Boss Mama CEO Story: Keeping It Simple

Courtney’s story shows how clearly you can see God working behind the scenes. A simple conversation with her husband led to the name of her business. A leap of faith after being laid off from her 9-5 led to a thriving photography career that eventually surpassed her corporate income. That’s the entrepreneurial dream so many of us are chasing.

Today, Courtney has built a life with more flexibility and freedom. One where she gets to make the rules. She can structure her business around her family, not the other way around. And if you’re a mompreneur, you know exactly how powerful that is.

We start these businesses because we want more control over our time, and to be there for school drop-offs, afternoon park trips, family dinners, and bedtime stories while still pursuing our dreams. We want the freedom to build something meaningful without sacrificing the moments that matter most.

I’m sure many of you will relate to Courtney’s story in one way or another. As a former military spouse myself, I can absolutely relate to the challenge of having to start over in a new place. In 2027, Courtney will experience that for the first time as a business owner after building her photography business from the ground up.

As someone who has also worked in a service-based business, I know firsthand how difficult that transition can be. You’re suddenly rebuilding your network, introducing yourself to a new community, and finding creative ways to spread the word about your business. It can feel overwhelming and, at times, even discouraging. But there’s also something incredibly exciting about a fresh start. New opportunities, new connections, and a chance to grow in ways you never expected.

Courtney’s journey is proof that while the road isn’t always easy, it can absolutely be worth it.

Check out her story below, and don’t forget to give her a follow on social media!

YOUR STORY

Tell us who you are!

My name is Courtney Wilson and I’m the owner of Keep It Simple Photography.

We love a good origin story, but first, give us your short + sweet intro!

I specialize in studio maternity, newborn, and milestone photography! As a mom myself, I know how quickly these seasons pass. One moment you’re soaking in those precious newborn snuggles, and before you know it, you’re celebrating milestones you never want to forget.

Every boss mama has a ‘day one.’ What was yours?

I’ve always been that friend who’s constantly taking photos of everyone and everything! I’ve always believed that our memories won’t last forever, but photos will.

In 2024, a friend of mine was pregnant and wanted maternity photos. I told her I had a little DSLR camera and could probably follow a Pinterest board well enough to make it happen. Later that week, we headed out for her session, and I took her photos. I instantly fell in love with the experience, but even more than that, I fell in love with how it made my friend feel.

From there, things took off. I started offering free practice sessions in Facebook groups, and people kept signing up. Before I knew it, I was photographing families almost every day!

Around that time, my own family photographer reached out and asked if my friend would be interested in newborn photos. She offered to show me the ropes of newborn photography to see if it was something I’d enjoy. I took her up on the offer and absolutely FELL IN LOVE. As I continued booking more sessions, what started as a hobby quickly blossomed into a real business.

Of course, once I decided to create social media pages, I needed a name for my photography business. After going back and forth on countless creative ideas, I finally asked my husband what he thought. His response?

“I don’t know, just keep it simple, babe.”

And just like that, it CLICKED.

Keep It Simple Photography was born.

Which came first—the business or the babies? Tell us how your family + business journeys intersected.

After! My son was born August 2023 and my business was started May 2024. He was only 8 months old.

We know it’s a wild ride—tell us how you’ve balanced building your dream biz while raising your crew. The good, the tough, the real.

It was definitely hard. One of my biggest challenges was trying to be fully present for my own family while also dedicating so much time to capturing memories for other families. I was working evenings and weekends, which meant missing important moments with my own family.

After six months of renting a studio space, I took a huge leap and opened my own studio. While it was an exciting milestone, it also came with long days, late nights, and even more time away from home. Eventually, I found a rhythm that seemed to work, until it didn’t.

After taking a hard look at how much family time I was sacrificing, I made the decision to stop offering evenings on Fridays and weekend sessions. I also don’t offer outdoor sessions June – August and December – February. It wasn’t an easy choice, but I knew something had to change. Of course, that meant shifting my work into daytime hours.

At the time, my son wasn’t in daycare, and honestly, I wasn’t ready for that step yet. Instead, I found an amazing babysitter who came in the mornings when I had sessions. It was the perfect balance for a while. I could focus on my business while still being present for my family and not missing those precious evenings together.

After a few months, however, childcare costs started to add up, and I had to make another difficult decision. It was time for daycare.

I didn’t want daycare at first, but after doing our research, we found an incredible program through CYS. Now my son attends daycare Monday through Thursday, and I work Monday through Thursday as well.

It took a long time to get where I am today. There were plenty of hard days, difficult decisions, and moments that broke my heart. I often felt guilty about the family time I missed, but I was also working toward something bigger, building a business and a future for my family.

Looking back now, every challenge taught me something valuable. It wasn’t always pretty, but it was worth it. I’ve built a business I love, found a schedule that works for my family, and created a life that allows me to pursue my passion without losing sight of what matters most.

