As I stepped up the familiar staircase to Revolution Hall, I could hear the gradual crescendo of voices emanating from the nearby lawn. I walked under an arch emblazoned with flowers to retrieve my nametag for the weekend.
This was XOXO, “an experimental festival for independent artists who live and work online” and on August 22, 2024, I was about to experience it for the last time.
I first stumbled upon XOXO in 2015 via a random tweet and registered immediately. Little did I know that this chance decision would evolve into a transformative journey spanning five festivals over nearly a decade of my life.
XOXO wasn’t just a conference; it was a safe haven for vulnerability, and a celebration of creativity. I’d love to unpack the magic of XOXO and what it has meant to me.
What is it
The place
XOXO drew from the city it has been held in. Portland has been called the Hipster Capital of the World, earning itself a whole television show (Portlandia) around that central theme.
I won’t try to sum up Portland, but I will state some of my observations. I consistently see a creative, artistic spirit in the city, lacking the uptightness you may see in a world landmark like New York or London. There’s great Thai food and inventive plant-based cafes. There’s a surprisingly wide-reaching public transit system and tons of bike lanes. Wall after wall is covered in beautiful murals. It’s a great place to run through.
Two recurring XOXO venues — Revolution Hall and Yale Union — were built in the early 20th century and later converted into event venues. Each subtly set XOXO apart from events held in convention centers and hotel ballrooms.
Of course, there are also the offices of Panic, the software company that feels like a spiritual sibling of XOXO. I loved the unending craft on display at their offices and the delicious tiki drinks they served us.
XOXO drew unique energy from the very specific place it was held in.
In-between spaces
Most places I visit are a collection of smaller places — friends’ houses, museums, restaurants, parks, landmarks. Sidewalks, streets, trains, and cars are the connective tissue holding it all together.
On other vacations, the visits to places are when I’m actively engaged, whether having a conversation over dinner, or perusing a museum exhibition. The in-between time when I’m walking to the next stop, or aimlessly looking out the window of a train are my times to recharge.
At XOXO, the roles felt reversed. I originally came in thinking I’d be most affected by the talks, video and board games on display, musicians, etc. These are the “places to visit” at XOXO.
Instead, it was the waves and hellos in passing, the small talk that leads to hours-long conversations, the “thank you”s and “i love your work”s that changed me. Those conversations were the connective tissue holding XOXO together.
I knew it the moment I stepped onto the grass outside Revolution Hall that something was different. Business cards were replaced with pins and stickers, little corporate swag in sight. The event was designed with enough down time for people to bump into each other and mingle.
The people
These surprise conversations wouldn’t have been possible without the people of XOXO. They came from all over the world, but were united by a strange web of feelings, aspirations, and values. No matter what, every person I met opened themselves to me, and as a result, helped me see the world differently. Often, I’d strike up a conversation with someone only to find out that I already know their work. Other times, I’d state one of my thoughts, to then be rebuffed in the kindest way possible.
Above all, the Andys (organizers Andy Baio and Andy McMillan), worked very hard to make XOXO as inclusive as possible. They screened every applicant. They established and strictly enforced a code of conduct. My friend, Josh Rubenoff, has written beautifully about the topic of inclusivity at XOXO.
Personal Growth
If there is a commonality among the diverse reactions attendees have to XOXO, it’s the sheer quantity of emotions felt.
FOMO
I felt FOMO immediately once I took a look at the 2015 schedule. It all overlapped! Some events were across the river from each other. There was no way I’d see them all. I had to let my gut decide where to go.
Sometimes, I’d leave an engaging conversation to go back indoors for a talk, immediately regretting my decision. I’d think to myself that I could watch the recording of the talk on YouTube in a few months.
Once the talk started, I’d be immediately reminded of the power of the collective experience.
When Amit Gupta concluded his moving talk in 2015 , I looked around and saw that nearly all of us were in tears. This year, when Cabel Sasser (CEO of Panic) delivered his talk, the crowd erupted in a mixture of laughter, praise, awe, and tears. The crowd was as much a creator of the experience as the speaker was.
This isn’t to say that you won’t get anything out of watching the recordings yourself. Go check a few out, you are bound to come away with something.
What I’m saying is that XOXO taught me every time that there is always opportunity cost in everything I do. I can’t see it all, and I shouldn’t fool myself into believing otherwise.
Imposter Syndrome
Of the things I felt, the loose set of feelings and thoughts commonly labeled as “imposter syndrome”, is at the top.
In 2015, I felt like a nobody. Every person I met seemed so interesting, yet I felt I had nothing to say. Twitter was still a popular way for creatives to keep in touch. Every time I exchanged handles with someone else, I’d see their comparatively massive follower count and again feel like a nobody.
Every night, I’d retreat to my bed and decompress.
Being accepted
Sometimes, I’d see someone famous and accomplished exhibit the same behaviors I saw in myself as they approached someone they admired.
Other times, someone I was eyeing from afar, but too scared to approach, would approach me and strike up conversation. Through the process, I’d come away realizing that there is nothing that truly separates me from them. We are all just a bunch of humans.
I remember befriending artist Brendan Monroe and chatting with him as he spent the entirety of the 2015 conference painting murals. I remember when Scott Hanselman quickly saw my imposter syndrome for what it was and inspired me to keep creating and sharing.
Every year that I returned to XOXO, the emotional burden posed by imposter syndrome reduced. The people I met inspired me to create and put more out into the world, which would give me more to talk about. This virtuous cycle mostly removed the debilitating aspects of imposter syndrome.
So, this last time, while I still hesitated at times, I felt no fear in striking up conversation.
Shifting perspectives
The intros the Andys gave and the talks on stage set the tone for the side conversations. While there was plenty of optimism and celebration of success, there was also plenty of exploration of the dark side. People talked about being stalked and abused. People talked about the real tradeoffs they had to make along their journey.
Coming from Silicon Valley, it’s hard not to see the outsized outcomes and forget about the long journeys that preceded. It’s hard not to get caught up among the people optimizing every detail to climb the ladder as high as possible.
In reality, many of Silicon Valley’s biggest successes started out looking like toys.
At XOXO, I got reminded to slow down and enjoy the journey. Cabel’s first talk from 2013 revolved around the idea that we can’t know the ending of our lives, so we should instead fill it up with as much weird stuff as possible.
This year, I asked Vincent Woo what the common thread among his various projects has been. He told me that he likes hitting a journeyman level of competence in a particular skill and then moving on to the next thing. There is no grand plan.
The future
Weird, creative places continue
XOXO is gone and won’t be coming back. I’ll miss it, but I don’t want to let nostalgia take over. It’s easy to think back to previous XOXOs and say “those were the days,” without acknowledging that there remain on the horizon new ways that we can continue playing, working, and living together.
The fracturing of the social internet may be making us more isolated, but XOXO has proved time and time again that it’s still possible to gather people from the far corners of the world and the internet for a magical weekend.
I’d like to focus on what is happening now. The XOXO community is thriving online more than ever. I heard several people discussing hosting their own take on XOXO with a personal twist.
Thank you Andys
Thank you Andy and Andy. You two are so talented and could have been doing so many other things. Yet, you chose to create a community and serve it. You made a space for us all to connect and learn. You kept iterating and improving.
Of all the people in the world that I would love to see a talk from on the XOXO stage, it’s you two. Until then, know that the impact you have made on the community will continue to ripple for decades to come.
XOXO,
Arun
P.S. I know XOXO was founded as and has always been an experiment. So, if you ever decide this experiment of ending XOXO isn’t working out, we’ll be happy to come back!
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Thanks to Q for reading drafts of this.