Meet Holly Roberson

Alright – so today we’ve got the honor of introducing you to Holly Roberson. We think you’ll enjoy our conversation, we’ve shared it below.

Hi Holly, thanks for sharing your insights with our community today. Part of your success, no doubt, is due to your work ethic and so we’d love if you could open up about where you got your work ethic from?

Growing up, like many latchkey kids, I was home by myself every day after school until dinner, from age 10 to 18. I saw what it was like for both parents to work a steady 9-5, Monday through Friday, almost 52 weeks a year. They lived for the weekends and the once-a-year vacation. They got up each day, tended to their routines, and did the thing—day after day, year after year. They didn’t love what they did, but it kept a roof over our heads and gave us a ‘nice life.’ From this, I learned the foundation of work ethic: you do what you have to do to support the life you want for your family, ensuring they have what they need (and want), a home, and a future. Cool, copy that.

Around age 15, I began to question it all. I yearned for something different, something more meaningful. Something was missing—I felt it deep in my gut.

The eight years after high school, I was ‘doing the thing’ in the form of working in the entertainment industry in Los Angeles—music video and commercial production, to be exact. I went from receptionist to graphic design department manager to production assistant and everything in between, with my sights set on becoming a producer someday. There I was: going to a job, spending loads of time working to level up (in a really male-dominated industry at the time), paying rent and bills in a big city, buying nice things, coming home tired (okay, maybe it was fun at first, having LA-inspired late nights), living for the weekends and once-a-year vacations. But by 27, I’d had enough. That longing for something more meaningful—the one I’d felt as early as 15—was still there, gnawing at me. Some days, I could barely bring myself back to the office after lunch. The stress, pressure, egos, and long hours had me dreading each new day. Then one day, I just stopped.

Now, before I tell you just how I stopped—and believe me, it was kinda epic—I have to say I had a plan in place. With a solid sense of work ethic under my belt, it felt irresponsible to simply quit. So, I gave it a little time, waited until I could use the two weeks of vacation I’d earned (ya know, the two I saw my parents live for), thinking I’d use that, return to work, and then resign soon after. But I didn’t make it that long. While on vacation, I stayed at the property of a woman who was a massage therapist, owned six little cabanas on the beach, and had left the States to live a life in Belize. I spent hours in her library, took books to the beach, practiced mindfulness exercises in my cabana, and asked her endless questions about her journey. She spoke of the calm joy she’d found in a simple life and the meaningful work that came with it—along with a work ethic grounded in passion rather than obligation. That was it—I saw another way. I sent my resignation from the beach. I would not be returning to my job.

At 27, I left the entertainment industry, good pay, and all I’d accomplished, with absolutely no clue what I’d do next. But I knew I’d apply myself in anything I chose to pursue—and that’s when my work ethic really kicked in.

Moving forward, I leaned on the memory of witnessing my parents ‘do the grind’ for 18 years, knowing that I, too, had the strength to work hard, even when the hustle didn’t fully align with me (remember that gut tug?). But now, I began shaping a life I truly wanted and working in ways that felt right. I applied my work ethic to a new golden standard—one that I alone would define. And you know where I started? Making sandwiches at a health food store. I needed space to sort my thoughts, and spreading vegan mayo was just the way. Pure bliss.

Appreciate the insights and wisdom. Before we dig deeper and ask you about the skills that matter and more, maybe you can tell our readers about yourself?

My career is shaped by three major cornerstones. First, I own With Soul Agency, a small business marketing agency founded in 2014 that focuses on helping women in the well-being and retreat space. Next, I am the owner and guide of Sip, Savor, Explore Oregon, a travel experience business I launched in 2022 as a way to step away and from the computer and into the world, helping people explore all that Oregon has to offer. Finally, I am part of the retreat team at Hidden Leaf Baja, a retreat destination in Todos Santos, Baja California Sur, Mexico.

Each of these cornerstones holds its own excitement for me, but for the purpose of this interview, I’ll focus on Sip, Savor, Explore Oregon as it’s ‘my baby’—the business I want to scale, nurture, and have truly sustain me long-term. It’s the venture that feels the most aligned with who I am, blending my love of the outdoors, designing trips and travel experiences, meeting new people, and ensuring they have a memorable time. Here, I excel at making connections, sharing the beauty of Oregon, and welcoming people from all over the world. At its heart, this business brings me the most ease and joy.

