Behind every achievement is a moment of reckoning: a shift in mindset, a leap of faith, or a hard truth faced head-on. For these Black women entrepreneurs and leaders, those moments turned into lessons they carry with them every day.
Here, they share the truths that helped them grow, the experiences that shaped their success, and how they continue to apply that wisdom as they build careers, companies, and communities. Let these stories from inside the Dreamers & Doers community inspire you to reflect on your own journey—and the lessons that might already be shaping your next chapter.
Christina Blacken
Founder & Chief Narrative Strategist of The New Quo, a social impact and behavior change training company.
Traci Elaine
Following your own values is so important in a system that conflates business practices based on inequality and exploitation with doing good business. When you build your products and services on integrity and core values, the impact and success is better for your well-being and longevity.
Although my work has been under attack from federal policies dismantling community- and DEI-based work, I’ve kept to my values to pivot my business. I’ve found creative ways to serve the public outside of institutions through community-building storytelling events funded by the New York City government, as well as an online learning community that shares engaging and original social justice education.
Hawwa Muhammad
Founder & CEO of Pink Trumpet, providing project management and communications support for mission-driven work so that good ideas for social change move from concept to completion.
DAG Images
Failure is inevitable, but it’s also an invitation to pivot. As a business owner, I’ve lost contracts and faced stalled deals, but I’ve learned that the faster I reframe those moments, the more I recognize my capacity to adapt and overcome. Once I stopped seeing failure as final, I gave myself permission to be more creative, resourceful, and resilient.
I actively try to create a culture internally and with my team where mistakes are viewed as learning curves, starting with being less hard on myself and with my team.
Lakeya Cherry
Founder & CEO of Changemakers of Color and Lakeya Cherry LLC, dynamic executive coaching and consulting businesses that empower leaders and organizations to maximize their potential through one-on-one and group coaching, leadership development workshops, and strategic offsites.
Danielle Finney
The most important lessons I’ve learned on the path to success are that I am a non-negotiable and that sustainable success requires alignment—not just ambition. I learned this during the transition from nonprofit CEO to solopreneur when I finally stopped overperforming to prove my worth and started leading from a place of purpose, clarity, and wholeness. That journey required me to redefine what success truly meant on my own terms and to reconnect with who I was beyond any title, expectation, or performance trap.
I protect my peace as if it were part of my job because it is. Whether I’m coaching a high-achieving leader, facilitating a workshop, or planning a new offering, I lead from alignment first and support others in doing the same.
Julia Fofanah
Founder of Sà Wea, a luxury ancillary e-commence platform.
Mavrk
The most important lesson I’ve learned is that clarity of purpose is stronger than fear. I discovered this while building Sà Wea from the ground up—bootstrapping, pitching, and showing up even when I felt unprepared or unseen. That lesson gave me the confidence to lead boldly and to share my vision with authenticity.
I remind myself daily that my why is bigger than any obstacle. This mindset allows me to keep taking up space as a founder, a mother, and a voice for cultural representation in cannabis.
Yemi Oluseun
Founder & Retention-Led Growth Strategist of The Change Hive, a boutique consulting firm that partners with B2B SaaS and service businesses to plug the leaks in their customer journeys.
Tina Ogunmilua
The most important lesson I’ve learned is that all work works. Sometimes it works on you—but it always works. I’ve launched funnels that flopped, offers that didn’t convert, and invested in assets that never saw the light of day. But none of it was wasted, because every misstep refined the IP and systems for which I now charge premium rates. The pain became a process.
The false starts became frameworks.
Now, I don’t rush to label things as failure. I harvest them. Whether I’m designing growth strategies for SaaS founders or navigating my own personal pivots, I remind myself that nothing is wasted when you stay in the room long enough to learn.
Gracelyn Woods
Chief Operating Officer of Bellweather Agency, a woman- and POC-owned creative agency that amplifies mission-driven brands through inclusive storytelling, bold campaigns, and award-winning impact across the nonprofit, civic, and cultural sectors.
