Female entrepreneurs often face a unique set of challenges with many shaped by societal expectations, subtle biases, and internalized beliefs. The stories of these four leaders reveal not just the obstacles they encountered but the pivotal lessons that reshaped their approach to leadership. From battling impostor syndrome to reclaiming one’s voice, these insights provide a roadmap for resilience and growth.
Jenna Renfroe: Breaking Free from the “Play Small” Mindset
As Jenna Renfroe, Clinical Neuropsychologist and owner of Tailored Brain Health, explains, many women are conditioned to be “nice” and avoid ruffling feathers—a tendency that can hinder leadership. Early in her career, Renfroe found herself overcompensating, holding back opinions to avoid being perceived as overzealous or overly critical. This self-censorship was stifling both her progress and her team’s growth.
Her turning point came after reading the book Compassionate Leadership, where she learned about the “empathetic hijack” that often occurs when leaders fear difficult conversations. The key lesson? “Clear is kind.” By embracing direct, transparent communication, Renfroe realized that avoiding discomfort only thwarts progress. Today, she leads with clarity, knowing that authenticity and constructive dialogue are essential for growth.
Jessie Brooks: Trusting Intuition Over Seeking Approval
For Jessie Brooks, Product Manager at Davincified, the greatest challenge wasn’t overt hostility—it was the persistent, discreet undermining that often goes unnoticed. From delayed bill approvals to subtle second-guessing, these microaggressions pushed her to over-prepare and over-deliver. While effective in the short term, this approach left her drained and failed to address the root issue.
Brooks’ breakthrough came when she shifted her priorities, no longer seeking external validation but instead trusting her own intuition. “I trained myself to speak not loudly, but with intention,” she says, “and to fill the room without making myself smaller to fit it.” An unexpected hurdle was creative disconnection, which she overcame by engaging with art purely for personal fulfillment. This reconnection reinforced that leadership is about vision, not just outcomes—a philosophy that now shapes her entire approach.
Keesia Wirt: Defeating Impostor Syndrome Through Collaboration
After two decades in corporate environments where women’s voices were often overlooked, Keesia Wirt, founder of Circa Legacy, struggled with impostor syndrome. She believed she was destined to remain a solo operator, undervaluing her skills and avoiding public leadership roles. The shift began when she joined startup communities, engaged with other female founders, and absorbed the insights of women leaders through podcasts and webinars.
One surprising obstacle was her belief that doing everything herself was a strength. In reality, it limited her growth. By seeking mentorship, collaborating with skilled peers, and delegating effectively, Wirt transformed her leadership style into one that is empowering and collaborative. Today, she surrounds herself with people who challenge and inspire her, confident that this diversity of talent elevates both her business and her leadership.
Amy Bos: Overcoming Challenges with Vision
Amy Bos, Co-Founder and COO of Mediumchat Group, launched her first business fresh out of university at just twenty-two. Walking into rooms filled with professionals twice her age, and with decades more experience, triggered intense impostor syndrome. She found herself second-guessing decisions, hesitating in discussions, and feeling overwhelmed by the pressure to prove herself.
Everything changed when a fellow entrepreneur offered to mentor her. Bos realized she didn’t need to mirror the voices around her—she needed to own her unique perspective. She knew her audience, understood the people she served, and could build a team to meet their needs. This shift led her to embrace curiosity over control, prioritize listening over performing, and commit to following her own vision. The result was a leadership style that is both authentic and deeply connected to her team’s and clients’ needs.
These stories showcase a universal truth for women in business: breaking free from limiting beliefs and external biases is as much an internal battle as it is an external one. Whether it’s through direct communication, self-trust, collaborative leadership, or visionary thinking, the journey of overcoming these challenges shapes not just careers, but the future of female entrepreneurship itself.
