After being turned down for two master’s degrees and a job at Big Lots, our latest podcast guest was at the end of her rope–but she wasn’t ready to give up.
Kaitie Bryant has never been afraid to take the ideas in her head and pursue them. From pitching fashion ideas to the GAP, to wedding photography and launching a side business with her husband.
She is a successful photographer, serial entrepreneur, and mom of two. Her work has been featured in magazines such as Real Simple Magnolia and The Knot. Her latest venture, The Known Project, includes a series of books co-authored with her husband to foster deeper connection and more meaningful conversations.
Kaitie joined the show to share her journey from history teacher to entrepreneur, her best mindset tips, and everything she’s learned about creating a budget for your business and your personal life.
Growing up as the youngest of three children, Kaitie never saw herself as particularly creative. “I’m a bit of a late bloomer,” she jokes. “I wanted to be different from my siblings.”
With two older brothers in the film industry, a photographer father, and an entrepreneur mother, Kaitie was content to leave the creativity to the rest of her family and focus on school.
After graduating from the University of Georgia, she applied for two different Master’s programs but was rejected from both.
Frustrated and still needing an income, she applied for a job at Big Lots–where she was denied on the grounds of being overeducated. “That was the apex of my denials. It was a really low point in my life.”
But Kaitie wasn’t ready to give up yet. “I’d always had a very optimistic outlook, and I truly believed I could do anything.” That positive perspective led her to start a creative side business and take the first steps toward becoming an entrepreneur.
Kaitie’s first product, Fickle Flops, were sandals with removable straps that could be changed to match your outfit. “My mom and I bought out all the flip-flops at Old Navy,” she laughs, looking back at that first product.
From there, she moved on to designing T-shirts for kids, then onesies, going so far as to pitch the GAP on her unique onesie design. “I had such confidence in my idea.”
When the GAP didn’t respond, Kaitie didn’t let that stop her. She went on to sell her children’s clothes in local stores in Athens, Georgia. When the excitement wore off, she simply moved on to the next idea.
Finally, Kaitie connected with a local photographer and found a business idea that would stick. She started taking photos for free to gauge interest, and when people responded and she started charging for sessions, it became her most profitable side business yet.
“I wouldn’t call myself ambitious,” Kaitie says, “but I get bored easily and look for ways to be excited.” When she thought of a product that didn’t exist yet, she went and created it.
Kaitie was working as a high school history teacher, but as a new mom, she craved more flexibility. “I wanted to be able to be in the driver’s seat. I didn’t want to work on someone else’s schedule.”
Many of the married women around her had taken up multi-level marketing, hosting Tupperware parties from their living rooms. “I had this fear I would have to do that–like that was the only option for women with kids who wanted a flexible job.”
When she discovered photography, it was a light bulb moment.
Kaitie booked her first wedding in 2010 for $250. With many of her recently graduated friends getting married, it wasn’t long before she had a full calendar of bookings. And with her husband still looking for the right job, they needed the extra income.
“I just started saying yes to everything, which probably wasn’t ideal with a young child, and while I was pregnant with our second.”
Not only did Kaitie replace her teaching salary, but she went on to double it the next year. Despite her success, she still didn’t feel confident with the numbers side of her business. She wasn’t sure when to spend and when to save.
“I was always too busy to look at the numbers, which was really unfortunate. I didn’t understand taxes and I had no idea how to make an Excel spreadsheet. Business was good, but I didn’t know how to make sense of any of it. I was drowning.”
Most entrepreneurs love the freedom of self-employment, but to create a sustainable business you also need some amount of structure. Without organized systems in place, that sense of freedom can quickly turn to chaos.
For Kaitie, the first step out of overwhelm was to get clear on what “enough” meant to her family and define a household budget.
After reading finance books that only talked about the business side of things, she wanted a way to connect that to her home life. Once she understood her family’s needs, she was able to work backward to price her photography services in a way that felt right to her.
