Three years ago, I couldn't take a photo of a stranger without my hands literally shaking. I'd see this amazing old guy feeding pigeons in perfect golden hour light, or a kid with the most incredible expression, and I'd just... walk past them like a complete coward.
The worst part? I'd go home knowing I'd missed incredible shots because I was too chickenshit to approach people.
You know what's funny? I used to think confident photographers were just born that way - naturally outgoing people who never felt awkward.
Then I met this photographer I really admired at a workshop. Guy shoots incredible street portraits, works for magazines, the whole deal. He told me he still gets nervous before every shoot. Still second-guesses himself. Still worried about bothering people.
The difference? He does it anyway.
Most of your fear has nothing to do with photography. It's about looking like an idiot in public, getting told off by strangers, or having someone laugh at you. That's normal human shit, not a photography problem.
New Orleans street festival. Three hours. Zero photos of people.
I kept seeing incredible subjects - this old jazz musician with the most expressive face, kids dancing in crazy costumes, couples laughing together. Every single time, I'd start to raise my camera, then lose my nerve and pretend I was photographing some boring building.
Came home with 300 photos of architecture. Not one interesting human moment. That's when I knew something had to change.
I know you want to skip straight to street photography. Don't. That's like trying to deadlift 300 pounds on your first day at the gym.
I started with my family at barbecues. Then my friends. Then friends of friends at parties. Each time got a little easier because these people already liked me and weren't going to tell me to fuck off.
You're learning to direct people, handle your camera under pressure, and deal with the social weirdness - all with a safety net.
You can't be confident with people if you're still fumbling with your settings. When I was constantly thinking about ISO, aperture, and shutter speed, I had zero brain space left for connecting with subjects.
Spent boring weekends practicing at home until I could change settings without looking. Only then could I focus on people instead of buttons.
Yeah, it's lame. But I started by asking permission for every photo. "Hey, I'm working on a project about street musicians. Mind if I take some shots?"
Got rid of that guilty, sneaky feeling. Most people said yes. The ones who said no were usually nice about it. Baby steps.
Musicians, artists, people performing in public - they want attention. That's literally why they're there.
Spent two months only photographing performers. Learned to work with movement, weird lighting, chaotic situations - all while knowing these people expected cameras.
Places where everyone has cameras out. You're not the weird guy with a camera - you're just another tourist.
Street photography made me improve faster than anything else. Can't hide behind controlled lighting or posed subjects. React fast or miss the moment.
Biggest realization? Most people don't actually care about being photographed. I was way more worried about it than they were.
This is what I teach in my Fearless Faces course - how to approach strangers and connect with them instead of sneaking around like a creep.
Formal portrait sessions taught me to give people direction, make them comfortable, and create good photos even when someone's awkward.
Big lesson: people want to look good. When you're helping them look awesome, they're usually happy to work with you.
Most people are too busy with their own shit to judge random photographers.
Real talk: three years of street photography, maybe five negative interactions out of thousands of photos. Most people don't notice or don't care.
Kept me in auto mode forever. Fix: practice manual mode at home until automatic.
Every photographer thinks this. You get better by taking lots of photos, not by taking perfect photos.
One week, one conversation with a stranger each day while carrying your camera. Not to photograph them - just to get comfortable talking to people with photography gear.
Photograph 50 different strangers over a month. Start easy (performers, tourist attractions) and gradually get harder.
By person 30, walking up to strangers feels normal.
Morocco. Marrakech market. Crazy busy, overwhelming, perfect.
Instead of trying to be invisible, I started showing people photos on my camera. Laughing with them. Using hand gestures when we didn't speak the same language.
People started calling friends over. They invited me to photograph their shops. Posing for me.
Photography became about connection instead of capture. That's when everything clicked.
Can't go from terrified to confident overnight. But you can build it step by step.
Start where you're comfortable. Friends at parties? Start there. Build on success instead of jumping into stuff that paralyzes you.
Make it gradually harder. Comfortable with friends? Try acquaintances. Then, friendly strangers in easy situations.
Understanding composition and perspective helps, but confidence comes just as much from people skills.
If you're serious about getting comfortable photographing people, my Fearless Faces course covers everything - approaching strangers without being creepy, handling rejection, and creating photos that capture real moments.
Building confidence isn't just about better pictures. It's about getting comfortable connecting with people and seeing the world with curiosity instead of fear.
Photographers who get fearless aren't naturally outgoing or talented. They're just willing to feel uncomfortable while building skills one awkward interaction at a time.
Took me about six months of regular practice before I stopped feeling like I'd throw up every time I approached someone. But everyone's different - some of my students get comfortable in weeks, others need a year. The key is consistency. Photographing one stranger a week won't build confidence nearly as fast as photographing five strangers a day for a month straight.
I keep it simple and honest: "I'm working on a street photography project" or "The light on your face right now is incredible, mind if I take a quick portrait?" People appreciate the straight talk way more than some pretentious artistic explanation. If they ask what you'll do with the photo, just tell them the truth - personal project, portfolio, learning exercise, whatever it actually is.
Happened to me maybe five times in three years. When it does, I apologize, delete the photo if they ask, and move on. Don't argue about your rights or try to convince them - just be respectful and leave them alone. One awkward moment isn't worth destroying your confidence or ruining someone's day.
Depends on what you're after. Asking permission builds confidence when you're starting out, but it changes the whole vibe, and you lose those natural, spontaneous moments. I asked permission for everything at first, then slowly moved to more candid work as I got comfortable. There's no universal right answer - just what feels authentic to you and respectful to your subjects.
Almost every photographer deals with this. What helped me was changing how I thought about it - from "I'm sneaking photos" to "I'm genuinely interested in people and documenting real moments." Being open about what you're doing helps too. If you're not hiding or acting shady, you feel less uncomfortable. The feeling fades with practice. By the time you hit stranger number 50, it feels pretty normal.