Lessons from a failed attempt to address homelessness

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I first met Joanne* one Friday morning at 5:45am on a San Francisco street corner. By ‘met’ I mean we stood next to each other in awkward silence.

Eager to break the ice, I tried out one of my usual conversation openers—an innocuous, bland question I’d use at any other social event. “So, where in the city do you live?” I asked.

Joanne just stared at me as my embarrassment drained the color from my face. Where she lived was a homeless shelter, and I knew that.

We met on a street corner that morning because of Back on My Feet, an organization that addresses homelessness through running. I’ve done seven marathons, so when I was looking for a way to volunteer, this felt like a no-brainer. Three mornings a week at 5:45am, Back on My Feet's volunteers join its members who are experiencing homelessness to run (yes, run) and walk together around San Francisco. After the runs, Back on My Feet’s staff helps each member secure anything it takes to get out of homelessness—from housing to education and job training.

“So, where in the city do you live?” I asked. Joanne just stared at me as my embarrassment drained the color from my face. Where she lived was a homeless shelter, and I knew that.

I’d shown up to Back on My Feet in an attempt to rid myself of my growing sense of guilt that my lifestyle, filled with its tech-bestowed riches and opportunities, had hastened inequality’s grip on San Francisco. Joanne showed up hoping that one of Back on My Feet’s staff would be able to help her find a job and a place to live.

Later that morning, Joanne told me she wasn’t much of a runner, and that the group’s excited energy was a bit overwhelming, especially considering the sun hadn’t even come up yet. She wasn’t as sociable as some of the other participants in the group, but she intrigued me, and I wanted to get to know her better.

In our first few walks together Joanne always left a considerable buffer between us as we passed under the dim street lamps of San Francisco’s SOMA neighborhood. I was used to the group’s typically close, bubbly energy, so her distance made me uncomfortable. But as we kept walking together every week I learned more about her life, and she began to open up.

Not long after we met, Joanne told me she’d be interviewing for a bread delivery job. I congratulated her.

She let out a half-smile, and I followed with, “Let’s practice for your interview together!"

“Now?”

“No better time than now!” I said.

I sifted through my mental Rolodex of interview tips and tricks that I’d collected over the course of my career. “Let’s start by listing out some of the things you’re good at, qualities that’d be appealing to an employer.”

Tears welled in Joanne’s eyes. Unsure of what I’d done I started spewing out apologies. She told me to stop. She apologized for crying in front of me, and told me I couldn't have known that thinking about what she was good at wasn’t something she was used to.

I surprised Joanne with homemade cookies on one of our walks. I think that was the first time she ever gave me a hug. I thought that maybe we were becoming real friends.

A few weeks later, Joanne found a job washing cars. It was part-time, though, and she told me she needed more money to be able to make rent. I knew better than anyone that tech companies are always hiring, and that they don’t seem to care about peoples' backgrounds—many of tech's most prominent leaders didn’t even go to college.

Wanting to do anything I could to help Joanne, I reached out to a close friend who’s the head chef at a tech company in San Francisco that serves meals to its employees. He had a number of positions open in his kitchen, so I made the connection that Joanne could be one of those employees.

When I told Joanne about the opportunity she was cautiously optimistic. But I insisted that it’d be the right thing for her. I assumed that the tech industry’s privilege and perks would work for her in the way that they worked for me. I thought if she just got the job and worked hard everything would be okay.

After a bit of coaxing, Joanne took a full-time job washing dishes and making coffee.

At first the job seemed great—Joanne started it just in time to make money for rent before she lost her free 90-day shelter bed placement from the city. It felt like a real victory.

But Joanne told me the job wasn’t what I’d thought it would be for her. Her paycheck barely covered her shared room in Richmond, California. She had to spend 4 hours commuting every day using a BART pass she couldn’t afford. Saving enough money to finish the few remaining college credits between her and her four-year degree, let alone finding the time to do it, was a distant dream.

