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

Jennifer , looking forward to hearing all of your stories today. So let’s jump to your mission – what’s the backstory behind how you developed the mission that drives your brand?

Heart & Sole Performing Arts, LLC was founded in 2018 by Ms. Jennifer D. Dickerson, initially as an after-school step team at Glen Avenue Elementary. The program began with a focus on promoting behavioral improvement and academic motivation among students. Since then, Heart & Sole has experienced tremendous growth, expanding to serve 8 schools across 4 counties and 2 states on the Eastern Shore.

Our mission is to empower youth through the transformative power of creative expression. Heart & Sole works to revive the “it takes a village” mindset by offering children a safe space to grow, develop essential life skills, and build resilience against the challenges of poverty. We aim to break down barriers of affordability and accessibility by partnering with schools and community organizations, offering scholarships, and providing sliding fee scales for families in need.

Our program is actively engaged in the community, participating in parades, festivals, school rallies, and various service initiatives. Heart & Sole has been recognized with multiple accolades, including the “Best Marching Unit” award at the Salisbury Christmas Parade in 2019 and 2022, as well as being selected for the 2024 Coastal Style Magazine “Best of” awards in the Best Youth Organization category. The group has also received the Lifetime Achievement Award and the NAACP Humanitarian Award. Founder and CEO Ms. Jennifer Dickerson was honored as Best Youth Coach in Wicomico County by Coastal Style Magazine and received the Champion Leadership Award from London, UK.

At Heart & Sole Performing Arts, we are dedicated to the holistic development of our youth. Through the arts, we nurture character, self-confidence, effective communication, innovation, and leadership—empowering the next generation to thrive in all aspects of life.

Jennifer , 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?

Heart & Sole Performing Arts stands as a testament to the core value of “Making a Difference.” Founded with a deep commitment to supporting children and families, the organization not only strives to meet immediate needs but also empowers children holistically, fostering their growth emotionally, academically, behaviorally, physically, and spiritually.
Jennifer Dickerson, the CEO and founder, initially created the program with a focus on dance and family. Over time, she expanded the mission to ensure that every child entrusted to Heart & Sole has the resources to succeed both in school and in life. “We make sure every child has all the support and resources possible to thrive,” says Jennifer, emphasizing the organization’s focus on building self-confidence and a love of learning through academic mentoring and individualized tutoring.
Beyond academics, Heart & Sole recognizes the importance of addressing emotional and behavioral needs. The organization provides a safe space where children can express and process their emotions, teaching them how to navigate their feelings and build resilience. This emotional support is essential to helping children grow into responsible, empathetic individuals, equipped with positive coping skills that serve them beyond the program.
Heart & Sole’s approach to behavioral support goes beyond mere discipline. By addressing the root causes of behaviors, the organization helps children take accountability for their actions and fosters lasting personal growth. This focus on responsibility and emotional intelligence is what sets Heart & Sole apart in its ability to produce long-term positive change.
In addition to academic and emotional support, Heart & Sole recognizes the importance of physical well-being. Through fitness programs, movement activities, and the provision of food and snacks, children are ensured the energy and nourishment they need to stay focused and engaged in both their studies and extracurricular activities. The organization also integrates spiritual development, nurturing each child’s sense of self, identity, and belonging.
Understanding that family support is just as vital to a child’s success, Heart & Sole provides resources for parents as well. The organization offers spa-like services and a general store for essentials, reducing the burdens on families and allowing them to focus more on their children’s needs and their own well-being.
The impact of Heart & Sole is measurable, with a recorded 45% increase in academic success and a 73% improvement in student behavior. These statistics speak volumes about the effectiveness of the program in transforming the lives of children and their families.
Ultimately, Heart & Sole demonstrates that “Making a Difference” is more than just a value—it’s a promise fulfilled through comprehensive, holistic support. From academics and emotional well-being to physical fitness, spiritual growth, and family support, the organization is helping children and families thrive in every aspect of life, creating meaningful and sustainable changes in their futures.

We’d love to hear a story of resilience from your journey.

In 2016, Heart and Sole began as an afterschool program with a mission to reduce behavioral issues and improve academic performance during the critical fourth term. I quickly realized that holding students accountable for behaviors that had never been addressed before—during just the final nine weeks of school—was challenging. The “three strikes, you’re out” approach, especially when tied to something students were passionate about, often left them feeling rejected.

I approached the principal at the time with a proposal: Could we extend the program to a full year? This would give students more time to develop discipline in their actions, so by the fourth term, they would have a better understanding of how their choices led to the consequences they faced. It was important to me that they didn’t just see discipline as punishment, but as a direct result of their own behavior.

When changes within the school system made it difficult to continue the program there, I faced a crossroad. I had to adapt, moving Heart and Sole from the school setting to the community. Lacking financial support for this transition, I had to push harder and dig deeper to make the vision a reality. My resilience became my superpower.

In 2019, I successfully established Heart and Sole Performing Arts, LLC. Through this, we made a real impact in the community—feeding the homeless, performing at nursing homes, participating in parades, and sharing our talents at local schools. These efforts became a testament to our mission: giving back to the community and empowering those in need.

Although the shutdown in 2020 forced us to pause, we came back stronger than ever. From 2021 to 2025, Heart and Sole has been unstoppable, continuing to grow and serve the community in new ways.

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

Recently, the day after Thanksgiving, I lost my mother. Then, not even 24 hours later, I lost my mentor. The person who allowed Heart & Sole to even exist. Two incredible women who were instrumental in shaping who I am and what Heart & Sole has become. It has been the hardest challenge I’ve faced, and truthfully, there were times when I wanted to retreat from everything. But, in those moments of deep sorrow, I realized that my business, Heart & Sole, still needed me. I had spent so much time giving to others that I forgot to take the necessary time to nurture myself.

This loss led me to a pivotal moment, both in my life and within my business. The incredible young people I’ve poured into over the years, in their own ways, found ways to pour back into me. Whether through text messages, hugs, letters, or just uplifting words, they reminded me of the strength and resilience within and I found courage I didn’t know I had.

This journey has reminded me of the very mission of Heart & Sole to equip our youth, empowering them to discover their own potential while giving them tools they need to effectively communicate while fostering leadership. Just as I have always strived to help them realize their worth, I’ve had to do the same for myself in this difficult time.

As we continue to grow, Heart and Sole will continue to grow, adapt, and support the next generation, just as it will continue to help me grow as a person and as a coach. Together we are building something stronger and I’m grateful for those who are a part of this journey.

Contact Info:

• Website: https://www.heartandsole18.org
• Instagram: https://www.instagram.com/heartsolestep
• Facebook: https://www.facebook.com/heartsolestep
• Twitter: https://www.twitter.com/heartsolestep

Image Credits

Photos by BJ Hyland & Megan Outten