Street portraiture is absolutely, unequivocally, why-would-anybody-do-this-for-a-living terrifying… in my opinion. The thought of approaching a complete stranger on the streets of New York City and asking if they would let me take their photo seems about as appealing to me as asking a mamma bear if she would mind me riding her 2 week old cub for a few miles.

That said, I also want to learn. I want to be able to go up to the man sitting on the stoop with a far-off look in his eye and ask him for his picture and… just maybe… his story.

This is what Humans of New York creator, photographer, and #1 New York Times bestselling author Brandon Stanton does better than anybody else in the world. A skill he generously demonstrated about a year ago at the UCD Literary & Historical Society at University College Dublin in Ireland:

We’ll forgive you if you want to watch that several times. And if you want to see Brandon put these techniques in action, check out this behind-the-scenes video put together by the folks at Mashable in October of 2013:

In the end, Brandon attributes his success approaching strangers to two things: fearlessness, which is born out of a mind-boggling amount of practice. Mama bear or human on the streets of New York City, neither will have the chance to tell you yes until you ask.

Hockey icon Wayne Gretzky once said, “You miss 100% of the shots you don’t take.” If you aspire to capture amazing street portraits like the 500px photographers who took the photos below, go outside and start taking shots. Side note: start with the humans… the bear is a bit tougher to convince.