But when it comes down to making work that really sings, I don’t know if I can teach any of it. I don’t even know if I can do any of it half the time. It’s so much about failure, it’s so much about making pictures that are so utterly boring and overstated, you’re endlessly disappointed. And in that process you hopefully find something that draws you back and calls to you. – Larry Sultan

It’s really easy to take a competent photograph. Buy a digital SLR, shoot a lot, get people to tell you how you are messing up and in a year, maybe 2, you’ll be producing pictures that are in focus and properly exposed, your skin tones will be decent and your images will follow basic rules of composition.

It’s really hard to take a good photograph.

It’s rather like writing. Learning to write a complete sentence that follows standard grammar is easy. Even learning basic rhetorical forms is easy, though it takes a bit longer. But being a writer, having a voice, saying something interesting and saying it well, that’s trickier. There are a lot of variations on My High School Vampire Lover for every Charlotte’s Web.

So what do you do, once you can turn out 30+ tidily conventional images from every shoot? How do you get from “here’s your kid, in focus, looking at the camera, and look how shiny her eyes are” to an image that moves not only people related to the subject but strangers as well?

You fail.

You push yourself out of your comfort zone over and over again and screw it up so badly you want to kick yourself. You mangle it. You make really, really awful images. You back up. You get closer. You copy people whose work you like in order to deconstruct what they are doing that speaks to you and then see if you can duplicate that element in your own pictures. You get in your head and ask what you are trying to say anyway. You get out of your head and shoot every day whether you are inspired or not. You flail around like an idiot. You try new stuff. You fail. Repeatedly. And then you don’t, at least a little. You fail less. And then a little less.

What can I say?

Here’s how…

1. Buy a DSLR. Check.
2. Put it on full auto. The people who work for Canon and Nikon are smarter than you and they made a camera smarter than you. The sooner you accept that, the happier you’ll be.
3. Get some great props. Wagons are always popular. So are washtubs. Also, giant lolly pops, tutus and train tracks. Bonus tip: take the child off the tracks before the train gets there.
4. Oh, you don’t like props? Then get some cute clothes. If you are so deeply lame you live in an area that doesn’t have a vintage store where you can pick up some pristine designer children’s clothing from the 40s, 50s and 60s I guess you could go slumming with Zara or Mini Boden. However, this will compromise your awesomeness.
5. Get yourself Photo Shop. You don’t need to get it right in the camera when you can spend hours at the computer making it passable with software. Remember – “photoshop” – it’s not just a product, it’s a verb.
6. Download some actions! Funky processing is like a Pucci print – it hides a lot of lumps.
7. Selective color adds a classy, timeless feel, like the laser backdrop or your wedding portrait on a wine glass.
8. Getting your models to cooperate is an important part of children’s photography. Bribery is often a good technique. Some people use stickers, lollypops or baskets of crappy toys but you may find tens and twenties to be more effective, especially with older kids.
9. If you can’t bribe the child into cooperating, you need to contain him or her in one spot. I tried cages but it’s hard to shoot around the bars. Duct tape, however, is a great solution!
10. The most important part of a portrait session is making a connection with your subject. Ask the child cliched questions about school or friends to really show you care. Failing that, asking the toddler’s analysis of the current banking crisis in Greece or whom she thinks would be a good candidate for state office is always good.

Now and again things happen at photography sessions that make one laugh, though usually not until a bit later after a glass of wine or two. A small sampling…

1. I was doing a very casual portfolio building shoot of a friend’s 3-month old son at my house on my back deck. She took her glasses off to get some pictures holding her child without the specs and my own child grabbed her glasses, broke them, and dropped them under the deck. We had to fish them out (or rather, I did, as she really is basically blind without her glasses) using a hook AFTER we located where they were by peering through the wooden boards at the assorted dead leaves below. Finding patterned brown glasses in dead leaves with almost no light is, well, interesting. I told her to let me pay for new ones. Did she? No. They are STILL taped together and that boy is 18 months old now. Every time I see them I feel glasses-guilt. Lesson learned: don’t ever try to do even the most casual shoot with your kids around. This just doesn’t end well.
2. I did a maternity session for one woman and was doing a set of rapid fire pictures, one after another, of the same pose. When I went back to proof the pictures, as I flipped from one to the next, I realized I could see the baby shifting around inside her womb and causing her abdomen to change shape. I’ve also had a woman have contractions during the shoot; she was a trooper and hiked all over West Hartford Center – in high heeled boots – pausing only briefly during contractions. She admitted she hoped the walking would bring on full labor. No such luck. I did, however, once have a mother go into full labor about 5 hours after our session.
3. Babies pee on my ALL THE TIME. It’s just part of the job and one reason I wear very casual clothes to shoots. Only once, however, did I manage to actually catch an arc of pee in the air when I pushed the shutter RIGHT as the baby peed. If this happens to you I will add a complimentary 4X6 of that shot for you to tuck away until your child’s wedding rehearsal dinner when you can add it to the slideshow of cute childhood pictures. This will be payback for the sleep deprivation.
4. At a wedding I once, camera gear hanging from my neck, jumped down a river bank to grab a blow-away ketubah that the wind had snatched and was attempting to introduce to the water, not 15 minutes after every single person in the family had signed it. This was not in the fine print of “How to be a wedding photographer.” I’ve also helped a bride into her dress, which eliminated any sweet “the bride getting dressed” shots but ensured that she actually DID get zipped into her dress.