made was to structure the trial so it would be part-time for everyone. We used to allow folks to take their 5-week trial full-time or part-time. Obviously, that ended up giving people who could invest all their time into the trial an advantage. So by reducing the trial to fewer than 20 hours a week, and gating each week very specifically, everyone has the same opportunity for input and output. Particularly in COVID-times, we were very concerned about how to make the trial as equitable as we could for people who may be teaching their kids all day at home, or caring for a sick family member, or who may just be stressed out of their mind. Reducing the time input and being super clear about our expectations upfront (both in terms of input and output) means that candidates can more easily decide if moving forward with a trial is right for them.

By February 2021, we were ready to launch our new program. So we did. We went through constant iteration on our pipeline process, and indeed, we still are tweaking and iterating our application questions to help us best ask for the exact things we want candidates to show us. We also brought onto the team an Onboarding Lead to build a formal onboarding program for new HEs that was universal. Previously, our onboarding was homespun, developed by the different divisions (WooCommerce Happiness onboarding was different from WP.com Happiness onboarding, for example). We also developed an understanding of how to handle onboarding for our smaller divisions (Tumblr Happiness and Trust & Safety, for example), and how to allow for necessary organic development of style and sense of community between the divisions, without actually leading to vastly different experiences.

We decided to start with the broadest possible onboarding, and narrow from there. Today, new HEs are onboarded into Automattic, then Happiness, then their division and team. They are invited onto their team from day one, so they know where they’ll be working, and who their lead is and their team mates, but we want them to feel at home as Automatticians first. Before the end of March 2021, our first new HE started in our new Happiness Onboarding (HappOn) program. We created a team to work exclusively on onboarding, with these folks responsible for staying very close to the work in their own division, and making sure that the onboarding for each division aligns where it makes sense to, and also helps folks set up for success as early as possible in their new team. To date we’ve graduated around 30 Happiness Engineers from onboarding, and have nearly 40 in the program (or starting soon).

Leadership Development

Something that Happiness has been invested in for a long time is leadership cultivation. This is a program that I helped to run for a few years when I was a lead-of-leads (LOL) in Happiness itself (through a curiosity of org charts, I no longer am technically in the Happiness organization; I’m in Talent, though my heart firmly resides in Happiness). Leadership cultivation is a program that helps folks who are unfamiliar with leading at Automattic how to be successful in the role, and what to expect. We like to say that if someone goes through leadership cultivation (a several months investment) and decides that they don’t want to be a lead, that is a good result! They will have gained new skills, new perspective, and they’re not in a role they don’t actually want to be in. Our intention with leadership cultivation is primarily to build our bench of available leads within Happiness. This intention is primary because it’s the most pressing. We are constantly filling leadership roles, both permanently and temporarily, so maintaining a bench of folks across all regions who are well trained and feel confident about leadership is vital to Happiness. Our secondary intention (which is not less important, but is necessarily less urgent) is to afford new skills across Happiness around leadership. Everyone can benefit from leadership training! Lead cultivation, however, is incredibly time intensive — which of course is a main benefit of it. Clear, direct attention from a tenured lead who coaches the candidate through the process, helps them develop their instincts around leadership, and gives them tools/resources to work through the rest. We ran lead cultivation in a one-to-one manner for years, and it worked okay.

Late in 2020, we recognized that if we were going to hire so many more Happiness Engineers, we were going to need to figure out a new way to run lead cultivation so it was one-to-many. In January, we launched leadership cultivation cohorts. To date, we have 14 graduates, 20 people in cohorts, and a similar amount interested in starting. Our leadership development program also includes support during leadership tenure. We call these leadership dens, and each den comprises 5-7 leads across Happiness with a mix of tenure and experience. Our (HappEx) role in dens is to facilitate; really, leads help each other more than anything. This gives them a safe space to provide support, ask for help, and psychologically come to the realization that they’re not alone in this work.

Given the popularity (and importance) of these programs, we just recently brought on a second person to work on leadership development full-time!

Growth and Development

Training for Happiness Engineers has always been a homegrown affair. We create the training we wish we had had, and stash it in the field guide (the handbook for all Automatticians). With nearly 400 Happiness Engineers alone, we have far outgrown this haphazard arrangement. And to be fair, Happiness Engineers themselves have worked hard to keep relevant information readily available for their peers. We have a training guild who has worked tirelessly at this, and various subject-matter guilds (i.e., domains guild, account recovery guild, CSS guild) that build and maintain their own training. And that all works okay for the work right in front of you (and sometimes not, when things get outdated). But what about actual career growth? What about building a sense of accomplishment and ownership within the Happiness role over the course of a decade? For a long time, the “growth path” in Happiness was assumed to be “go into leadership.” At Automattic, we don’t give pay raises for leadership role changes. Compensation is tied directly to impact, so pay may follow, but it’s not a guarantee. Leadership definitely isn’t for everyone, and the opportunity to move back out of leadership without financial penalty is crucial. For awhile, folks began to assume that “growth” in Happiness meant becoming a developer (and for some people, that’s true! It’s a great next step for some of our HEs). But that’s again not right for everyone, and our internal Developer Apprenticeship program is a big time investment (rightly so). So we have a gap between the time when an HE leaves onboarding and gains proficiency in the role (we feel this should take one to two years), and the next phase of their career. It’s possible to do rotations to different divisions (from WP.com to Tumblr, for example), and that is absolutely career development, but we don’t have structured training with consistent evaluation and gating criteria. So we don’t have an ideal gauge of what all our Happiness Engineers know, today. Happiness, as an organization, works and it works pretty well. But “pretty well” is not good enough. We can do so much better, and serve Happiness Engineers far better with career growth and development. This is something we’re working on now. We’re currently hiring for an instructional designer to begin to get our arms properly around this work, and then we’ll build this team out to serve Happiness effectively for the next several years.

Future Happiness

It’s an incredibly exciting time to be part of Happiness and Automattic! Happiness is poised on the edge of something great and special, and all Happiness Engineers will be part of it. We’re going to continue to grow and become a true force for growth and acceleration within Automattic. Happiness Engineers are truly the best in the world at providing technical support, and are a deeply empathetic bunch to boot (as well as fun)! Everyday I’m deeply honored (and frankly humbled) to be able to work directly on growing our Happiness organization, while also being able to positively impact the happiness of Happiness. This in turn leads to greater efficiency and efficacy, which is good news for everyone.

Today is a great day to look at whether you’d be a good fit for Automattic. Maybe we’ll see you in Happiness soon!