Consider the Wildflowers

044. Courtney Cannon: Making the Leap to Full Time

May 11, 2023 Courtney Cannon
044. Courtney Cannon: Making the Leap to Full Time
Consider the Wildflowers
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Consider the Wildflowers
044. Courtney Cannon: Making the Leap to Full Time
May 11, 2023
Courtney Cannon

It’s time to take the leap! 

This husband and wife photography team spent almost a decade working as full time music teachers while also building up their photography business. Even with years of experience, today we dive into the hesitations, mindset shifts, challenges and triumphs that come with letting go of your intended profession to pursue a dream career, and this husband and wife team both made the leap. While we are only hearing from Courtney today, anyone who has left the comfort and security of a full time job to pursue entrepreneurship knows, taking the leap is not for the faint of heart! Hear how they did it, how it’s going, and what they envision for the future, all in today’s episode!


Show Notes Transcript

It’s time to take the leap! 

This husband and wife photography team spent almost a decade working as full time music teachers while also building up their photography business. Even with years of experience, today we dive into the hesitations, mindset shifts, challenges and triumphs that come with letting go of your intended profession to pursue a dream career, and this husband and wife team both made the leap. While we are only hearing from Courtney today, anyone who has left the comfort and security of a full time job to pursue entrepreneurship knows, taking the leap is not for the faint of heart! Hear how they did it, how it’s going, and what they envision for the future, all in today’s episode!


Courtney Cannon (00:00):

We were going to wait until March to turn in my letter resignation so that we could make sure that we had the bookings on the calendar. And I ended up turning it in December because I just felt like we needed that push. We needed to know that there was no way out that this was happening and the money had to come in. And I do think that when we took that leap of faith, it really just kind of sprung us forward.

Shanna Skidmore (00:26):

You are listening to Consider the Wildflowers, the podcast episode 44. It's time to take the leap. This husband and wife photography team spent almost a decade working as full-time music teachers while also building up their photography business even with years of experience. Today we dive into the hesitations mindset shifts, challenges and triumphs that come with letting go of your intended profession to pursue a dream career. And this husband and wife team both made the leap. While we are only here from Courtney today, anyone who has left the comfort and security of a full-time job to pursue entrepreneurship knows taking the leap is not for the faint of heart. Hear how they did it, how it's going, and what they envision for the future. All in today's episode, if you dig professional bios, here it goes. 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 multi-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, and yes, they do use Cannon. Formal introductions over, let's dive in. Hey, it's Shannon and this is Consider the Wildflowers, the podcast. For the past 15 plus years, I've had the honor to hear thousands of stories from entrepreneurs around the world. As a former Fortune 100 financial advisor, turn business consultant, I have a unique opportunity to see the reel. Behind the highlight reel.
I'm talking profit and loss statements, unpaid taxes, moments of burnout, and those of utter victory. Or as my husband says, the content everyone is wondering but not many are talking about. And now I'm bringing these private conversations to you. Hear the untold stories of how industry leaders, founders, and up and coming entrepreneurs got their start, the experiences that shape them and the journey to building the brands they have today. Stories that will inspire and reignite encourage to redefine success and build a life in business on your own terms. Welcome Wildflower. I'm so glad you're here. Hey Courtney, welcome to the show. I'm so glad you're here.

Courtney Cannon (02:39):

Hello. Thank you so much for having me today.

Shanna Skidmore (02:42):

I just locked the door to my studio,

Courtney Cannon (02:46):


Shanna Skidmore (02:47):

Sweet. Little Madelyn, we might have a cameo appearance from her today. That would be cute, but I feel bad. I like locked her out. That is mom life with toddler. Courtney Cannon (02:59):

Yes. We have a four and seven year old, so I totally get it. S

hanna Skidmore (03:03):

Yeah, I love working from home and I love getting to see her throughout the day. We have talked back and forth about getting a studio outside of our house and I'm like, I can definitely see how that would help my productivity, but I would miss, I'm just so grateful. So my husband and I work together and it sounds like you and your husband work together as well.

