Last week, I helped build Super Bowl activations for DraftKings, Bud Light, and Spotify, turning San Francisco into a vice-centric Disneyland for the rich and famous. It was plastic. It was loud. It was profitable.

On Wednesday, I traveled from Berkeley to the Tenderloin. The rain was rushing down as I exited the Civic Center BART Station. I walked past the Main Library and water started filling my shoe through a hole I didn’t know existed. My sock got heavy. My foot got damp. Is there anything quite as awful?

The discomfort catapulted me back.

March 2025.

I stepped off a Greyhound into the shadow of the Salesforce Tower. It is the second tallest tower on the West Coast. It’s a giant glass needle that penetrates the clouds. Sometimes it looks the eye of Sauron. It’s a monument to a corporation that monetizes human connection. It is a machine that measures a human being’s worth based on how much money they can make you.

I arrived at its base with no money, no phone, and an empty backpack.

Time was ticking. The sky was gray. I didn’t want to sleep on the ground, or venture to the airport, or have to nod off on short bus routes that ended at nowheres in the middle of the night.

I walked up Market Street to the Main Library. As I sat in front of the computer, it was the first time I truly acknowledged the harsh truth I had been avoiding: I was homeless.

I found a list of shelters. I started with what I believed to be the nicest one.

Dignity Moves on Gough Street. Seventy private rooms. A staff member looked at me through the fence as if I was an invasive species. He told me there was no one to talk to. I had to call The SFHOT line. I had to wait for the van to pick me up and drop me off where they find fit.

“I am in front of you right now,” I said. “I am a person. I don’t have a phone. I don’t want a phone. I am here. I am tired. This is a shelter. I need shelter.”

“Can’t help you.” he said.

He walked away. I walked away. Did dignity move?

I drifted south to SOMA. I passed a tent handing out clean needles. I thought of Huxley’s Brave New World. Soma: the government-produced drug for artificial happiness. An opiate for the masses. I arrived at the next shelter. They asked if I was an addict. I told them I had a couple beers in a couple months.

“This place is only for addicts,” they said. “Try the Human Services Agency.”

Sobriety was the disqualifier. And the Human Services Agency? The name felt wrong. Like how aliens might describe us. Or a department in a Kafka story.

It was getting close to dark. I went back to the library. I sat down in front of the computer again and found a temporary shelter a few blocks away at the Quaker’s Meeting Hall on 9th Street.

I joined the line. These were odd folks. I suppose I was an odd folk, too. A woman with purple hair held a clipboard like a shield. She pointed a thermometer at my head.

“Ninety-four degrees.”

“What?” I asked.

She wrote it down.

“Shouldn’t it be 97 or 98?”

“No. Ninety-four.”

She didn’t recognize the disconnect. I looked at her ledger. The temperatures ranged from eighty-eight to ninety-five.

It reaffirmed a delusion that had previously gripped my mind and begun my psychosis; I must be dead. This place, purgatory. I prayed for a quest or that my retribution was almost over, so that I could go back to land of the living.

I entered the hall.

The old lady’s came marching in, and fed us pasta and bread and cake and cookies. There was Coca Cola. I ate because I had no choice, but suspicious of the sugar they forced on us. We slept on green mats. Most of the folks, drenched theirs in Industrial Clorox. I thought they had it wrong. Embrace the filth. Do you trust the chemicals?

At 8:05 PM, the lights died. I had no blue light. I had no screen. Just exhaustion and the collective breathing of fifty souls. Tired souls. Hurting souls. I slept as deep as you can until 5:30 AM.

The morning crew felt like NPCs (for those older folks, an NPC is a character in a video game that is scripted or run by AI). This morning crew was Sneakerheads. Starbucks and Air Force Ones, tracksuits and the chit chat of urban culture. I wonder how much they were getting paid?

One man marched in every morning and kept repeating, “Drago! Drago! Drago!” at an invisible enemy in the air. They brought French toast in white containers. Some of the people around me drenched theirs in mountains of maple syrup. Is sugar the enemy?

Out by 7am. I entered Mission Mode. Survival is a series of small, concrete objectives.

Find a shower. Find laundry. Find food.

There was a shelter in the Mission that offered laundry and showers on Tuesdays, but only for women.

“I identify as a woman,” I said.

She smiled. She said ok. You are smart. The gate opened.

I sat with some older women who knitted and shared some pizza. I looked around. I had a small breath of relief.

“Your turn.” I had five minutes to shower. I shaved too fast and cut my face. I watched the blood mix with the water.

