Sally Gupta shared their story and experiences with us recently and you can find our conversation below.
Hi Sally, thank you for taking the time to reflect back on your journey with us. I think our readers are in for a real treat. There is so much we can all learn from each other and so thank you again for opening up with us. Let’s get into it: What is something outside of work that is bringing you joy lately?
Outside of my day-to-day as a Cloud Solution Architect, what’s been bringing me a lot of joy is building and growing my Instagram handle, @chicbysally. It started as a creative outlet, but it’s evolved into an entrepreneurial venture where AI meets fashion—where technology enhances personal style, and where I remind women that they can be both brilliant and fashionable. It’s been incredibly fulfilling to blend two worlds I’m passionate about: innovation and self-expression. It challenges me in new ways, keeps my creativity flowing, and gives me the joy of connecting with a like-minded community.
Can you briefly introduce yourself and share what makes you or your brand unique?
Hi! I’m the founder of ChicBySally, a digital fashion brand where technology meets personal style—and a proud Cloud Solution Architect and AI strategist by profession.
As early as I can remember, fashion was my first language. By age 10, I was styling not just myself but also friends, family—even my mom’s friends! For me, fashion was never just about clothes—it was about confidence, creativity, and helping people feel their absolute best.
But life took me on a different path—one paved with code, cloud, and cutting-edge tech. I built a career in IT, eventually diving deep into AI strategy, where I thrived solving complex problems and building scalable innovations. Yet, even after the most technical of days, I found myself recharging the same way: scrolling through curated outfits, analyzing trends, and rewatching iconic fashion films like Legally Blonde and The Devil Wears Prada (yes, I’ve seen them more than 20 times!). Those films always reminded me of one truth: intelligence and style aren’t opposites—they’re a power combo.
That realization led me to merge both worlds, and ChicBySally was born—a passion project turned entrepreneurial venture where AI fuels fashion storytelling. You can explore it at chicbysally.org.
At ChicBySally, we believe fashion is a story waiting to be told. From user-generated content to bespoke curation services, we’re building a community rooted in collaboration, empowerment, and innovation.
We recently launched an AI-powered fashion chatbot that browses through all our curations to help users discover their perfect look instantly—and there’s more AI-driven magic on the way.
At the heart of it all, I’m on a mission to remind women that they can be both brilliant and stylish—and that self-expression doesn’t have to live in a box. Fashion is smart. Fashion is tech-powered. And fashion is for everyone.
Appreciate your sharing that. Let’s talk about your life, growing up and some of topics and learnings around that. Who taught you the most about work?
It’s hard to name just one person—because my understanding of work, dedication, and purpose has been shaped by many people across different stages of my life.
As early as I can remember, I watched my father work incredibly hard to provide for our family. He instilled in me the values of honesty, loyalty, integrity, and grit. His discipline and commitment taught me what it means to set a goal and follow through, no matter the obstacles.
At the same time, I saw my mother, a homemaker, work just as relentlessly—quietly and gracefully holding the family together, making sure every need was met, every detail remembered. Her selflessness showed me that work isn’t always about titles or paychecks—it’s about care, resilience, and showing up with love.
My parents always encouraged me to pursue higher education and push for more. That support led me into the world of IT, where I’ve been fortunate to build a meaningful career. Along the way, I’ve had amazing mentors—people who guided me, challenged me, and helped me grow in ways I never expected.
But if I had to name one person who continues to shape how I work today, it’s my husband. He’s a seasoned architect in the IT space, and his curiosity and passion for learning—especially in the AI field—have deeply inspired me. He’s the reason I began exploring the intersection of technology and fashion, and without his support and insight, ChicBySally wouldn’t exist.
So, I guess my story is shaped by many teachers—some who raised me, some who coached me, and one who walks beside me every day.
What did suffering teach you that success never could?
Suffering has a way of slowing everything down—forcing you to sit with yourself, with your thoughts, and ask the questions we often ignore in the busyness of life. For me, it became a space of introspection. It taught me to look inward and ask, Who am I, really? What do I like? What matters to me? What is my purpose?—questions I’m still exploring, if I’m being honest.
Through difficult seasons, I learned to see things more clearly—not just situations, but people, relationships, and my own truth. There’s a certain clarity that only pain can bring. It strips away the noise, the pretense, and what’s left is raw, real, and eye-opening.
Suffering also taught me presence. That life doesn’t begin after the next milestone, or when everything aligns. It’s happening now. I learned to enjoy life as it is—not in anticipation of some perfect moment, but in the quiet, imperfect, everyday ones.
Success, on the other hand, is a moment. A beautiful one. It’s the visible tip of the iceberg—made of hard work, discipline, perseverance. And when it comes, I’ve learned to celebrate it, to pause and feel proud. But it’s in the suffering where I truly grew. Where I became more honest, more grounded, and more aware of who I am becoming.
Suffering may not feel like a gift in the moment—but it gave me lessons success never could.
Alright, so if you are open to it, let’s explore some philosophical questions that touch on your values and worldview. What would your closest friends say really matters to you?
My closest friends would say that what really matters to me is authenticity—showing up as my true self, staying loyal to my values, and creating meaningful connections. They’d also say I care deeply about balancing ambition with heart—whether it’s in my career, my creative work, or the relationships I invest in
Before we go, we’d love to hear your thoughts on some longer-run, legacy type questions. What do you understand deeply that most people don’t?
What I understand deeply—something I feel many people overlook—is how much unspoken emotion lives beneath the surface. I’ve always been spiritually inclined and emotionally sensitive, and I can often sense what someone is going through, even when they don’t say it out loud. What I wish more people knew is that it’s okay to feel things like insecurity, jealousy, or anxiety—they don’t make you weak or flawed. But it’s important to acknowledge those feelings, not bury them. Because beneath all those layers, every human being is beautiful, worthy, and capable of healing. I’ve learned that when we allow space for honesty and compassion, we not only understand others better—we understand ourselves.
Contact Info:
- Website: https://chicbysally.org/
- Instagram: https://www.instagram.com/chicbysally/
- Youtube: https://www.youtube.com/@ChicBySally
- Other: https://shopmy.us/savvyfashionista