Courtney Cannon (03:24):

We do. That is actually recent, which I will tell you more about here soon, but we've been working together at home now since May. It's wonderful.

Shanna Skidmore (03:34):

Oh my goodness. Okay. I can't wait to hear all the things. So Courtney, hi. We don't actually know each other and I'm very excited to get to know you and hear more of your story and your journey. So we just tell everybody quickly who you are, and then I want to kind of kick it back to life before business.

Courtney Cannon (03:51):

Yes. So I am Courtney Cannon, part of the Cannons Photography, and my husband and I are wedding photographers for kindhearted couples. And we also host a conference called the Graceful Gathering, which is a conference for kindhearted wedding vendors. And we just love serving people, we love pouring into them and helping them to create their memories, whether that be for our couples or for our students on the side of education.

Shanna Skidmore (04:25):

Yeah, okay, I love that. Now tell me, what were you doing before you started your photography business? How long ago did you start your photography business? It's fun to be on a call with somebody I don't know anything about. Yes, so

Courtney Cannon (04:39):

I'm going to take it back to when Robert and I met. Okay. We met when we were sophomores in high school and we started taking pictures just with the Kodak disposables, which were not $40 a piece back then. And we would take photos of each other all the time then. And then once we were in college, we took a class for photography. We actually both majored in music, so we were both music teachers. And I taught for nine years in Robert Top for 10 years. And we were also building our business and building our family in the same time span that we were newly married and teaching. So it all kind of came together at the same time.

Shanna Skidmore (05:24):

Were you teaching in the same school or different schools? Same area. Did you date that whole time?

Courtney Cannon (05:31):

Oh, the dating story was a rollercoaster, but we ended up back together, so not quite as perfect as some people might like it to sound, but that's okay. That's real life. But we did start dating and then once we were dating a second time in college, we pretty much knew we were going to get married at that point. So we got married right out of college and then we started our teaching jobs, got married in July, started our teaching jobs in August, and then we started our business, I think the following August. It was officially legal in all the things. So yeah, a lot happened in just within one year for us. It was amazing. Yeah,

Shanna Skidmore (06:16):

It sounds like it. So did you know that you wanted to have a photography career? What made you go into music education? I'm interested of, you know, did both, it sounds like at the same time you were launching two careers all at the same

Courtney Cannon (06:29):

Time. Yeah, so we did both and we loved both. And so I'm totally an achiever, technically Enneagram two, but my wing three is hard, so I'm just constantly doing all the things. And I remember when I first said to Robert, we need to make this a business and actually do something with this. He was like, are you sure? This is our hobby. We're having fun with this. We're both teaching. We don't need that on top of everything. And I'm so glad I did it. It was a slow start at first. We literally had $25 mini sessions when we started, actually 10 years ago now, and it just grew from there.

Shanna Skidmore (07:11):

Okay. So tell me about, you say you're teaching, you have that career and you're doing photography, also building a career. It's not like, maybe technically it's a side hustle, but it's wanting this to be a career. So how did you come up with your offers and your pricing? Did you go into wedding photography first or it sounds like portraits. How did you get started in photography?

Courtney Cannon (07:34):

I feel like we did all the things. So when we first started the photography business, we were doing bridal shows. We were second shooting with other wedding photographers. We were going to as many networking events as we possibly could, creating relationship, asking all the questions. I've always been a question asker and just really growing as quickly as we could. We started, I still have some wedding flyers that have packages that were as low as $700. And then I think within a year we booked around 15 weddings closer to a thousand. And then the next year we were closer to 2000 with 20 weddings and it just kept going up from there.

Shanna Skidmore (08:15):

Did you feel good, Courtney, about the growth or was there ever a point where you were like, this isn't sustainable, or I need to increase pricing? How did you learn the business side of photography?

Courtney Cannon (08:27):

So we have just done so many different courses and poured ourselves into so much education that at this point I don't even know that I could create a list that would truly showcase all of the different courses that we've taken, mostly as wedding photographers from other wedding photographers or going to workshops, going to conferences and just pouring ourselves into the idea that we could always learn more.

