As women leaders, we navigate a world filled with incredible opportunities but also distinct challenges that can sometimes feel overwhelming. Throughout my journey of mentoring and guiding women, I’ve identified ten key barriers that consistently stand in our way. These challenges are deeply rooted in societal expectations, systemic inequities, and the immense pressures we place on ourselves. But here’s the good news: they’re not insurmountable. With the right tools and mindset, we can transform these obstacles into stepping stones for growth and authentic leadership.

Let’s take a closer look at these challenges and how we can overcome them together.

1. Burnout and Overwhelm

Many of us feel the crushing weight of trying to “do it all.” We overwork, overachieve, and still worry that it’s not enough. To move beyond burnout, we need to embrace emotional regulation and energy management. I teach concepts like “The Millisecond Technique™” to help you pause, reflect, and respond thoughtfully instead of reacting impulsively. Setting boundaries and prioritizing self-care without guilt are also crucial for maintaining balance.

2. Lack of Confidence in Leadership Styles

For too long, women have been told that to lead effectively, we need to emulate traditional, masculine styles of leadership. But this pressure to suppress our natural tendencies toward collaboration and intuition leaves us feeling inauthentic. It’s time to embrace your feminine energy as a strength, not a liability. Through storytelling, experiential exercises, and real-world examples, I help women discover their unique leadership styles and lead with confidence.

3. Difficulty Setting Boundaries

Saying “no” can be one of the hardest things to do, but it’s essential for preserving our energy and focus. I often remind women that every “no” creates space for a more impactful “yes.” Visualizing boundaries as forcefields—a concept I call “Boundaries as Forcefields”—is a simple yet powerful way to protect your time and energy while staying aligned with your priorities.

4. Hustle Culture and Constant Busyness

Society glorifies busyness as a badge of honor, but it’s an exhausting and unsustainable way to live. I challenge this mindset by teaching women to balance effort with rest and alignment. Tools like “Playing Volleyball with the Universe” encourage you to partner with the flow of life rather than pushing against it. This shift creates space for joy and fulfillment, allowing you to pursue success on your terms.

5. Emotional Suppression and Lack of Emotional Intelligence

How often have you heard the phrase “leave your emotions at the door”? This outdated mentality disconnects us from our intuition and creativity. I encourage women to reframe emotions as strengths. By mastering emotional intelligence, you can navigate highs and lows with grace and use your emotions as powerful tools for connection and decision-making.

6. Living in Survival Mode

Many women feel trapped in survival mode, constantly reacting to demands without ever taking the time to design the lives they truly want. Shifting from reactive to proactive living requires clarity and focus. I share strategies and real-world examples of how to break free from this cycle and create a life driven by intention and purpose.

7. Navigating Patriarchal Systems

Systemic challenges in male-dominated environments are a reality we cannot ignore. Microaggressions, lack of recognition, and limited opportunities can wear us down. That’s why I focus on helping women lead authentically and advocate for themselves effectively. Building a community of like-minded women is also key to navigating these systems with strength and resilience.

8. Feeling Disconnected from Purpose

Even when we achieve great success, it’s not uncommon to feel a sense of emptiness or disconnection. Reconnecting with your purpose starts with introspection. I guide women through journaling exercises and frameworks to explore their passions and values, creating a leadership approach that integrates personal fulfillment with professional achievement.

9. Lack of Mentorship and Support

Leadership can be isolating, but it doesn’t have to be. Building a network of mentors and peers is one of the most powerful things you can do. In my work, I create opportunities for women to connect, collaborate, and learn from one another, tapping into the collective wisdom of a supportive community.

10. Fear of Taking Bold Risks

Fear is a natural part of stepping outside your comfort zone, but it doesn’t have to hold you back. Through tools like “The Courage Walk,” I help women build resilience and take intentional, aligned risks. Bold leadership often means doing the thing that scares you most—and discovering your greatest growth on the other side.

These ten challenges may feel daunting, but they’re also opportunities for transformation. By addressing them head-on, we can reclaim our authenticity, confidence, and power as leaders. My mission is to help women like you break through these barriers and lead with purpose, strength, and joy.

If you’re ready to explore these ideas further and take the next step in your leadership journey, I invite you to learn more at Lead Like a Woman.

When Kim Davis joined C-Sweet in early 2023, she was at a pivotal point in her career. After serving as CFO of Wilbraham & Monson Academy for a decade, she was stepping away in a few months to take care of personal matters and consider her next move. "I was contemplating what was next—whether to remain in the nonprofit world, transition back to corporate, or pursue something entirely new," she shared. At the recommendation of a colleague, Kim joined C-Sweet and soon discovered the Women in Transition group, a monthly forum designed to support executives navigating career changes. 

This group became instrumental in Kim’s journey. “It was a place where women contemplating career shifts or job searches could share their experiences and support one another,” she explained. With the help of expert coaches and peer discussions, Kim refined her personal mission statement, bolstered her confidence, and gained insights into networking and job search strategies—key tools for someone who had rarely needed to actively job hunt. “The idea of a job search felt overwhelming, but the group helped me clarify my priorities and navigate the process.”

While in transition, Kim worked as an interim CFO for nonprofits, weighing options between corporate and nonprofit opportunities. When a recruiter approached her about a role at the Sisters of Providence Ministry Corp. (SPMC), she initially declined. However, upon learning more about the organization’s impactful legacy—serving the community through elder care, transitional housing, and food security—Kim reconsidered. "It felt providential," she reflected. After a series of presentations to SPMC’s board—a process she admits was daunting—Kim was offered the role of President and CEO.

Reflecting on the support she received from C-Sweet, Kim emphasized how the Transition group helped her articulate her value and navigate the challenging board presentation process. “They helped me with soundbites, crafting my story, and building confidence in presenting my accomplishments. The group gave me clarity about what I truly wanted in my next role, helping me intentionally align my career path with my core values and aspirations—a decision I couldn’t have made without their support.”

