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Following the Rules

Homeless Experiment: Living for Free on the Streets of New York

In June of 2013 I spent 28 hours on the streets of New York as an exercise in stoicism.

“Set aside a certain number of days, during which you shall be content with the scantiest and cheapest fare, with coarse and rough dress, saying to yourself the while: “Is this the condition that I feared?”


I wanted to see how it felt to go completely without money or shelter for 28 hours.

This is the Homelessness Experiment.

NOTE: Before reading this, check out these two posts for context:
I’m Two Weeks From Living On The Streets
Experiences in Growing a Beard

“All creativity should be exploratory. If we know what we’re doing completely, we’re not in the right place.”

-Jerry Seinfeld

I wake up to the sound of my iPhone buzzing at four in the morning. My alter ego’s late on his rent payment for the last time. All my friends are on vacation, and I have no place to go.

No time to stay, the landlord’s yelling at me to leave; I’ll need to come back for my things next week. I take a notepad and pen, that’s all I have for the next 28 hours.

I leave the house with only my clothes from the night before: no money, no deodorant, no direction, and nowhere to spend the night.

I walk out into the street and move toward the nearest Metro Station.  Somebody threw a bunch of boxes out, so I take one and rip it into pieces.

I don’t have a bag with me, so I fold up one small section and stick it in my pocket. There’s no money in Harlem, so I need to get downtown, but I’m still not sure where I’m going to sleep tonight.

I have this intense desire not to tell other people I’m homeless. A guy walked past who I could have asked for change, but I couldn’t say anything.

Begging’s going to be a lot harder than I thought. I’ll just have to remember that the worst thing they can do is say no or ignore me. Begging is just like sales; it’s actually identical to cold calling.

Begging is just like sales; it’s actually identical to cold calling

I walk down a side street trying to find a safe place to pee without being seen. People keep passing on both sides, and the sun’s coming up.

There’s a brick wall between two houses that I’ll make my pee zone.

The Pzone is not good.

Not to be confused with a P’zone, though very similar.

The wall already smells like urine; somebody’s been here before. I mark the territory; the first time I’ve ever gone outside while sober.

I walk by a grocery store and get the insatiable urge to buy a box of cereal. I almost walk in before remembering I have no money. Six hours ago I bought a paper notebook for $8; it’s funny how quickly priorities change.

A pair of black men and a fully dressed drag queen are arguing in the street. The queen keeps yelling: “You owe me five minutes!  You owe me five minutes!”

One of the men runs down the street to get away, but the queen chases him. He gets away, and the drag queen stop chasing. She goes back to her corner, defeated.

I pass by a Wendy’s with a bunch of trash bags out front. It looks gross in there, but if someone was really hungry I could see how they’d be able to survive off what was in there.

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