We recently connected with Courtney Cannon and have shared our conversation below.

Courtney, thanks for taking the time to share your stories with us today Do you take vacations? How do you keep things going – any advice for entrepreneurs who feel like they can’t step away from their business for a short vacation?

We plan 4 vacations or getaways a year with our family. Some are closer to home and some are full vacations. They often include some sort of business connection but can also be a true trip away as a family. It is one of the many things that help to give back to our family and make all of the long hours of work that we put in worth it for our entire family.

Walking away from your small business for any period of time can be difficult.
Here are sharing a few pieces of insight that allow us to successfully continue to serve our clients well, while we are out of the office.
-have an assistant who can oversee things behind the scenes
-understand what is truly urgent and what is not
-prepare before you leave, be proactive with client’s needs before you leave
-schedule your social media
-schedule any emails you need to send out
-put up an out of office for your email
-schedule a few times throughout your time away to check your inbox for anything urgent: I prefer once a day to keep it manageable when I return.
-schedule a catch up day with no meetings when you return

Courtney, before we move on to more of these sorts of questions, can you take some time to bring our readers up to speed on you and what you do?

Courtney & Robert Cannon make up the highly-sought after, multi-six figure husband & wife photography team, The Cannons. Based in their hometown in Ohio (where the two were high school sweethearts!), they now travel coast to coast photographing elevated destination weddings & engagements for their kind-hearted couples. Guided by their one core principle—to find their people, and serve them well— these two former music teachers have grown their business from a $25 mini-session side hustle into a powerhouse brand, now commanding over $10,000 a wedding. Still teachers at heart and fueled by the desire to help other photographers build sustainable, servant-hearted businesses that last, they founded The Graceful Gathering Conference in 2020 which has hosted hundreds of photographers from all over the country. They have since gone on to launch their six-figure Mastermind and Coaching programs, continuing to pour into their people… all while showing them that it IS possible to work hard and build a balanced life you love.

Can you tell us about a time you’ve had to pivot?

In order for us to go full time as wedding photographers, we had to approach our entire business in a new way. Before, our profits were our “fun money.” Our teaching salaries covered our personal expenses, so the business was able to invest in itself. When we shifted to running The Cannons Photography full time, everything changed.

We couldn’t just hope the business would sustain us—we had to know it could. That meant getting clear on exactly what we needed to bring in, not just to cover costs, but to support our family, pay ourselves consistently, save for the future, and still reinvest in the business.

We built out our budget starting with our personal needs—our mortgage, groceries, insurance, childcare—and then layered on our business expenses: gear, software, education, client experience, and taxes. Once we saw the full picture, it gave us a realistic view of what we needed to charge, how many weddings we could sustainably take, and where to focus our energy.

That pivot—going from side hustle to sustainable business—only worked because we took the time to know our numbers. And honestly, it gave us the confidence to move forward without second-guessing every decision. We weren’t guessing anymore—we were building something with clarity and intention.

What do you think helped you build your reputation within your market?

Honestly, it’s always come back to service. From the very beginning, we knew that beautiful images were only part of the experience—we wanted our couples to feel taken care of every step of the way. Whether that meant helping with timelines, fixing a boutonniere, or offering a calming presence on a hectic morning, we’ve always tried to go above and beyond the role of “just” photographers.

But it hasn’t just been about serving our couples—it’s also been about caring deeply for the vendor teams we work alongside. We know how much heart and energy goes into a wedding day, and we do our best to support planners, florists, videographers, DJs, and every vendor involved. Whether that means sharing galleries promptly, cheering each other on, or simply being a kind and collaborative presence, we’re all about creating a team environment where everyone can thrive.

Over time, that consistent care and reliability have led to trust—not just with our couples, but within the vendor community too. Word travels fast when people feel seen, supported, and genuinely appreciated—and that’s something we’re really proud of.

In short, people may come for the photos, but they remember how we made them feel. That’s what builds a lasting reputation.

Contact Info:

• Website: thecannonsphotography.com
• Instagram: https://www.instagram.com/thecannonsphotography/
• Facebook: https://www.facebook.com/thecannonsphotography/

Image Credits
Headshot: Rachael Leigh Photography All portfolio images: The Cannons Photography