We recently had the chance to connect with Jennifer Dickerson and have shared our conversation below.
Jennifer , a huge thanks to you for investing the time to share your wisdom with those who are seeking it. We think it’s so important for us to share stories with our neighbors, friends and community because knowledge multiples when we share with each other. Let’s jump in: What is a normal day like for you right now?
A normal day in my life looks anything but ordinary…it’s purpose in motion.
I start my day grounded in intention. Before the world asks anything of me, I center myself through prayer, reflection, or a quiet moment that reminds me why I do what I do. I’m not just waking up to tasks; I’m waking up to a mission.
My mornings quickly shift into leadership mode. As the CEO of Heart & Sole, I’m answering emails, coordinating programs, checking in with students, parents, and community partners, and making sure every moving piece aligns with the bigger vision, bridging the gap between students, families, and the community. I’m thinking about impact, outcomes, and sustainability, not just for today, but for the future.
Somewhere between meetings and messages, I’m also a mother first. Becoming a mom at 17 shaped me in ways nothing else could. That journey taught me resilience, empathy, and determination, and those lessons guide how I lead, mentor, and show up for others who feel overlooked or underestimated.
My afternoons are often filled with service and visibility…school visits, mentoring moments, community conversations, or preparing for speaking engagements and my responsibilities as 2026 Ms. Salisbury, MD. I don’t take that role lightly. I know that when I walk into a room, someone may be watching me as proof that their story doesn’t have to end where it started.
Evenings are about building. I’m writing, planning, creating content, refining speeches, or working on my book….telling the truth about survival, faith, and becoming. Even when I’m tired, my heart stays engaged because this work is personal.
At the end of the day, when things finally quiet down, I reflect on progress. I rest knowing that lives were touched, seeds were planted, and tasks were complete.
My normal day is a balance of faith, family, leadership, service, and legacy.
It’s busy. It’s demanding. But it’s exactly the life I fought for and now use to help others rise.
Can you briefly introduce yourself and share what makes you or your brand unique?
I’m Jennifer Dickerson, a community leader, entrepreneur, and advocate proudly serving as 2026 Ms. Salisbury, MD. I’m also the founder and CEO of Heart & Sole Performing Arts, LLC, a community organization dedicated to bridging the gap between students, parents, and the community through mentorship, step/dance education, and character development.
My work is deeply personal. I became a mother at 17, and what could have been the end of my story became the foundation of my purpose. That lived experience fuels everything I do…from empowering youth and families to creating programs that produce real, measurable impact in behavior, academics, and confidence.
What makes my journey and my platform unique is that I don’t just speak about possibilities, I create solutions. As the reigning, 2026 Ms. Salisbury, MD for the Miss Corporate America-Maryland pageant, I use my voice, visibility, and leadership to show that your beginning does not define your destiny, and that service, faith, and consistency can transform lives. My mission is simple but powerful: to turn obstacles into opportunities and ensure the next generation knows they are seen, supported, and capable of more than they imagine.
Okay, so here’s a deep one: What relationship most shaped how you see yourself?
The relationship that most shaped how I see myself was with Toneisha Harris. She showed me my life had value before I could see it for myself.
At a time when I was young, overwhelmed, and questioning whether I even belonged in this world, that relationship became a lifeline. It was built on trust, consistency, and genuine unconditional love. A trusted individual who listened when I couldn’t find the words, who saw strength in me when I only saw struggle, and who refused to let my pain define my future.
That relationship taught me that I was worth saving, worth investing in, and capable of more than my circumstances suggested. It reshaped my self-image from survival to purpose, from broken to becoming. It’s the reason I now lead with empathy, pour into others, and create safe spaces through Heart & Sole…because I know firsthand how one meaningful connection can change the trajectory of a life.
It didn’t just influence how I see myself, it changed how I show up for others.
Was there ever a time you almost gave up?
Oh absolutely!
I was young, overwhelmed, and carrying more than I knew how to name. At 16, facing pressure, fear, and uncertainty all at once, I reached a moment where the weight of everything felt unbearable. I couldn’t yet see purpose, promise, or a future beyond the pain I was in. I questioned my worth, my direction, and whether my life truly mattered. I was carrying pain I didn’t have words for, expectations I didn’t think I could live up to. My only way out was to end my own life…so I thought.
What stopped me wasn’t that everything suddenly got better…it was that someone believed in me when I didn’t believe in myself. In that fragile space, I realized that giving up would silence a story that hadn’t fully been told yet. I chose, moment by moment, to stay, to fight, to live.
That moment didn’t break me…it built me. It became the turning point that fuels my compassion, my leadership, and my commitment to making sure others never feel invisible or alone. I stand today not because I never struggled, but because I lived through it.
So a lot of these questions go deep, but if you are open to it, we’ve got a few more questions that we’d love to get your take on. Is the public version of you the real you?
The public view of me is very real…authentic….but incomplete.
What people see is real: my strength, leadership, faith, service, and resilience. They see 2026 Ms. Salisbury, MD, a CEO, a community advocate, a woman who shows up polished, confident, and purposeful. That version of me isn’t a performance, it’s earned. I worked hard to become her.
What they don’t always see is the full weight of my journey, the quiet battles, the moments of doubt, the nights I questioned myself, and the younger version of me who had to grow up fast just to survive. Not because I’m hiding it, but because not everyone is privileged to walk the entire journey with me.
I lead with grace, but my foundation is grit.
I speak hope, but it’s rooted in lived experience.
I inspire others, not because my life was easy, but because I kept going when it wasn’t.
So yes…the public sees the real me.
They just see the chapter where I’m standing in my purpose, not every page it took to get here.
Thank you so much for all of your openness so far. Maybe we can close with a future oriented question. Could you give everything your best, even if no one ever praised you for it?
Oh, absolutely! I could, and I did.
I gave everything my best even when no one was clapping or supporting. I showed up when the work was quiet, when the rooms were small, and when the impact wasn’t immediately visible. I poured into people who may never say thank you, who used my presence for their own personal gain, and poured into communities that needed consistency more than recognition.
I always show up as my authentic self…. nothing fancy or extra. Anything I do is never for acknowledgment. It has always come from a place of genuine love and care. My desire is that the people I encounter leave my presence better than they arrived.
I want individuals to know that even in their darkest or most broken moments, I am willing to sit in the trenches with them; to hold space for their pain without judgment, without rushing their healing, and without needing to fix anything. Sometimes presence is the ministry, and love is the work.
I am driven by knowing that what I do matters, even if one life is changed. My standard is never praise….it’s about fulfilling purpose.
I gave and still give my best because it aligns with who I am, not because of how it’s received. And that part of my story may never make headlines, but it’s the part that made everything else possible.
Contact Info:
- Website: https://beacons.ai/heartandsole/home
- Instagram: https://www.instagram.com/heartsolestep
- Twitter: https://x.com/heartsolestep
- Facebook: https://www.facebook.com/heartsolestep
- Youtube: https://www.youtube.com/@HeartSoleStep
Image Credits
Jenna Wright; Megan Outten