“There are real formulas for pricing. It doesn’t need to be a shot in the dark.”
Once she was confident in her pricing, Kaitie experienced more freedom in her business. She was able to map out new goals and how many weddings she needed to book to reach those goals–which turned out to be far fewer than she expected.
With two kids at home, the hustle from her early days of business was no longer sustainable. She didn’t want to stay married to her computer.
So Kaitie worked to find a sweet spot that would allow her to make a comfortable income and cut back her working hours. That sweet spot is the key: finding what works for you, your family, and the type of lifestyle you want to live.
Having multiple sources of revenue helped Kaitie feel more secure in her business when the photography side of things slowed down. That flexibility was key to helping her achieve a better family life as well. Before, Kaitie struggled with a lot of guilt about working.
Learning her numbers helped her come to another realization: being a good parent doesn’t need to be in conflict with growing your business. Instead of paying attention to what everyone else was doing, Kaitie focused on what worked for her family.
One strategy she recommends is to have structure around when you work. Create boundaries for yourself and your family, and know that those may shift over time.
Before working through Blueprint at Home, Kaitie never used to think of herself as a numbers person.
“Now I’m a nerd with Excel spreadsheets and the numbers help ground me. They don’t tell an emotional story about what’s good and what’s bad. They just help me see where I’m at and where I’ve grown.”
This perspective has helped Kaitie appreciate her growth, rather than getting sucked into other vanity metrics. “I have real data that says this worked, this went well, or this didn’t go as well.”
Getting a handle on her finances has also helped Kaitie feel more organized.
“Before, all my money was in this really messy closet. Working through Blueprint at Home was like going to the Container Store. I used to have to look at 10 different accounts, but now I have containers for everything. So when I open up our financial closet, everything has labels and it’s beautiful.”
It should come as no surprise that Kaitie is a firm believer in creative side projects–although she stresses that you don’t need to turn everything into an income stream. “Growth doesn’t always need to have a dollar sign next to it.”
Give yourself permission to pursue new ideas whether they’re financially successful or not. If there’s an untapped area you want to explore, start there and see where it leads you. For Kaitie, that’s writing. Her next project will be a coffee table book.
But even for this experienced entrepreneur, there’s still the fear of trying something new. “I know I’m going to face resistance, and when I do, I need to lean into it because I want to see the end product.”
With so many projects on the go, how does Kaitie stay motivated?
“I’ve learned I have a million ideas, but there’s no shortage of ideas. The shortage is of people who follow through. So I just need to follow through.”
She hopes to pass the same passion on to her kids. “A huge motivation for me is I want my kids to use their gifts, their interests, and their curiosity to be a maker, not just a consumer.”
“It doesn’t matter if the end product is successful in sales. What matters is that you followed through and developed the work ethic to bring to life what was inside of you.”
If Kaitie could go back in time and give advice to her younger self, “I would say to find the people you want to serve and to focus on serving with your work. Don’t get lost in all the noise. If you can focus on serving your people, then it will feel meaningful and worth it.”
To hear our full conversation, press play above or click here to download the transcript.
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Kaitie is a photographer who has worked primarily in the wedding industry while also shooting fine art photography in collaboration with Minted, an online marketplace for independent artists. She has also worked with her husband in creating small booklets of questions as a resource to help people connect on a deeper level, called Well Known. Kaitie and her husband live in Athens, GA and are avid Georgia fans. She has two boys, a 14 year old and 11 year old, and they spend most of their days on a soccer field or basketball court. She is honored to have photographed all over the country, including weddings in New York City, Los Angeles, Chicago, and Mexico while having her art featured in magazines such as Real Simple, Magnolia, The Knot, and in stores such as West Elm. Kaitie & Jared continue to grow their side business, i.e. The Known Project, with the total sales of Well Known books over 18,000 and new editions to be released in 2023.
January 27, 2023