On WordPress, career development, productivity, and life goals. (Hallway Chats)

Do what you love and get paid for it. Success means looking forward to going to work every day, looking forward to getting up every morning, really entwining what you do professionally with your interests personally so that it complements each other. With what I’m doing now at GoDaddy, I feel like I’ve finally hit that point.

Source: Episode 12: Andy McIlwain – Hallway Chats

Thanks to the crew at Hallway Chats for having me on the show. Really enjoyed the conversation. Even though it’s a WordPress-centric community podcast, I liked how we went deep on other topics. 🙂

A few of the tools I mentioned:

(I’m a sucker for tools and systems.)

From a production standpoint: I love how Tara and Liam are running this show like a well-oiled machine. From the guest onboarding and question prep to the follow-up postcard I got in the mail (!!!), it’s clear that they’ve put a lot of thought and care into their process.

Let’s start with empathy.

We slaughtered nuance in favour of knee-jerk reactions. But that isn’t anything new for society.

What’s new is the web. In the last ten years the web has accelerated how knee-jerk reactions spread.

The great equalizer, the “level playing field”, has removed the filter of reasonable discourse.

We don’t have a dozen press/media organizations respecting journalistic integrity. Instead we have hundreds/thousands/millions/billions of voices all making a ruckus.

Traditional media has eroded. Their survival depends on attention. Now they’re forced to compete with the likes of bloggers and trolls and people who don’t give a damn about the truth.

Now we have this endless loop of hysteria and clickbait coming at us from every direction. It’s all fueled by outrage and emotional triggers.

It’s overwhelming. So what happens? People retreat further and further into their “teams” or “tribes” or “camps” (or whatever you want to call it).

I consider myself a centrist, though I do lean left of most American politics (Canadian here, sup?). It’s a hard position to be in. It would be a lot easier to choose a team.

Don’t think about it. Side with that team every single time. Go team go!

But I don’t want to do that. It wouldn’t solve anything. It would only feed the beast of polarization.

So what do we do? The only thing close to a solution that I can think of is pushing for greater exposure and empathy on both sides.

Keep asking “why?” and trying to understand.

It’s hard to do. I’m a straight, able-bodied white male. I live a comfortable life in a great city. I work in tech with a stable job and benefits. My family’s been here since the 1850s or 1860s.

I’m pretty sure I fall right in that target definition of “white privilege”. I don’t know what it’s like to be in a minority group. I don’t know what it’s like to be a target. I don’t know what it’s like to get profiled for no reason other than my race, religion, or ethnicity. I don’t know what it’s like to have my life upended by war or famine or natural disasters. I don’t know what it’s like to flee, trying to survive or protect my family.

But I can try to imagine. I can read and listen to others share their experiences.

Is that the missing piece? Empathy?

I’m convinced that the less exposure we have to “others”, the more we retreat into our bubbles. We listen to the echo chamber. We feed the vitriol. We dismiss the many because of the few.

It’s like trying to put out an electrical fire with buckets of water.

And it’s messed up. The web was supposed to make empathy easier. It was supposed to connect us with people around the world.

Instead we’re using it to build up mental barriers.

And yes, I believe that the tech industry holds a fair share of blame here. When the almighty algorithm reinforces everything you already believe? When it’s “personalized” to only shows you things that align to your worldview? And when it happens at a scale touching billions of lives every day?

Yeah. That feels like a problem to me.

This is all a big problem. There isn’t a single patch that’ll fix it. But empathy… I think empathy is the right direction. Can we start there, at least?

Planning, timeboxing, and setting goals.

I’m doing a lot of planning right now. It started with planning for work, looking at what needed to get done in the coming months and year ahead. But then I started looking at how I could apply that to other items outside of work.

As a remote worker, deciding how I structure my day and spend my time is an ongoing task. Timeboxing has been helpful for that.

For years I’ve been using my calendar to log my time spent on tasks. But blocking my time out, days or weeks in advance, is something I’ve started doing only in the last year or so.

I don’t always stick to the blocks of time I lay out. But I do try to make sure that the blocks get taken care of before the week is over. So if something comes up, or if I decide to work on something else, I’m not pushing off my to-do items.

I’ve been following this routine of disciplined timeboxing for the last three months. Now I’m thinking about how timeboxing can work at a higher level, months and years into the future.

For example, what about a five year plan? So that’s five big blocks. What five big things do I want to accomplish?


Zooming in – for each quarter of each year, what are my goals?


  • January – March
  • April – June
  • July – September
  • October – December


And for each month? Each week?

You can see how the granularity of timeboxing can scale up to encompass broader goals.

I turn 30 next year, and one of my big goals is to pay off the last of my student debt before I do. And then, from there, I’m timeboxing the future. I’m taking things from my bucket list and putting them on the calendar.

A world of decentralized fun to be had.

There’s a whole world of fun potential consumer products that let people do computer things that don’t involve reading ads on Facebook or viewing promoted tweets.

A decentralized web is harder to create than a centralized web, especially when overcoming non-technical user adoption. Is the upside of a decentralized model worth the effort? (Or rather, will time and changing circumstances create the perfect opportunity for a stable decentralized web to emerge?)

From the same article:

A precondition for the success of these distributed platforms is a shift towards user-controlled data, the ownership of a user’s social graph and her intellectual property created online.

Will there come a time when the average person will have more concern over the ownership of their personal information and personal IP?

Development of the WordPress REST API is under-resourced.

The toughest challenge facing the REST API team right now is resourcing. There are only a few people working on the API regularly, and we need help to build out our projects—which is hopefully where you come in.

Source: REST API Roadmap – Make WordPress Core

WordPress is shaped by its contributors. These are the people who show up and do the work. But when contributors don’t have interest in an aspect of the project, that aspect gets neglected, e.g. data collection and user testing.

This wouldn’t be big issue if it wasn’t for the ecosystem that’s built up around WordPress. We have large businesses (like GoDaddy, where I work) and small businesses (like the agencies and freelancers in GoDaddy Pro) building products and services that depend on WordPress.

Cue Five for the Future, a call to action from Matt Mullenweg. Back in 2014, Matt started asking for organizations to contribute 5% of their people to working on something to do with core development.

Contribution comes in many forms. My skills are by no means core-worthy, but I’m trying to do my part through hosting user meetups and sharing product education. At the other end of the spectrum, my colleague Aaron Campbell is a full-time core contributor. And I know freelance contractors who regularly contribute bits and pieces when they can.

If you’ve got the developer chops, the REST API could really use your help. This is a core feature of WordPress that’s been dragging out for a long while now (development started around 2012/2013). It finally shipped to core in 4.7 and there’s more to be done. You can get involved.