family + business operations for parent entrepreneurs


We're Kevin + Courtney Gilroy: married best friends turned parent entrepreneurs. is the resource hub + like-minded community we were missing in our first days of new parenthood + business ownership.

Becoming a profitable stay-at-home family changed our life. Now, we help other current + soon-to-be parents have a healthy start to parenthood + entrepreneurship.

Learn more about our systems for running the business of family alongside the family business here or ask us questions here.




How to Prep for Your Parent Branding Photoshoot

We’re sharing how we prep for our parent branding photoshoots, including some of our simple planning checklists.

Created by potrace 1.15, written by Peter Selinger 2001-2017
Reading Time: 8 minutes

Branding your business as a parent is an incredible feeling. You’re merging two of the most important parts of your life — it’s like a marriage!

And like any wedding worth photographing, you’re going to want to pick a quality photographer + have a plan in-place for the big day. 

In this post, we’re sharing how we prep for our branding photoshoots, including some of our simple planning checklists.

Let’s go!

Set Your Childcare Plan + Backup Plan

This part isn’t the most fun + potentially the most frustrating, so let’s get that out of the way!

Someone you genuinely trust (+ don’t have to hover over) needs to be on-location to watch your children if they will be getting into some pictures with you.

If the kids are staying home while you go out on-location, make the detailed arrangements they need to have a great time away from you + that you need in order to mentally step away for that amount of time. 

There’s nothing more obvious on-camera than a distracted, concerned parent — whether obsessively checking the phone for babysitter messages or looking around the photographer to watch the babysitter on-site.

For us, this means having Kevin on-location to hang out with the kids while Courtney gets solo photos taken. They jump into some pictures (more on that later), but they’re otherwise on their own exploring around the photoshoot location. 

Kevin makes sure that the kids don’t get too messy, to feed them what they can snack on safely + to be in-tune to the flow of the day. Their behavior cues help us gauge when they should step in + out of photos.

Brand Color Palette

Pick your shoot colors based on both your brand color palette + the season you’re in. 

Spring/summer sessions coordinate best with pastel-based palettes, whereas fall/winter sessions coordinate best with more jewel-toned palettes.

If you’re brand new to business, stick to 2 neutral colors (like black + tan, or white + navy blue) + 1 accent color.

As you go deeper into branding over time, you’ll pick more colors that match your business, but you don’t want to commit too early to a palette that won’t be timeless for you. 

Use this color palette as the theme in your outfit choices, your props + your location backdrops (like the walls you stand against or furniture you sit on).

Curate Your Pinterest Board

We’ve found that the best way to share our visual goals with our photographer is to share a Pinterest board.

Use the sorting features of Pinterest to divide up a “Photoshoot Board” into the following sections:

  • Headshots
  • Behind-the-Scenes
  • Product/Service Engagement

Then add any unique elements as sections, such as:

  • Props
  • Outfit Inspiration (color palette in mind)
  • General Office Poses — like sitting at a desk or holding a laptop
  • General Outdoor Poses — like a headshot with a greenery background

For some sample boards, check out our OrganicFamilyCEO Pinterest.

Start Your Shot List

We take our favorite “must-have” Pinterest inspiration images + write out the descriptions of what they look like in a spreadsheet or an Asana project board. 

Some of our descriptions are hilariously awkward, but the point is that our photographer knows exactly what we’re aiming for. This strategy works!

The virtual list (like Google Sheets or an Asana board) is a worthwhile effort because it’s easy to pull up in the middle of the photoshoot itself + acts as a checklist. When you’re in-between outfit or location changes, your photographer can pull that list up for a quick reference before you take the next round of images. 

Make sure to allow your photographer to edit the list, so that they can note any comments, questions or concerns for you well in-advance of the photoshoot. You can rule out your must-have shots + bonus would-be-nice-to-have shots together in-advance, too. 

An additional bonus tip: Make your lists sortable by “location type”, which will help in the event of an unexpected venue or time change.

For example, we originally scheduled a photoshoot at our house, but when renovations weren’t finished in time, we switched to an outdoor location last-minute. What would normally be a big, stressful switch actually wasn’t at all. 

And because we switched to a new outdoor location, we ended up with more time for photos overall + Courtney knew exactly what extra photos she wanted to capture using that bonus time. 

A second bonus tip: We also run a packing list alongside her shot list.

This way, we’re able to triple-check if we need any props, certain clothing items, multiple quantities, etc. This helps us to not over-shop for missing items we need for the shoot + spares us or an assistant having to do returns later.

What to Wear

Lay out your outfit choices — coordinating with your brand color palette — at least 1 week in-advance in a kid-safe, low-traffic area. For us, that’s on top of a dining room banquet cabinet. 

Set aside any cleaned items you need for the shoot throughout the days leading up to the shoot: as laundry gets finished, dry cleaning gets returned, online shopping packages arrive, etc. + take an inventory of anything you need to buy to make a complete outfit. 

