An exploration of how effective leaders embrace uncertainty and complexity by engaging with unclear projects, conflicting perspectives, and evolving ideas—discovering that true leadership thrives in the messy spaces where answers aren't obvious.
Her Story
About Natalie
Natalie Caro, MBA, is a cross-functional professional with seven years in hospitality and nearly a decade in nonprofit healthcare. Her experience spans digital communications, major project leadership, workplace and real estate initiatives, safety, operations, and entrepreneurship—including directing improvements across approximately 20,000 square feet of Foundation space and roughly $250,000 in workplace enhancements.
She brings experience from across disciplines to look at systems, root issues, and the bigger picture. Natalie is drawn to messy, undefined work—creating structure, connecting teams and resources, and building solutions with lasting impact. Thinking beyond herself is central to how she leads: listening to the individual need while also considering the greater organizational need.
Outside of her professional work, she remains deeply committed to philanthropy and community service through organizations including Give Kids The World Village, Pet Alliance, Habitat for Humanity, ASPCA, Canine Companions, and the American Foundation for Suicide Prevention.
Her Interview
Ten minutes with Natalie
01What do you attribute your success to?
I attribute much of my success to my willingness to step into unfamiliar spaces, ask questions, understand how systems work, and take ownership of challenges that do not always arrive with a clear solution. Curiosity and adaptability have allowed me to grow across different roles, disciplines, and responsibilities while continuing to build on what I learn.
I also credit the mentors who have supported and challenged me throughout my career. Amanda Walker, Community Relations Director of Brevard, gave me my first leadership opportunity during my hospitality career and helped shape my early understanding of leadership, accountability, and how to bring out the best in others. My current leader, Tracey Choroco, VP - Foundation Communications, has continued to help me grow professionally by encouraging me to recognize my value, stretch beyond the boundaries of my role, and pursue opportunities aligned with my strengths and ambitions.
Just as mentorship has shaped me, I value sharing what I have learned by informally guiding and supporting people I care about and helping others recognize their own strengths.
02What advice would you give to young women entering your industry?
Stay curious about what naturally draws your attention. Your career does not have to develop in a perfectly straight line for your experience to compound. Learn how different parts of an organization work, build relationships outside your immediate role, and pay attention to the problems you consistently enjoy solving. Often, that pattern tells you more about your strengths than a job title does.
03What are the biggest challenges or opportunities in your field right now?
One of the greatest opportunities in nonprofit healthcare is connecting systems that have traditionally operated separately. Digital communication, fundraising technology, operations, patient experience, data, facilities, and community engagement increasingly influence one another. Professionals who can understand those intersections, translate needs across teams, and build sustainable processes have an opportunity to create impact well beyond the boundaries of a traditional role.
04What values are most important to you in your work and personal life?
I value continuous learning, service, community involvement, and personal responsibility. I believe growth comes from staying curious, being willing to learn from people and experiences outside of your immediate role, and using what you learn to create something meaningful for others.
My education, including an MBA with a healthcare concentration, has strengthened that foundation, but many of my most important lessons have also come through hands-on experiences. Volunteering with organizations such as Habitat for Humanity, Give Kids the World, Alliance of Greater Orlando, and the ASPCA has reinforced the importance of empathy, contribution, and showing up for needs beyond my own.
Professionally, I value collaboration, accountability, and leaving systems, processes, and teams stronger than I found them. There is immense value in listening closely to the individual need while also considering the larger organizational impact. Whether I am working on a digital initiative, an operational challenge, a community project, or something entirely new, I want my contribution to be thoughtful, useful, and sustainable.
Personally, I carry those same values into how I approach relationships, growth, and community. I believe in continuing to evolve while staying grounded in purpose, compassion, and the responsibility we each have to contribute where we can.
Her Content Hub
Articles by Natalie
The Leadership Value of Taking On the Messy Work
Finding Leadership in Uncertainty: Why Embracing Messy Work Matters
I've learned that I'm often drawn to the work that doesn't have a clean starting point: the unclear project, the process that mostly works until it doesn't, the idea that sounds promising but inconvenient, or the conversation where two people are technically talking about the same goal but seeing it completely differently. None of this is a new leadership philosophy. Plenty of women before me have built careers by questioning the obvious path, taking calculated risks, and trusting themselves enough to explore what others might leave alone. What I've been learning is how much leadership can live inside that mess.
What Does "Messy Work" Actually Mean?
Messy work is not chaos for the sake of chaos. It is the work where the answer is not immediately obvious, ownership is unclear, or the path forward requires more listening than directing. Sometimes it means exploring an idea you are not sure will work. Sometimes it means taking someone else's idea seriously even when you are skeptical. Sometimes it means recognizing that a process has become rigid enough that people are starting to create their own workarounds. The mess is often not the process itself. It is the combination of people, priorities, constraints, expectations, and perspectives.
Why Take It On?
Because curiosity has value. I tend to notice patterns. If something keeps creating friction, I want to understand why. If one team has solved something differently than another, I want to know what they learned. If a small inefficiency keeps resurfacing, I start wondering whether it points to something larger. That investigation is often where I feel most energized, not because I need to be the person who fixes everything, but because I like discovering what is actually happening beneath the surface.
What If the Idea Doesn't Work?
Then you learn something. I think one of the hardest lessons in leadership is becoming comfortable enough to let an idea begin imperfectly. That does not mean being reckless with time, money, or trust. It means accepting that some information only becomes visible once you start moving. Sometimes the result confirms that the existing process is already the right one. Sometimes it exposes an opportunity no one was looking for. And sometimes the goal changes entirely. That is not always failure. Sometimes it is simply evidence.
What Does Alignment Have to Do With Ambition?
A lot. Ambition can push you toward opportunities, but alignment tells you whether those opportunities actually belong to you. I use the word selfish loosely here, but I think there is a healthy form of selfishness in leadership: being willing to ask whether something aligns with your values, your capacity, your interests, and the life you are trying to build before giving it your energy. There are many women leading boldly, building businesses, challenging expectations, taking up more space, and choosing themselves in ways previous generations were often discouraged from doing. That does not mean ambition should always win. Sometimes the strongest decision is saying yes. Sometimes it is saying no. Sometimes it is saying, not this version.
How Do You Know When to Keep Pushing?
For me, passion is usually the clue. If I continue thinking about an idea after the initial excitement fades, if I keep noticing supporting patterns, and if I am still willing to ask questions after hearing "not yet," then I know there may be something worth exploring. That does not mean the original vision survives unchanged, and it usually should not. The goal is not to defend the first idea. The goal is to stay curious enough to find the best one.
What Has Messy Work Taught Me About Leadership?
That leadership is not proving how much you can carry. It is knowing when to investigate, when to listen, when to connect people, when to challenge a process, when to let an idea evolve, and when to hand something off. It is also learning to trust yourself enough to be imperfect. The more comfortable I have become with uncertainty, the less I need every project to end exactly where I imagined it would. That flexibility has made me more patient, more confident, and more willing to let the work reveal what it actually needs.
My Philosophy
Leadership is not having all the answers. It is allowing the answers to exist in forms different from what you expected, rather than forcing them to become what you needed them to be. That is where the messy work becomes valuable, and sometimes that is where the most interesting version of the work begins.
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