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Story & Lesson Highlights with Barbara Gillespie of Maui, Hawaii

We’re looking forward to introducing you to Barbara Gillespie. Check out our conversation below.

Hi Barbara, 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 a normal day like for you right now?
I wake up at around 6:00 am to start with a good workout. I play with my 2 black cats and then make sure they have food and water for the day. I answer emails and makeup requests from brides or families. I enjoy a good breakfast with friends or by myself close to town. Later on the afternoon I normally have a big wedding party to do makeup on. That normally takes me the rest of the day and once I arrive home I have to clean my kit and go to sleep for the next day.

Can you briefly introduce yourself and share what makes you or your brand unique?

Hi! I’m Barbara, a 23-year-old makeup artist based on the beautiful island of Maui. I specialize in creating effortless, glowing looks that enhance natural beauty — whether it’s for weddings, photo shoots, special events, or just because you deserve to feel amazing.

What started as a passion quickly turned into a career, and now I’m proud to lead a talented team of hairstylists who share my vision for elevated, modern beauty. Together, we bring a calm, professional, and fun energy to every glam session, making our clients feel confident, radiant, and truly seen.

Living on Maui has shaped so much of my style — inspired by the island’s natural light, vibrant colors, and relaxed vibe. I believe makeup should never hide who you are — it should highlight your unique features and personality.

Right now, I’m growing my brand, expanding into destination weddings, collaborating with photographers and local creatives, and building a beauty experience that feels personal, luxurious, and grounded in aloha. Whether you’re a bride, a model, or just someone wanting to treat yourself, I’m here to make you feel your absolute best.

Thanks for sharing that. Would love to go back in time and hear about how your past might have impacted who you are today. Who saw you clearly before you could see yourself?
My mom saw me clearly before I could see myself. Back when I was just playing with eyeshadow palettes in my room, she told me, *“You’re going to do this for real one day.”* At the time, I brushed it off — I didn’t think I was “good enough” or ready. But she kept encouraging me, hyping me up, even volunteering to be my practice face again and again. Her belief in me helped me take that first leap, and every step since then has been because someone saw the vision before I did.

What did suffering teach you that success never could?

Suffering taught me patience, humility, and resilience in a way success never could. When things weren’t working — when I had slow months, lost confidence in my craft, or questioned if I was on the right path — I had to sit with the discomfort and find strength in myself, not in external validation.

It showed me that growth isn’t always glamorous. That showing up when no one’s clapping is where the real work happens. Success feels good, but suffering is what shaped my character, sharpened my focus, and deepened my empathy — especially for others navigating their own battles behind the scenes.

Suffering made me real. And that’s something success alone could never teach.

Sure, so let’s go deeper into your values and how you think. What important truth do very few people agree with you on?

An important truth that very few people seem to agree with me on is that *beauty is not just surface — it’s energy.*

I truly believe that makeup and hair are just tools. The real glow comes from how someone feels inside. You can apply the most flawless glam, but if someone doesn’t feel seen, safe, or celebrated, it won’t shine the same.

A lot of people see beauty work as just aesthetic — but I see it as emotional, even spiritual. When someone sits in my chair, I’m not just enhancing features; I’m helping them reconnect with their power, their softness, their joy. That’s the kind of beauty that lasts. And not everyone understands that — but it’s the truth I stand by every day.

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 10 years left, I’d stop doubting myself immediately. I’d stop shrinking to make other people comfortable, second-guessing my worth, or waiting for the “perfect moment” to do something bold.

I’d stop saying yes out of guilt or fear, and start saying yes to what actually lights me up — creatively, emotionally, spiritually. I’d stop working just to prove something, and start working from a place of joy, presence, and purpose.

Time is too precious to spend it being anything other than real, aligned, and fully awake in your own life.

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