Which Side Are You On

It started with a song.

It was a cool and foggy night in San Francisco, late May 2025. My bandmates and I had rented out Music City SF for the night, putting on a benefit concert for institutions that were opposing Trump's agenda: Indivisible, ACLU, NAACP, HRC, Planned Parenthood. The place was packed. The energy was electric. Folks clearly needed an outlet, and we had given it to them. A place to connect with friends and fellow travelers. A way to show folks that they were not alone in their opposition to this hateful regime.

We rocked through our set, crowd thoroughly entertained, until we finally came to our closer: a medley of the old union song "Which Side Are You On", followed by CSNY's "Ohio". We have some amazing vocalists in our scene, and we invited them all up on stage with us. It was beautiful. 4-part harmony, crowd singing along, the works. It was one of those magical moments where chills run up your spine and deep down into your soul.

The night ended with applause and hugs and smiles and drinks. Great time all around. And we ended up raising just over $6K for those folks -- not bad for a small-time gig!

But as I lay in bed that night, ears still ringing and body still buzzing, the ghostly echoes of one song kept running through my head:

🎶 Which side are you on? 🎶

I thought I knew the answer. I'm a Berkeley leftie from the 90s. I've read my Chomsky. I've smashed my share of TV sets. I go to protests, give to progressive organizations, and sort my recycling. I believe in a fair, just, and free society. I'm willing to sacrifice to help make that happen. Folks know where I stand.

🎶 Which side are you on, boys? 🎶

But that was thirty years ago, I say to myself, and a lot has happened in the meantime. Here in 2025, I'm an midlevel exec at one of BigTechs. Nice gig to be sure, but I saw my CEO line up with all the rest at the inauguration. I heard the demands from the president. I saw how quickly his minions moved to consolidate power and silence opposition. And I saw how quickly our vaunted tech leaders, all those supposedly brilliant freethinking visionaries, I saw how they all fell in line to kiss the ring of the Mad King.

🎶 Which side are you on? 🎶

Back in 2016, I worked at a major online media company. This gave me a ringside seat for the firehose of misinformation and conspiracy theories that were starting to clog the Internet. I saw our algorithms hacked to become microtargeted propaganda machines, complete with built-in A/B testing platforms to fine-tune messaging. For the next four years, it was like watching a slow-motion car crash. Don't get me wrong – our leadership meant well. They tried their best to stop it. But anyone with eyes to see knew where it was heading. When Jan 6 finally happened, all we could do was watch with sickening dread from our screens.

🎶 Which side are you on, boys? 🎶

I was politically active during the 2024 election. I knew the stakes. The other side had been busy laying their groundwork during the Biden years. Orban was their template, Project 2025 was their plan. And personally, I liked Harris – she was smart, eloquent, and tough as nails. So I worked phonebanks, donated, and spoke to everyone I could. But it always felt like the fix was in. I remember frantically making calls the night of Nov 3rd, trying to get people to understand. Few did. The din of Twitter and TikTok was just too loud. Trans panic and the price of eggs won. Now we get to watch the consequences play out every day.

🎶 Which side are you on? 🎶

I work at a self-driving car company now. One of my many jobs is leading our Developer and Agentic AI initiatives. I have decidedly mixed feelings about this. Sure, it's a hot space, and LLMs are a fascinating technology. It still blows my mind that we can encode human concepts and knowledge as vectors in a billion-dimension space, and then use transformers and self-attention to extract them out as text indistinguishable from human writing. But deep down, I know I'm automating the craft I love out of existence, and replacing it with a tech debt machine. I don't think we're going to be happy with the long-term consequences.

🎶 Which side are you on, boys? 🎶

More than that, I fear the consequences of conquering the Turing Test. It was always computing's Holy Grail, but the reality seems closer to Sauron's One Ring. Last month, I met a young woman at Molasses Books in Bushwick. We had a great conversation about LLMs and AI. But at the end, she confessed something that chilled me to my bone: "You know, I think ChatGPT has become my best friend". She's not the only one. I laugh nervously with my co-workers about how creepy our SVP's enthusiasm for AGI and the Singularity is, as we put in another budget request for ever-scarce GPU training quota.

🎶 Which side are you on? 🎶

I lie awake in the darkness, wondering if I still know.