Shanna Skidmore (08:54):

Yeah. Is there anything looking back that you'd say in those early years you feel like, what would you say you feel like you guys did really well, maybe one to two things you feel like you did really well. And then what were a couple things, one thing, two things that you feel like were harder lessons to learn for you all?

Courtney Cannon (09:12):

I feel like we have always done a great job of challenging ourselves and leveling up and recognizing that even in the moment, no matter how confident we may feel, there's always something else that we can learn. And I think that that has really allowed us to continue to blossom and grow throughout the years. And then something that I wish we would've done more of, honestly, probably just have a better understanding of all the backend things that no one likes to talk about as creatives, like taxes and hiring a CPA from the beginning and just really having the QuickBooks account or something to take care of all of those backend numbers from the time that you start instead of waiting until you're in a place where you have no choice.

Shanna Skidmore (10:00):

Yeah, speak of my language, Courtney. Yes. That's truly why I do. When I first started most of my clients and then students when I started the education side had been in business for a few years at least. And they were in this situation where it hurt enough, yeah, oh, we have to figure out this business side and like you said, taxes, c p, a, QuickBooks. So I often feel like in those early days for me, I was talking to clients when they were having to dig out of maybe yes, where they were, if that makes sense. And then now it's interesting because I would say it's pretty 50 50 and I love that. I wish everyone would, we have a program called the Blueprint Model, and it's all about creating a business plan for your business and getting, yes, the foundations of the business set up bank accounts, CPAs, who needs to be on your text, all that. And I'm like, I wish everyone would take that before they started the business in the first year of business because it would save so much. You had to learn trial and error and oh, I guess we need to figure this out. So it's an interesting mix. Now I love, we have some people that are coming in right out of the gate and still work with a lot of clients that are like, oh wow, this hurts a little bit. I need to figure this out.

Courtney Cannon (11:16):

Even just understanding your expenses, we work with so many students that have no idea what's actually coming in and going out. So while they maybe feel successful that they're booking weddings at 2000 or $3,000 when they really flush out all the numbers, they realize that they're not making anything.

Shanna Skidmore (11:36):

Yeah, that's a hard one. That's a hard hit. Yes. I always say though, I practice, I have all my students go through is I've forced them to really look at the numbers, what's coming in, what's going out. And I always say awareness is the key to change because once you can see those numbers on paper, it really does empower you to understand, is my pricing profitable? Am I spending too much on expenses? So I love that you're doing that, Courtney, and helping people, helping photographers build their business. So talk me through, after those first few years in business, it sounds like, did you start mainly taking on weddings and then just talk through the next few years of growth in your business? Were you doing mainly weddings? When did you start the conference and the education? I, I'd love to hear just how it grew. It sounds like you've been in business now 10 years, so yes, let's hear about the growth.

Courtney Cannon (12:25):

Yes. So we were essentially doing only weddings with some maybe mini sessions on the side for our past couples to continue to serve them. And we were at a place where I was still teaching. I would probably work from two hours in the morning before I went to teach at school, then I'd work all day and then I'd come home and I'd try to take care of our kids because in the midst of all of that we had some kids too, and then also work in the evening. And it just came to the point where as much as I loved teaching, something had to give. And we were looking at our numbers before we had our conference before 2020, and there was just no way. It was extra money for us at that point. It was covering our vacations, covering our house projects, and there was no way that we could foresee it being an actual income for us at that point.
But we were very successful. We were really essentially running a full-time wedding photography business while we were still working our full-time teaching jobs. And because of our teacher's hearts, we knew we wanted to get into some sort of in-person education. Honestly, this was probably, I guess it wasn't before courses, but it was 2019 is when we started to dream up, let's have a workshop. And the graceful gathering at first was supposed to be a workshop with the two of us, and then we thought, oh, let's bring in some guest speakers. And all of a sudden a few guest speakers turned into this entire conference that then almost didn't happen because it was in 2020, I think. Yeah, I can't even believe that it did happen. Somehow it did all as well. Everything went perfectly. So we started in June of 2020, the graceville gathering, and then we took a year off for obvious reasons, and then we started again last year. And in the midst of that time during Covid, we were able to save a lot of money and then felt confident in me going, we also completely leveled up our business. So we went from an average investment of 4,000, which at the time was very average for successful wedding photographers in northeast Ohio. And it went from that to 6,000 in probably about two months all at the same time that I had turned in my teaching resignation. And things just exploded from there, really, essentially when we made the decision to take the leap. Yeah,

