Overcoming Awkward in Street Photography? + Asking strangers for their portrait

A no fear approach?

A question I often get is: how do you approach strangers on the street for a portrait without feeling awkward? It’s a fair question, and like i said it’s one that surfaces frequently. The reality is that comfort and street photography rarely coexist. It’s inherently uncomfortable. Even after 14 years of shooting street portraits, I’m still uncomfortable every time I approach someone.

Don’t believe the con!

Many will sell you a story—YouTube tips and tricks promising to ease this discomfort. But confidence isn’t the absence of discomfort; it’s operating in spite of it. Real confidence is acknowledging the discomfort and moving forward anyway. The idea that you can become entirely comfortable with asking strangers for their photo is a con.

Heightened Awareness

Street photography requires a heightened sense of awareness—a sort of internal radar. Comfort, in this context, can be dangerous, dulling the edge necessary to capture the spontaneity of life on the streets. Many street photographers lean into comfort, and it shows in their work. My workshops, particularly the Dare Photography Workshop, aim to help photographers embrace their discomfort, not eradicate it. It’s about integrating all aspects of ourselves, even the ones we’d rather push away.

What if?

Often, we hold ourselves back with self-talk: “I’ll start when I’m ready,” or “What if it doesn’t work out?” But waiting for comfort is a barrier to creativity. In street photography—and in life—there will always be an internal dialogue. It’s about recognizing this, accepting it, and moving forward anyway.

Dare

The Dare workshop isn’t about teaching you to shoot like me; it’s about supporting you to see that you’re already enough. It’s not about positive thinking or empty affirmations. It’s about confronting the truth: that underneath it all, we’re all dealing with insecurities, shaped by the false realities we see on social media. What’s mostly projected online isn’t real, it’s a facade.

At the heart of my workshop is a liberating truth: when we let go of the bullshit, the need to fit into these fabricated ideals, we start seeing the world as it truly is. And from that place, photography becomes something extraordinary.