A New Backpack, a Big Goodbye

This August, my youngest goes to kindergarten here in Chesterfield. She’s been counting down the days since her brother went to Big Kid school two years ago, and I have mixed feelings about sending her out after him (but thankful that the nightly countdown is nearly over).

This big transition reminds me of when we moved across Chesterfield County two years ago - mere days before my son went off to kindergarten himself. The chaos of leaving one rhythm and stepping into the next, the abruptness of a new era while still saying goodbye to the old.

And just like back then, I want to remember this moment too - not just what it looked like, but what it felt like.

That’s where candid photos come in.

A nervous little girl picks at her fingernails at the bus stop on the first day of school in Chesterfield County.

Back-to-School Photos Don’t Have to Be Perfect (In Fact, They Shouldn’t Be)

Instagram is about to be full of sweet, beaming kiddos proudly holding up their “First Day of Kindergarten” signs, decked out in fresh new shoes and pressed outfits. There’s absolutely nothing wrong with that. We do those here too. They’re a great way to mark the milestone.

But if your goal is to remember this season - to be able to close your eyes 10 years from now and truly feel what it was like - the posed photos aren’t going to take you there.

Emotions don’t pose well.

What does take you back? The cereal milk mustache at breakfast. The crazy untamed bedhead of a child who struggled with sleep leading up to their big day (let’s be honest). The bookbag that looks bigger than them. The nerves at the bus stop. The goodbye hug that lingers just a beat longer. These are the photos you'll cherish later.

So today, I’m sharing a few ways to capture the true essence of the first day of school with simple, meaningful candid photos - whether you have a fancy camera or just your phone handy.

A boy grabs the pole at the playground and prepares to slide down at kindergarten open house

How to Capture First Day Magic Through Candid Photos

1. Document the Days Before

The first day of school doesn’t actually begin when the backpack goes on - it starts when the preparations do.

Grab your phone and catch:

The new clothes laid out for tomorrow
The back-to-school haircut
The Open House tour and apprehension
You or your partner prepping lunches and writing lunchbox notes

This quiet anticipation is part of the story.

A diptych of a little boy laughing while getting a haircut and sitting in a school cafeteria chewing on his bottom lip during open house at his new school in Chesterfield.

2. Photograph the In-Between Moments

Not every photo has to start and end with “cheese.” Honestly, the most memorable images are the ones in between.

Things to look out for:

Breakfast time and busy hands
A sibling helping with shoelaces
A quiet moment at the front door before walking out
The look back at school drop-off

Don’t ask your child to smile. Don’t call their name. Just take the photo. It might feel strange at first if you're used to asking for a pose, but give it some time. You'll adjust, and the moment will thank you.

A fuzzy phone picture of a little boy sitting in his pajamas in a dark bedroom the night before school started.

3. Capture Your Own Emotions, Too

This one’s a little harder. But hand your phone to your partner or a friend if they’re with you - or set up a self-timer - and get in the frame. You, in your robe, waving goodbye. You, teary in the carpool lane (no judgment, I’ll be right there with you). That stuff matters too.

This is your story as much as theirs.

Photo of a parent's hand holding her child's hand on their walk to the bus stop.

4. Think Like a Memory-Collector, Not a Director

You're not making a highlight reel - you're preserving a chapter.

So instead of aiming for a “perfect” photo, shift your focus to:

Honest expression over polished appearance
Natural light over bright filters
Emotion over composition

Let go of the urge to angle your child toward the sun or fix their hair. Candid photos work best when you're capturing things as they are, not as they should be.

A little boy wearing rainboots and a big smile sits on an ABC rug in his new kindergarten class.

Why These Moments Matter

In the whirlwind of backpacks, bus stops, and new beginnings, small things tend to blur. And one day, when they’ve moved farther down the path, these simple, candid images become anchors.

They remind you of the rollercoaster of emotions. How their fingers barely reached the doorknob. What they chose to wear on that very important first day. How brave they were. How brave you were too.

Want More Gentle Family Photo Ideas?

If this resonates with you, and you’re someone who values honest, emotionally rich photos of your family life - not just posed highlights but the beauty of the every day - then we’d probably make a great match.

Candid and cozy photo sessions are what I do best. I'm an in-home family photographer based in Richmond, VA, specializing in those everyday-yet-extraordinary moments. So if you're looking for someone to help you remember the rhythms of your life in a beautifully real way, I’d love to talk.

And if not? Just remember this: you don’t need a perfect picture to have a beautiful memory. You just need to be in it.

This school year, grab the photo: mid-hug, mid-laugh, mid-meltdown, mid-whatever. No poses required.

Capturing the First Day of School: Why Candid Beats Perfect Every Time