Shanna Skidmore (15:08):

So do you think that was the turning point? I mean, knowing now, okay, we can't rely on our teacher's, Sal, at least for you, Courtney, your teacher's salary, is that what made you increase your pricing? Was that scary? Now you said you were able to save a lot of money. I always find, and I'm interested Courtney, if you would say the same thing, when people need the money, their mindset can shift around it. And also just knowing exactly, having that plan in place. There's some like fairy dust, there's some magic in yes, knowing exactly what your target is and can get you maybe. I mean that's what I do every day, financial planning. So yes. How did you save the money? Why did you increase price? Was that all just around, I want to quit my full-time teaching job.

Courtney Cannon (15:57):

So we were going to wait until March to turn in my letter of resignation so that we could make sure that we had the bookings on the calendar. And I ended up turning it in December because I just felt like we needed that push. We needed to know that there was no way out that this was happening and the money had to come in. And I do think that when we took that leap of faith, it really just kind of sprung us forward and it gave us, mindset is huge. It gave me the confidence to push forward, but also know that we had no choice to push forward. So we already knew that we had the experience in place that we were giving the quality product to our couples. So that wasn't a concern at all. But we started booking and then every few bookings, we would just raise our prices a little bit more as we went. And then it skyrocketed from there. And then since then, that was two years ago. We've now added, our average booking now is 8,000. So we essentially went from four to eight in two years.

Shanna Skidmore (17:05):

That's incredible. Now my follow up question, and I think everyone listening is did people still book? Were you scared? Did you see a drop off in bookings? This is the number one question I get when I tell people it's time to double your prize. And they're like, I can't. Yeah. How did you do that?

Courtney Cannon (17:21):

So people did still book less bookings come in, less inquiries come in, and we have our system set up to where we're not trying to sell every single person who comes through the door because of the life that we live for so long. I just didn't have time for that. We needed to know that if they were contacting us, they were able to invest in us and they really wanted to work with us. So we do get less inquiries, but because they're more, we do do not, we don't have to take on as many. Right. And it gives us more time back in our family, more time to pour into the education side and essentially more time to take better care of the couples that we are working with. Shanna Skidmore (18:02):

Yeah. Okay. So when you quit your teaching job, so I'm going off script here, but did you guys create a financial plan for your business? Did you know your sales goal? How were you comfortable knowing we're doing this? There's no looking back. Yeah, like you said, how did you know those numbers at that point? I mean, just by doing business at that point, it sounds like eight years.

Courtney Cannon (18:27):

Yes. So we knew what our numbers were. We knew what we could really wisely project. We kind of set three tiers of goals, our goals based on what we already see coming in our goals based on very standard projections and then kind of our dream goals. And we look at our numbers in that way so that we know we're safe and we're taken care of, and then this is what's realistic and this is what we're going to reach for the stars on. So when I went, it was much easier to take that leap of faith because my husband was still teaching, we still had insurance with him, and at the end of the day, we knew that the business would bring in enough to make up what we needed just to pay our bills and take care of our family. But then when Robert went, it was way more of a different story because yes, we did have the financial plea and we knew everything was going to be in aligned. It was going to be just fine with me, but with him leaving as well, it was this whole other world of, I mean, it was definitely scarier when we decided for him to go.

Shanna Skidmore (19:40):

And now you're, I'm going to ask how it's going. Yes,

Courtney Cannon (19:45):

It's going very well for any wedding photographers. This is our down season. We're in Ohio, so most people don't get married in the snow. So January, February, March has been a little weird just because we have the funds in our account, but there's no fresh funds coming in until the weddings start back up again. So that's always a little interesting just to navigate when you're so used to your paychecks coming every other week and consistently no matter what, just learning how to organize, how we're paying ourselves and how we're making sure that we're breaking everything up accordingly so that it makes sense.