As CEO, Kim now leads the organization through its own transformation, working to ensure the Sisters’ legacy of helping others endure for decades. “I’m humbled and inspired to be entrusted with their mission of hope and healing. This role is above and beyond what I envisioned for myself, and I feel truly aligned with their values.”

Kim’s journey is a testament to the power of C-Sweet’s community. “I’ve formed meaningful relationships with other members, and the programs are incredibly relevant to women in executive roles. Even though I can’t always attend in-person events, I feel connected to Beth, Dianne, and the network. Their enthusiasm and passion for supporting women is infectious.”

As C-Sweet prepares to embark on its 2025 theme of Women in Leadership, Kim's story exemplifies the transformative power of connection, support, and strategic career development. “I’m so grateful for C-Sweet. They’ve helped me see not only what’s next, but what’s possible,” she said.

When Wendy Fletcher joined C-Sweet in early 2024, she was at a significant turning point in her career. After serving as the Vice President of Finance at Playboy Group, where her work spanned team building, consumer business strategies, and financial planning, she was exploring what might come next. "I knew I was at the end of my role and wondered if I should pursue board positions or look for a new executive opportunity," she recalled. A recommendation led her to C-Sweet, where she found the support and resources she needed.

The Women in Transition group became a cornerstone of Wendy’s journey. The monthly sessions provided a confidential space for women to share their experiences, explore career aspirations, and receive expert coaching. "It wasn’t just about finding a new job," Wendy explained. "It was about understanding the barriers I faced and figuring out how to overcome them." The group's coaches helped her reframe her career narrative, refine her LinkedIn profile, and craft a compelling story, boosting her confidence in presenting herself as a valuable asset to prospective employers.

The skills and insights Wendy gained from the Women in Transition group played a crucial role in her decision to pursue a new leadership position. She now leads finance for a sports team and stadium preparing to lead the organization through significant transformational change. "This new role involves redesigning everything within the scope of finance, with a short to medium term focus on transforming processes and stabilizing the organization, while focusing on driving growth and profitability in the longer term,” she said. Wendy views this experience as an opportunity to build the skills and experience needed for future board positions. "It’s setting me up for the next phase of my career and will give me the additional heft to be attractive to boards in the future."

C-Sweet’s board readiness resources have also been valuable to Wendy. "I didn’t feel confident at first that I had what it took, but through C-Sweet, I’ve learned about the skills needed and how to prepare myself. It’s more than just sending out a resume; it’s about building the right experiences and connections," Wendy said.

Reflecting on her journey, Wendy emphasized the importance of community and mutual support. "The Women in Transition group wasn’t just about professional development; it was about forming relationships and supporting one another," she noted. The network she built within C-Sweet helped her stay accountable, share challenges, and celebrate achievements with peers who understood her experiences.

Wendy also expressed her gratitude for C-Sweet’s co-CEOs, Beth Hilbing and Dianne Gubin. "Their enthusiasm and dedication to the organization are truly inspiring. They’ve created a space where women in executive roles can find the resources and support they need to succeed," she said. "They are real champions for women, and their passion for C-Sweet is contagious. They make the C-Sweet community and its mission real for all of us."

For Wendy, C-Sweet has been more than just a professional network; it has been a place to grow, learn, and prepare for the future. Whether navigating transitions, seeking board opportunities, or expanding her leadership skills, the organization has provided invaluable tools and a supportive community. "It’s been a journey of self-discovery and professional growth," Wendy concluded. "I’m grateful for the guidance, the network, and the confidence I’ve gained along the way."

Wendy’s story exemplifies how C-Sweet’s Women in Transition group empowers executives to embrace change, enhance their skill sets and find clarity in the next steps of their careers. As she continues her journey, Wendy is more prepared than ever to pursue her goals and make a significant impact in her new role and beyond.

As leaders in the DEI space, we recognize the importance of evolving our strategies to meet the changing landscape. Recently, we sat down with Rachel Ann Williams, Chief Diversity and Inclusion officer at The Motley Fool for a discussion on the state of DEI programs on our podcast, C-Sweet Talks.. Rachel Ann offers invaluable insights and we believe that the future of DEI requires a multifaceted approach that goes beyond traditional methods. Rachel's emphasis on "quiet work"—auditing internal processes for equity without performative gestures—is a powerful reminder that real change often happens behind the scenes. This resonates deeply with our own philosophy at C-Sweet, where we advocate for a balanced approach that marries bold initiatives with subtle, systemic shifts.

However, the journey doesn’t stop there. As we look ahead, it’s crucial to expand the conversation to include not just underrepresented groups but also those who have traditionally held power. Engaging majority groups, particularly straight white men, in DEI efforts is not about diluting the focus but about broadening the impact. By making them active participants in the process, we can leverage their influence to drive meaningful change across the board.

Furthermore, in the realm of venture capital, where diverse networks are often lacking, it’s essential to both build connections and invest in those who already have them. As Rachel suggested, funding managers who are embedded in underrepresented communities is a practical step forward. But beyond that, corporate leaders must commit to long-term strategies that prioritize diversity not just as a goal but as a fundamental business imperative.

At C-Sweet, we see the path forward as one that embraces both innovation and inclusivity, ensuring that DEI is not just a checkbox but a cornerstone of corporate culture. As we continue to lead in this space, we encourage our peers to adopt a proactive, inclusive, and strategic approach to DEI—one that prepares our organizations for the complexities of tomorrow’s workforce.

Join us in shaping the future of DEI. Engage with C-Sweet’s leadership programs and resources designed to empower executives in creating inclusive and equitable workplaces. Let’s lead the charge together.