Being a Street Artist

The Good, the Bad and the Ugly

Boston's very own Downtown Crossing.

This summer I was working as a remote software developer in Boston. Without the regular hours of an office, I found my schedule slipping into the early AMs, and then the late AMs. I also started to feel quite isolated. I decided that I needed to do something that:

  1. required lots of socializing,
  2. would get me outside during the day, and
  3. would help me improve at something I was interested in.

I decided to be a portrait artist, like the ones I used to idolize as a kid in Times Square. It fulfilled all conditions easily. That afternoon, I picked up:

  • Two camping seats. Small enough to fold and put into my bag. One for me, one for my customer.
  • A canvas stand. Not to use for drawing, but to hold up my sign.
  • A drawing pad, 18” x 24”. Again, not for actual drawing but to use as my sign.
  • A bucket hat and sunscreen.

Filled with trepidation and excitement, I stepped out of the Red Line station into Boston’s Downtown Crossing. And so began my life as a street artist.


How much money did you make?

Haha. This is always the first question. I initially charged $10 a portrait but messaged it as a suggested donation. This means that a third of people who really like their portraits will pay me $20 or more. The most I got paid was $100 (true 80/20 curve in action). For simplification, let’s say this is $15/portrait.

A portrait takes me 15 minutes. Given a chit-chat time of 5 minutes per person, this caps me at 3 portraits per hour, or $45/hour…assuming that people are lining up to get drawn.

But people aren’t lining up to be drawn. Musicians and breakdancers can draw crowds with their energy and showmanship. Artist don’t have the same option. My best bet is try to engage people to make them stop, making other people stop in the process. I didn’t figure this part out until after a painful first week.

But anyways. Here are some stats from week 1:

Not so great, huh? I was bummed too.

Here’s week 6:

A lot better!

Short answer: Enough to pay the rent.

Long answer: I was surprised that after the first week I was making a livable income. After I had learned my initial lessons though, my hourly revenue didn’t change very much. By FAR the most meaningful change I made was upping my suggested donation from $10 to $20, and using a thicker, more official looking card-stock material.

I also acknowledge there were a number of optimizations I could have made. A larger, printed sign. More examples of my work. Portraits on canvases that could sell for $40. Mass-produced pop art canvases on the side. I wanted to stay light though, so I go move around and do things after I was done working. That meant everything had to fit in my bag.

One could argue that you don’t do something like this for the money. From talking to the other street performers though, I get the sense that it is purely for the money, because it allows them pursue their art on the side without the obligation of employment. This brings me to the next question:

Make any friends out there?

I would frequently see The Human DJ, one of the more popular street performers in Boston. He told me it was the quickest way to make money for now, and as soon as he saved enough, he would leave Boston and produce music full time. He’s had a lot worse experiences than me because he’s been doing this for so long, like getting shut down by police and getting robbed.

Mr. Not Art was a grafitti artist. He sold his prints on the street while working on his own pieces in the meantime. He’s been doing the same concept for 7 years now, and is having a hard time coming up with something new.

Ming doesn’t have an online presence, but at one point I’d stop by and talk to him every day. He’s one of those OG graduates of the Central Academy of Fine Art in Beijing in Painting. He works on his own paintings in the winter and draws realistic pastels in the summer. He’s not too invested in his own work though. He just likes being able to go home when he wants to and the fact that MassHealth is so cheap.

I got acquainted with a lot of the homeless people in the area. In the beginning I was afraid they would resent me for being invasive competition. But I’d bring them cigarettes, food and small bills and we became friendly. Once, Jack, a local homeless man, brought me a burrito.

Who gets their portrait drawn?

I realized early on that my drawing style wasn’t popular with the tourist families. My audience skewed towards younger - lots of high schoolers and college students. I got a lot of people with creative, niche interests. A lot more locals. Otherwise, I got a fairly even split of gender and race.

I had lots of people who said they liked to draw too and wished they kept at it.

Any interesting people out there?

Oh gosh. Plenty. Lot of weirdos. Lot of nice weirdos too. Some kids who worked at the Downtown Crossing Primark would stop by every day and shill for me. They were fun.

Was it enjoyable?

I liked talking to people about their days and their lives, and the part where I got paid. I didn’t actually like doing the actual portraits.

It’s pretty mentally taxing for me go for accuracy with such a short time constraint. Sometimes I got into a flow but this was rare.

I thought of it as free drawing practice, which made the whole thing go more smoothly.

Worst Experience?

Teenagers on dirtbikes hanging out on the street all evening and scaring all my customers away with the noise.

Or, that customer that walked off without giving the “suggested donation”. Haha. My fault really.

Nothing that was too bad. I had a lot stranger experiences when hitchhiking.

Any tips for aspiring street artists?

Experiment with times and locations. I thought I would to better in Faneuil Hall, Boston’s most touristy spot, but I rarely got any customers when I set up there (there was also more established competition).

The weekend evenings worked best for me. This was when things were slowing down, and it was starting to get dark. Thursdays were always better than Fridays - I think people chill out on Thursdays, but are too eager to get drunk on Fridays.

I realized that my mood would get lower when I went for long stretches without getting customers. I told myself that it was okay to take a break, buy some water, sit down, and do some light sketching while I got my energy back. I found that chatting with strangers without the intent of drawing them always boosted my mood. Your mood is important because it’s most of the reason why people want or don’t want to engage with you!

It’s very empowering to realize that you can make money completely independently, and with a creative skill nonetheless. So yes, hone your craft, but more importantly, work on your sales, because that’ll account for 80% of your results.

And don’t forget:

You’re basically a bus driver. You’re aren’t really a part of the lives of any of your passengers, but you do have the unique ability to make all of their days :)