The Most Beautiful Memory I have

I'll never forget this

While I was working on Omnivore.io, our office was out of a corner Penthouse we were lucky to get in a coworking space in the financial district of San Francisco.

I worked long days into the night and long after everyone else had gone home. So I’d be sitting there coding in the dark in the glow of three monitors furiously pushing the ship forward.

And I had one special moment I looked forward to every day that grounded me.

Somewhere between 7 and 8pm, a mentally ill homeless man would start playing the Trumpet. And he was very good.

It was quintessentially San Francisco. The songs were somber and slow and each note echoed up the towering skyscrapers and somehow reached into my office.

And when it started every night, I’d stop what I was doing, lean back as far as I could, and listen. As I said, he was very good and his music selection was very moving. As a huge music lover, it was one of the few things at the time that completely disconnected me from work.

Occasionally when work was not too demanding, I would decide to walk home during this time so I could go and watch him play. I’d sit on the steps right infront of him and listen for and hour or more before dropping a $20 or more into his cup. He was incapable of making eye contact and had difficult communicating, but you could see the gratitude in his face. Not just for the money, but that at least one goddamn person stopped and appreciated his divine gift.

Because thousands of other people would walk by this person who could draw me to tears without even thinking or looking every single day. He’d be lucky to have a few dollars and some change besides what I dropped in there.

And there was one song...just one song every night that I’d look forward to. For some reason, Arlen’s “Over the Rainbow” has always held a special place in my heart from a young age. It’s always moved me almost like nothing else. Maybe it’s because I had a rough childhood, but the thought of escaping to a better life rings home to me.

And every night, at some point, this homeless virtuoso would play the single most beautiful and moving rendition of Over the Rainbow I have ever heard in my life. It was slow. It was delicate. It conveyed more emotion than any other piece of live music I have ever heard. And you could feel it was him playing from his own pain and longing for a better life. There was so much of his own experience in that solo when he played it and apart perhaps from Jeff Buckley’s Hallelujah, I have never heard so much of a musician’s heart and soul in a piece of music.

And every night, I’d break down crying, whether I was in my office or sitting a few feet away. The sheer beauty and sadness of the moment nearly brought me to my knees on a nightly basis. It put so much into perspective about how pointless this rat race we call life is. About the endless hours I was putting into work. Shouldn’t we all feel so lucky to experience something so moving as to be brought involuntarily to tears?

We eventually outgrew that office and the next time I went back to specifically hear him play, he was gone. I never found him again.

But I will never, ever forget those nights listening to that trumpet and waiting for those first few notes that would make my heart ache for love, comfort, and a place where dreams really do come true.