We’re looking forward to introducing you to Ashley Callaway . Check out our conversation below.
Hi Ashley , thank you so much for joining us today. We’re thrilled to learn more about your journey, values and what you are currently working on. Let’s start with an ice breaker: What do you think others are secretly struggling with—but never say?
I think a lot of people are struggling with feeling seen. We live in a world that praises productivity, perfection, and performance, but deep down so many of us just want to be understood beyond the surface. Through my work, I’ve learned that beauty isn’t just about makeup—it’s about helping people feel visible, valued, and reminded of who they really are.
Can you briefly introduce yourself and share what makes you or your brand unique?
I’m Ashley Callaway, the artist and founder of Ashley Callaway Beauty, a Maryland-based brand specializing in luxury bridal, TV, film, and editorial makeup. My mission is to create an experience that goes beyond beauty — where each client feels seen, valued, and celebrated in their most confident light.
I’ve had the honor of working with incredible women, from brides to public figures, including the First Lady of Maryland. Today, I’m expanding my brand through educational experiences and mentorship, helping others discover the power in their own glow.
Appreciate your sharing that. Let’s talk about your life, growing up and some of topics and learnings around that. Who saw you clearly before you could see yourself?
My godmother, Aunt Oxy — Miss Roxane Whipple — saw me clearly before I ever saw myself. She worked at a popular salon back in the 90s, and I spent a lot of time there with her. Every time she did my hair, she made me feel beautiful, loved, and like I mattered. Watching her in that environment showed me how powerful beauty could be — not just in appearance, but in how it makes people feel. Those moments with her planted the seed for what I do today and taught me that true artistry starts with heart.
Was there ever a time you almost gave up?
Yes, there were moments I almost gave up — especially when my health challenges, motherhood, and career pressures all collided at once. I was pouring into everyone else while silently fighting battles of my own. But every time I reached my breaking point, God reminded me of the purpose behind my pain. I realized I wasn’t being buried, I was being planted. Those hard seasons taught me resilience, faith, and the power of grace. Now, I use what I’ve overcome to inspire and pour back into others who might be fighting their own silent battles.
Alright, so if you are open to it, let’s explore some philosophical questions that touch on your values and worldview. Whom do you admire for their character, not their power?
I admire women who lead with grace and stay grounded no matter the spotlight — women who don’t need a title to walk in purpose. One person who embodies that for me is Cheryl Polote-Williamson. Her spirit, generosity, and faith remind me that true power is service. She carries light wherever she goes, and that’s the kind of legacy I want ….. one that changes lives through love, not ego.
Okay, so before we go, let’s tackle one more area. What light inside you have you been dimming?
I think for a while, I dimmed the part of me that loves out loud. I’ve always been that person who naturally pours into others and speaks life into them, especially when they can’t see it for themselves. When life is heavy or people are feeling defeated, something in me just wants to lift them up. I truly believe the mind is a powerful tool — you have to shift your mindset before you can step into new beginnings. I’ve always felt called to help people see themselves in a better light, to remind them that their story isn’t over.
But along the way, I realized I was pouring so much into others that I forgot to pour back into myself. I had to learn that my light, my words, and my energy are gifts — and that it’s okay to protect them. Now I give from a place of balance and peace. My heart still loves to uplift others, but I’ve learned to include myself in that grace too.
Contact Info:
- Website: https://Www.AshleyCallawayBeauty.com
- Instagram: AshleyCallawayBeauty
- Linkedin: Ashley J. Callaway
- Facebook: Ashley Callaway Beauty
