Alright – so today we’ve got the honor of introducing you to Caeli Richter. We think you’ll enjoy our conversation, we’ve shared it below.

Hi Caeli, thanks for joining us today. Folks often look at a successful business and imagine it was an overnight success, but from what we’ve seen this is often far from the truth. We’d love to hear your scaling up story – walk us through how you grew over time – what were some of the big things you had to do to grow and what was that scaling up journey like?

Three years ago, I left a corporate job that I loved to pour all my time and energy into launching my photography business full-time. I am naturally cautious, far from a risk-taker, and I tend to overanalyze everything. But I knew that building a business from the ground up would take time, and I prepared myself for that reality. Instead of focusing on overnight success, I focused on what was within my control and what I could do that would ultimately set myself up for success.

Stepping into the biggest professional change of my life was daunting. I no longer had a team to strategize with, lean on, or celebrate wins with. I was incredibly anxious about whether I would succeed, and I knew I needed structure, support, and accountability. One of the first steps I took was joining a business mastermind with Elena S. Blair. This gave me exactly what I was looking for — a community of like-minded entrepreneurs, guidance from experienced mentors, and a structured approach to building my business strategically.

One of the smartest decisions I made early on was focusing on school photography. With my background in sales, I knew that exposure to as many potential clients as possible was key. Schools gave me a direct line to hundreds of families – many of whom were in the exact stage of life where family photography was a priority. These parents were already investing in capturing their children’s milestones, making them an ideal audience for my work. By delivering a high-quality, personalized school portrait experience, something many families are not accustomed to, it helped build trust and created a natural pathway for them to consider me for their family and newborn photography needs. This approach allowed me to establish a strong client base early on, which became the foundation for scaling my business.

Another critical strategy was structuring the first year of my business a little differently. Instead of trying to hit the gas from the start, I treated Q1 and Q2 as my building blocks, using that time to lay the groundwork for what would inevitably become a busy Q3 and Q4. Each year, my business has grown exponentially – but at a steady, sustainable pace, allowing me to take on more and more work in Q1 and Q2. I truly feel I am able to do this because I focused on creating a strong foundation from the start rather than chasing short-term wins.

Even as my business has grown, I have remained committed to mentorship and surrounding myself with a supportive community of photographers. Staying engaged with others who push me to grow, both in my craft and in business, has been invaluable. Sure there have been obstacles along the way, but having a clear strategy, building strong relationships, and staying disciplined about my short and long-term goals has been the key factors in my ability to scale successfully.

Caeli, love having you share your insights with us. Before we ask you more questions, maybe you can take a moment to introduce yourself to our readers who might have missed our earlier conversations?

I am a lifestyle family, newborn and school photographer serving Greater Boston and Nantucket. My goal with photography is to capture genuine and joyful moments for the families I work with – the fleeting, everyday magic of childhood, the closed-eye laughs, the tiny hands wrapped around your finger, the moments that may feel small now but will mean everything to you years down the road.

Looking back, my love for photography, and the understanding of the power of photographs, started long before I ever picked up a camera. As a child, I spent hours sitting in my Grandma’s “fancy living room,” paging through the albums she meticulously assembled and labeled by hand. Each album told a story, not just of the big milestones but of the everyday moments that made up our lives. Those albums were more than just pictures, they were a tangible record of love, connection, and the experiences that shaped our family. Photography is so much more than beautiful pictures. I believe it is about preserving memories, about giving our children and future generations a way to see and understand the love and life that came before them.

My journey into photography was not a straight path. Sure, I grew up as the family documentarian, the one in my friend group always taking pictures. I studied photography in high school and college, but upon graduation, I entered the corporate world and my first “real job.” After about 15 years in the “real world,” I left a corporate career I truly loved to pursue photography full-time. I am naturally risk-averse and tend to overanalyze everything, so stepping away from a stable career was daunting. But, I also knew I had a deep passion for storytelling through images, and I wanted to build something that not only brought me fulfillment, but also created lasting value for families and gave my own family more flexibility and support.

From the start of my business, I focused on what I could control – building relationships, creating a seamless client experience, and developing a strong foundation. A key part of that strategy was school photography. Partnering with schools allowed me to introduce my work to hundreds of families, many of whom were at a stage where capturing their family’s story through photos was a priority. I treated school photography not just as a way to take portraits but as an opportunity to provide families with a more personal and meaningful experience than they were used to. This approach helped me quickly build trust and connect with families, many of whom later hired me for their own family and newborn sessions.

What sets my work apart is my ability to create images that feel both timeless and deeply personal. My goal is to capture the essence of your family as you truly are. Whether it is an in-home newborn session, a sunset beach session on Nantucket, or school portraits that reflect a child’s true personality, I want my photos to feel like a piece of your family’s history.

Have any books or other resources had a big impact on you?

I read the book The Big Leap by Gay Hendricks, as recommended by Elena S Blair. To say it had a tremendous impact on my entrepreneurial mindset is an understatement. As someone who is naturally risk-averse and tends to overanalyze everything, stepping away from a stable corporate career to pursue photography full-time felt overwhelming. I started reading The Big Leap within days after leaving my corporate career and it helped me recognize and identify the self-imposed limits I was placing on myself and gave me the extra push to move beyond my comfort zone.

The book talks about the “Upper Limit Problem”, the idea we often subconsciously hold ourselves back from achieving our full potential because of fear, self-doubt, or a belief that success in one area will come at the cost of something else. Reading this helped me shift my thinking and realize I was not just building a business, but creating a life that aligned with my passion, values, and goals.

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

The biggest pivot I have made—both in my career and in my life—was leaving my corporate job to pursue photography full-time. I had a career that I truly loved, but as my daughters were getting older and starting school, our family’s needs were shifting. My corporate job was returning to more in-office work post-COVID, and I knew that balancing that with school pick-ups and the demands of family life would be challenging. Starting my own business felt like a way to create more flexibility while also building something meaningful.

At the time, framing this change as a way to support my family helped me justify what felt like a selfish risk. I am naturally cautious, so stepping away from a stable, structured career was daunting. But now, three years post-pivot, I can see that this decision has added so much to the quality of my life and the lives of everyone in my family. My daughters get to see me doing something I love, something that brings me fulfillment and purpose. I am present for them in ways I never could have been in a traditional corporate role, and I have built a career that allows me to be both creative and strategic.

This shift was not just about work; it was about designing a life that aligns with my values. And while there have been challenges along the way, I have never regretted taking the leap.

Contact Info:

• Website: https://www.caelirichterphotography.com
• Instagram: https://www.instagram.com/caelirichter.photography/
• Facebook: https://www.facebook.com/profile.php?id=100090166916861