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Courtney Cannon: Making the Leap to Full Time

APPLE PODCASTS | SPOTIFY | STITCHER Courtney Cannon: Making the Leap to Full-Time After almost a decade of building a photography business alongside her teaching career, Courtney Cannon knows making the leap to entrepreneurship isn’t for the faint of heart.  Courtney and her husband Robert are wedding photographers, educators, and hosts of The Graceful Gathering […]




Courtney Cannon: Making the Leap to Full-Time

After almost a decade of building a photography business alongside her teaching career, Courtney Cannon knows making the leap to entrepreneurship isn’t for the faint of heart. 

Courtney and her husband Robert are wedding photographers, educators, and hosts of The Graceful Gathering conference. Courtney is an expert at building a business while working full-time – and now that she’s taken the leap, she’s able to share all the triumphs, missteps, and lessons learned along the way.

If you’ve been thinking about leaving your 9-5 or wondering if it’s time, you won’t want to miss this episode! Press play above for the full interview or keep reading below.

Launching Two Careers at Once

Courtney and Robert have been taking photos together since they were in high school, but it wasn’t until after they graduated college and got married that they decided to start a business – while beginning their teaching careers at the same time. 

It was Courtney who advocated for doing both. “I’m an Enneagram 3, The Achiever,” she says with a laugh. “So we did both and we loved both.” They started off charging $25 for mini-sessions, and things grew slowly but surely from there.

“We did all the things,” Courtney says about their early days in business. She and Robert attended bridal shows, conferences, and networking events, and did everything they could to build relationships.

When it came to learning the business side of things, “We invested in so many different courses. We poured ourselves into education and to the idea that there’s always something new to learn.” 

Business Finances 101

One area Courtney wishes they would have invested more time into is finances. “I wish we had a better understanding of all the backend things that no one likes to talk about as creatives, like taxes and hiring a CPA.”

Like many creative business owners, Courtney and Robert waited until they had no choice but to ask for help – but by then, you’ve already established financial habits that are hard to break.

This is why it’s better to learn about the financial side of your business early on! The best time to take a course like The Blueprint Model is in your first year of business, or even before you’ve launched.

How to Manage Money as an Entrepreneur

The first step is to determine exactly how much money is coming in and out of the business. Awareness is key. Once you see those numbers on paper, you can see if your pricing is truly profitable or if you need to cut back on expenses.

Courtney’s advice for anyone thinking of making the leap to entrepreneurship would be to seek out financial advice sooner rather than later, rather than trying to do it all yourself. 

“Instead of relying on what you think you know, go to a professional and figure out what you need to know.”

Building a Business While Working Full-Time

Courtney and Robert started with weddings as their main package, although they continued to offer mini-sessions on the side. 

As for building a business alongside a full-time job, Courtney would get up early to work for two hours in the morning, then head to school and teach all day, before returning home to take care of the kids and work on the business again in the evening.

Sound busy? It was. “We were essentially running a full-time wedding photography business while teaching full-time.”

Courtney knew she couldn’t stay in her teaching role forever, especially as they added an education side to the business. What started as a small workshop hosted by her and Robert soon grew into a full-blown conference with guest speakers.

The first year they hosted The Graceful Gathering in 2020, Courtney began to seriously consider making the leap.

Making the Leap to Entrepreneurship

During the Covid lockdowns, Courtney and Robert were able to save money and work on leveling up the business. 

Their average investment for wedding packages went from $4,000 to $6,000 within two months, which allowed Courtney to feel more confident making the leap. Still, she needed one extra push.

Originally they planned for Courtney to hand in her letter of resignation in March, but she decided to turn it in three months early. “We needed to know that there was no way out that this was happening – the money had to come in.” 

Taking that leap of faith gave Courtney the mindset she needed to push forward and the business skyrocketed from there.

Leveling Up The Business

Courtney and Robert knew they were providing a quality experience and product to their couples. 

They started raising their prices with each new booking until they reached an average investment of $8,000, which was double the amount they’d charged just two years earlier. Although they received fewer inquiries, those who did book were quality clients.

“We’re not trying to sell every person who comes in the door. We needed to know if they contacted us that they were able to work with us and afford our rates.” 

