Teaching and mentoring youth in the era of gentrification and mass incarceration.

The children’s section of the library was cold. Someone had left a window open and the North Berkeley fog was riding the frigid bay breeze. Kyle, my 14-year-old writing student, one of those kids who wears shorts in just about any weather, was antsy. His legs jumped and his gaze roamed the rafters like a cat tracking a moth. I offered him some gum—one of the few carrots, besides casual profanity and pictures of my adorable kid, with which I can coerce him into writing.

My phone vibrated. X was calling. I stuffed it in my bag, deciding that whatever X needed must wait. If I replied, Kyle would notice and then he’d think of his own phone.

His gaze still in the rafters, Kyle said, “Can I ask you something?”

I smiled. “That’s what we’re here for, bud.”

X didn’t give up. My bag failed to smother the phone’s persistent buzz.  

Kyle looked at me and chewed his lip. “Don’t take this the wrong way, okay?”

He does this from time to time—asks for permission to say something problematic. As alarmed as I am by some of the stuff that comes out of his mouth, I admire his courage. He knows who he’s talking to.

You said that homelessness directly affects me, but I don’t see how. I mean, I don’t mean to sound like…heartless or whatever, but why should I care? They made their choices…right?”

The question mark at the end of his statement might have been a product of doubt, or it might have been a response to my pained expression—the longer he’d gone on, the more contorted it had become, so that, in the end, it must have registered somewhere between grief and irritable bowel. 

“I said something wrong?”

The last thing I want is to discourage questions for fear of being judged, but the durability of this myth of personal responsibility—especially at a time when tent cities are sprouting around the Bay Area faster than coffee shops and art galleries after an IPO—is maddening. 

“No. You said something honest and that’s the most important thing.” I put my hand on his shoulder. “It’s just that, not only should you care about them, deeply, but the reason you should care should be obvious.” 

“Really? I don’t get it.”

I was suddenly extremely tired. It happens at some point every evening during my rounds. Fatigue drapes its shadow over me and it takes all my strength to keep my eyes from closing. And sometimes, especially when I’m tired, it’s just so hard not to be disappointed—not in my students, but in whatever prejudices have been drilled into them—and it’s so tempting to correct their mistakes, to do the work for them, to tell them all the ways they’ve got it wrong. 

But people only practice ideas they work for. 

I clicked one of the many tabs in my browser, revealing an open letter to people of privilege from a homeless mother of two. 

“Take five minutes to read this,” I said. “Then we’ll talk.”

Once he was started, I fished my phone out of my bag. There was a notification for three missed calls accompanied by a text. 

Calling to let you know we moved into our place. 

I exhaled.

 This was good news. It was also bait—as good as the news was, it didn’t warrant three phone calls. But I didn’t care. I was going to respond because I was happy for him. If I’m being honest, I was happy for myself, too. A roof over X’s head was one worry to scratch off a long list.

 Amazing news! You like your place?  

 Yeah it’s quiet and big, townhouse.

I met X at the Alameda County Juvenile Detention Center where I facilitate weekly writing workshops. After his release, he’d reached out and, since then, I’d become a kind of unofficial mentor. Life for a disconnected transition-age youth who’s spent the lion’s share of his adolescence in detention is unimaginably hard. The fact that X had managed to stay out of prison for four years made him an outlier. Things became especially precarious when, a few months before this, he, his partner, her six-year-old daughter, and their infant son got kicked out of government-assisted housing and moved into a shelter.

 I asked about his job in the city, the length of the commute from his new home. He acknowledged that it was long, about two hours each way on BART, and he was looking for something new.

 Meanwhile, Kyle—frowning and brow-furrowed—was finishing the open letter. “There’s some people out there who think the homeless should be moved to reservations in the desert.” 

“Keep reading,” I said.

Despite having been out of detention for four years, the hall still cast a shadow over everything in X’s daily life, putting him at great risk for homelessness. Years of incarceration strained his relationships with family members. It cemented his function in their lives as a bottomless source of need, an emotional and financial drain—a simple phone call from X could cost them as much as $1/minute; court dates meant taking days off work and sacrificing income; probation officers and judges squinted through disapproving eyes, and asked that they (X’s family) make them (court officials) believe in the sincerity of their desire to care for their own nephew, grandson, son.

