Stepping Out of My Bubble: Meeting the Homeless in Silicon Valley by@fiiine

Stepping Out of My Bubble: Meeting the Homeless in Silicon Valley

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Steffany Boldrini


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Charlie Joe, Dominique, Tiffany, John, Carlos, Alex. I’m very bad with names. Bad as in, I already forgot your name after you just told me, especially after meeting a lot of people in a short period of time. But when I spoke with each of these lovely human beings that are living in the streets of the Tenderloin, I was humbled, touched, and overwhelmed enough to have their names etched in my memory. I felt a strong desire to somehow, someway, help them.

I’ve been meaning to volunteer my time for-e-va. But I figured that as long as I donated to a charity, I was being charitable enough with my money instead of time, and this covered my volunteering duties. But the day finally arrived when my church had a volunteering program going on, and I decided to take the opportunity right away.

“You will be walking in groups, you will have a team leader, and you will always have a partner with you when approaching someone. We all know that these streets are dangerous, so if your team leader tells everyone to go, you go. You don’t ask questions. If you feel you are getting into a dangerous situation, give your team leader the look and everyone will leave right away. Don’t get too close, because you will be entering their personal space, this is their homes and you need to respect that. If they start hate talking, you politely say that you have a different point of view and leave. Also, do not talk to anyone who is shooting up drugs.” It was 7pm, a couple of people in the group were admittedly scared (and secretly myself). And we were all “God is with us!” and I thought….“and please save us God”!

My partner was one of the admittedly scared ones, so I had to get the courage to start talking with the first person. - What’s your name? - Charlie Joe, and this is my friend Dominick.- You both have beautiful names. Would you like a muffin? - Sure. - Would you like, hmmmmm, a prayer? I’m sorry, it’s the first time I do this…

She calmly looked at me, as in to say don’t be nervous, put the muffin away, and said yes.I held her gentle hands, dirtied with black street marks, and surprisingly had absolutely no nervousness of holding them (I have barely changed one diaper in my life, might as well held someone’s hands who is likely on drugs and hasn’t showered in a very long time). Charlie Joe was probably in her early 20’s, a beautiful person, and her eyes showed that she was under the influence of something. I wanted to know what got her there, and if anything could have stopped it from happening. But I didn’t know how to ask.

After I was done praying for her, she surprisingly took the stage and prayed for me, asking God to make all my dreams come true. Wow, Charlie Joe, this homeless person, who is part of a group of people that I have purposefully ignored even looking at, cared about my dreams coming true when she knows I already have so much more than she does. My heart froze, cracked into a million pieces and sank to the deepest part of the ocean.

We had a box of small snacks like bananas, muffins, and some flowers for the ladies. Each person we encountered humbly took only 1 item, clearly leaving some for others that needed it as well. One of them just stopped, looked at the flowers in the box with a focus that nobody that owns a phone has left, picked a single stem, raised it up and looked at it like it was a piece of art, smelled it, carefully put it next to his bag, and said thank you as he walked away. No snacks, just one flower. I was watching that with the same focus he was looking at the flower (a focus I haven’t had in a while) as if nothing else around me mattered, thinking of the abundance of flowers I buy for myself, put in a vase and leave them there, not really stopping to appreciate the bouquet.

The next person we approached was Alex, a young man probably in his early 30’s. I asked him if he wanted a snack and he promptly accepted. Where are you from Alex? “San Francisco”. Unsure of what to respond (as I typically respond with “It’s such a beautiful and awesome city, isn’t it?!”) I quickly asked him if he wanted a prayer. He said yes. Alex was a bit quieter and I felt that maybe Alex was ashamed of being there as a man, having a woman around his age offering him food and a prayer. We quickly left so Alex wouldn’t feel uncomfortable.

By now my partner tells me to “Keep it up Steffany, you’re doing great” as she is still a bit nervous about the situation, and the night settles in.

We then approached Tiffany, another young girl probably in her mid twenties. Tiffany told us that she had some emotional challenges, as her mother was using drugs when she was pregnant with her. Tiffany had problems holding jobs because, as soon as a challenge was presented, she couldn’t deal with the problems and would quit. She went on to say that she has a son who is going to be six next week. Her son was taken away from her after he was 1 year old. She said that she wishes her son was with her, as tears started streaming from her eyes, followed by “But I know that it’s very selfish of me, because, if I can’t even give myself one meal a day, how can I take care of my son?”. Needless to say, I was bawling too. What an amazing mom to say that it was selfish of her to wish that the human that she loves and longs for the most in this world was with her, because she can’t even take care of herself.

Riding back home in my Uber had a very different feeling this time around, as we passed through the Westfield Mall on Market Street, with my iPhone in hand, looking outside of the window and seeing all of the frivolous things we buy being heavily marketed to us as “Falls Must Have’s” on storefront after storefront. What has our world come to, that these sweaters had homes with a roof, when so many other human beings slept just outside of it, in the cold?

As I arrived in my warm apartment building, I remembered I had to pickup an Amazon box in the “Amazon-boxes-overflowing-mail-room”, knowing that all of the box owners will get strangely excited to open their newly arrived box, taking what is inside, getting a kick from their new “toy” followed by immediately loosing that kick, and throwing away the box — that very discarded box will become someone’s mattress, and blanket…

Silicon Valley was put in the spotlight when we woke up completely baffled after America decided who should be our president. This volunteering experience showed me that we have a long way to go. If we don’t acknowledge the situation in our own backyard, and choose to turn our heads, how could we even begin to fix the disparity between us and the middle of America? How can we even attempt to fix the problem?

I know that most of us would also be shaken by an experience like this. And we can make an impact in these human being’s lives by creating and supporting programs in our organizations that can help train and employ them, give them a chance, a chance that we were all just handed. If every organization makes it a point to help even just one human being per, say, 500 employees, imagine the exponential effect this can have in our own backyard. Empathy also makes us more emotionally intelligent and informed leaders, and it is very important for every organization to have a team with a broader perspective on life. — Otherwise, we work in silos, inside our echo chamber, out of touch with the reality around us, and we make mistakes that seem like basic common sense in hindsight. Can I get a clap clap or a comment for every person who will propose this at their next All Hands meeting? Shall we call it “Meet the Homeless”?

Here are a few organizations that you can get started to #MeetTheHomeless:

  1. Lava Mae
  2. Miracle Messages
  3. SF Food Bank
  4. Glide
  5. Defy Ventures
  6. Because Justice Matters

  7. My lovely Canvas Church__

Thank you Chandini Ammineni and Lecole Cole for reading drafts of this article.

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