To minimize stress, we recommend not shopping for new items.

Instead, prioritize replacing “fresh” new pieces of items you already know + love.

For example, now isn’t the time to try a new bra, but it is a great time to buy a fresh white basic tee to replace the one you’ve worn out to a dull beige. 

Choose the following pieces:

  • 1 solid bottom
  • 1 solid oversized top
  • 1 solid fitted top
  • 1 patterned fitted top
  • 1 formal jacket, like a blazer, that fits comfortably over the fitted tops
  • 1 casual jacket, like a denim jacket or cardigan sweater, that can be changed out over the fitted tops
  • 1 pair of neutral dress shoes
  • 1 pair of statement flats or loafers
  • 1 pair of casual shoes
  • 1 set of formal accessories (jewelry, etc.)
  • 1 set of casual accessories (jewelry, etc.
  • 1 hair elastic
  • 1 hair clip or hat

By doing so, you’re giving yourself an interchangeable set of on-brand outfits that are easy to maneuver on photoshoot day. 

Some interchanging ideas:

  • Fitted shirt, blazer, statement accessories, hair down, statement flats or loafers
  • Fitted shirt, no blazer, simple accessories, hair up (clip or hat), neutral dress shoes
  • Oversized shirt, statement accessories, hair up (clip or hat), casual shoes

The possibilities are nearly endless when you start interchanging hairstyles, shoes + accessories with your basic clothing choices from that list. 

Choose Singular Family Outfits (optional)

Our children are always in our brand photoshoots because that’s what’s true in our life: they’re always there!

As full-time stay-at-home parents + entrepreneurs, we’re working in the part-time hours + playing in the main ones.

So, we choose one “elevated casual” look for everyone in the family that can coordinate with our brand palette + chosen outfit pieces. 

For example, Kevin will wear a button-down shirt without a blazer or suit jacket. Our daughter will wear sneakers with her tutu dress. No matter when they jump in + out of the shoot, they’ll match the scene. 

Kevin + Kenzie

Makeup + Skincare Prep

Now is not the time to test out feeling glamorous with a makeup artist you don’t work with often or taking a stab at DIY-ing your own false eyelashes or attempting eyeliner for a few reasons:

  1. You will most likely run out of time on photoshoot day + the added stress will do nothing for your steady hand;
  2. You won’t have adjustment time to “feel comfortable” + LOOK like you’re comfortable when you’re wearing lots extra.

“Arguably, the most important part of looking great in your photos, apart from taking them in natural light, is you feeling as much like your day-to-day self as possible.”

Your brand photos represent who you ARE so that your potential customers can get to know, like + trust you — where you’re at right now.

Note: If your intention is to show an elevated version of yourself — that’s outside of what’s reasonable for you everyday — then we encourage you to consider what that false precedent might attract for your business.

Dial it up one small notch or two + plan to do that in steady increments over time as your business grows (+ as you step into that brand vision for real!).

Communicating with Your Photographer

We send a photo or video description of whatever we’re planning to wear + pack to our photographer via text on the day or two before the shoot. 

And we share a quick reminder description of the “look/vibe” we’re trying to achieve, too.

For example, our most recent text was “Think J. Crew, working parent, green smoothies” + that’s exactly what got delivered!

We also ask for the crew’s coffee order or breakfast sandwich or usual go-to lunch order, etc.

Budget for that. Treat your vendors!

They don’t expect being treated, but they are humans who appreciate the small acts of kindness. And it usually always gets reflected in your final images!

Post-Shoot Family Plans

Speaking of food, plan for a food carryout order for the rest of the day. Even the shortest photoshoots are exhausting!

Outsource dinner. Bank on paper plates + skipping bath time. Make it a family pizza + movie night! You all deserve the treat. 

Share the Love on Social

If you had a fun session, then say so on social media.

Tag your photographer + any other vendors — no matter how much you might not want to share your good hires with others! — + share what you genuinely loved about working with each of them. 

They will likely reciprocate the sweet gesture + you’ll both gain new followers.

You’re also showing an honest look at life behind-the-scenes with your parent branding.

These posts don’t have to be shared in “real time” because you’ll want to maximize your camera time + respect your vendors’ schedules as much as your own, but keep a few BTS shots on your phone to share socially after the shoot.

They’re always fun to look back on years later to see how far you’ve come! We love looking back on our branding shoots (especially those behind-the-scenes moments!) + reminiscing just like we do with regular family photos.

Seeing how much progress we make in those little time frames when we feel like every day is the same is incredible — trust us!

Now we’d love to hear from you: do you have a parent brand?

Drop a comment below + share how you best prepare for your branding photoshoots. Interested in our brand photoshoot template? Let us know in the comments + maybe we’ll share ours here!