 Imagine needing to prove to people who didn’t know your son’s nickname, his favorite food, what kind of music he listened to, the sound of his laughter, that you cared.

 Then there were the lessons. Incarceration taught X little more than how to identify threats and obey authority. It robbed him of social skills, agency, autonomy. It taught him how to make quick calculations such as—if I take the bait and fight this kid in front of me, will the benefits outweigh the consequences? And then it taught him to apologize, to say he was working on himself, to say that he was going to try harder, be better, change who he was into something that no one ever showed him how to be. 

The homeless and the incarcerated share the same insane mandate—first: Acknowledge and accept our assessment of you as broken, and second: With little to no help from us, build yourselves up into the very thing we keep insisting you are not. 

X texted again.

hey zach can I please please ask you for a favor please?

 I knew it was going to be important. He doesn’t ask for money that often, despite there always being a need.

 I need diapers please for my son today please and food please.

 If mass incarceration is an atomic bomb dropped on poor neighborhoods, gentrification is the radioactive cloud that scatters the survivors. X had no community. That was why he was coming to me. There were no neighbors to go to in a pinch for diapers, no family to go to for a home-cooked meal.

I had two more students after Kyle and X didn’t have a bank account, so Venmo and PayPal were useless to us. He suggested Western Union, but a cursory examination of their website on my phone revealed it was going to take me a few minutes to set up the transaction and of course there would be a fee.

 I wished he’d contacted me sooner. I wished he could have gotten out ahead of his need. But anticipating needs is nothing the juvenile justice system ever saw fit to teach him.

 Teaching now, I said. Gimme a couple hours.  

 Cool thank you zach thank you

“Do you know any homeless people?” asked Kyle. 

“I live in this world,” I said.

Kyle scrunched up his face.

“Yes.” 

“How did they end up that way?”

“I’m not sure that one person’s story really matters. Not in this case.” 

“But you’re a writer,” he said. “Isn’t telling one person’s story what you do?”

I smiled. “Yes and no.” 

“I don’t understand,” he said.

“I tell stories,” I said. “Not anecdotes.”

“What’s the difference?”

“Well, I guess the difference is that a story is longer. It’s immersive. It’s supposed to manifest empathy. Anecdotes may illustrate a point but they don’t immerse you in a point of view. And because they’re so short, definitionally, and because they lack nuance, the other side has an easy time dismissing them. Also, the other side, if they’re at all invested in their position, is armed with plenty of anecdotes of their own.”

I could tell from the vacant expression that I’d lost him, but my little speech had been as much for me as for Kyle. The serendipity here—X texting me at the precise moment that I was having this conversation—was noteworthy, but it wasn’t my place to tell Kyle about X’s struggles. My proximity to X’s suffering did not make it anywhere close to mine, and, given that it wasn’t mine, I had no right to make a neat little anecdote out of it that Kyle could then recycle for peers, family, teachers, or whomever he wanted to impress his worldliness upon. 

I chewed my lip and squinted. “What I mean is that, in this case, what I could tell you about this or that person shouldn’t become the reason you sympathize with the plight of the homeless. You need to ask your own questions. And, after asking those tough questions, you need to read and talk to different people with firsthand knowledge. You need to do a lot of listening and reflecting.”

Kyle groaned and thumped his forehead on the tabletop. “I’m so tired. Can’t you just tell me what to write?”

I laughed. I typed a prompt into the document: Write about a time that someone made an assumption about you. Describe the truth that this assumption prevented them from seeing. 

Kyle sighed. 

“You’ve got this,” I said. 

He slumped in his seat, sighed again, sat up, cracked his knuckles and began to type.

This is the process. There are no shortcuts. As teachers and mentors, we have to trust it. Kyle would compose and share a piece of writing and be commended for his efforts. That approval—a material benefit—would boost his confidence. He’d start identifying as a thinker and a writer. And, as a person who identifies as a thinker and a writer, he’d be less likely to accept the hateful fearmongering of the right or the reductive moralizing of liberals. He’d know that in order to know something fully, he’d need to listen to the people whom it affects. 

