Why I Love XOXO, or,
“Don’t Cry, Organize”

Erin McKean
XOXO 2015
Published in
3 min readSep 8, 2015


Tomorrow I’m headed back to Portland, Oregon, to attend XOXO. (I’ve been looking forward to this year’s conference since the last day of last year’s XOXO.)

It’s not because Portland is lovely (it is) or because the people attending are awesome (they are) or even because I’ll be drinking the equivalent of my own blood volume in cold-brew coffee (I will). I look forward to XOXO because there’s really nothing else like it in the world.

XOXO, to me, is the unofficial union meeting for independent makers.

A union for independent makers might sound like an oxymoron, or at the very least a contradiction in terms, but bear with me for a minute.

Independent creators might own the means of production, but they’re also labor. And in our culture — even our independent, creative, all-the-cold-brew-you-can-drink culture — labor isn’t always treated as well as it should be.

The best thing about independent work is being your own boss. The worst thing about independent work is being your own boss. Because, frankly, when you’re your own boss, sometimes you can be a real pointy-haired asshole.

All the things you internalized about work when working for other people don’t just magically disappear once you strike out on your own. (That’s what ‘internalized’ means.) When you’re your own boss, you can end up demanding that you be your own perfect worker.

And it’s not just your own expectations: you have customers, users, fans, an audience … and you feel responsible to them all. You’ve taken “boss” from being one manageable human person and changed it into both an omniscient overseer and a thin coating of boss-ness smeared across everyone you interact with.

So maybe you think eighteen-hour days, every day, are just what you “owe” to your project. Or maybe you treat every random one-off email from a Disgruntled Internet Person as your annual performance review. Or perhaps you’re still uncomfortable charging enough to fairly compensate your own labor — after all, aren’t you living the (independent Internet creator) dream? It’s all too easy to exploit yourself.

Indie creators are not alienated workers by any means; we’re lucky in that we’re deeply connected to meaningful — even joyful — work. But when the dominant model of work is that of the cubicle or the assembly line (or the Red-Bull-fueled startup wunderkind, or the “gig economy worker”, always on call), we tend to keep following those models, even where they no longer apply.

At last year’s conference, Andy Baio said “We just want more people making amazing things and pushing through the noise.” He was talking about external noise, but it’s equally important to push through the noise in your own head.

There’s been a lot of focus on the changes in technology and new economic structures that have made indie work more possible today than ever before — democratization of distribution, crowdfunding, heck, even honest-to-god LASERS you can keep on your desk — but XOXO also talks about how these changes in working conditions affect the daily lives and relationships of the people doing this work, at more than just the “you can work on the beach with your laptop!” level.

At XOXO, personal struggles aren’t treated as convenient plot points in the (inevitable) success narrative; they are the narrative. XOXO is where we try to figure out how we can create our life’s work without losing our lives in the process.

XOXO is where we bring our demands for better working conditions … to ourselves. Where we can talk about both how awesome it is to be spending all our time on the work we love and how hard it is to be spending all our time on the work we love. Where we can strategize about how to burn bright instead of burn out. Where we can let our fellow workers’ voices rally and shout over the voice of the Big Boss in our heads.

Despite the title of this piece, it’s actually okay to cry at XOXO, because XOXO is a place where we acknowledge how difficult this kind of work can be. But XOXO isn’t just about sympathy — it’s about action. By openly discussing what independent, creative labor looks like, we organize to create a new model of work, together.



Erin McKean
XOXO 2015

Founder, Wordnik.com. Recovering lexicographer. Full Stack-Overflow Developer. Developer Advocate, IBM.