Life, Values & Legacy: Our Chat with May O’Connor of Manhattan

We recently had the chance to connect with May O’Connor and have shared our conversation below.

Hi May , thank you so much for taking time out of your busy day to share your story, experiences and insights with our readers. Let’s jump right in with an interesting one: What are you being called to do now, that you may have been afraid of before?
I’m being called to show up more, specifically, to be more present on social media. I’ve always thrived in one-on-one connections with my clients. I love hopping on video calls, diving into their businesses, and helping them see what’s possible. But I know that to expand my impact, I need to show up on a bigger stage. That means being seen, sharing my perspective, and letting people experience the energy behind what I do. It’s not about perfection- it’s about presence. So I’m learning to push past any insecurities and treat social media as an extension of those face-to-face conversations I already love so much.

Can you briefly introduce yourself and share what makes you or your brand unique?
I’m May O’Connor, the founder of Magnolia Digital, a full-service digital agency that helps entrepreneurs and brands look as good online as they do in real life. My background is a bit unconventional. I spent eight years working on yachts around the world before transitioning to tech. I often say building websites feels a lot like crafting a great meal: it’s about creativity, flow, and presentation.

At Magnolia Digital, we don’t just design websites. We create digital ecosystems that help businesses grow. What makes us unique is that we combine aesthetics with strategy. Every site we build is designed to convert, tell a story, and reflect the heart of the brand behind it.

Over the past decade, I’ve had the privilege of helping hundreds of clients streamline their systems, elevate their presence, and build businesses that truly work for them. As we approach our 12th year, I’m especially focused on expanding our educational side, helping business owners get “web ready” through tools, templates, and training that simplify the process and make digital feel less intimidating.

Great, so let’s dive into your journey a bit more. Who taught you the most about work?
My dad taught me the most about work. He was an entrepreneur and business owner, and from an early age I watched him build something meaningful from the ground up. He showed me the value of creating something for yourself, taking pride in your craft, and staying committed even when things get hard. That mindset shaped everything I do today. It taught me that work is more than a paycheck. It’s about creating something that matters, standing behind it fully, and leaving your mark in the process.

If you could say one kind thing to your younger self, what would it be?
I’d tell myself to just do the thing instead of overthinking it. Trust your intuition and move forward, even if you feel scared. Fear is something we create in our minds, and it doesn’t deserve the power to hold us back from our biggest dreams. Every great thing in my life has come from taking a leap before I felt ready. The courage to start is what changes everything.

So a lot of these questions go deep, but if you are open to it, we’ve got a few more questions that we’d love to get your take on. Is the public version of you the real you?
Yes, one hundred percent. What you see is what you get with me. I’m authentic, open, and social, and I’ve never been afraid to speak my truth. I genuinely enjoy connecting with people and sharing who I am. I’m also a bit of a showman at heart. I love being seen, bringing energy into a room, and creating moments that people remember. It’s not about performance, it’s about presence, and that’s something I’ve learned to fully embrace.

Thank you so much for all of your openness so far. Maybe we can close with a future oriented question. When do you feel most at peace?
I feel most at peace when I’m surrounded by friends at the dinner table in my home. I love cooking, nurturing, and creating an experience for the people I care about. There’s something magical about good food, laughter, and connection all happening in the same space. For me, that’s where joy and creativity meet, sharing something I’ve created and watching it bring people together.

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Image Credits
Vanessa Rogers Photography

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