Shanna Skidmore (20:24):

Yeah, that's so good. And I know I think every entrepreneur's fear is people will continue to pay me or buy from me or Yeah, I wonder if there's any entrepreneurs email me if you're out there and you're like, I never worry about that.
Because yeah, every year it's kind of fresh start. When I worked in finance, we built up residuals. So you would start the year already with residuals, so you kind of created your base salary that way. And so it's been interesting as we have built out, this is our 10th year in business as well, structuring offers in a way to how can we create that consistent kind of residual. We have a membership mastermind community now that is starting, and that's been exciting then. So it's just fun to think about different ways to add in new offers. But it sounds like I'm going to talk about the conference a little bit and then education. It sounds like with the conference this was an offer, not necessarily a strategic offer of diversifying your income, but just something you all wanted to do for impact. Is that, would you say that's kind of correct?

Courtney Cannon (21:35):

Yes. So the conference is definitely a work of hearts. It is not something that we rely on for profit at all. We pour almost every single dime right back into it. And it really just allows us to serve our community well and come together with others and network. And it has helped us, and I think we'll continue to do so to create our reputation as educators and to get our name out there just in that role and be recognized as educators as we continue to, we're going to be launching a shop and then creating some courses here soon just because we definitely have a heart to serve and to teach. So it does serve that role as well, but it has just been so wonderful to be able to connect with the community.

Shanna Skidmore (22:28):

Yeah, that's so awesome. I love getting to see people in real life is such a gift. So I always love when I get asked to speak at conferences or we host an annual conference for our students called Blueprint Summit, so it's just so fun. Yeah. Okay. Courtney, I want to dig into it. I'm going to put you in the hot seat a little bit and let's dig into the numbers just a little bit. I would love if you would share just a little bit about your relationship with money, maybe when you first got started as a teacher and then launching your business and now how would you characterize your relationship with money?

Courtney Cannon (23:01):

I think that when we started teaching, even though our paychecks were very low, looking back, we were thrilled because we had gone from working high school, college jobs to an actual salary with benefits. And we started our retirement funds right away when we started teaching and we were putting more aside for that. And so even though it was way less than many people would consider even substantial to live on, it was wonderful for us. So I think that was kind of where as we continued to grow, we were getting raises for our teaching salaries, but our business was also, and we really just learned how to manage our money and be able to still do all of the fun, enjoyable traveling or going out to eat or shopping within our means. And I think that that was definitely a huge part of being able to go, because if we needed to pull back, we knew where and how to do that.

Shanna Skidmore (24:08):

Yeah. Well, that's so good. Do you feel like starting with a salaried position in their teaching role that it taught you habits for money management, like you said, saving for retirement, that you were able to then carry over when you went now full-time entrepreneurship, paying your own salary, that you were able to maintain those same habits?

Courtney Cannon (24:32):

100%. And actually my husband Robert, is on a call with our financial advisor that we've been working with since we started teaching. And honestly, if we wouldn't have taught, I don't know that we would've ever thought to hire a financial advisor when we were 23 years old. So I think it definitely has given us so many tools to even just learning how to talk to people and continue to work with people and diving into all of those savings for sure.

Shanna Skidmore (25:05):

Yeah. Well, that's so good. What would you say when it comes to money came naturally for you or for your husband, and then what were things that were harder to learn?

Courtney Cannon (25:16):

Yeah, I'm the spender, Robert's the Saber, and we have Target in our backyard. No. So for me, definitely just learning how to save. We have a fantastic relationship to where he just knows that monthly I'm probably going to go shopping, but he knows that there's a certain point when he tells me not to do that anymore.
He created when he was in college, actually what he calls is New Zero. So as he built his account, he decided that in his mind, the account was at zero, if it was at 500 and then it was at zero once it got to a thousand and just so on and so forth. So he continued to grow that. So essentially when we were looking at going full-time, we already had that savings just kind of naturally there ready for us. And so he obviously has way more of a budget minded mind and was able to prepare us and just look at the numbers in a way that were very practical. And that helped me a lot to control where I was investing too, because it's, as a business owner, it's easy to say, well, we have to get this lens and it's going to be an investment, but if the funds aren't there, then it's not time to get it.

