[Bloganuary] Dream Job

This post is part of my attempt at Bloganuary 2024. Today’s prompt is:

What’s your dream job?

It feels like a bit of a cop-out to say I’m already doing it, but that’s true. Well, mostly (read on and I’ll make a counterpoint!).

Automattic

I’m incredibly fortunate that my job gets to tick so many of the boxes I’d put on a “dream job wishlist”:

• I work on things that really matter. Automattic’s products make Web publishing and eCommerce available to the world without “lock-in” or proprietary bullshit. I genuinely believe that Automattic’s work helps to democratise the Internet and acts, in a small way, as a counterbalance to the dominance of the big social media silos.
• I get to make the world a better place by giving away as much intellectual property as possible. Automattic’s internal policy is basically “you don’t have to ask to open source something; give away anything you like so long as it’s not the passwords”.¹ Open Source is one of the most powerful ideas of our generation, and all that.
• We work in a distributed, asynchronous way. I work from where I want, when I want. I’m given the autonomy to understand what my ideal working environment is and make the most of it. Some mornings I’m just not feeling that coding flow, so I cycle somewhere different and try working the afternoon in a different location. Some weekends I’m struck by inspiration and fire up my work laptop to make the most of it, because, y’know, I’m working on things that really matter and I care about them.
• I work with amazing people who I learn from and inspire me. Automattic’s home to some incredibly talented people and I love that I’ve managed to find a place that actively pushes me to study new things every day.
• Automattic’s commitment to diversity & inclusion is very good-to-excellent. As well as getting work work alongside people from a hundred different countries and with amazingly different backgrounds, I love that I get to work in one of the queerest and most queer-affirming environments I’ve ever been paid to be in.

Did I mention that we’re hiring?²

Three Rings

But you know where else ticks all of those boxes? My voluntary work with Three Rings. Let me talk you through that wishlist again:

• I work on things that really matter. We produce the longest-running volunteer management system in the world³ We produce it as volunteers ourselves, because we believe that volunteering matters and we want to make it as easy as possible for as many people as possible to do as much good as possible, and this allows us to give it away as cheaply as possible: for free, to the smallest and poorest charities.
• I get to make the world a better place by facilitating the work of suicide helplines, citizens advice bureaus, child support services, environmental charities, community libraries and similar enterprises, museums, theatres,  charity fundraisers, and so many more good works. Back when I used to to helpline volunteering I might do a three hour shift and help one or two people, and I was… okay at it. Now I get to spend those three hours making tools that facilitate many tens of thousands of volunteers to provide services that benefit an even greater number of people across six countries.
• We work in a distributed, asynchronous way. Mostly I work from home; sometimes we get together and do things as a team (like in the photo above). Either way, I’m trusted with the autonomy to produce awesome things in the way that works best for me, backed with the help and support of a team that care with all their hearts about what we do.
• I work with amazing people who I learn from and inspire me. I mentioned one of them yesterday. But seriously, I could sing the praises of any one of our two-dozen strong team, whether for their commitment to our goals, their dedication to making the world better, their passion for quality and improvement, their focus when producing things that meet our goals, or their commitment to sticking with us for years or decades, without pay, simply because they know that what we do is important and necessary for so many worthy causes. And my fellow development/devops volunteers continue to introduce me to new things, which scratches my “drive-to-learn” itch.
• Three Rings’ commitment to diversity & inclusion is very good, and improving. We skew slightly queer and have moderately-diverse gender mix, but I’m especially impressed with our age range these days: there’s at least 50 years between our oldest and youngest volunteers with a reasonably-even spread throughout, which is super cool (and the kind of thing many voluntary organisations dream of!).

The difference

The biggest difference between these two amazing things I get to work on is… only one of them pays me. It’s hard to disregard that.

Sometimes at Automattic, I have to work on something that’s not my favourite project in the world. Or the company’s priorities clash with my own, and I end up implementing something that my gut tells me isn’t the best use of my time from a “make the world a better place” perspective. Occasionally they take a punt on something that really pisses me off.

That’s all okay, of course, because they pay me, and I have a mortgage to settle. That’s fine. That’s part of the deal.

My voluntary work at Three Rings is more… mine. I’m the founder of the project; I 100% believe in what it’s trying to achieve. Even though I’ve worked to undermine the power of my “founder privilege” by entrusting the organisation to a board and exec that I know will push back and challenge me, I feel safe fully trusting that everything I give to Three Rings will be used in the spirit of the original mission. And even though I might sometimes disagree with others on the best way forward, I accept that whatever decision is made comes from a stronger backing than if I’d acted alone.

Three Rings, of course, doesn’t pay me⁴. That’s why I can only give them a few hours a week of my time. If I could give more, I would, but I have bills to pay so my “day job” is important too: I’m just so incredibly fortunate that that “day job” touches upon many of the same drives that are similarly satisfied by my voluntary work.

If I didn’t have bills to pay, I could happily just volunteer for Three Rings. I’d miss Automattic, of course: there are some amazing folks there whom I love very much, and I love the work. But if they paid me as little as Three Rings did – that is, nothing! – I’d choose Three Rings in a heartbeat.

But man, what a privileged position I’m in that I can be asked what my dream job is and I can answer “well, it’s either this thing that I already do, or this other thing that I already do, depending on whether this hypothetical scenario considers money to be a relevant factor.” I’m a lucky, lucky man.

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