Since launching in 2022, Sip, Savor, Explore Oregon has been my way of encouraging people to experience Oregon through a personal lens, moving beyond typical tourist paths to explore hidden gems and unique regional experiences. As I continue to grow this brand, I’m focused on expanding our offerings—adding new routes, exploring unique partnerships, and creating curated events that bring people closer to the region’s farms, wineries, natural beauty, stunning coastline, and cultural landmarks. This year, I’m especially excited to be launching a seasonal series, including urban wine tours in SE Portland (my home base) and private tours that are thoughtfully curated to specific travel preferences.

My goal is for Sip, Savor, Explore Oregon to become a trusted travel brand known for thoughtful itineraries, authentic connections, and experiences that create lasting memories. I envision this as a business that not only scales but also evolves into a sustainable, joyful venture that allows me to keep doing what I love—sharing the best of Oregon with others.

If you had to pick three qualities that are most important to develop, which three would you say matter most?

In reflecting on the qualities, skills, and knowledge that have shaped my journey, three core principles stand out as both guides and strengths: stick-to-itiveness, alignment, and intuitiveness. Here’s how each applies for me:

Stick-to-itiveness. Building a business isn’t something that happens overnight; it’s a journey that takes endurance, patience, grit, and the commitment to just keep going. In my experience, the rewards often come after the 12th or even 18th month, with peaks, valleys, and new iterations along the way. I’ve experienced this firsthand and witnessed it with many other women in business—success demands persistence and resilience. This has held true for both With Soul Agency and Sip, Savor, Explore Oregon—the work requires a commitment to see it through. My advice for those just starting is simple: stay patient and keep showing up, even when progress feels slow. Perseverance is often what separates those who succeed from those who give up too soon.

Alignment. I began my solopreneur journey over 20 years ago, and a few years later, when my son was born, my commitment to being fully present with him became my guiding principle. It wasn’t just about having a flexible schedule; it was about designing a career that allowed me to be engaged and available. This vision shaped my path as I built a business aligned with my strengths and personal goals, prioritizing a life that balanced my professional ambitions with raising my child. This alignment wasn’t just a goal—it was essential to my journey as both a parent and an entrepreneur.

To others, I’d say: take the time to understand what truly aligns with your values, strengths, and life goals, and build your career around them. It may take effort and some unconventional paths, but when your work aligns with who you are and what you prioritize, you’re more likely to find both success and deep fulfillment.

Intuitiveness. After leaving the entertainment industry in my twenties, I studied the healing arts for two years. Though I eventually moved into other fields, the intuitiveness I developed during that time has influenced how I connect with people, read situations, and understand others’ needs. This intuitive sense has been invaluable, especially in customer-centered businesses. For those early in their journey, my advice is to trust your gut—whether it’s about an opportunity, a connection, or a decision. Cultivating intuition and empathy can help you build meaningful relationships and better serve others.

What’s been one of your main areas of growth this year?

Over the past 12 months, my biggest area of growth has been learning to expand my vision beyond the initial reasons I had for carving my own path while still holding onto them as my true north. When I first stepped away from the traditional 9-5 and the entertainment industry, my goal was clear: to find meaningful work outside the grind, to work for myself, and to create a life that aligned with my strengths and values. Five years later, when my son came along, that purpose deepened—I wanted the flexibility to be present, to truly be there for him as he grew. Those priorities shaped everything I did.

Now, with my son grown, my focus has shifted. This year, my biggest growth has been in managing multiple endeavors at different phases—With Soul Agency at 10 years in and Sip, Savor, Explore Oregon at just 2.5 years in—and believing in my ability to scale them, even when it’s often just me doing the work. It’s taken resilience, confidence, and a renewed trust in my work ethic to juggle these evolving roles. Learning to navigate each business’s unique demands and envisioning their growth potential has been challenging yet empowering.

This past year has shown me that I can go beyond simply maintaining my vision; I can expand it. I can trust that the foundations I laid early on—flexibility, alignment, and the commitment to meaningful work—are strong enough to support my bigger ambitions. And as I scale these ventures, I remain grounded in the purpose that first set me on this journey.

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