Shanna Skidmore (26:36):

I just wrote down New Zero because I am obsessed with that concept. I'm totally going to credit your husband news. That's such a cool way to think about, this is my new zero. We're not going below this. Yeah, yeah. That's so good. And I also love how you brought up, I hear this from entrepreneurs almost every single day about reinvesting in the business, and I think reinvesting in the business is needed and necessary, but I always advocate for doing that with an intentional plan because habits, just like you created habits in your teaching job of saving systematically, incrementally that you carried over and how you were paid systematically, incrementally and consistently. Those habits that we create early on in our business are hard to break later. So we want to create good habits from the beginning. And so when people say like, oh, I reinvested everything in the back of the business, I'm like, well, let's just go in with an intentional plan because that's hard to break later on. So I love that you guys thought about that. I always like to ask all of our guests, Courtney, what would you say is the best thing you have learned about money?

Courtney Cannon (27:44):

I feel like when you stop feeling, it's totally a mindset thing. When you stop feeling like it's never going to come and you start to feel grateful for what you have and what is coming, it starts to naturally flow.

Shanna Skidmore (28:00):

Yes, that's so good. Gratitude,

Courtney Cannon (28:02):

And that sounds kind of woowoo. I don't mean for it too, but it's just valid when you start to look at money in a way of we are successful, we are grateful, we do have what we need, instead of the scarcity mindset of we need more and more and more. Where's it at? Why isn't it coming? It just starts to flow. It really does.

Shanna Skidmore (28:24):

Yeah. Ooh, that's good. I feel like I'm, I'm going to listen to that one again. We talk so much about scarcity versus abundant mindset. I think it's hard almost sometimes to get your mind around or it's easy to dismiss, but gratitude is such an important piece, and I could go on and on about this, but thank you for sharing that. That's so good. Courtney, would, before we go into kind of a quick fire round, I would love for you to talk about just you work together, husband and wife team. We have two kiddos at home. How would you say, and for a lot of this time, you had a full-time job as well.

Courtney Cannon (29:00):


Shanna Skidmore (29:01):

How would you say that in a world that asks us to do all the things really well, how have you found harmony in your work life? The mom, you want to be the wife, you want to be your home life. What does that harmony look like for you?

Courtney Cannon (29:16):

I would say first of all, just that both Robert and I are in it. We've had a lot of mentors who guided us to say that our life is not the canons photography. Our life is not the graceful gathering our life. We are the CEOs of the cannons and our home. And so whether I'm answering emails or my husband's doing the dishes or making dinner, every single task that we have is valid and is part of the success of our lives. And so we have really just divvied up the roles, but not put any one role 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 and post on social media and check our emails as well. And another thing that has really helped me, I'm a list maker.
I'm a planner and I like to feel like I've accomplished task. So we created a bucket list for our family and the kids can see it. It's hanging up in our kitchen and there are four different activities each month. Some are very practical, some are more like, Hey, we're going to go to this place. But it allows the kids to see that even while we're working, we're still pouring into them and we're still doing active things with them as well. So that has really helped me just to find that harmony, because it's so easy to have mom guilt and feel like I'm always at my computer in their home. Now I should. I need to close it and put it away, but there is a balance. If I work from home, I have to work from home, and I need to still make sure that I'm giving them the time and attention that they need as well.

Shanna Skidmore (31:03):

Yeah. I love the idea of a bucket list for your family. So is that monthly things, do you have a big bucket list, yearly, forever things?

Courtney Cannon (31:13):

Yeah, so last year I had 15 things, and sometimes it was as easy as indoor snowball fights or build a snowman, but this year I broke it down to four things and it's making it very easy to do one activity a week. And some of them are very simple. Some of 'em are more going somewhere and doing something. I think in March we have a Yes day, which is a modified yes day. I don't know if you know what that is, but where essentially we take the kids out and we say, here are some options. What would you like to do? And whatever they say, we say yes to. And so each month now, the kids have gotten really excited about just making sure that we're checking off all of the activities. And I think it just gives them the opportunity to see that we are really pouring into them too.

