Does Your Discomfort Photographing Strangers Keep You From Being a Good Street Photographer? (2025)

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by Gordon Webster 3 Comments

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It takes a combination of courage, self-confidence, and a relaxed, easygoing nature to feel comfortable approaching and photographing strangers. For some of us, this comes more naturally than for others, but is this a skill that we can develop with a view to becoming better street photographers?

I don’t know about you, but I would definitely count myself among those who experience a certain degree of nervousness and discomfort when it comes to photographing strangers in the street. I actually do quite a lot of street photography because I love it—to the point that my wife has sometimes complained that I take more pictures of strangers than I do of our family (not true, by the way). But like Thomas Heaton, the photographer who made the video presented here, I struggle with some level of anxiety when it comes to approaching strangers to take their pictures. It is perhaps no coincidence that both Thomas and I were raised in the UK, where a brand of modest diffidence tends to be encouraged by our culture, in contrast with the more outgoing and affable ethos promoted in many other cultures.

In the video presented here, Thomas talks quite openly and frankly about his own anxiety when it comes to street photography and the steps he has taken to overcome it. Thomas contrasts his own experience in street photography with that of another photographer featured in the video—somebody for whom approaching strangers to photograph them comes far more naturally as a result of his easygoing and relaxed approach. And even if this relaxed approach to street photography might not be second nature to us, it is something that we can strive for and develop over time if we are serious about upping our street photography game.

What I really like about this video is that it demonstrates the extent to which our own issues, hangups, and lack of self-confidence in certain areas can be an impediment to our creative process if we allow them to be. But it also reminds us that this is nothing that cannot be remedied with a little effort and a willingness to step outside our comfort zone in order to grow as photographers.

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About Gordon Webster Follow

Gordon Webster is a professional photographer based in New England. He has worked with clients from a wide range of sectors, including retail, publishing, music, independent film production, technology, hospitality, law, energy, agriculture, construction, manufacturing, medical, veterinary, and education.

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3 Comments

Milton Holmes

If there is a way to get paid for this it might be worthwhile. I just don’t see much of an income stream from this.

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Timothy Kieper Milton Holmes

Like most things on YouTube. Can make more money by selling the advice, than you can by following it !

Timothy Kieper

So when Thomas got the free Hasselblad, it didn't make him a better photographer ?

Does Your Discomfort Photographing Strangers Keep You From Being a Good Street Photographer? (2025)
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