Most of us are not natural extroverts and some of us are scared by the idea of approaching a stranger on the street and asking for something as unusual and personal as taking their portrait with a camera.

This fear is completely irrational and unfounded. What’s the best thing that can happen if you don’t ask someone for a photo? You don’t get a photo. What’s the worst thing that can happen if you as someone for a photo and they say no? You don’t get a photo! In the vast majority of cases, if you ask kindly and with a smile, they will say yes.

The fact is, no matter how many times we repeat the above truth to ourselves, no amount of self-persuasion will take completely away the gripping fear most of us experience when approaching a stranger. The only way to overcome the fear is to stare it in the face it not once, but many times.

Up until a few years ago, I was just like that. Shy, introverted and fearful. Then I heard of a photography project called 100 strangers and resolved to do something similar to vanquish my fears. The goal I set for myself was to publish at least one portrait of a stranger every day for one year. Of course I had to ask my subject permission to take their portrait. Stealth photography with a telephoto was not allowed.

The first few times were really hard and I would wander for hours without mustering the courage necessary to stop someone on the street and ask, but now I felt an obligation and just before my time was out, I had to do it or admit failure.

A gentleman from El Salvador, my first stranger portrait

The most surprising thing, for me, was that most of my subjects said yes without hesitation. Sometimes I got a puzzled look, in which case I explained candidly what I was doing. This thing alone was almost always sufficient to break the ice.

After a few weeks, I felt my confidence had dramatically improved and fear was completely gone and I could ask anyone for a portrait without sweating even a little bit. I came to the point where I would keep shooting portraits with the aim of getting at least one refusal. Sometimes that meant getting ten portraits before stopping.

In the end, I didn’t stick to my project for a full year, but abandoned it at about 150 portraits in 150 days. At that point, my purpose had been reached and I wanted to try new things and not go out every day with a fixed idea in mind. The exercise however had been incredibly useful for me. Not one of my friends and family would have thought I could do something like that, if you had asked them before I started, as I was known as Mr. Introvert. So, if I could do it, you can do it as well.

The Tailor of Chefchaouen, Morocco

Do’s

Smile. Trust me, there is no better way to gain the trust of your subjects than approaching them with a smile. To some people, me included, it takes a conscious effort to smile to people, so make a mental note to do it and practice often.

Show the back of your camera. After you’ve taken a photo of your subject, show it to them on the back of your camera. Besides creating more of a rapport, this lets them see how they look and they might even suggest that you take another one, turning their best side to the lens. This will potentially teach you something about taking better portraits.

Send prints. This is especially important in developing countries, where many people can’t afford a printed portrait and they might have never held in their hands a photo of themselves or of their loved ones. An instant printer can be a wonderful tool for this. In a technologically advanced society you can limit yourself to giving out a business card with your email address and offer to send a digital copy if they write to you.

Learn a few words of your subjects’ language. This of course applies when you are visiting foreign countries and no, it doesn’t count if you’re an American traveling to Canada or the UK.

Portrait of a gentleman from Meknés, Morocco. I had to speak what little French I know to get this one

Don’ts

Be sneaky. You might get away with stealing a portrait a few times, especially if you use a long lens, but I can assure you that the more you try to pretend you’re not photographing someone, the more likely it is that your body language will give you away. You also don’t have a chance to capture the eye contact that makes many portraits come alive and besides, where are the fun and the challenge?

Fiddle with your camera controls. When you finally muster the courage to ask a stranger for a portrait, don’t spoil the moment and make them impatient by wasting a lot of time changing aperture, shutter speed, ISO or white balance. Think about your settings before asking and then just focus and click. There is nothing wrong with using Auto mode either, if it makes you act faster.

Portrait of a waitress at my favorite bar

Exercise: Photograph strangers in your home town

It would be a pity if you traveled to a country like Cuba, which is full of great characters who are generally very happy to be photographed, and spent the first week of your trip without taking a single portrait because of shyness and fear.

This is why you must practice the art of photographing strangers and learn to overcome your fears before you leave on that trip you’ve long dreamed of.

In London

Don’t wait until next week to start doing it. If you need to go out to buy groceries today, take your camera with you and ask someone on the street or the lady at the cash register. If you had no plans to go out, do it now and aim to get at least one good portrait.

Do this for ten days or more and upload one image per day to the Web. Create a Facebook album, post to Instagram or Flickr or wherever you like and then leave us a comment with a link to the album and share your impressions. We want to hear from you!

Editor’s note: Ugo runs photo tours to Europe and beyond. Find out more at Ugo Cei Photo Tours.

Further reading

• How Finding a Rich Environment Improves Your Street Photography

• What is a Candid Portrait?