Gracelyn Woods
The most important lesson I’ve learned is that real sustainability begins with emotional safety. I had to unlearn the belief that burnout was the cost of ambition. I apply that lesson by leading with intention—building systems that make space for people to thrive, not just perform. At Bellweather, this is reflected in how we manage our projects, protect our team’s time, and prioritize relationships over urgency. In my personal life, it means honoring seasons of rest, trusting my internal rhythm, and modeling what it looks like to succeed without self-sacrifice.
Becoming more intentional didn’t just change how I work. It changed how I live. It reminded me that leadership and success aren’t about pushing harder, but about making space for people to show up fully and still have something left for themselves at the end of the day.
Catharine Montgomery
Founder & CEO of Better Together Agency, a Black woman-founded, full-service, AI-forward communications agency that creates integrated campaigns for mission-driven work.
Catharine Montgomery
The single most important lesson I’ve learned is that your values must drive your business decisions, even when it’s uncomfortable or costly. I learned this when I left my previous job due to a racist employee, which forced me to confront whether I would compromise my principles for financial security. That experience taught me that building a business grounded in justice and equity isn’t optional for me; it’s the foundation of everything I do. Ultimately, it led to creating the Better Together Agency, where we help organizations align their actions with their stated values.
Today, I turn away potential clients who don’t align with our values—even when we need the revenue—because I’ve learned that compromising on principles always costs more than the short-term financial gain. This values-first approach has built the Better Together Agency into a trusted partner for organizations that want to create real change, not just check boxes.
Charmaine Green-Forde
Founder & CEO of Chapter tOO, LLC, a data-backed, people-first coaching and consulting practice, helping organizations and people design their best chapters by optimizing performance, engagement, and organizational processes.
@nicolemondestinphotography
I never regret staying true to myself and my values—no exceptions. I respond to values, not money. If an opportunity requires that a value be compromised (even slightly!), it’s a no. I’ve turned down business deals when something felt off with the leadership or culture. The reward? Peace of mind and a clear conscience.
That filter still guides every decision I make in business and in life. Whether I’m advising a client or shaping a new offer, I check: Does this align with what I believe and how I lead? If the answer is no, I walk away, no matter the dollar amount. Staying rooted in my values has protected my peace, my brand, and my reputation.
Rozella White
CEO of The Waymaker Agency, helping mission-driven organizations and visionary leaders untangle dysfunction, navigate change, and build the capacity to thrive with strategy, soul, and structure.
Katie Simbala – Kap2ure Studios
The single most important lesson I’ve learned is that I can only take people as far as I’ve gone myself. I can only lead people and organizations through culture change and personal transformation if I am willing to go there myself, both personally and professionally. Addressing my own history, trauma, and limiting beliefs was crucial for my healing journey. It also made me a better leader.
Ongoing reflection is a tangible activity that comes from this lesson—one that requires me to intentionally pause, reflect, and shift as needed every year. When I come up against a challenge, it invites me to go deeper in order to uncover what stumbling blocks exist in me that might inhibit the work I do with others.
Adebukola Ajao
CEO & Digital Marketing Consultant of B.D.Y. CONSULT LLC, a marketing agency providing small businesses and badass brands with creative and efficient marketing services—without breaking the bank, of course!
Northeastern University Women Who Empower
The most important lesson I’ve learned is to always remain a student of the game. I used to believe I had to know everything to lead, but experience—especially building teams and launching projects—taught me that real growth comes from being honest about what I don’t know and staying curious enough to learn. No CEO has all the answers, but the best ones know how to listen, adapt, and build with intention. That’s the energy I bring into every room.
Today, I surround myself with people who challenge my thinking, and I lead like a conductor, focused not on playing every instrument, but on ensuring the whole orchestra moves in sync.
All individuals featured in this article are members of Dreamers & Doers, an award-winning community that amplifies extraordinary women entrepreneurs, investors, and leaders by securing PR, forging authentic connections, and curating high-impact resources. Learn more about Dreamers & Doers and get involved here.
