Meet Rochelle Cheever

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

Rochelle , we’re thrilled to have you sharing your thoughts and lessons with our community. So, for folks who are at a stage in their life or career where they are trying to be more resilient, can you share where you get your resilience from?

My resilience comes from trusting my own path, even when it didn’t look like anyone else’s. I never followed the conventional route—I built my life and career through intuition, reinvention, and an unwavering belief that I could do something I loved and make a living from it.
I wasn’t raised to be independent. No one taught me how to run a business or build financial security—I had to figure it out myself. And that’s exactly what I did. I started from nothing and learned how to create a career that supported me, first as a fine art painter, then as a photographer, then as a wedding designer specializing in luxury elopements. Every pivot required resilience. Every step meant learning, evolving, and refusing to let fear stop me.
But I never pursued work just for the sake of making money. I’ve known too many people who are financially successful but miserable because they hate what they do. That was never an option for me. I pursued my passion and purpose—and I found a way to make a living doing what I love. That’s the win-win.
Now, I’m pivoting again—this time, to teaching other creatives how to build a business in luxury elopements. After years of experience, I know the challenges wedding professionals face, and I want to help them skip the trial-and-error and step confidently into success. Just like I had to carve my own way, I now want to help others do the same—on their own terms, doing work they love, without following outdated industry rules.
But resilience isn’t just about pushing through difficulties—it’s about listening to your inner wisdom, knowing when to evolve, when to let go of something, and trusting that every step is leading you where you’re meant to be. I’ve never let circumstances define me, and I never will. That’s the mindset I bring into everything I do—and now, it’s the mindset I help others cultivate, too.

Thanks for sharing that. So, before we get any further into our conversation, can you tell our readers a bit about yourself and what you’re working on?

I specialize in luxury elopement design—creating intimate, intentional, and artfully curated wedding experiences for couples who value beauty, meaning, and exclusivity over tradition. My brand is built around the idea that a wedding should feel effortless, deeply personal, and reflective of the couple’s unique story, not just a formulaic event.
What makes my work special is my eye for design and my ability to curate experiences that feel both refined and deeply emotional. I don’t follow trends—I design each intimate wedding to fit seamlessly with the couple’s vision, the location, and the essence of quiet luxury.
Beyond designing elopements, I’m now expanding into teaching other wedding professionals how to create successful businesses in luxury elopements. Over the years, I’ve seen so many talented creatives struggle to break into this space because they weren’t sure how to price their work, attract high-value clients, or build a brand that stands out. I want to change that.
Through coaching and education, I help wedding professionals:
Understand the business side of luxury elopements so they can charge their worth.
Curate truly bespoke experiences instead of following generic planning templates.
Attract the right clients—those who value artistry, experience, and intentional design.
What excites me most about this transition is that I get to help others create a career they love, just like I did. So many people in this industry get stuck in a cycle of undercharging, burnout, or constantly chasing bookings. My goal is to give them the tools and confidence to build a sustainable, fulfilling business—one that supports their lifestyle and creative passions.
What’s Next?
I’m currently focused on expanding my coaching and education offerings, helping more wedding professionals step into the luxury elopement space with clarity, confidence, and a strong business foundation.
For anyone looking to elevate their wedding business or step into the world of luxury elopements, I’d love to connect and help them create a path that’s aligned with their passion and expertise.

There is so much advice out there about all the different skills and qualities folks need to develop in order to succeed in today’s highly competitive environment and often it can feel overwhelming. So, if we had to break it down to just the three that matter most, which three skills or qualities would you focus on?

Looking back, there are three key things that have been essential to my journey.
The Ability to Pivot & Reinvent Yourself
The wedding industry—and entrepreneurship in general—never stays the same. Trends shift, client expectations evolve, and what worked five years ago may not work today. The ability to adapt, learn, and pivot has been one of the most important skills in my career.
Advice:
Don’t get too attached to how things should be—stay open to reinvention.
Learn to read the market and adjust your approach instead of waiting for things to improve.
Trust your own instincts and creative evolution—it’s okay to change paths if something no longer aligns.
But most importantly, keep moving, keep learning, and keep creating. Whether it’s learning SEO, launching a YouTube channel, writing a book, or improving your craft, the moment you stop growing, your business stops growing. The most successful entrepreneurs aren’t just talented; they are relentless about learning and evolving.
Understanding Luxury & High-Value Clients
Early on, I realized that designing luxury elopements isn’t just about planning a wedding—it’s about curating an experience. High-value clients don’t just want logistics; they want thoughtful curation, personalization, and someone who understands their vision without them having to spell it out. Mastering this has been a game-changer.
Advice:
Luxury isn’t about opulence—it’s about refinement, ease, and intentionality. Learn to recognize the difference.
Focus on experience over execution. A well-planned timeline is great, but the way a couple feels during their day is what makes it luxury.
Refine your brand messaging to attract the right clients—speak to exclusivity, experience, and artistry, not just pricing or services.
Having a Strong Business Foundation
Many creative entrepreneurs are incredibly talented but struggle with the business side. Knowing how to price your work, attract the right clients, and market yourself effectively is what allows you to turn a passion into a profitable career.
Advice:
Learn pricing strategies that reflect your expertise, not just the going rate in your area.
Branding and marketing matter. If you’re not attracting the clients you want, revisit your messaging, visuals, and positioning.
Boundaries create longevity. Charging appropriately and setting clear expectations keeps you from burning out.

Final Thoughts
If I had to sum it up, the biggest lesson is this: Success in luxury elopements or business in general isn’t just about planning—it’s about positioning. The creatives who thrive in this space are the ones who stay adaptable, deeply understand their clients, and treat their work like a business, not just a passion.
And most importantly, never stop learning, improving, and evolving. Whether it’s expanding your skills, trying new platforms, or refining your brand, success is about staying in motion.
For those just starting out, my advice is to focus as much on business and brand strategy as you do on creativity, you need to keep the passion fire alive. When those two things come together, that’s when real success happens.

As we end our chat, is there a book you can leave people with that’s been meaningful to you and your development?

The book that has had the most impact on my journey is The Artist’s Way by Julia Cameron. I return to it every time I feel stuck, and without fail, it helps me move forward.

One of the most powerful lessons from the book is the idea that creativity isn’t just inspiration—it’s discipline, self-trust, and a daily practice. The two core exercises, Morning Pages and the Artist Date, have been game-changers for me.

Morning Pages help clear out mental clutter. Writing freely, without judgment, allows me to process fears, doubts, and creative blocks so I can move forward with clarity.
The Artist Date encourages stepping outside routine—engaging in something new, playful, or inspiring. It reminds me that creativity thrives when we step outside of the norm and allow ourselves to explore without an agenda.
This book also reinforces the importance of trusting your artistic instincts and breaking free from perfectionism. It teaches that creativity is something we nurture, not something we wait for.

Every time I feel uninspired or stuck in a cycle of overthinking, The Artist’s Way helps me reconnect with my artist soul. It reminds me that creativity is meant to be fluid, joyful, and ever-evolving—just like life.

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Rochelle Cheever

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