Four years ago, when X was released and placed in AB-12 housing—a subsidized apartment with another 19-year-old system-impacted kid who also had no clue how to live with a roommate—he was eating nothing but fast food each month until his money ran out and then subsisting on the instant Ramen noodles that the on-site manager gave him, preparing them in a roach-infested kitchen littered with crumpled take-out bags, rotting food and unwashed dishes.

One day we made a shopping list together and I took him to Trader Joe’s. He came back to my apartment and I taught him how to make scrambled eggs and toast. X cracked the eggs into a mixing bowl, poured in some milk, stirred, added salt and pepper, stirred again. He chopped and sautéed some onions. He toasted bread and buttered it before halving the slices. Then he set a spot at my dining table, arranged his food on the plate, sat down and, with a fork in his hand and a huge smile on his face, he posed for a picture.

Later that day, he later posted the pic to Instagram with a caption: I made this.

That post was concrete evidence for X—proof that he was an adult who could go to the store, buy some ingredients, and transform those ingredients into a meal. 

Kyle slumped in his seat and sighed. He had successfully written a paragraph. I patted his back before reading it because the school day is long and doing this kind of work after a long day is hard. Then I discovered that he’d written thoughtfully about a time when some kids, who’d thought he was stupid because he’d had a hard time reading, had given him a hurtful nickname. He said that the nickname prevented them from seeing that he thought deeply about things and asked good questions. He said they didn’t realize that asking questions was more important than repeating back what the teacher told them.

I congratulated Kyle on a solid start, gave him dap. He’d reflected on someone else’s struggles, connected them to his own, and put some words on the page. Our job now would be to get him read more, reflect more, ask questions and shape his responses to those questions into an essay, with the goal of sharing his work in some sort of public forum. 

The act of sharing wouldn’t be for others. Sure, there’d be a chance that some young person would come across Kyle’s work and reflect on their own prejudices. But the sharing would be for Kyle. So he might begin to see himself as the kind of person who recognized injustice, and so he might grow into an advocate for people whom his society tried to convince him were unimportant. 

Darkness fell as I drove the single-lane Berkeley streets to my next session. I turned off the radio. I rolled down my window. I missed my kid. It hurt to be away from home during the slow evening hours. On the passenger seat, the face of my phone lit up.

Hey Zach? Is it still alright? 

At a red light, I wrote back. Patience, buddy. I got you.

Thank you Zach thank you.

Our young navigate completely different worlds. They know of one another’s existence but they experience each other only as the other. That this is not right makes no difference because this is what is. Their lives require no direct contact with one another, and, for the most part, they’re conditioned to avoid contact for fear of the loss of their liberty or their lives. And, because they are taught not to question the design, the structure makes the reality feel, if not right, at least grounded in something true. 

Many of us are a nexus between these worlds. We watch people living out their lives on opposite sides of a chasm. Occasionally, the chasm winks, reminding us of our responsibility to keep delivering messages to the other side. 

But the message cannot be: Listen to me because I have the answers. 

Our unfaltering message must be: See the world with clear eyes and question the answers given to you. It must be: Every discovery, upon further reflection, yields more questions—and this is both right and good. Our message must be: You are more than they expect of you. 

And then our job is to show them that we are right in our conviction. To give them evidence that will stand up against doubt and hate and despair, and tether them to love, which is to say, to one another, because, while we may be powerless to save them, we can provide the tools that will enable them to save themselves.

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Zach Wyner is a writer and educator who works with incarcerated youth in the San Francisco Bay Area. His debut novel, What We Never Had, was published by Rare Bird Books in 2016. He is a contributor to The Good Men Project, Curly Red Stories, Unbroken Journal, Atticus Review and Your Impossible Voice. Zach received an MFA in Creative Writing from the University of San Francisco and lives in El Cerrito with his wife and children.

Photo: Don Ross III