Shanna Skidmore (32:00):

Yeah. Oh, I love this idea. Given me so many ideas. I want to incorporate myself new zero bucket list for family, check, check. Let's do it. I love that, Courtney. And how would you say that things have shifted now that your husband is full-time in the business as well? Have you all created certain boundaries? No work after this time, or, I also love the idea of boundaries can be a yes to. So we're saying yes to four activities a month, or how has that shifted since now that your husband's full-time as well?

Courtney Cannon (32:34):

It has been wonderful. We decided we need a calendar just to mark how many times we say, is this our life? Is this happening? We were able to go and do, we went to top golf with the kids on a random Tuesday, and we just looked at each other and we said, we would never have done this. If we were both teaching they're, we would've been exhausted. I tend to work a lot. So for me, I try to make sure I close the computer at dinner dinnertime and sit down and eat with them. We'll play a board game or watch a movie almost every night. So as much as we are very busy in our businesses, it has definitely allowed us to just have that very intentional family time every evening, whether we play a game or go for a walk together or go to the park, we make sure no matter what, that those two hours between dinner and bedtime are for family.

Shanna Skidmore (33:26):

Courtney, this has been so wonderful to hear about your business and the growth of your companies and getting to work with your husband, how you're doing your fam. It's just been a joy to get to know you. And I want to go into kind of a quick fire round. These are just some fun questions that I love to ask all of our guests, so I'm going to fire away.

Courtney Cannon (33:48):


Shanna Skidmore (33:49):

Okay. So first question, what is one thing that you would be embarrassed if people knew?

Courtney Cannon (33:55):

People used to ask me how we did it all, and I would tell them our house was a disaster. It was true. I wasn't joking.

Shanna Skidmore (34:03):

You're like not, please don't come over today.

Courtney Cannon (34:06):


Shanna Skidmore (34:07):

Man, it is hard to keep up with dishes and grocery shopping and all the things. So yes, I'm grateful that we have help with, we have an amazing, Ruth is our house cleaner. She comes every two weeks and our toilets would not be cleaned. So many things. Our floors would not be mobbed without Ruth. Thank the Lord for Ruth.

Courtney Cannon (34:27):

I am still trying to convince Robert that we need a Ruth. Yeah. So we'll see.

Shanna Skidmore (34:32):

Okay. He can call me because it is the best. She is just the sweetest lady. She's such a gift to our family, the best investment we make in our home. Yeah, absolutely. Okay. Any regrets or wish you could do over moments?

Courtney Cannon (34:47):

I think we would've hired a CPA sooner to just know all the rules right away.

Shanna Skidmore (34:52):

Yeah, that's helpful.

Courtney Cannon (34:54):

I know that that sounds cliche, and some people are like, really? Do we need it? But yes, you do, and you end up ahead when you actually know what all the steps are to do. Yeah.

Shanna Skidmore (35:05):

I have a follow up question with that, Courtney. Yeah. What would you say kept you from hiring a cpa?

Courtney Cannon (35:11):

I think we just felt like it was easy to take care of on our own, and we just recently switched from filing as a sole prop to an S corp, and it was really in that moment that we needed to have that backbone to understand what we were getting into. And I think it just is so valuable for people to not rely on what they think they know and instead go to the professionals and figure what they need to know.

Shanna Skidmore (35:38):

That's so good. And so we launched, this is still, it's not publicly launched now. Maybe by the time your podcast comes out it will be. But we started this idea of the Money Club. It's our new mastermind membership. We've been doing it for almost a year now just with our students. But it's so interesting because there are so many questions in business. Should it be a sole proprietor or an LLC or like you said, an S Corp or how do we have all these things? And so I have a background degree in finance, but it's so funny because I'm like, there are times I love the Money Club membership because it's a place where we can just ask these questions. You don't know who to who else to ask. But still, I always tell my students that you have to have professional help in your area that understands your business because even with my background and the fact that I am in talking about finance every single day, there are still things because I don't read the tax code. Everything changes so often that you need to talk with someone that knows you and your situation and your location and your business. So I love how you said it can be easy to rely on our own knowledge, but when you find someone that's a great asset to your company, they're going to be able to answer questions that absolutely I can't even find as a finance professional. Right. So that's so good. Okay. Third, what is a big win or a pinch Me moment?

