Most stories about leading begin with a promotion, a title, or a breakthrough moment.
Dr. Shakenna K. Williams’ story begins on a fishing boat.
Before she became Executive Director of the Frank & Eileenâ„¢ Center for Women’s Entrepreneurial Leadership (CWEL) at Babson College, before she earned a doctorate, and before she became a recognised voice in entrepreneurship and education, she was a little girl learning lessons from her father.
Shakenna loved catching fish. What she didn’t love was baiting the hook. The worms were slimy, unpleasant, and messy. Yet her father taught her that if she wanted the reward, she had to be willing to do the uncomfortable parts too. Years later, she would recognise the same lesson in leading.
Looking back, Shakenna now sees her journey not as a series of positions or achievements, but as a collection of chapters. Each chapter taught her something about confidence, mentorship, resilience, and finding her own approach to leading.
Leading Often Starts Before We Recognise It
One of the earliest chapters in Shakenna’s story is what she calls Leading the Boys’ Club.
As the oldest grandchild and the only girl among a group of younger boys, she naturally became the organiser, teacher, and guide. She found herself creating games, keeping everyone engaged, and learning how to motivate different personalities. At the time, she wasn’t thinking about leading. She was simply helping those around her.
Yet those early experiences shaped the way she approaches leading today.
Too often, we associate leading with formal authority or senior positions. Shakenna’s story suggests something different. Leading often begins with influence. It begins when people trust us, follow our example, or look to us for guidance.
Many women spend years waiting for permission to recognise that they are already leading in their families, communities, and workplaces.
Why Mentorship and Community Matter
If leading was planted by her father, it was nurtured by the mentors who appeared throughout her life.
One of the most powerful lessons from Shakenna’s story is the importance of mentorship and community in personal growth.
As a teenager, she navigated challenges that many people around her never saw. While she was often viewed as the high-achieving student, there were struggles beneath the surface. It was an English teacher who noticed something was wrong and took the time to intervene.
That moment stayed with her. Later, when she arrived at Babson College, another chapter of growth began. Accustomed to academic success, she suddenly found herself surrounded by exceptionally talented peers. For the first time, she questioned whether she truly belonged. What helped her move forward was not determination alone. It was community.
Faculty members, mentors, faith leaders, and supporters helped her navigate uncertainty and rebuild her confidence. Today, as she works with entrepreneurs, she carries that lesson forward. She encourages women to build support systems with the same intention they bring to building careers or businesses. Success rarely happens alone. Community matters because none of us are meant to navigate life’s challenges in isolation.
Self-Awareness Before Entrepreneurship
Through her work supporting entrepreneurs, Shakenna has become convinced that understanding yourself is just as important as understanding your business.
Many people spend years developing strategies, plans, and goals while paying little attention to their own habits, fears, and motivations. Yet the challenges we avoid personally often show up professionally.
When working with entrepreneurs, she encourages them to think beyond their business plans. Do they understand their purpose? Are they resilient enough to navigate setbacks? Do they know what drives them? Do they have people around them who can provide support when things become difficult?
For Shakenna, self-awareness is not separate from success. It is often the foundation of it. The more we understand ourselves, the better equipped we are to influence, support, and inspire others.
Confidence Doesn’t Always Arrive First
Like many women, Shakenna’s journey has included moments of being overlooked. Despite her qualifications, experience, and ability to create impact, there were times when opportunities passed her by. Those experiences were frustrating, but they also revealed an important truth. Confidence does not always come before opportunity. Sometimes confidence develops afterwards. Sometimes it grows through experience, through setbacks, and through continuing to show up even when recognition is slow to arrive.
For many women, speaking about achievements can feel uncomfortable. Yet Shakenna learned that advocating for yourself is not arrogance. It is helping others understand the value you bring and the contribution you are capable of making.
Her story is a reminder that confidence is not about believing you have all the answers. It is about trusting yourself enough to keep moving forward.
What Shakenna Leaves Us Thinking About
- Leading often begins long before formal recognition.
- Mentorship can change the direction of a life.
- Community helps us navigate uncertainty and build resilience.
- Self-awareness is often the foundation for personal growth and influence.
- Confidence develops through experience, not perfection.
- Everyday experiences can shape the way we lead in ways we only recognise later.
Perhaps the most moving lesson from Shakenna’s story is that the foundations of leading are often built in ordinary moments. A conversation with a teacher, support from a mentor, a hallenge that forces us to grow. Or a fishing trip with a parent who sees something in us long before we see it ourselves. At the time, Shakenna thought she was learning how to catch fish. Years later, she realised she was learning how to lead.
To hear Dr. Shakenna K. Williams reflect on confidence, mentorship, resilience, entrepreneurship, and the experiences that shaped her approach to leading, listen to the full episode of the Women Emerging podcast.
