Over the first weekend of last June, I attended a two-day street photography workshop with the renowned photographer Phil Penman in New York City. In retrospect, I regret that I did not record my thoughts right after the workshop, but I flew on the day after the workshop to Italy, a wonderful trip — another long overdue blog post. I will catch up someday, maybe.

As someone who has long admired Phil’s work capturing candid moments and unique street scenes in the city, I was excited to learn directly from him. Phil proved to be as friendly, open, and gracious as his public persona suggests, sharing not only his approach to the craft but also invaluable advice on where to shoot, when to catch the best light, and how to find those iconic New York scenes.

Phil's teaching style was straightforward and encouraging. He spoke about his journey and broke down his process, emphasizing the importance of patience, observation, and intuition in creating compelling images. I quickly learned that knowledge and experience garnered over 25 years in the city were a key part of his success. New York, of course, offers endless opportunities, but Phil’s insights on finding those “sweet spots” when the light is right, researching events, and just being out there offered lessons for how I prepare to shoot on my next visit to the city.

For me, the biggest challenge in street photography is working up the courage to capture people in their natural element—particularly in New York, where people can be as intimidating as they are interesting. I hoped this workshop might help me overcome my insecurity about photographing and, occasionally, engaging with strangers. While that fear didn’t disappear in two days, watching Phil’s calm, respectful approach gave me confidence. I observed that building trust through small gestures and showing genuine interest can go a long way in street photography.

Ultimately, I left the workshop feeling more inspired and more equipped to face my fear of engaging with the unknown on the streets of New York. Phil’s generosity in sharing his knowledge reminded me that good street photography isn’t just about technical skill—it’s about being open, empathetic, and unafraid to connect with the world around you.

Over the interval of time since the workshop, while Phil’s examples and teaching have helped but damn it all, I am still hesitant to ask someone if I can take their photo!

I cannot recommend Phil's workshops highly enough. While not inexpensive, the two day workshop was a relative bargain compared to other workshops I have attended. The information and insight provided was priceless. I also recommend Phil's book, New York Street Diaries, which can be purchased on Phil's website, https://www.philpenman.com. or through Amazon and other online vendors.