Navigating the Highs, Lows, and Unexpected in Photography and Entrepreneurship with Heather Leicy

Entrepreneurship is a journey full of challenges, triumphs, and moments of unexpected growth. But for many, the road is more complex—especially for those who are balancing family, business, and self-discovery. In this episode of High, Low, and Unexpected, I had the pleasure of chatting with Heather Leicy, a photographer, educator, and passionate advocate for fellow creatives. Heather's journey is an inspiring reminder of the power of persistence, community, and finding your own pace in the chaotic world of business.
Heather’s story is one of resilience, ambition, and self-discovery. As a full-time photographer, Heather didn't just focus on her craft—she also found a way to combine her love for numbers with her passion for helping others. From starting her business to becoming an advocate for financial literacy in the creative space, Heather has found a unique way to thrive in the intersection of art and business. Here are the takeaways from our conversation that truly resonated with me:
1. Celebrate Your Wins, No Matter How Small
As entrepreneurs, we often rush through our wins without truly appreciating them. Heather shared her high moment of going full-time in her photography business—a massive milestone, especially considering her background in architecture. The moment she was able to tell her parents that she was making more as a photographer than she did in her previous job was a personal victory. But it wasn't just about proving something to her parents—it was about realizing the power of trusting her passion, stepping into the unknown, and building a business that reflected her true calling.
It's easy to get caught up in the hustle and overlook these milestones, but Heather's story is a reminder to celebrate the highs, big and small. Whether it's booking your first client or finally reaching a financial goal, those moments of progress are worth acknowledging.
2. Embrace the Challenges of Motherhood and Business
Heather's vulnerability in sharing the challenges she's faced as a new mother and business owner really stuck with me. After the birth of her daughter, she realized that the predictable schedule she once thrived on was completely upended. From disrupted nap times to constant appointments, she found herself juggling motherhood and business in a way she never expected.
For many entrepreneurs, especially those with young children, the pressure to "do it all" can be overwhelming. But Heather is learning to embrace this new season and give herself grace. She is still figuring out how to balance her roles as a mom and a business owner, and it's a powerful reminder that it's okay to not have everything figured out. Some seasons will require more effort than others, and sometimes it's about finding peace in the chaos.
3. Comparisons Can Steal Your Joy—And Your Energy
One of the most relatable struggles Heather shared was the temptation to compare herself to others in her industry. It's easy to look at others' successes and feel like you're falling behind, but Heather is learning to quiet the noise. Her experience with comparison has made her realize that every entrepreneur has their own pace, and that's okay.
As Heather works through the challenges of being a business owner with a young child, she's learning to focus on what she can control and let go of external expectations. The path to success isn't a race—it's a journey, and it's important to go at your own pace, regardless of where others may be.
4. The Unexpected Can Lead to Unlikely Passions
If you had told Heather a few years ago that she would be teaching other photographers about taxes, she probably would've laughed. Yet, here she is, using her love of numbers to help others navigate the often overwhelming world of taxes.
It was through the Conquer Community that Heather's passion for helping other photographers with tax prep began. What started as a side interest slowly turned into an unexpected business venture. Now, Heather helps photographers organize their finances, save money, and navigate the often confusing world of tax laws—all with a smile on her face.
This unexpected twist in her career shows that sometimes the things we least expect to become our passion can provide some of the greatest fulfillment. For Heather, it's all about finding the joy in helping others achieve financial freedom and confidence.
5. Community is Key to Growth
One of Heather's biggest takeaways is the importance of surrounding yourself with a supportive community. She credits the Conquer Community as a key factor in her ability to push forward through tough times. By joining forces with like-minded individuals who share her goals and values, Heather has been able to overcome obstacles and build a business she loves.
As entrepreneurs, it’s easy to feel isolated, but Heather’s story reminds us of the power of community. Whether it’s through masterminds, online groups, or local meetups, connecting with others in your field can provide the support, accountability, and inspiration you need to succeed.
If you're in the midst of a challenging season, feeling overwhelmed by the highs and lows of entrepreneurship, Heather's story is a powerful reminder that you're not alone. Her willingness to share her struggles, growth, and victories makes her a true example of perseverance and heart.
Want to hear more from Heather?
Check out the full podcast episode of High, Low, and Unexpected to hear Heather’s inspiring journey in more detail!
And here’s the best part: If tax season gives you anxiety, Heather is giving our audience 20% OFF her Make Taxes Suck Less course! Use code “KISS20” for 20% off the go-to guide for photographers who want to keep more of their hard-earned money and actually feel confident about taxes. Seriously, it is a GAME CHANGER!