An Inspired Chat with Monica Challingsworth of Carlsbad

We’re looking forward to introducing you to Monica Challingsworth. Check out our conversation below.

Good morning Monica, we’re so happy to have you here with us and we’d love to explore your story and how you think about life and legacy and so much more. So let’s start with a question we often ask: What are you being called to do now, that you may have been afraid of before?
I’m being called to step into a new kind of vulnerability. For so long, I defined myself by how much I could build, fix, and carry for others, with Eustress & Demeter, my focus was on holding up clients and making their brands shine, and with Dink & Dine, it was about creating a space for the community. But in all that, I kept a lot of me tucked away.

What I was afraid of before was letting people see beyond the polished exterior. The truth is, there have been nights where I’ve cried on the bathroom floor from exhaustion, moments I felt like I was drowning in the weight of expectation, and seasons where I questioned if I was worthy of the dreams I carried. I’ve always been strong in business, but I wasn’t always strong with myself.

Now I feel called to stop hiding those parts. To share that I’m learning self-love in deeper ways, that I journal when I’m scared, that I find healing in quiet mornings with my coffee and the people or animals I love the most. To show that the same woman who can negotiate with investors and design a multi-million-dollar concept is also the woman who sometimes just wants to cook a big breakfast for the people she loves, or sit in a hammock and breathe.

What I’ve realized is that people don’t connect to perfection, they connect to humanity. And the parts of me I was once afraid to share are the very things that make me real, approachable, and whole.

Can you briefly introduce yourself and share what makes you or your brand unique?
My name is Monica Challingsworth, and at my core I’m a hospitality visionary who believes in creating spaces where people feel seen, cared for, and connected. I wear a few hats. As co-founder of Eustress & Demeter, I’ve spent years guiding restaurants and hospitality brands through consulting, operations, and marketing, helping them not just grow but thrive in a way that feels authentic. As co-founder of Dink & Dine Pickle Park in Mesa, Arizona, I’ve poured my energy into building something that merges two of my loves: food and community. It isn’t just pickleball and dining, it’s an experience designed to bring people together, whether they are families, friends, or people discovering the sport for the first time.

What makes my work unique is that it has never been just about business. Hospitality is personal for me. My first company, Eustress & Demeter, began as a mother and daughter project with my mom Darlene and grew out of a shared desire to take care of people. That spirit of care has stayed with me through every venture, whether I’m helping a restaurant tell its story or opening the doors to Dink & Dine and watching strangers become friends over a game and a cocktail.

My story has never been perfectly linear. I’ve had to navigate the messy and unglamorous parts of building and scaling companies while staying rooted in what I value most: love, connection, and creating experiences that people carry with them long after they’ve left the room. Right now, I’m focused on growing Dink & Dine into a model that can expand nationally while continuing to nurture the consulting side of my work through Eustress & Demeter. At the same time, I’m allowing myself to dream about what comes next, whether that’s building wellness retreats, supporting mentorship programs, or creating more spaces that blend wellness and hospitality, all with the same heartbeat of bringing people together.

At the end of the day my work is about more than food or pickleball. It is about creating moments where people feel joy, community, and a little bit of magic.

Amazing, so let’s take a moment to go back in time. Who were you before the world told you who you had to be?
Before the world told me who I had to be, I was a girl who loved creating joy out of simple moments. I hosted dinners for friends, made spaces feel warm, and dreamed of ideas larger than the world around me. I was playful, curious, and endlessly creative. Over time, the business world asked me to be sharper, more polished, and more professional. I learned to lead with vision and strategy, to build credibility in industries where being young and female did not always mean being invited in. I became skilled at driving growth, launching new revenue programs, and creating opportunities from the ground up. Yet even as I proved myself, I worked hard not to lose touch with the part of me that believed in the softer magic of details, imagination, and joy.

That younger version of me also loved animals with her whole heart, spent hours outside in the dirt and sunshine, and carried the lessons of growing up in Pennsylvania where life felt grounded and close to nature. She was spiritual, generous, and quick to volunteer her time. None of this was about achievement. It was about connection, joy, and the meaning found in small things. She believed a good day could be defined by something as simple as a favorite song, a great movie, or the laughter that comes with friends around a table.

