What Fourteen Years of Family Photos Taught Me About Letting Go of Perfect

My daughter was two and my son was four the first time we bribed the kids with candy to get through a photo shoot. I'd brought suckers, the plan was simple, they get one when we're done, and then they did not understand the concept of "when we're done" and they absolutely could not wait one more second. So I caved. Mid-shoot. They have suckers in their hand in some of those photos, cheeks still round with toddler & little kid, very happy and completely unbothered by the fact that this was supposed to be a polished family portrait.

They're some of my favorite photos we've ever taken.

That's the thing nobody tells you before you start doing this every year - the moments you'll actually treasure are almost never the ones where everything went according to plan. We've done a family photo shoot every single year for fourteen years now, and if last week's post was about the outfits, this one's about everything that happens once everyone's actually dressed and standing in a field together for an hour. Because that part is where it either falls apart or comes together, and I've picked up a few things about which way it tends to go.

Say the quiet part out loud to your family first

Before we even get to the field, we set the expectation as a family: we're doing this once a year, it takes about an hour, we're going to laugh and connect while we do it, and I do need everyone to cooperate and take direction for that hour. That's it. That's the ask.

My husband has been the one to really carry this, honestly. He's told our kids more than once, some version of "hey, this is important to Mom, she doesn't ask a lot of us for things that are just for her, so let's be respectful and give her this." I didn't ask him to say that. He just did. And it's made more of a difference than any outfit or location ever has, because when your partner sets that tone, the kids follow it. And now the boys tolerate we (we try to make it fun) but my daughter is now on team photoshoot!

If you're doing this solo, you can say a version of it yourself - not as a threat, just as the actual plan. Kids do better with an hour that has an ending in sight than with an open-ended "just be good."

Know your shot list before you show up

This one's simple but it saves so much regret later: know what groupings you actually want before the camera comes out. You and your husband alone. Just the kids. You alone. A parent with just one kid. If you don't decide this ahead of time, you'll get home, love the photos, and still think "wait, why don't we have a single one of just me and my husband" - and by then it's too late for a year.

The other thing that I let my photographer know is that I need a mix of portrait and landscape style images with negative space in the background. The reason this is important comes down to a Christmas card where I want to be able to write words in the background or a blog post that I need in a specific format or a family photo gallery where I need a portrait photo. It's really good to have a mix of both.

Take the two-second observer pause

Right before your photographer starts clicking, just step back for a second and actually look at your family like a stranger would. A collar flipped wrong, a button skipped, a piece of hair doing something wild - you'll catch it in two seconds if you look, and you won't catch it at all if you don't, and then you'll have forty photos with the same thing wrong in every single one. Quick look, quick fix, then let them shoot.

Move, don't freeze

If I don't love how my hair looks in one shot, staying frozen in that exact position just guarantees I won't love the next nineteen either. So between clicks, I move things - hair over one shoulder, then behind it, hands through it, a different head tilt, a different angle of my chin. Same idea for your body. If a pose feels off, shift it before the next click instead of holding still and hoping. You've got way better odds of landing on a shot you love if you're actually giving the camera different options to choose from.

Make them laugh for real

Fake smiles look like fake smiles, every time, no matter how good anyone is at faking it. The photos I love most are the ones where someone actually cracked up - an inside joke, a joke about myself, whatever gets a real laugh out of the group. That's the smile you want on your wall, not the "say cheese" one.

Ask your kids what they want too

Last year my daughter wanted her shirt hanging off one shoulder in a way it wasn't really designed to do, so before pretty much every photo, I'd quietly adjust it back to how she wanted it. Same with her hair - I'd check in, "is this how you want it," before we started. It sounds small, but if your teenager or tween has an opinion about how they look in the photos that are going to represent them for the year, let them have a say. They'll actually enjoy the process more, and you'll get a version of them they recognize.

Let candid beat posed, most of the time

Our photographer is genuinely great at creating moments instead of just poses - walking through the meadow together, walking toward the camera, just talking and laughing while she catches it. Those in-between moments, the ones that are more about connection than about "everyone look here," are almost always the ones that end up meaning the most later. Use your photographer's direction, absolutely, but leave room for the unposed minutes in between the posed ones. Also, if something doesn't feel natural it also won't read as natural so no weird post positions.

You don't have to look at the camera

Some of my favorite photos of us, nobody's eyes are on the lens. I'm looking at my husband, or up and off into the distance, or just caught mid-laugh looking at one of the kids. Let your photographer guide you on when this works, but don't feel like every shot has to be a direct-eye-contact moment to count. The ones that aren't are often the ones that feel the most like you.

None of this means the photo shoot itself won't have a rough ten minutes somewhere in the hour. Ours usually do. But the years I remember most fondly aren't the years where everything went perfectly - they're the years with a sucker in someone's hand, or a shirt adjusted eleven times, or a joke that made everyone actually crack up right as the shutter clicked. That's the stuff you'll actually want to remember. Let it happen.

Actually film the photo shoot

We just had our family photo shoot a couple of days ago and last minute, I threw our iPhone tripod in the car on the way to the shoot. I set it up, hit record, and just left it alone - it was such an afterthought, but it ended up being the best decision of the whole day. We laughed so hard watching it back later: there's a clip of us taking the leash off the dog (yes, we made the questionable decision to bring the dog), and for one beat she just paused, realized she was free, and took off in full zoomies around all of us. Obviously the photographer couldn't do anything with that moment, but it set the tone for the entire shoot - just get what you can get, and let it be fun. We found other little snippets buried in that footage too: Lilah dancing in front of the camera, the dog going straight at the photographer’s camera, Clay awkwardly sidestepping out of frame every time it caught him.

But my favorite thing happened at the very end. We took fifteen seconds, stood about thirty feet back, and faced the tripod together - and it's the first video we have of all four of us in one frame. I know that sounds small, but it genuinely floored me. There's always one of us behind the camera, so when I look back at years of family videos, I know I was there- but there's no actual footage of me being there. This is the year I'm reclaiming proof that I existed in these moments too, not just the person capturing them. Fifteen seconds, and I'll take it.