We caught up with the brilliant and insightful Rachael Dickhute a few weeks ago and have shared our conversation below.
Rachael, we’re so excited for our community to get to know you and learn from your journey and the wisdom you’ve acquired over time. Let’s kick things off with a discussion on self-confidence and self-esteem. How did you develop yours?
I built much of my confidence through two early experiences: sports in high school and my first real job in sales. Sports taught me discipline, teamwork, and how to push through discomfort. But it was my sales job in my early twenties that truly shaped my self-esteem.
I worked for a company selling office supplies completely on commission, which meant if I didn’t sell, I didn’t get paid. Every day, I would walk into offices unannounced, start conversations with complete strangers, handle rejections, and turn those moments into sales, sometimes a few hundred dollars, sometimes a few thousand. It was intense, but incredibly rewarding.
That job taught me how to talk to people, navigate rejection, and find common ground through conversation. It also showed me that success comes from persistence and connection. I even sold office supplies to Michael Bay’s production offices at one point. Knowing I could thrive in a job most people wouldn’t even attempt gave me a lasting sense of confidence and resilience that’s carried into everything I’ve done since.
Let’s take a small detour – maybe you can share a bit about yourself before we dive back into some of the other questions we had for you?
What I find most exciting about what I do is that I get to provide small businesses and entrepreneurs with the kind of insight and expertise they’d typically receive from a full-time marketing director, but at a fractional cost. There’s a growing movement of “fractional” roles, where seasoned executives and CMOs lend their experience to multiple companies at once. Through my agency, I essentially serve as a fractional marketing director, helping businesses access high-level strategy, structure, and growth without the six-figure salary of a traditional CMO.
It’s incredibly rewarding to work closely with business owners in this way. Many of my clients have stayed with me for years because I truly get to know their brands inside and out, acting as an extension of their leadership team. Marketing is most effective when it’s consistent and rooted in long-term vision, so I value those ongoing relationships deeply.
Beyond my agency work, I’m also expanding into film production, a natural evolution of my experience producing creative campaigns and storytelling-driven content. I’ve stepped into a producer role for several short films and documentaries, applying my marketing background to help bring these stories to life. In fact, my first short film is currently in production in Nepal. Even after 17 years in my career, I’m still learning, evolving, and finding new ways to tell meaningful stories, and that’s what keeps it all exciting.
If you had to pick three qualities that are most important to develop, which three would you say matter most?
The three qualities that have had the biggest impact on my journey are communication, resilience, and curiosity.
Communication has been essential in every part of my career. Whether it was cold-calling businesses in my early twenties or leading high-level strategy meetings with clients today, being able to communicate clearly and confidently changes everything. My advice for anyone starting out is to practice speaking with intention, whether that’s through public speaking, writing, or even having more thoughtful everyday conversations. The more you communicate, the more you refine your voice.
Resilience has kept me grounded through every stage of my career. Entrepreneurship can be unpredictable, and creative industries especially come with highs and lows. Learning to take feedback, rejection, or setbacks without losing your drive is what separates those who sustain success from those who burn out. Resilience grows with experience, so take risks and allow yourself to fail forward.
And finally, curiosity has been my greatest teacher. I’ve never stopped asking questions or wanting to learn how things work, whether it’s a new platform, a marketing trend, or now, film production. Staying curious keeps you evolving. My advice is to approach every opportunity like a student, even when you’re the expert. I’ve been really diving into AI the past year in order to stay ahead of things for my clients as well as be able to streamline my effectiveness and time.
Those three qualities, communicate, persevere, and stay curious, have shaped not just my career, but how I approach life and creativity as a whole.
I think the first and most important step is being honest with yourself about what you’re actually good at. For me, that meant recognizing that communication was my strongest skill. Once I understood that, I realized I needed to be out in the world—meeting people, taking coffee meetings, attending events, and finding opportunities through connection. Every time I stepped outside, something positive happened for my business. The more I stayed behind a desk, the less momentum I had.
That level of self-awareness completely changed how I built my career. I stopped trying to fit into a traditional work model and started designing my workflow around my strengths. It’s not always easy to be on the go, but it’s the environment where I thrive.
And that’s really the advice I’d give to anyone early in their journey: be brutally honest with yourself. If you’re not great at communication, don’t force it, lean into what is natural to you. If you’re highly organized or strong on the administrative side, amplify that. Dive into AI tools, find ways to systematize your processes, and set yourself apart by staying ahead of the curve and self-teaching constantly. Success comes from self-awareness and the willingness to build around your strengths instead of trying to emulate someone else’s.
One of our goals is to help like-minded folks with similar goals connect and so before we go we want to ask if you are looking to partner or collab with others – and if so, what would make the ideal collaborator or partner?
Absolutely. Collaboration is at the heart of everything I do. I’m always interested in connecting with other creatives, brands, and entrepreneurs who value storytelling, design, and intentional marketing. Through Wayward Creative Studio, I partner with clients and collaborators across industries, hospitality, design, travel, and lifestyle, to create campaigns, content, and experiences that resonate deeply. Storytelling and intention is at the forefront of everything we produce.
I’m especially drawn to partnerships that blend creativity with purpose: artists, filmmakers, small business owners, and brands who want to do things differently and tell stories that matter. I’m also expanding my work as a producer, so I’m looking to connect with filmmakers, production teams, and brands interested in supporting short films and documentary storytelling around art, travel, and culture.
If you’re reading this and think we might align, I’d love to hear from you. You can connect with me through my agency website at www.waywardcreative.com
or on Instagram @waywardroamer
Contact Info:
- Website: https://www.waywardcreativestudio.com
- Instagram: https://www.instagram.com/waywardroamer
- Linkedin: https://www.linkedin.com/in/rachaeldickhute/
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