Those same values remain at the center of my work today. I build systems and strategies that allow organizations to grow, but I also know that real success is measured in more than revenue. The most sustainable outcomes come when strategy and humanity work together. The girl who loved rom com marathons, sang along to every 2000’s rap artist, and appreciated a well-made Old Fashioned still lives in me. She reminds me that even in high stakes business, creativity, humor, and heart are often what open the door to the most lasting results.

Was there ever a time you almost gave up?
Yes. In the early days of Eustress & Demeter, I had moments when I thought I could not keep going. The highs and lows were extreme. One day I felt unstoppable, convinced momentum would carry me anywhere, and the next I was questioning every choice and wondering if I was in over my head. Wins felt electric, but setbacks cut deep because I cared so much and tied the results to my own sense of worth.

The hardest part was not just solving business challenges but carrying the emotional weight of the vision. I felt the pressure of not wanting to let people down, the fear that I might not be enough, and the loneliness that comes from being the one expected to hold everything together. There were days when that weight left me sitting on the shower floor, letting the water run until my mind quieted.

What kept me going was remembering why I started. I am someone who builds joy from small things, who values connection, and who believes purpose matters more than perfection. Reconnecting to that truth reminded me that entrepreneurship is not only about building companies. It is about creating a life and body of work that feel aligned and meaningful.

There were moments I nearly walked away, and I am sure there will be more. But I have learned that breaking down is not the same as giving up. Often it is the pause before a breakthrough, the space where resilience is formed, and the reminder that strength is not in never falling but in choosing to rise again.

Alright, so if you are open to it, let’s explore some philosophical questions that touch on your values and worldview. What are the biggest lies your industry tells itself?
One of the biggest lies my industry tells itself is that success is all about growth at any cost. That if you expand fast enough, raise enough money, or chase the hottest trend, you’ve “made it.” The truth is, I’ve watched too many businesses grow wide before they grew deep, and eventually collapse because there was no soul or foundation holding it together. Growth without intention isn’t sustainable, and it’s definitely not hospitality.

Another lie is that hospitality is only about the guest experience. Of course the guest matters, but if your team is burnt out, unsupported, or treated as disposable, that energy seeps into every plate, every drink, every interaction. You can’t create joy for the public while your people are silently drowning. Taking care of the team is the heartbeat of real hospitality, yet the industry often glorifies burnout as a badge of honor.

And maybe the hardest truth is this: we glamorize resilience to the point of self-destruction. There’s this unspoken belief that you have to suffer, grind, and sacrifice yourself in order to prove your worth. But I don’t believe resilience should mean breaking yourself to hold everything up. Real resilience is about balance, boundaries, and building systems that let people thrive rather than just survive.

Before we go, we’d love to hear your thoughts on some longer-run, legacy type questions. Have you ever gotten what you wanted, and found it did not satisfy you?
Yes. If I am being honest, one of my greatest challenges is actually celebrating the wins. There have been so many moments where I achieved something I had been working toward, whether it was a new client, a successful opening, or an investment milestone, and instead of pausing to really feel it, I immediately moved on to the next goal. It often feels like the finish line keeps moving, so I never allow myself the joy of arriving.

The truth is that even when I get what I thought I wanted, there is a quiet voice that asks, what is next. That voice has pushed me forward and shaped who I am, but it has also stolen moments that should have been celebrated. It is something I am actively working on now, because I do not want to look back and realize I missed the sweetness of the very things I once dreamed of.

For me, the practice has been slowing down and really noticing the small human moments of success. My team laughing together. My parents telling me they are proud. My partner reminding me to breathe. Even just sitting with a glass of wine and letting myself say, you did it. Those moments may not look like a headline, but they are the real milestones.

So yes, I have gotten what I wanted and found it did not satisfy me in the way I expected. What I have learned is that the missing piece was never the goal itself, it was my willingness to celebrate the journey along the way.

Contact Info:

• Website: https://www.dinkanddine.com
• Linkedin: https://www.linkedin.com/in/monicachallingsworth/
• Other: https://www.eustressanddemeter.com