What’s one obstacle you’ve overcome?

Fun fact – I was working for IBM as an audit analyst while also doing photography for 1 year. I was laid off in July 2025. I exceeded my IBM corporate income within my first 20 months of Keep It Simple Photography!!

YOUR BUSINESS

Tell us your superpower—what’s your product, service, or special offering?

I provide photography services, specifically specializing in studio maternity, newborn and milestone photography.

What’s the magic that sets you apart?

Being a military spouse, a mom, and a developing photographer at my current skill level gives me a unique perspective that helps me stand out.

Spill the tea — any big milestones, press shoutouts, or launches on the horizon? 

Milestones: Opened my own studio just six months after starting. Expanded into a studio twice the size within one year. And ultimately, surpassed my corporate salary.

Shoutouts: 

My loving husband, Joshua – Through the hard days, doubts and challenges, he was always there

supporting me in everything I do. I truly wouldn’t have been able to build this empire without him! 

Christy Silva with Lasting Memories Photography—my mentor and friend. She has taught me everything I know and has played a huge role in my growth.

Melissa Tomlin – my friend and family photographer. Out of the goodness of her heart, she introduced me to newborn photography and generously allowed me to use her studio for the first six months of my career!

Launches: I will be expecting military orders in Spring 2027 and will be relocating.

Give us a Day in the Life of being both Mom and CEO!

I usually wake up to my 3-year-old’s room already wrecked with toys because he’s been up before me. We battle the “outfit of the day” discussion and I almost always lose to mismatched clothes (lol).

Breakfast is usually pancakes and a banana—the same exact thing he’s had for the past six months. I grab my homemade iced coffee, we get shoes on, and head out the door.

I drop my son off at daycare at 8:45am and arrive at the studio by 9am. From there, it’s studio prep and sanitizing before clients arrive. Sessions begin, clients leave, and then I reset the space by cleaning and prepping for the next day.

I pick my son up from daycare around 2pm. After that, we usually head to the park, run errands like the grocery store, or just go home and relax.

My husband, Joshua, gets home from work around 5–6pm, and dinner is on the table by 6:30pm. After dinner, we always go on a 2.5-mile walk with our husky, Kyra.

Bedtime is… well, a battle (LOL). It hasn’t changed, yet somehow it’s always a struggle. Bath, pajamas, teeth, bedtime story, running hugs and kisses, and then Tonie time.

The biggest daily challenge is that even when I’m not physically at the studio in the afternoon, I’m still always working. Inquiries, client messages, and social media notifications are constantly dinging. Balancing being present in mom life and business life is the hardest part.

ADVICE FOR MOMPRENEURS

What’s the single best piece of advice or favorite tool you’d share with other mamas building their businesses?

Find people who relate, whether that’s other photographers or just other business owners! I organize a monthly military spouse photographer dinner. We get together and yap! No kids, no husbands, no phones… just girls.

What’s been your biggest challenge juggling motherhood and running a business?

Being present and the best version of myself for both my son and my clients.

What’s your approach to balancing business and family? We love the real, unfiltered stories!

Setting boundaries and sticking to them! For me, this is not working evenings and weekends.

Looking back, what’s something you wish you had known before starting your business?

Don’t compare yourself to those in the same field.

What tool, resource, or habit has completely changed the game for you?

In person mentorship classes and training!! Changed the GAME! The before and after is drastic.

What mindset shifts have helped you keep going during hard seasons?

I remind myself I built this from nothing while also being a mom to a pretty cool kid!! I can do anything. Hard seasons will come and go.

What words of encouragement would you give a Mom tempted to give up on her business dream?

Find the source of the doubt and CRUSH IT. You started this journey for a reason, your story is not done yet. Keep going!

What I find most inspiring about Courtney’s story is that she has intentionally built her business around her life, not the other way around. Along the way, she realized what truly mattered to her and wasn’t afraid to set boundaries that allowed her to be present for both the big milestones and the everyday moments with her family.

That commitment to her priorities has helped her create a life that feels balanced and fulfilling. Of course, “balance” looks different for everyone, and there is no one-size-fits-all approach. But Courtney’s journey is a great reminder that it’s possible to build a successful business without sacrificing the things that matter most.

Her story is proof that you can create a life where both your family and financial freedom can flourish and she’s done it her way, on her terms.

I’d love to feature more Boss Mamas like Courtney. If you know someone who deserves the spotlight, please reach out and send me their info at ashley@bossmamaceo.com or via my contact form here. And hey, if that’s you, I love a little self-brag too! Send me your details so we can shine the spotlight on you as well.

Here’s to all the incredible Moms juggling a million things—keep shining bright, cheering each other on, and building the life you love!

Ashley

Friendly Note: I’m simply sharing my journey, experiences, and lessons learned as a Mom in business. This isn’t legal, financial, or professional advice. Always check with a qualified pro for guidance tailored to you.