We caught up with the brilliant and insightful Caitlyn Cloud a few weeks ago and have shared our conversation below.
Caitlyn, appreciate you joining us today. Before we get into specifics, let’s talk about success more generally. What do you think it takes to be successful?
Success in our society is usually defined by how much money you make. And while I do believe earning money contributes to success, I’ve come to realize that I don’t define success in the same way.
So what does it take to be successful? Knowing what you want out of life, and then setting the boundaries and expectations for yourself so you achieve your version of success. For me, that means setting a hard limit on how many weddings I take each month so I know I won’t overwork myself. This gives me the freedom that I wanted from owning my own business.

As always, we appreciate you sharing your insights and we’ve got a few more questions for you, but before we get to all of that can you take a minute to introduce yourself and give our readers some of your back background and context?
I am a wedding, couples, and senior portraits photographer. I specialize in documentary wedding photography.
Weddings have become a victim of social media. We started to value cool photos more than the actual wedding. But my style of photography, the documentary-style in general, allows the couple to bring the focus back to the important part, getting married and celebrating with loved ones. I approach the day as a witness, meaning I do not interfere I simply photograph everything, document all the memories.
So I’m most proud of the moments captured. Photos are moments frozen in time. They have the power to transport you right back any time you look through your wedding photos. The documentary approach to wedding days is what sets me apart.
I actually went to college to be an event planner, and the ultimate goal was to work in weddings. I’ve been in love with weddings since I was little. My introduction to the wedding industry was my grandma’s bridal shop. Visiting the shop and going to her wedding expos always felt magical. The wedding industry just always felt like where I’m meant to be. Wedding planning felt like the right path because of my Type A personality. However, planning my own wedding showed me that being a wedding planner was not my dream job. So, I either had to give up on working in weddings or find a new avenue.
I was straight out of college, living in a new city with no connections and struggling to find a job, when I saw a friend of a friend who had started up a photography business and I literally thought to myself, “I could do that.” So I spent a good chunk of my savings on my first DSLR and started asking my friends and family to model for me. I taught myself how to use my camera and how to frame a photo. Pinterest and Youtube were great resources, but practicing is what helped most. When my husband and I moved to Kansas City in May 2018, I decided to take the leap and go full time with photography.
It’s been almost 5 years since I went full time and I’ve come to realize that the part of my job that lights me up the most is working with my amazing clients. My job is to be with you while you celebrate joyous moments in your life. Graduating school, celebrating your love. It’s such an honor to be trusted with documenting these important memories. Photography has brought the best people into my life, some past clients have even become good friends. I am so thankful I followed a random whim and bought that first camera.
We often hear about learning lessons – but just as important is unlearning lessons. Have you ever had to unlearn a lesson?
I had to unlearn some capitalist values in order to find joy in my business. When I started, all of my goals had to do with how much money I earned. How many sessions or weddings I booked. Constantly grinding and hustling. We’re sold on the “American Dream” from such a young age, it’s basically engrained into our brains to work hard and earn money so we can buy all the things that equate success. I burned out in less than two years.
Luckily, I found a wedding photography workshop called All You Witness. I’ve always preferred candid photos over posed photos, but All You Witness introduced me to documentary photography. During this workshop, I realized I find the most fulfillment when I’m able to witness humanity happen in front of my lens. Humanity is so beautiful, especially on wedding days. From a mother helping her daughter into her wedding dress, to kids playing hide and seek with the wedding party, to those quiet moments before walking down the aisle into their new chapter of life, to the tired but excited exit at the end of the night. Being able to witness and document all these memories and the in between moments fills my cup so completely. After this realization, I worked on reframing my mindset around my business. My goals were no longer solely about income, but rather about how I could better serve my clients. Letting go of the capitalist need to always be hustling, always be earning money, that money over happiness mentality, freed me up to focus on what I enjoy about my job instead. Obviously, there’s nothing wrong with keeping the hustle mentality if it works for you, but now that I’ve unlearned this behavior I am so much happier. And my clients benefit too.

Is there something you think non-creatives will struggle to understand about your journey as a creative? Maybe you can provide some insight – you never know who might benefit from the enlightenment.
I don’t think this is limited to only non-creatives, I think it’s something people who don’t own a client facing business might struggle to understand.
Social media changed the game when it comes to how people spend their money. 2020 was also a huge catalyst that changed consumer behavior. People want to support a cause or a person and they take company values into consideration when making a purchase.
I have a pop-up on my website that tells people a few important things I believe in. Like Black Lives Matter, I am an ally to the LGBTQ+ community, I believe women have the right to make decisions about their own bodies, I believe in vaccine science, etc. They’re all controversial topics, which businesses would have shied away from in the past. I’ve had people tell me that I should take the pop-up down because it drives business away. What they don’t understand is that putting those beliefs front and center actually drives the right clients to me. It’s so important to be transparent, and to be yourself. It’s also important to understand that I am not the right photographer for every single person, and that’s okay.
Contact Info:
- Website: https://caitlyncloud.com
- Instagram: https://www.instagram.com/caitlyncloudphotography/
- Facebook: https://www.facebook.com/CaitlynCloudPhotography
- Other: Pinterest: https://www.pinterest.com/caitlyncloudphotography/
Image Credits
Caitlyn Cloud Photography

