Eight short-ish thoughts about XOXO 2016

Elizabeth pinged me and asked if she could get a ride down to Portland. Given I had had a rough month, I wasn’t looking forward to a three hour drive alone with my thoughts, so I gladly invited her along.

And so we talked, of jobs that had gone bad, of our love for our kids and the struggles we went through with them and for them, of friends and their health struggles, of the terrible semi drivers, as we rolled south on I-5.

I had been trying to get to XOXO for years, but every year it seemed ill-starred. One year I missed out on a ticket because I was stuck in a meeting. But this year, this year, I somehow wrangled my way in. The “final” XOXO, perhaps.


I spent most of Thursday evening talking to Rachel, someone who I’d known from the internet for years but never met. She’d made the mistake, once, of saying the right thing about a very powerful person in my vocation. As a result, she’d been punished for her insubordination. The righteous do not always win.

There was this fluctuation in our conversation that was one part Aaron Sorkin single-take walking conversation, one part Judd Apatow emotional human revelation. We would show our strengths, then bare our insecurities. We would curse the machinery of our industry that creates powerful gatekeepers, then wonder how we were going to get around their power.

Rachel is vim and moxie, courage and strength, creativity and determination. She is going to soar higher than the birds of prey that have come for her.


2016 has been a hard year for almost everyone, but in different ways for each of us. For me, it’s been the return of my ancient war with anxiety disorders. In daily life it can be a struggle. At a conference of 1200 people, it’s near paralysis.

On the one hand, there was support. Slack had an #anxiety channel where all the anxious sorts openly talked about how they were feeling and giving support to one another. The Andys had also set aside the roof space of the hall, with a small bar and a grand view of downtown Portland, for introverts to chill out and hide.

On the other hand, it was still hard. I usually lean into the discomfort at big events, but I lacked the emotional energy to pull it off. And that led to FOLO — fear of losing out on the opportunities presented at such a grand gathering.

I spent a lot of the conference feeling like Vincent Adultman, the three kids in a trenchcoat on BoJack Horseman — only I was not blissfully unaware I was failing at adulting.

It was a conference full of impostor syndrome, of people scared of being the uncool one in a place filled with the truly cool kids. And then you start talking to them. And you start realizing they think exactly the same — how did they get to be in this space with all the cool kids?

Everyone was a little scared. But that’s the weird genius of XOXO. It’s a conference that, quietly, tells you it’s OK to be scared. You’re not the only one who is scared.


This was the first time I truly reflected on how the last 25 years of the web has changed us as a society.

I certainly ran older than most of the crowd, who was mostly in their upper 20s and low 30s. They were creators and artists that were living in the web world that my generation help create back in that first Boom, and they were rolling with the joys and pains of our good and bad decisions.

But they weren’t content with our work! They were building, transforming. They were focused on fulfilling the promise we had struggled to bring to life — and they were making it their own.

Listening to Talia Jane describe how she chose to blow the whistle on Yelp’s shady pay practices, suffer dearly, then win in the end was a true Millennial redemption story. The Millennials that the Boomers so deride are strong and powerful. And I’m not just saying that because, at long last, there is a generation of baristas that can spell my name correctly.


We were an overwhelmingly white crowd (welcome to the Pacific Northwest, here’s your sunblock), but among us were people of color, LGBTQ folks, people of very high and very low incomes, even… gamers.

I could feel my own discomfort at times, being one of those rich cishet white guys that felt antithetical to this crowd. It couldn’t be dismissed. But I needed to confront it, and this was a space that demanded it. Even as we laughed at Homestar Runner, in the back of my mind I felt like some of the jokes, especially the transphobic ones, hadn’t aged well.

But this was a place where we could all meet on even footing and laugh and think at the same time.

This year featured women of color like Star Simpson, the rapper Sammus, Heben Nigatu, Sarah Jeong, Esra’a Al Shafei. All of them challenged the sphere of privilege we have due to our gender, our race, our nationality… our income level.


Lucy Bellwood ran down the litany of big events she had this year: The new book, the signing, the book tour.

“But the biggest thing I did this year?” she asked. “I got off food stamps.”

For me, it was a gut punch.

I grew up upper middle class, until my parents lost a lot of business during the mid-1980s Oil Bust in Oklahoma. One year, my father did what the instructions said and entered $0 on our taxable income line because he’d essentially made nothing.

I was poor after college, living off borrowed money from Mom. And then, somehow, I got a job working on the web. And then another. And then I was making far, far more than I ever have before.

I thought that I was doing the right thing: Giving as much as I could to charity. But I hadn’t thought of the creators.

We don’t know our worth as creators. We think people make outsized amounts as Big Internet Celebrities when they’re making less than a penny per YouTube view. Meanwhile, we give away our work and our creative rights because we don’t know better.

And I’ve been guilty in both directions. Heck, I wrote a piece for a magazine recently and got paid nothing. Meanwhile, I’m streaming songs on Spotify as I write this, passing fractions of a cent to musicians and songwriters along the way.

I am trying to figure out how best to share my wealth. I guess I’m in Medici territory now (for as much as you can be in a super-expensive town like Seattle). Time to be a patron of creators.


Some of us stayed up very late Friday night for the Fray Cafe, an outgrowth of Derek Powazek’s glorious storytelling site that started 20 years ago. Stories of pain, heartbreak, redemption, success, and just getting through.

In a sense, this is what XOXO truly was. It was telling our stories, through art, through podcasts, through games (video and board), through slidedecks, through the intimate conversations over beer and Fried Egg I’m In Love.

I told my story here. But it was one of so many. And it was in a space where everyone was comfortable to share as much as they wanted, from a simple idea to the thoughts that came to them in the loneliness.

Story brings shared experience. Shared experience builds empathy and community, a parallel of the Biblical “sharing one another’s burdens.” Andy Baio, at the end of the conference, talked of his revelation that XOXO was now much bigger than him. It’s become a community of generous, creative people of all races, genders, sexual identities, and love of games.

And this is the community that continues even as XOXO pauses. I hope that XOXO the conference returns one day. But I know that XOXO the community continues on.

Frank Chimero’s closing talk resonated with this, that we are all independent creators, some truly indie, some with day jobs. But independence is a lonely thing. Community comes when we truly are independent together, relying on one another for support in our quests for the good of the crafts we do. So, in the end, how can we be independent together?


As I left Portland and headed north, I reflected on what the anxiety I took in and the unsettling burden I took out of there. I need to create more. I need to give more. I need to build up those who create. I need to stand with those who suffer injustice at the hands of malicious governments, companies, and people on the Internet. I need to support those who suffer from their own insecurities even as I suffer from mine.

The recessional song running through my head, thanks to Lucy Bellwood’s ship fetish, was about sailing in the darkness of life:

We’re all battered people, we who create this internet you love. May we build a better internet, build a better society with it, and most of all, build better people.

And so the outside, it bashes us in
Bashes us about a bit
Feel it tugging you, ploughing you flat
Then feel it filling your sails
And warm on your back