Digital photography is perfect for those who—like myself—used to waste roll after roll of film. Yet despite never-ending takes, my pictures still end up looking like they were shot by the office drunk at the Christmas party: blurry, foreheads chopped off, no sense of perspective. This is no way to shoot New York.

For help, I enlisted the services of Phil Toledano—a photographer who shoots for Vanity Fair and Details, among others. Armed with an ordinary Canon PowerShot SD400, we started out in Times Square, moved on to a few darkly lit New York bars, and found out what we’re doing wrong.

Outside, on the street

Don’t try to get as much crap in each picture as possible. Toledano calls this “a typically American attitude.” Focus on particulars; capturing the minutiae of the city—like street signs or graffiti. In the photo on the right, I focused on this lost-looking woman in red, and let Times Square fall around her.

Don’t use the viewfinder. It promotes eye-level picture taking, which tends to promote static picture taking.

Take loads of pictures. Important for someone like me, “such a bollocks photographer,” says Toledano. This pic was the best of 120.

Overcast days are better than sunny days. Shadows from buildings can wreak havoc. It’s better to take pictures earlier or later in the day, rather than when the sun is directly overhead. I took this at 7:45am.

It’s bad form to take pictures of homeless people. They’ve already got it bad enough without you using them as props. If you’re looking for strangers to shoot, try tourists and people who look like celebrities. Your friends will be impressed.

Indoors, at a bar

Don’t spend a lot of time setting up shots. Toledano says: “Be invisible. People get uncomfortable and awkward if you stick a camera in their face for too long.” Also, drink more. The drunker everyone gets, the more natural the pictures seem. In the moody self-portrait on the right, I am very drunk.

Most bars are lit moodily. And taking pictures in low light can be tricky business. Toledano tells us to use what photographers call the old “Joan of Arc”: Take the candle on the table and set the person sitting next to you on fire (that tip is presumably droll British “humour”). Failing that, switch your digital camera to indoor mode or adjust the ISO setting (the light sensitivity of the camera’s image sensor) manually—lower ISO settings generally result in a higher-quality photograph, but it is worth experimenting with different speeds at different light levels.

Master the white balance. It’s important to be able to adjust your camera’s white balance (which will decrease the blue or orange hue that often appears with default settings) and different color modes (vivid, neutral, sepia, etc.). Experimentation with manual settings can help prevent loss of detail. (If nothing else, at least switch your camera to the indoor setting.)

Don’t use the zoom function. The images generally become more pixelated the more you zoom in.

Don’t use black and white. He’s right. It just makes you seem like—in Toledano’s words—“a wanker.” The shot above is well composed but makes me look like a pretentious Ansel Adams.

Now that you know how to take a pic, learn how to show it off. Check out Seek for display tips.