Positioning their business as a premium service has given Courtney and Robert back more time with family, to work on the business, and to serve their clients.

The Upside of Having Two Careers

Courtney’s nine-year teaching career helped her better understand how to manage money as an entrepreneur. 

“When we started teaching, even though our paychecks were very low, looking back, we were thrilled because we had gone from working high school and college jobs to an actual salary with benefits.” 

She and Robert were diligent about saving for retirement and started working with a financial advisor at just 23 years old. Starting with salaried positions in their teaching roles gave them both strong habits for money management, which they carried with them into entrepreneurship. 

The New Zero System

In their marriage, Courtney tends to be the spender and Robert is the saver. With her love for education, Courtney was eager to reinvest every penny into the business, but Robert helped her stay intentional about when to reinvest and when to save.

“He created this system in college, what he calls the New Zero. So as he built his account, he decided that in his mind, the account was at zero. If it was at $500, then it was at zero. Once it got to $1,000, that was the New Zero, and so on and so forth.” 

The New Zero method is a powerful way to grow your savings – to establish a new amount as your baseline and decide that your balance will never dip below that number. When Courtney and Robert went full-time, they knew they had those savings to support them.

Developing an Entrepreneurial Mindset

One of the most difficult parts of making the leap to entrepreneurship is learning to manage your mindset, especially if you’re leaving a stable paycheck for an unknown future. 

When Courtney left teaching, she had the added security of Robert’s full-time salary. But when he joined her full-time in the business, there was much more at stake, and so Courtney had to consciously shift her mindset to a place of gratitude.

“When you stop feeling like the money is never going to come and you start to feel grateful for what you have and what is coming, then it starts to flow naturally.”

Courtney has also leaned on the support of mentors like Mary Marantz to help her challenge her imposter syndrome. “Having someone who’s willing to listen and help you to continue to be brave and push forward is so valuable.”

How to Run a Business and Be a Mom

Despite the fact that she and Robert are now both full-time in the business, Courtney is quick to point out, “Our life is not Cannon Photography. Our life is not the Graceful Gathering. We are the CEOs of the Cannons and our home.” 

Every task she performs at home, whether it’s doing the dishes or making dinner, she considers an integral part of their lives. She’s careful not to put one role (wife, mother, entrepreneur) above another. 

“It’s important that our kids are fed breakfast before they get put on the bus, and it’s important that we’re able to take care of ourselves, post on social media, and check our emails as well.”

Making a Family Bucket List

As a planner and list maker, Courtney likes to create bucket lists for her family. Every month, they make a list of activities, whether it’s building a snowman or watching a movie.

“Each month now, the kids have gotten excited about making sure that we’re checking off all of the activities. That’s helped me find that harmony because it’s so easy to have mom guilt and feel like I’m always at my computer.” 

Courtney tends to work a lot, but she keeps firm boundaries around family time. She closes the computer at dinnertime, and each night the family has two hours of intentional time together.

Is It Time for You to Make The Leap?

Even with years of experience and a supportive partner, there are still hesitations, mindset shifts, and challenges that come with leaving your day job. But for Courtney, making the leap to entrepreneurship was one of the best decisions she’s ever made.

Not only is she able to spend more time with her children, but the business has grown exponentially. She and Robert are branching into education for other wedding photographers and they’re planning to open a shop in the next few months.

To any creatives out there considering going full-time, Courtney says: “Education is key. Continue to pour into yourself and continue to find ways to grow.”

More from this Episode

To hear the rest of the story and what Courtney is up to now, press play on the player above for the full interview or click here to download the transcript.



Mary Marantz

Ep. 012: Mary Marantz on Consider the Wildflowers Podcast

The Graceful Gathering Conference


Meet the Cannons

The Cannons, also known as Courtney and Robert Cannon are husband and wife wedding photographers and educators. Known for their unwavering dedication to their kindhearted couples, this dynamic duo truly cares. They have developed a multiple six figure business through a personalized client experience. After a decade of also working in the public school classroom as music teachers these two have loved pouring into other photographers and creative businesses to help them grow as professionals. Through their mastermind, one on one coaching, and a boutique conference, The Graceful Gathering these two are busy serving and spending time with their family. Oh, and yes, they do use Canon.


Website | Instagram




May 11, 2023

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