Courtney Cannon (37:04):

I think our biggest win was definitely when Robert went full-time with us as well. We never in a million years thought that I would go, so that was huge. But then he was in his dream job at his dream school in an incredible program that just continued to grow and for him to leave was really, really hard. But it has completely changed our life and our lifestyle and our day-to-day, and we're just so thankful. Shanna Skidmore (37:33):

What a gift. I tell Kala all the time, it is a gift. We get to spend so much time together with Madelyn. It is a massive privilege and gift to both be entrepreneurs, and it's not for everyone, of course, but it's so sweet that you can go to Top Golf on a Tuesday.

Courtney Cannon (37:48):

Yeah. Yeah. He loves even just putting them on and off the bus every day. Yeah, it's wonderful.

Shanna Skidmore (37:54):

It's sweet. Yeah. Okay. What is the best advice or just really good advice that you have received?

Courtney Cannon (38:01):

I think recently as we are diving into being educators, Mary Marz has really challenged us as to the line of imposter syndrome, and are we really good enough and is this really something that we should be teaching, and are we the experts on this or do we only know these answers because X, Y, Z told us? And she really just continually challenges us to question why we feel that way and helps us to validate what we do know and what we have learned. And I think just having a person who's willing to listen and pour into you and challenge you to continue to be brave and push forward is so valuable.

Shanna Skidmore (38:50):

I think Mary Moran is such a wonderful human. Do we did an episode, if you haven't listened to it yet on the podcast with Mary. Oh, yeah. It is so good. I think I was tearing up in the first three minutes because she

Courtney Cannon (39:02):

Just, hundred percent, I'm

Shanna Skidmore (39:03):

Sorry. Goes straight to the heart. Yeah, listen to it if you haven't, and I'll link it below. For everybody listening, if you haven't listened to Mary's episode on Consider the Wildflowers podcast. It's so good. All right. Last quickfire question. Courtney, what are you working on now or one resource that you would love to share?

Courtney Cannon (39:19):

So right now we are in the thick of it with the Graceful Gathering because it is almost one month away. We're so excited for that. But we are also going to be launching a shop in the next few months, and then we will be launching some courses along with our Mastermind. So for any wedding photographers or for wedding creatives, there are tons of resources that we are just so excited to share, and I think just for people to know that we're here for them, that we're happy to chat. I know sometimes even just reaching out via email or Instagram can be intimidating, but our hearts are truly to serve, so we are here to serve.

Shanna Skidmore (40:01):

Yeah. Ooh, I'm so excited for you all and good luck with the Graceful Gathering Conference. That's going to be

Courtney Cannon (40:06):

So fun. Thank you.

Shanna Skidmore (40:07):

All right, let's send it off. Courtney, this has been so fun, but what would you tell yourself, looking back 10 years on day one of starting your teaching career, and then a year later officially starting photography, what would you tell yourself just at the beginning of your business journey?

Courtney Cannon (40:25):

Education is key. Continue to pour into yourself and continue to find ways to grow and don't be afraid to push forward.

Shanna Skidmore (40:34):

I love it. Thank you so much, Courtney, for coming on the show and for sharing your journey and business, and it's just been a joy to get to know you.

Courtney Cannon (40:43):

Thank you so much. I enjoyed it.

Shanna Skidmore (40:45):

Hey, wildflower, you just finished another episode of Consider the Wildflowers the podcast. Head over to consider the wildflowers for show notes, resource links, and to learn how you can connect with Courtney and Rob. One final thought for today from GK Chesterton, I would maintain that thanks are the highest form of thought and gratitude is happiness doubled by wonder. As always, thank you for listening. I'll see you next time.