I had found a shower. I had found laundry. I had food. Missions accomplished. I went back to the Quaker’s Meeting Hall that evening.

In the margins of the day, I started reading a lot and building a website for time travelers. I thought I might be able to communicate that way.

One day, I went to the St. Vincent’s clothing pantry. I tried on Miami Vice-like Hawaiian shirts that felt like Grand Theft Auto outfits. However after a few blocks with my new clothes, I decided they must be cursed. Filled with the bad energy of their previous owners. I wore them 30 or so blocks. And donated my new clothes at a Goodwill. I stuck to my original avatar. Jeans and a Marine Layer hoodie.

I needed a guide. I stole Don Quixote from the library.

One night, in the Quaker Meeting Hall, I thought I found my Sancho Panza: an older Chinese man who waddled with three plastic bags filled with Pringles containers. I don’t know what he did during the day. Or why he always carried those plastic bags. Or why the contents of those plastic bags never changed. I thought we might be knights.

The end of March happened and so did the temporary shelter. I needed to find a new place.

I remembered a place in San Mateo I rejected back in February. It hadn’t crossed my mind when I first arrived back in San Francisco. When I had been offered it in February, I rejected the offer because I thought it was ludicrous to think I was homeless. I come from a relatively privileged upbringing, and the idea of homelessness was a distant concept to my naive brain.

Now that I was beginning to land in reality,

I hopped on the Cal Train to Redwood City and walked to LifeMoves Navigation Center. They accepted me for a night but said I needed an official recommendation from the Human Service Agency to stay. I would do it after my court case the next morning.

April 2nd, 2025

I stood in a courtroom. Four felonies.

My public defender reminded me of a woman I did ayahuasca with in upstate New York. But she didn’t like me the same as the ayahuasca friend. She hadn’t responded to my emails. She was never in her office. I didn’t like the lack of communication.

I told her I wanted to represent myself.

She looked at me like I was insane. “You might not even be allowed to represent yourself.”

If there is one thing to know about me, it’s this: as soon as the words, “You can’t” or “You aren’t allowed” are spoken - especially when there is objective truth- it becomes my mission to prove the right way, to prove a truth. Purpose endowed.

The judge looked down from the bench. “Are you sure? If convicted, you could spend three to five years in prison.”

“I am sure,” I said. “I am capable. I understand the charges. I understand the possibility of the consequences. And I understand the process. I want to represent myself.”

She said, “Ok. I’ll see you at the end of the month.”

I walked out of the courtroom, a homeless felon acting as his own attorney.

I took the Caltrain back to Redwood City. I went to the library. I saw the email from my mom.

Your grandma passed away this morning.

Twenty-two days in hospice. Supposedly she broke the record in that hospice. She couldn’t die without winning.

I went to the Human Services Agency in Redwood City. My paranoia of the place had dissipated slightly as the idea of having my own room felt pretty nice. But they denied me from the LifeMoves Navigation Center. Instead they offered me a bed in a room with twenty men in Menlo Park. She pointed to 3 guys who were missing their teeth and I summed them up to be probable meth users.

“You can join them. I’m calling them an Uber right now.”

“No,” I said.

I was done with barracks and shared rooms in homeless shelters. I walked out.

I walked into a Savers. I didn’t have money. Since that 94 degree reading, I had refused to steal, convinced I was in purgatory and doing the “right thing” was the only way to pass the test. But standing there, the rules dissolved. The moral guardrails of our broken systems suddenly felt absurd. Today, survival wasn’t a sin. It was a step in this journey. I felt a wink from my grandma.

I took a sleeping bag, and a Thermos. I walked out.

I walked into a Sports Basement. I grabbed a portable stove and a small propane tank.

I walked into a Safeway and grabbed some taro roots, tortillas, beans, and a steak.

I found a bridge in Redwood City. Concrete. Brutalist. A bit damp.

I unrolled my sleeping bag in the dirt. The moon came up. A raccoon walked on the other side of the river. I turned on the mini propane tank, cut and cooked the taro, the steak, and the beans - and made myself some delicious steak tacos.

A couple months ago, I found that particular bridge was next to an office building inhabited by some of my old colleagues. A start-up I had been a part of in New York. Where I was the first employee. I had owned equity. They had eventually sold for $350 million. At that moment, they were raising $140 million to build robots for the future.

And here I was, a man facing felony charges, homeless, penniless, sleeping in the dirt just a stone’s throw away from a future that could have been.

It was funny.

I closed my eyes. I could defend myself. I could fend for myself. I could survive.