Above all, Joanne said she couldn’t bear how out of place she felt in California, especially at work. “These people, Griffin,” she always said to me. “They’re not like me. They don’t get me. I’ll never feel at home here.”

She told me that someone at work once cornered her and asked, “Where do people like you sleep at night?”

One morning, a few days after I took her to lunch to celebrate her birthday, I texted Joanne to check in, “Hey! Everything okay today?” I asked.

“I’m back home in Louisiana,” she responded.

“Oh okay! Just for vacation?”

“For good. I’m with my family now.”

The news shocked me—I had no idea she was planning to leave San Francisco, let alone on such short notice. I wished I’d had an opportunity to talk to her before she left, or at least to say goodbye. I’ll never forget the immense feeling of guilt that washed over me as I read that text. I wanted to be the solution to Joanne’s problems. I wasn’t.

She told me that someone at work once cornered her and asked, “Where do people like you sleep at night?”

My experience with Joanne didn’t make me see inequality. I’ve already read all the headlines that a six-figure salary is “low income” in the Bay Area. That people like Joanne exist in San Francisco wasn't news to me.

What my experience with Joanne made me see was homelessness, up close. I’d observed it through the window of a Lyft but now the problem felt real. Even harmless questions like “where do you live?” were a delicate minefield defined by the stark contrast between our two experiences of San Francisco.

I, like many of my peers, have been quick to put the blame and burden of our homelessness crisis on the city. It’s hard not to considering that San Francisco spends hundreds of millions of dollars annually to reduce homelessness yet has seen a steady, if not increasing, population of between 7,350 and 7,500 people experiencing homelessness over the last five years.

But after Joanne left San Francisco, I became less sure that the problem is that simple. I wasn’t convinced that the solution was as easy as getting someone experiencing homelessness a place to sleep or even into a job. After all, Joanne had a shelter bed, and she eventually found employment. The system seemed to be working for her.

Looking to get to the bottom of what was really going on, I threw myself into the problem.

I started getting coffee with anyone who would respond to my cold outreach emails—friends, city and state elected officials, economists, leaders in tech, nonprofit and shelter directors, people experiencing homelessness firsthand. I read articles on the causes of homelessness and inequality, dozens at a time. I showed up to take notes at meetings in City Hall. I joined nonprofit boards and took on more volunteer gigs than I had time for. I volunteered for a local politician’s reelection campaign. I learned that there are countless people working tirelessly without praise or press to solve this problem.

Yet when I surveyed all of my tech peers for their perspectives they'd all agree that homelessness is a terrible crisis plaguing our city. But what could, and why would, we do anything about it?

Eventually I took what I learned and wrote a 10-page proposal for how I would design a program to help people like Joanne call San Francisco their permanent home. The idea I outlined was to guarantee people like Joanne living-wage employment at any company in the city while providing comprehensive supportive services like case management, mental health services, and job training that is geared toward sustainable, long-term employment. I thought it was radical. But after getting feedback on the proposal from dozens of experts of homelessness in the Bay Area and beyond, I learned the idea wasn’t revolutionary. Executing it, which would require focusing nonprofits, employers, elected officials, and the city on a singular goal, would be. Connecting those dots in a way that simplifies the complex web of navigating one's way out of homelessness, I was told, might be impossible.

Yet when I surveyed all of my tech peers for their perspectives they'd all agree that homelessness is a terrible crisis plaguing our city. But what could, and why would, we do anything about it?

Today LinkedIn is launching Series, which allows authors to regularly publish articles that anyone can subscribe to. I’ve been invited to write about homelessness in the Bay Area, an issue that since meeting Joanne I’m committed to helping solve.

Follow along as I document my learnings and embark on a journey with my co-leader and Bay Area social justice advocate Sheena Jain as we take that 10-page proposal from vision to reality.

*Joanne is not this person's real name. I have changed all personally-identifying information.

If you or someone you know are currently experiencing homelessness here’s a link to San Francisco’s emergency homelessness services.

If you’re looking to volunteer your time or money, you can find a list of nonprofits that address homelessness in the Bay Area here.