Deep Observation Assignment: Eleven Examples

Steven Bertram

Anna Ehart

Steven Bertram arrives at the men’s shelter with his black rolling suitcase and a rolled up tarp under his arm. The gray mop of hair on his head is greasy and unkempt and the denim of his gray skinny jeans is torn in places. He hasn’t bothered to put his only pair of shoes on for the long walk from the High Line to the shelter, his calloused feet tough from years of treading the Manhattan streets. The night is warm, and today October felt like mid-June. He pushes open the iron gates and the ivy covered brick of the old psychiatric hospital seems to be consuming him as he approaches the door. Inside there is the familiar filth and stench of unbathed men, which he’s grown accustomed to over the years.

“Hey, Bertram, how’d the interview go today?” The employee guarding the door asks.

“It was useless, thanks for asking.” He’s been applying for jobs in HR, but no one is hiring. He’s been applying for jobs since his media consulting firm went bankrupt after 9/11. He enters the dimly lit stairwell, his bare feet making a soft, thumping echo. He turns down the long white hallway to his usual room on the third floor, where six cots are made with thin cotton blankets. He sets his tarp on the cot and begins to unfold it.

Orange and yellow boards of plastic cut in panels of various sizes and shapes have managed to arrive at the shelter just a little bent. The boards are covered in small paintings, all on squares of cardboard of the same size. Contorted and monster-like portraits are shadowy in the partially illuminated room. One square reads “Make Peace Not War” and others have colorful peace signs. Geometric compositions painted by children and detailed mini artworks by practiced artists are displayed together on the panels. He unzips his suitcase and takes out the containers of paints, brushes, and palettes encrusted with dried colors and places them on the metal set of drawers next to his cot.

Before he stows away the street art for the night, he stops and puts his rough hands on his hips. He’s been setting up his miniature city in a busy park for a few years now, drawing in small crowds of tourists and locals alike who stop to look. The traveling structure has grown as more and more people have sat down to paint with the barefoot man with the yellowing teeth. Children ask their parents if they can paint and ask “What does art mean?” He tells the children it’s “anything you can get away with.” He’s hardened and gnarled compared to the young innocence of the children, like different species unsure of how to interact. The children kneel on the mats that he lays out along the edge of the green tarp covered in paint and use his globby acrylic paints. When they’re finished he tells parents that he is accepting donations for supplies in a small box attached to the structure. The box is labeled with a phrase he turned into a movement that started with the Occupy Wall Street protests. He protested the causes of his unemployment with his artwork, painting his slogan on a box and getting recognized by reporters and news outlets.

He packs up the panels, carefully tucking his most valuable possession away. He strips down to his soiled boxers, his calloused feet on the cool tile floor and eases his aging and thin body into bed. He sighs with relief, muscles relaxing. The only thing he has is his art. No family, no job, no house. He finds joy in painting signs for his traveling art, and spreading art around the city by having people paint. The support of his fellow protestors makes him feel at home, a support that money can’t buy.

Discussion Questions

  • Why would somebody want to read this piece (the “Who cares?” factor)?
  • Can you clearly identify the author’s intention for the piece?
  • How well does the author support the intention of the piece? Cite specific details that support or take away from the author’s intention.
  • Is there information missing from this piece that would make its intention clearer? What else would you like to know?
  • Does the author portray herself as a round character? How does she do this?
  • Do you trust the author of this piece? Why or why not?
  • How clearly does the author establish a sense of setting/space in this piece? Cite specific details that support your claim.
  • How clearly does the author establish characters other than the self in this piece? Cite specific details that support your claim.
  • Did you learn anything new from reading this piece? If so, what?
  • Are there particular passages with engaging language/description that stood out to you? Describe the appeal of these passages.
  • Would you read more writing from this author? Why or why not?

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