Last November I shot a campaign for Samsung’s NX20 camera using a video camera strapped to my head to record the footage of me shooting street portraits in Chicago with permission. It was a project that was intensive: I shot for 2 days straight from 5am-noon on little sleep.

The thing I loved most about the project is that although I certainly didn’t take photos that made it into my portfolio — it forced me to step outside of my comfort zone and interact with lots of people on the streets in a short period of time. The fact that the video was being played live in Amsterdam while I was shooting did give me healthy pressure which ended up being a great learning experience.

I was in Korea the last week and chatted with some of my buddies from Korea, and asked for some feedback on what I should focus more on my site. The majority of them (especially Ryan Cabal) shared that I should do more videos. With that conversation, I remembered I still had a ton of video footage from Chicago that I hadn’t uploaded yet. So while in Korea, I chopped up and edited this video for your learning pleasure.

I still have several of these videos to come in the next coming weeks – I anticipate at least another 2 or 3.

I also hope to start shooting more video, perhaps featuring other photographers in some sort of mini-documentary series (been really liking the stuff that VICE has been putting out). This feature on Magnum Photographer Christopher Anderson comes to mind. I certainly need to work on my video and editing, and it is a challenge I look forward to.

Regarding these street portrait videos, here are some tips I would give when asking strangers permission to take their photos:

1. Don’t hesitate

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I think one of the biggest issues I have is hesitating when wanting to take a photograph of someone. The second I hesitate, I freeze up and end up not taking the photo.

So if you see someone interesting you would like to photograph, don’t hesitate. Don’t think about rejection or anything like that– just go for it. Surprisingly very few people refused me to take a photo of them (9/10 said yes).

2. Smile and introduce yourself

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Nothing is more disarming than a smile. It shows to your subject that you are friendly and to be trusted. By also introducing yourself and saying what you are and what you do (a street photographer taking portraits) also makes them feel more comfortable with you.

If you tell them what you are all about, and your purpose of shooting (wanting to make a portrait series of the people of Chicago) they become more intrigued and open to your cause.

3. Tell people what you find fascinating about them

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I feel it is paramount to also tell people what you find interesting about them. To us, it is obvious what we find interesting about them — whether it be their outfit, smile, or expression. But our subjects have no idea. They don’t see the things we see that make them special or unique. Often they might think we are trying to mock them, or trying to show something ugly about them.

So tell them exactly what you find interesting and unique about them — and they will feel much more comfortable around you.

See My Other Chicago Street Portrait POV Videos

Chicago Street Portraits POV Volume #1

Chicago Street Portraits POV Volume #2

Chicago Street Portraits POV Volume #3

Stay tuned for the rest of videos that are coming up in the next few weeks. In the meanwhile, I suggest to go out and if you feel nervous shooting street photography — start off by asking for permission.

So how do you interact with people on the streets to make them more comfortable? Leave a comment below and share your tips with the rest of the street photography community.

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