Meet Orletta Caldwell

 

We caught up with the brilliant and insightful Orletta Caldwell a few weeks ago and have shared our conversation below.

Orletta, so good to have you with us today. We’ve got so much planned, so let’s jump right into it. We live in such a diverse world, and in many ways the world is getting better and more understanding but it’s far from perfect. There are so many times where folks find themselves in rooms or situations where they are the only ones that look like them – that might mean being the only woman of color in the room or the only person who grew up in a certain environment etc. Can you talk to us about how you’ve managed to thrive even in situations where you were the only one in the room?

Being the only one in the room has often meant navigating spaces where I am both seen and unseen—seen for my differences but unseen for my potential and contributions. Early in my career, I learned that success in such situations required an unwavering sense of self-worth and a deep understanding of my own value. I came to realize that while I might be the only one in the room who looks like me, I was never alone in spirit. I carried with me the lessons, strength, and resilience of those who came before me, and I used that as my foundation to thrive in environments that weren’t always welcoming.

To be effective, I developed strategies rooted in preparation, authenticity, and intentionality. I prepared relentlessly—knowing that being underestimated meant I had to overdeliver to be seen as equally capable. I remained authentic because trying to conform to expectations that didn’t honor my true self would have diluted the unique perspective I bring to the table. And I was intentional about building relationships, even in spaces where I initially felt like an outsider. I learned that creating allies and fostering mutual respect could shift perceptions and open doors for collaboration.

Perhaps most importantly, I reframed being “the only one” as an opportunity rather than a burden. My presence often disrupts the status quo, and with that disruption comes the chance to educate, to innovate, and to pave the way for others who will come after me. While it has not always been easy, I’ve learned that success in these moments lies in embracing my difference as a strength and using it to lead with confidence, compassion, and purpose. Each room I’ve entered, I’ve left a bit more open for others to follow.

Great, so let’s take a few minutes and cover your story. What should folks know about you and what you do?

I’ve dedicated my life to empowering nonprofit organizations to not just survive but thrive. Through my platforms, Beyond Existing Enterprises and The Urban Nonprofit, I help nonprofits build sustainable strategies, foster innovation, and create meaningful impact. I’ve spent over 35 years in the nonprofit world, and my passion is helping organizations overcome challenges and achieve their full potential. Whether it’s strategic planning, fundraising, or governance, I focus on equipping leaders with the tools they need to succeed.

What excites me most is witnessing the transformation of grassroots organizations. There’s nothing like seeing a nonprofit leader go from feeling overwhelmed to confidently navigating their organization’s path forward. With Beyond Existing Enterprises, I work one-on-one with nonprofit leaders, providing consulting and workshops tailored to their unique needs. On the other hand, The Urban Nonprofit is all about addressing the distinct challenges faced by organizations in African American communities. By offering practical tools and real-world solutions, I strive to help these nonprofits become pillars of their communities.

Right now, I’m especially excited about an upcoming three-day virtual summit for churches, designed to help them create or strengthen their community development centers as separate 501(c)(3) organizations. This summit will focus on compliance, sustainability, and organizational structure—key areas where I know many struggle. I’m also constantly updating www.beyondexisting.com and www.urbannonprofit.com with new resources to guide nonprofit leaders. At my core, I’m passionate about equipping others to lead with confidence and make a real difference in their communities.

Looking back, what do you think were the three qualities, skills, or areas of knowledge that were most impactful in your journey? What advice do you have for folks who are early in their journey in terms of how they can best develop or improve on these?

Looking back on my journey, the three qualities that stand out as the most impactful are resilience, emotional intelligence, and strategic thinking. Each of these has shaped how I approach challenges, lead others, and create meaningful change, both in my life and in the organizations I serve.

Resilience has been essential because the road in nonprofit leadership is rarely smooth. There were times when funding was uncertain, support was limited, or I was simply the only one in the room who looked like me. What got me through was the ability to adapt, push forward, and focus on the mission, even when things felt overwhelming. For those starting out, I’d say this: challenges will come, but don’t let them define you. Learn to lean on your community, take setbacks as lessons, and always keep your purpose front and center.

Emotional intelligence has been another cornerstone. Nonprofit work is deeply human—it’s about understanding people, building relationships, and leading with empathy. For me, being able to connect with individuals, whether they’re colleagues, clients, or funders, has been critical. For those starting out, I’d recommend practicing active listening and reflecting on how your emotions and actions impact others. The more you can understand and manage emotions—both yours and those of others—the better you’ll lead and collaborate.

Lastly, strategic thinking has made all the difference. In the nonprofit world, you have to see both the big picture and the small steps needed to get there. Early in my career, I learned to always ask, “What’s the long-term goal, and how do today’s decisions get us closer to it?” My advice is to study the field, understand trends, and always have a plan—but remain flexible. Strategy is about intention, but success also requires the ability to pivot when needed.

For anyone early in their journey, focus on developing these qualities through mentorship, continuous learning, and practice. Resilience comes from overcoming challenges, emotional intelligence grows with self-awareness, and strategic thinking sharpens with experience. Trust your process, invest in your growth, and remember that every step—no matter how small—adds to your journey.

How can folks who want to work with you connect?

Through Beyond Existing Enterprises and The Urban Nonprofit, my goal is to provide practical tools, strategies, and resources that help nonprofits thrive. To do that, I value collaboration with individuals and groups who bring fresh perspectives, innovative ideas, and a shared commitment to creating meaningful impact.

I’m particularly interested in collaborating with nonprofit leaders, consultants, educators, funders, and community organizers who focus on areas like organizational development, strategic planning, sustainability, and community empowerment. If you’re someone who is passionate about strengthening nonprofit ecosystems or helping grassroots organizations build their capacity, I’d love to hear from you. I’m also open to partnerships with organizations that support urban communities, faith-based initiatives, and those focused on leadership development or workforce training.

If this resonates with you, let’s connect! You can reach out to me through www.beyondexisting.com or www.urbannonprofit.com, where you can learn more about my work and contact me directly. Whether you’re interested in co-hosting workshops, collaborating on community projects, or simply sharing ideas, I’m always eager to explore how we can work together to make a difference. Let’s combine our strengths to empower nonprofits and create lasting change!

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