Subway Portrait

“Excuse me, m’am, may I draw your picture?” he says, white pad on his lap, fingers stained with charcoal.

“Pardon me?” says the woman sitting across from him on the subway, looking confused and a bit taken aback.

“Your picture…is it alright with you if I draw your picture?” he reiterates.


And then, as his hands glide across the page, his patter begins, not interrupting the drawing, which has to be complete in the two minutes before the last stop.

“This is what I do,” he says, “I draw pictures of people. Portraits. Been doing this for years, I’ve drawn 800 portraits of New Yorkers so far.”

She takes the bait: “All in one day?” she asks. Her guard is dropping just a little bit.

“No m’am, that would be impossible. Anyone who tells you they’ve drawn 800 portraits in one day, they’re lying to you. No, I’ve drawn 800 portraits since I started, and that’s why I can draw them so fast, because I’ve done it so many times. I’m an artist, you see, an artist. Don’t you like how that looks?” (he holds up the already – amazingly – half-finished sketch, which has gone from a few lines to, instantly, a pair of eyes, an outline of a mouth, a bit of expression, in about one minute).

She smiles, recognizing her likeness, the shape of her face, the crinkles around the outside of her almond-shaped eyes.

“See I knew that would make you smile! Now I can get that smile in the picture… Now I’m gonna give this portrait to you, that’s what I do, I’m gonna give it to you either way….Lots of people like these portraits, they hang them up, in their offices usually…And a lot of them pay me for them, even though I give them to ‘em either way, a lot of people pay me $10, or sometimes even $20…

(almost to himself) “Yeah, I try to get 10 people in a day to pay me $10 each, that’s what I try to do. Last guy I did this for he handed me a $10 bill, yes he did. And don’t tell me I’m not an artist, see? Artists make people smile and that’s what I’m doing here, I’m making something that will make people smile.”

Just a few more seconds for the finishing touches, and:

“So here you go, beautiful, here’s your portrait I hope you like it.” he says, handing it to her.

And she does.

And she pays $10.


In review: to create a situation where someone gives or buys, you must first create joy, a story, connection, a thing of beauty.

And in situations, like philanthropy, or busking, where it’s not clear what something is worth, it’s your job to tell them, to frame it for them, to say: this is what people who are happy and feeling a sense of connection in this moment typically pay. This is what the last 10 people did.

“I’m going to give this to you either way, but you gotta know that everyone else before you who liked their portrait gave $10 or $20 and hung the portrait in their office.”

Sure, she could decide not to pay, but if she does pay, you can bet it’s not going to be $1, which is what most people on the subway get when they ask for money.

His starting point was a $1 portrait. The story about the portrait, and the story about what people who like portraits pay, that’s what’s worth the other $9.


As I sprinted into the subway car, I noticed a woman on the platform stop, reach down, and pick a smartphone up from the ground.  She started waving it, saying loudly, “Someone dropped this phone!”

Just as the subway doors were about to close, she leaned in and handed the phone to a passenger standing next to me.  A third guy says, “I think it belongs to him,” gesturing to a man in a blue overcoat who was walking through a door to the next car.  A few gestures, a few shouts, and we get this guy’s attention.  The man standing next to me hands him his phone.

“Thanks,” he says, with a nod, and then turns away, nonplussed, as if dropping his phone on the platform and having it pass through three sets of hands while he walks away, oblivious, is just a normal occurrence.  As if people instantly dropping everything to help him isn’t worth more than a little acknowledgment.

And it occurred to me: it’s not that we don’t get touched by angels from time to time.  It’s just that we fail to notice.