YxYY 005

“I really admired the way Richard built up an entire political movement to address an issue of profound personal concern,” Sarah said, explaining her attraction to Stallman.

My wife immediately threw back the question: “What was the issue?”

“Crushing loneliness.”

Sam Williams, Free as in Freedom, 2002.

I thought it might be a good idea for me to capture some of my thoughts about YxYY 005 while they’re still fresh in my mind. It’s been a great weekend for me, and it’s an important event to me, so I figure it’s worth some decompressing over.

Yes and Yes Yes is an annual event that started 5 years ago and if the numbering system is any indication was maybe planned to continue for 1000 years. It came from a social group loosely associated with the San Francisco tech community — or, really, one branch of it. I think maybe a word cloud of tags on people involved in this network would have tags like “web20” and “sxsw” and maybe “foocamp” or “burningman” appearing. But it’s been loose, too — there are people who’ve been involved from lots of different communities.

It was intended to replicate, and extricate, the social experience from Austin’s South by Southwest Interactive conference from the mid-2000s (the “Web 2.0” heyday). 

What experience, exactly? Eating good food, in part. Drinking good beer and artisanal cocktails. Seeing the people that you admire over the Internet from afar and finding out they admire you in return. Appreciating and being appreciated. Laughing at obscure references. Reinforcing the ties of that compose the dispersed social network.

There was a general consensus around the turn of this decade that the explosive growth of SxSWi made this experience much harder to have at the event itself. The powerful and lucrative platforms that had come out of this event attracted too many people trying to capitalize on it. At least two events (YxYY and XOXO) rolled out of a desire to provide a venue for this experience.

Both events worked well. XOXO because it had amazing, intelligent, diverse and fantastic speakers and a deep integration with the hipster wonderland that is SE Portland. YxYY took a different tack: a mostly social event sited at the tony and Portland-ish Ace Hotel in Palm Springs, CA. With no official schedule and an agenda centered mostly around chatting in a big pool, it seems like the lightest possible take on “tech conference” imaginable.

But it’s worked really well. For a number of reasons:

1. A great network of intelligent and interesting people who branch out fractally from the root nodes of the 5 founders.
2. An emphasis on diversity and particularly female participation. At every event, women have been more than 50% of ticket-holders. As you’d expect, this gives a largely polite and  positive environment.
3. It’s only marginally technology-oriented. There are fun things to do, like the Maker Lounge and some sessions about technology, but mostly it’s a social event for tech people and their friends, rather than a tech event with some social stuff layered on top.
4. A central thesis that you should say “YES” to things. Leaping into the unknown, taking opportunities. People at the event are relentlessly positive without being pollyannaish, and they make a big deal about trying new things.

XOXO decided to stop its annual event after 5 years, and YxYY’s founders decided to end their run for YxYY 005. They’re wonderful people and they all work hard and I’m happy they are taking time to live their lives, but ending the conference runs raises a lot of questions.

Did these events have a bigger meaning or mission? If so, was that mission achieved, so the event is no longer necessary? Or did we fail to achieve it, and it’s no longer worthwhile to try? It’s hard to tell where things lie, or what groups will take up the mantle after these two events end.

On this year’s event: I had a great time. Several things mattered a lot to me. First, I’m in probably the best physical shape I’ve been in since my teen years. I don’t think I’ve ever felt as OK walking around in just my bathing suit as I do now. I realize that that’s incredibly shallow but it’s surprising how much feeling comfortable in your own skin affects your ability to enjoy an event.

Second, I had a project that I’d been planning to do for three years that finally came off. The idea was based on the Long Now Foundation‘s Long Conversation from 02010. (I called my version The Long Con, which was both a nice abbreviation and a call-out to my favourite episode of Lost). (There are some interesting overlaps between Long Now and YxYY, not least their use of aspirational leading zeroes.)

The project was a chain conversation, starting off with 2 people A and B speaking to each other, and after 10 minutes person C joins and person A leaves so B and C can talk for 10 minutes, then D joins and B leaves, and so on for about 4 hours.

It was a resounding success. We had about 25 participants talking together, which makes for a lot of conversations, perspectives, and discussions. Everyone who was part of it really loved it, and it was a real pleasure to see it unfold. I’m excited to get the audio up to share privately with the YxYY community.

I feel like there are a lot of friends for me at YxYY. Many of them I knew from pre-YxYY times. Some I’ve met at the event. I feel recognized and validated by this community. It’s something I feel part of. I have a lot of variance between together-time and alone-time at YxYY, but I feel like I’ve found a good balance between them.

I am sad to have the event be over. It’s a unique slice of the tech-ish Bay-Area-ish community that matters to me, and I’ll miss spending time with them in that particular place. The founders have some ideas about what they are going to do next, but I’m pretty sure they will take at least 1 year off. I don’t know yet what will fill that same role for me in my life, if anything. Maybe that’s just not something you can replicate exactly the same way again.