We caught up with the brilliant and insightful Cheyenne Underwood a few weeks ago and have shared our conversation below.

Hi Cheyenne, thanks for joining us today. Earning a full time living from one’s creative career can be incredibly difficult. Have you been able to do so and if so, can you share some of the key parts of your journey and any important advice or lessons that might help creatives who haven’t been able to yet?

Oh, absolutely, but let me be real with you, it didn’t happen overnight, and it definitely wasn’t linear. I’ve built a multi-six-figure photography business that has supported my family and allowed me to be fully present as a mom of three. But when I first started, I was hustling for a few hundred dollars here and there, taking on any client who would pay me, with no systems, no niche, and a whole lot of late nights editing while the rest of my house was asleep.

My breakthrough came when I stopped trying to do everything and started running my business like a CEO, not just a creative. I leaned into personal branding, content marketing, and client experience. I built workflows, implemented automation, raised my prices, and most importantly, got really clear on who I wanted to serve and why I was doing this. That mindset shift changed everything.

Some major milestones for me were:

Switching from offering everything to specializing in high-end boudoir and branding photography.
Learning how to sell with confidence (not pressure).

Embracing content as a way to connect and build trust, not just promote.

And eventually coaching and strategy services that allowed me to scale beyond just trading time for money.

Looking back, I could’ve sped things up if I had believed in myself sooner, set boundaries earlier, and stopped chasing perfection. But honestly, every twist and detour taught me something I now teach my clients.

Now, my mission is to help other women do what I did—build a business that works for them and their life, not the other way around.

Awesome – so before we get into the rest of our questions, can you briefly introduce yourself to our readers.

I’m Cheyenne Lenea—a mom of three, a multi-six-figure photographer, content strategist, and business coach for women who are ready to rewrite their story and build a business that works for their life, not just their to-do list.

I got into photography when I was 19 years old, armed with nothing but a borrowed camera and a deep desire to tell stories—especially the ones women didn’t know they were allowed to share. What started as a side hustle turned into a lifeline—a way to support my family, to heal, and to give other women a mirror to see their own strength. My work evolved from capturing beautiful images to helping women feel beautiful, powerful, and in control; on camera and in their businesses.

Today, I run a luxury boudoir and branding photography studio and coach female entrepreneurs on how to create confident content, attract aligned clients, and build systems that give them their time and power back. I’ve created courses, templates, strategy sessions, and digital products that simplify marketing, make business feel less like chaos, and help women show up fully in their purpose.

What sets me apart? I don’t just teach the strategy, I live it. I’ve built a six-figure business while raising babies, healing from trauma, and doing 99% of it on my own. I know what it’s like to feel burnt out, unseen, and like the success you’re chasing is costing you your peace. That’s why my entire brand is rooted in empowerment, simplicity, and alignment. I believe that when a woman steps into her confidence and builds from a place of purpose, everything changed; her income, her influence, her legacy.

I’m most proud of the fact that I didn’t give up, especially when life gave me every reason to.

Before I met my now-husband, I was a single mom raising two little boys with no support system. No backup. No family to fall back on. Just me, my dreams, and the deep conviction that I was meant for something more.

There were so many nights I wanted to quit—when the bills didn’t care about my goals, when the weight of motherhood and entrepreneurship felt too heavy, when I was scraping by and still showing up for my clients like everything was fine. But I kept going. Not because it was easy, but because my kids deserved to see what was possible when their mom refused to settle. I built my business during nap times, late nights, and in stolen moments between pickups and meltdowns. And that journey, as hard as it was, is the very reason I can now help other women do the same—build something real and aligned, even in the mess, even when it feels impossible.

I’ve built a thriving community of over 500,000 women online who are learning how to step into their confidence, build brands with soul, and create success on their own terms. That community is the heartbeat of my brand. They are the proof that this work matters.

If there’s one thing I want people to know about me and my brand, it’s this:
You don’t have to have it all figured out. You don’t need a huge team or a perfect plan. You need belief, strategy, and support. That’s what I create—for the women who are doing it scared, doing it tired, but doing it anyway.

This is for the woman who knows she was made for more, because I was her. And I turned my rock bottom into a launchpad. And now? I help others do the same.

Can you share a story from your journey that illustrates your resilience?

My entire life has been a story of resilience.

I grew up in a home shaped by addiction, chaos, and trauma. My childhood was filled with instability, emotional neglect, and the kind of survival mode that hardens you before you ever get a chance to be soft. Statistically, I wasn’t supposed to make it here. I wasn’t supposed to break the cycle. Kids raised in environments like mine often repeat the patterns, but I made a promise to myself early on: this ends with me.

And it did.

I became the first in my family to build a business, create financial growth, and raise children in a home filled with love, peace, and possibility. I’ve created a life that looks nothing like the one I came from. I’ve built a multi-six-figure business doing what I love, helping other women reclaim their confidence and build businesses on their terms.

But it hasn’t been easy.

The trauma I experienced didn’t just disappear, I had to fight to rewire my mind. I’ve had to learn how to reframe my thoughts, unlearn the belief that I wasn’t worthy of success, and release the shame and fear that were passed down to me. There were seasons where my inner critic was louder than my ambition, but I kept going. I kept healing, and I kept showing up for the future I knew I was meant to create.

That’s what resilience looks like to me. Not just pushing through, but rising above. Not just breaking cycles, but building something better in their place.

I’m raising my children in a world I once only dreamed of. And I remind myself every day: I am the proof that your past does not define your future.

For you, what’s the most rewarding aspect of being a creative?

The most rewarding part of being a creative is creating a space where women get to remember who they are—before the self-doubt, before the burnout, before the world told them they had to shrink.

Through my lens, I don’t just take photos—I help women see themselves differently. And sometimes the biggest transformation happens before they ever see a single image. It’s in the moment they let go. When they soften. When they laugh. When they step into the room nervous, but leave with their head held high, fully in their power.

I’ve watched women walk into my studio unsure, guarded, even disconnected from their bodies… and walk out changed. Not because of the images alone, but because of the experience. Because they felt seen. Safe. Celebrated.

And that’s the magic of what I do: I get to show women that they are art. That their bodies are not something to hide or fix, but something to honor. That their stretch marks, scars, curves, and stories are proof of their resilience. Every inch of them tells a story of survival, softness, strength—and I’m just lucky enough to capture it.

To me, that’s the gift: creating not just beautiful photos, but beautiful truths, and giving women the chance to embody them every day.

Contact Info:

• Website: www.cheyenneleneaboudoir.com www.cheyennelenea.com
• Instagram: @cheyenneleneastudios
• Other: Tiktok: @cheyennelenea_

Image Credits

My headshot: Tristian Michelle Collective