When I first began as a photographer I did so out of frustration with videography. This was back in the days just before the digital video explosion. You needed tapes to record your video to and it just wasn’t easy to endlessly waste tape trying new things.

Digital photography by the way of DSLRs was just coming of age. My first DSLR was a Nikon D70s which I bought instead of a mountain bike. Probably for the best because I’m certain that there are no professional wedding mountain bikers.

You might be the best news photographer around but you don’t have a press credential, have no access to a recurring event, you have no way to shoot any of this stuff.

But I digress.

The other reason I wanted to switch to photography was because you could and try a lot of new things which didn’t require people to accomplish or partake in.

In video if you had an idea it was generally people you would need to make it happen.

That sucked. I’d made a few videos here and there and became quite proficient with non linear editing tools such as Adobe Premiere and After Effects, but I was at the end of the road for video.

I’d been frequently messing with my dads old Canon AE-1 SLR along side video and eventually my desire to shoot photos grew. I bought a DSLR.

I happily set about taking pictures of landscapes and nature. The usual stuff most beginners snap pics of. Their family. Random birds. Rusty locks on sheds. Flowers. Their pets. And so on, till finally I felt pretty good about myself and some how lucked into a “portfolio” review with the legendary Paul Daly.

Paul was great to me, more than he will ever know. I left somewhat embarrassed but also challenged and I frikin’ love a challenge.

I put portfolio in quotes because it was less of a portfolio and more an album of random snaps of crappy subjects, none of which told a story… which was Paul’s first piece of advice he gave me.

Finally he said “you have to shoot more people” and showed me work from his portfolio as example.

It should be said, Paul isn’t a Street photographer. He’s a newspaper and commercial photographer and a very accomplished one at that. And nothing that he showed me was Street photography oriented, it was mostly news and commercial work. Quality stuff, but not anything I had access to.

You might be the best news photographer around but you don’t have a press credential and have no access to a recurring event, you have no way to shoot any of this stuff. You can’t just show up to a concert and get access to the press pit.

What was I to do?

I had direction. I had renewed focus. I had a challenge. I had no opportunity. Especially so in a city with so little occurring relative to other “big” cities.

Even working for free, there’s 20 other photogs also offering to work for free. We’re not in Manhattan where there’s a ton of photogs but also hundreds of events happening nightly, all attended by photography welcoming guests, without a camera jockey to snap them.

I turned to the only easily accessible outlet with a constant stream of the people all doing interesting things: the street.

It wasn’t easy. Learning to take photographs in close quarters to a random stranger is a huge thing most photogs never over come.

The fear of rejection second only to public speaking, which itself has many parallels to street photography. If you’re a photographer that fears rejection and public speaking you have to try it.

Personally I started slow, sticking mostly to the 100-200mm, only occasionally getting close to someone. Soon I began teasing the waters, engaging subjects in conversation, discovering out who they are and what they’re doing.

This is how I cut my teeth as a street photographer and got over my fears of rejection. Before I knew it was sticking the lens as close as I could to people and staging mini photo sessions on busy sidewalks.

I’ve asked homeless addicts on the streets of Ottawa for their picture. I broke language barriers in Manchester, approaching doormen of Indian restaurants for their photo in a part of town where I was in the minority. I’ve been yelled at by police, and yelled back. I shot street in Manhattan, a place so flooded with potential street photography subjects it was like shooting fish in a barrel. I’ve done pop up photography directly in front of people without their express permission — not that it was needed, because a photo had to be taken then and there without their knowledge.

Street photography taught me a lot of techniques and skills I use when I photograph weddings. And a lot of life skills that I’ve used in other aspects of non-photographic day to day life.

It taught me how to be fearless behind the lens. And how to persuade people, winning them over in an instant with a smile and a decent sense of humor.

That’s how I became a street photographer.

That’s how I became a better photographer.

Here’s some of my best and my favorite street photographs. And if you enjoy these than you should check out my huge collection of photographs from downtown St. John’s titled “Environs and Denizens“, a long side project I worked on for many years.

Enjoy.