We recently had the chance to connect with Ms. Kiswana Charmaine and have shared our conversation below.
Kiswana , really appreciate you sharing your stories and insights with us. The world would have so much more understanding and empathy if we all were a bit more open about our stories and how they have helped shaped our journey and worldview. Let’s jump in with a fun one: What do you think others are secretly struggling with—but never say?
I think many people quietly struggle with the fear that everything they’ve built could fall apart at any moment. Even when things are going well, there’s a lingering feeling of questioning whether they truly belong where they are or if their success is temporary. I deal with this daily. It’s the anxiety of not wanting to return to the version of life that existed before the consistency, growth, and momentum took hold. What I’ve learned is that this fear often shows up right alongside progress, and learning to move forward anyway is part of sustaining success.
Can you briefly introduce yourself and share what makes you or your brand unique?
I’m originally from San Diego, California. At 26, I left and moved to Memphis, Tennessee. The move taught me something important: not every place, role, or season is meant to be permanent. Memphis wasn’t the right fit for me, but it sharpened my sense of self, resilience, and direction, and it clarified what alignment actually feels like.
My life has been shaped by movement and pivots, and by learning when to pause and be honest with myself. I’ve learned that growth doesn’t always arrive with a plan. Over time, I’ve stopped labeling experiences as good or bad and started seeing them as purposeful.
Today, I work as a Solutions Specialist at Shift4, helping hospitality businesses grow through SkyTab technology. Before stepping into tech, I spent years as a server and bartender. At the time, I believed the only way to move forward in hospitality was management. That was the path I saw, and the ceiling I assumed existed.
What I didn’t realize then was that hospitality had already given me a powerful foundation. Working on the floor taught me how to read people, build trust quickly, adapt under pressure, and understand the rhythm of a business in real time. Those skills now guide how I approach technology.
At my core, I’m a connector. My larger goal is to help small businesses and emerging companies bring their technology to life by helping people understand not just how it works, but why it matters. I thrive on building relationships, educating along the way, and creating momentum that feels both practical and empowering.
Outside of work, I’m a mom to a little girl who constantly reminds me what genuine connection looks like. She naturally brings the kids in our neighborhood together, and in the process our home has become a safe, welcoming space. Watching her lead with curiosity and openness has influenced how I show up in my work and my community. It’s a reminder that connection, when approached with intention, creates trust, belonging, and opportunity.
Amazing, so let’s take a moment to go back in time. Who were you before the world told you who you had to be?
Before the world told me who I had to be, I was open and trusting, sometimes to my own detriment. I didn’t yet understand discernment, only belief. I was taught to see God in everyone, which led me to assume effort would always be met with fairness and that good intentions were enough to move forward.
Experience taught me otherwise. I learned the importance of boundaries, of asking better questions, and of trusting my own observations just as much as I trusted others.
Today, I still lead with openness, but it’s paired with wisdom. That balance has shaped how I move through both life and work, allowing me to stay compassionate without being unprotected.
What did suffering teach you that success never could?
Suffering taught me accountability in a way success never could. I had to confront how many of my choices, not just my circumstances, contributed to where I was. That awareness was uncomfortable, but it was also freeing.
I learned that no one will ever care about your life as much as you do, and that responsibility can’t be outsourced. At some point, I stopped seeing myself as a victim and moved into a growth mindset, learning to view challenges as feedback rather than failure.
That shift changed everything. It taught me clarity and self-trust. Today, I move with intention, knowing that accountability isn’t punishment, it’s power.
Next, maybe we can discuss some of your foundational philosophies and views? What truths are so foundational in your life that you rarely articulate them?
A foundational truth in my life is that clarity comes from action, not overthinking. I’ve learned that you don’t always need to have everything figured out before you move. Momentum has a way of teaching you what reflection alone cannot.
I also believe discernment is a skill that develops with experience. Learning when to pause, when to act, and when to walk away has been just as important as learning when to push forward. Those decisions, often quiet and unseen, shape outcomes more than any single moment of success.
Okay, so before we go, let’s tackle one more area. If you knew you had 10 years left, what would you stop doing immediately?
If I knew I had ten years left, I would stop postponing presence. I would choose joy more freely, say what needs to be said, and spend my time building what truly matters. I lost my mother to breast cancer when I was sixteen. She was only forty-one, and her life taught me how precious time is and how much meaning can be created within it.
Everything I do now is rooted in legacy, but it’s a hopeful one. My focus is on creating a life where my daughter feels supported, confident, and equipped to thrive, no matter what. That perspective fuels how I work, how I plan, and how I show up each day.
I move with intention, not fear. I believe legacy is built through love, stability, and the example you set while you’re here. To me, it’s about planting seeds that continue to grow, long after you’re gone.
Contact Info:
- Instagram: https://www.instagram.com/kiswana.charmaine?igsh=MWFkMDVwYjBseDltNw%3D%3D&utm_source=qr
- Linkedin: https://www.linkedin.com/in/kiswanacharmaine?utm_source=share&utm_campaign=share_via&utm_content=profile&utm_medium=ios_app
