Befriending Technology

Hi, my name is Rob, and I am confused about technology.

Some days, I’m glued to screens and despair at the state of the timeline as it’s seemingly all slop now.

Other days, I feel empowered by AI to build the tools and websites and experiences I’ve always wanted for myself.

Is this whole moment with AI utterly baffling to you as well? Please tell me I’m not the only one.

Because lemme tell you, I am excited and freaked out and I have no fucking idea what’s going on.

Wendell Berry’s death a few weeks ago hit me hard. I’ve been thinking about something he wrote for years.

It is easy for me to imagine that the next great division of the world will be between people who wish to live as creatures and people who wish to live as machines.

I can’t speak for anyone else, but I’m all in on relating to myself as a creature of this earth. It leaves me feeling more grounded and connected to life and generally okay, whereas when I try to outsource what I value to the machine and let digital environments shape my psyche, the more I’m filled with endless anxiety and a sense of disconnection from life.

And holy shit, I love technology right now.

AI for writing has been a nightmare for me. AI for building the apps, websites, and WORLDS I’ve always wanted has made me feel like a freaking wizard. I’m falling in love with computers at the very same time that I want less and less to do with computers. I’m excited by the possibilities and a little intoxicated by them, tbh. I can feel the Faustian bargains lurking around the edges.

Basically, I’m legit confused about technology, humanity, and how to gracefully hold the tensions between the two in my own life instead of collapsing into reductionism. I’m neither a neo-Luddite who wishes to live off the grid and sabotage data centers, nor am I some techno-utopian who believes we’re conjuring a new machine god that will magically fix everything. I’m a secret third thing.

What I want is something like friendship with technology. A relationship where I can be the creative human creature I am, machines can be what they are, and we can coexist and collaborate without me slowly surrendering everything that makes life worth living.

Idk if that’s possible. I want to live into the question with other curious, earnest people.

A very weird reading and writing club

For roughly two months, I’m going to read two books that approach technology from wildly different directions.

Both resonate with me. They also belong in tension with each other. One left me wanting nothing more than to go live in the woods and write unhinged manifestos raging against technologic society on a crickety old typewriter. No pipe bombs though. The other got me excited for the world we could create.

You’re welcome to read them alongside me. You’re equally welcome to bring another book, essay, artwork, spiritual tradition, lived experience, or stubborn question into the conversation. You won’t need to finish both books to participate.

We’ll gather for reading and writing sessions, conversations, and occasional show-and-tells about how technology is entering our actual lives. There will be a group chat, even though I’ve never quite figured out how to enjoy group chats. We’ll try small experiments with our habits, boundaries, creative practices, and tools. Then we’ll return and tell the truth about what happened.

This will be part book club, part writing and journaling group, part collective experiment, and part online retreat.

The question at the heart of it is this:

What does it mean to live a good, dignified human life in relationship with technology?

I have no neat answers. Over the course of the experience, I’ll invite each of us to develop a handful of personal principles for our relationship with technology — self-chosen, revisable, earned through experience.

The place

We’ll gather inside Dark Forest OS, Yancey Strickler’s strange and beautiful community platform. It already feels like a small example of the internet becoming interesting again.

The practical stuff

Roughly two months, beginning around early October and continuing into early December. Exact dates and gathering times are coming shortly.

• $50 reduced
• $100 standard
• $250 patron

Every price gives you the same experience. Choose the one that fits your circumstances. Patron places help support the work and make lower-cost access possible. Scholarships will be available for people who genuinely can’t afford to join. And of course, if this really calls to you and you can’t afford it, just shoot me an email.

Come live the questions with us