Women entrepreneurs across industries continue to face challenges that demand adaptability, strategic thinking, and resilience. While their industries, markets, and personal circumstances differ, many have reached similar conclusions about leadership: clear communication, trust in capable teams, and readiness for change are essential. The following accounts show how moments of difficulty became turning points that shaped their businesses and leadership styles.
Shaping Leadership Through Experience
Mary Case, founder of The Happy Food Company, says her early career was marked by entering rooms where her abilities were underestimated. She learned to “stop overexplaining” and instead focus on clarity, boundaries, and results. That shift, she notes, changed not only how others perceived her but also how she viewed herself as a leader.
For Jerrica Long, storyteller and show runner at Jerrica Says, the defining moment came after a period of burnout. She reframed her business to reflect her values, acknowledging that “in the long run, I needed to take care of myself if I wanted to do this work.” Both women found that sustainable leadership often begins with internal change.
Adapting Strategies to Unlock Growth
Attorney Jacqueline Salcines, founder of SALCINESLAW, discovered that delaying the hiring of top-level talent slowed her firm’s expansion. Once she began to bring in experienced professionals and delegate core responsibilities, revenue growth accelerated. “Hire quickly,” she advises, emphasizing that strong teams are vital to scaling effectively.
Dana Lewis, owner of DWD Travel & Destination Weddings, faced a different adjustment in presenting herself online. Frequent travel made her life seem distant from her audience, and she feared appearing out of touch. Over time, she developed a way of sharing that resonated with clients while maintaining her privacy, concluding that “authenticity doesn’t mean oversharing, but finding the rhythm that reflects who you are.”
Breaking New Ground in Unfamiliar Markets
Some entrepreneurs must create demand for services that are new to their markets. When Denise Iacona Stern launched Let Mommy Sleep, professional newborn care was not widely recognized in the United States. She focused on compassionate education and highlighting her team’s expertise to address both operational challenges and social stigma.
Katherine King, CEO and co-owner of Dazychain, has confronted a different obstacle: doubt. She describes it as “vacuuming the air out from under your wings,” and counters it by preparing alternative plans and pushing forward even when uncertain, reminding herself that the stakes are rarely as high as they feel in the moment.
Balancing Passion with Operational Demands
Diane Howard, founder of Esthetic Finesse, realized that without strong operational systems, the quality of client care could suffer. By revamping administrative processes, she freed more time to connect directly with patients without compromising business efficiency.
Similarly, Debra Hildebrand, owner of BARC Business, built her career in the male-dominated consulting industry while navigating a self-imposed expectation to handle every aspect of the work herself. She believed that taking on every task would prove her competence, but the approach led to burnout and inefficiencies.
The turning point came when she began to delegate, recognizing that trusting and valuing the skills and knowledge of her team not only improved results but also strengthened collaboration. This shift reshaped her leadership, focusing on strategic oversight rather than micromanagement, and reinforced the value of drawing on diverse expertise within her team.
Preparing for the Unexpected
Business coach Dielle Charon of For the 23% faced a sudden test when illness forced her to step back during a major launch. The absence exposed gaps in her systems and revealed which team members could adapt under pressure. She responded by creating stronger operational processes to ensure the business could function without her direct involvement, reflecting a lesson shared by many of these leaders — that preparing for the unexpected is as much a part of leadership as managing the day-to-day.
Together, these experiences show that while the details of each challenge differ, the strategies that emerge are remarkably consistent: focus on clarity, trust capable teams, and be willing to adapt. For these entrepreneurs, resilience is not simply enduring obstacles but using them to redefine how they lead and build their businesses.
