Embracing Courageous Leadership With Lisa B, the Life Changer

Starting and running a business can be frightening even for the bravest among us. It takes a special kind of grit to face the uncertainties and challenges you encounter on the road to startup.

Recently, Ramon Ray chatted with Lisa Blackmon, Esquire — aka Lisa B, the Life Changer — about how crucial courage is for business leaders. Lisa, who helps individuals become more courageous leaders, has a background in law and over 25 years of experience in running her own business. In this article, we’ll dig into Lisa’s insights, giving straightforward tips for entrepreneurs to be brave leaders and enhance their skills.

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Why Courageous Leadership Matters

Considering the nature of entrepreneurship, you can understand why courageous leadership is essential. Starting and growing a business requires taking risks, not playing it safe. “You have to be courageous to make a change,” says Lisa.

Often, making changes involves pushing beyond current boundaries to reach new heights. Whether in the corporate, nonprofit, or collegiate space, Lisa encounters leaders who know they need to get to the next level — not only to grow their organizations but also to leave a legacy for future generations.

So, if leaders know they need to make changes, what holds them back? It isn’t just fear that comes into play. Self-doubt, past experiences, victim mentality, mindset, and input from well-meaning family and friends can all hinder success.

“It takes courage to want to be a better version of yourself and then begin to make the steps,” Lisa acknowledges. “We had a first day of everything, right? And sometimes our hands were shaking. Our heart was beating fast. Maybe our voice even began to shake. And so we have to really have the tools that are necessary to move anyway.”

Action tip: Identify areas in your business that need to change, and commit to making courageous decisions. Reflect on your self-talk and challenge negative narratives, pushing yourself to embrace discomfort for growth.

Recognizing the Ebb and Flow of Professional Connections

Drawing from her extensive coaching experience, Lisa urges entrepreneurs to pause and take stock of their professional connections. According to Lisa, relationships, like seasons, can serve distinct purposes in our journey.

Lisa emphasizes the necessity of evaluating your current network with a discerning eye — and recognizing when individuals have fulfilled their roles in your professional life. As you evolve and your goals shift, so should the composition of your support network.

Action tip: As you reflect on whether existing relationships align with your current goals and aspirations, ask yourself:

  • Is this connection still contributing to my professional growth?
  • Does this relationship align with my current business objectives?
  • Have the dynamics of this relationship evolved along with my entrepreneurial journey?
  • Is there mutual value and reciprocity in this professional alliance?
  • Are there new goals or challenges where I might need different perspectives or support?
  • Does this connection foster a positive and conducive professional environment?
  • Have I outgrown certain aspects of this relationship, and is it hindering or aiding my progress?

Asking these questions provides a structured approach to evaluating your professional connections, ensuring your network aligns with the evolving seasons of your entrepreneurial journey.

Building Trust and Delegating

Entrepreneurs can learn from Lisa’s coaching experience, focusing on building trust and delegating tasks. Lisa encourages entrepreneurs to confront the fear of relinquishing control and embrace the power of collaboration.

Lisa shares an example from a recent client who struggled to let go of the reins despite her successful entrepreneurial tenure. Because she was reluctant to delegate, she grappled with handling every aspect of her business.

Despite a satisfactory bottom line, the client found herself overworked and limited in her ability to expand. Lisa’s coaching intervention focused on instilling trust in others and delegating tasks. This transformation allowed the entrepreneur to transition from being immersed in daily tasks to expanding her business.

Action tip: Identify tasks you can delegate within your team. Begin by assessing your current workload and pinpointing tasks others can handle effectively. Trusting your team alleviates your burden and empowers your colleagues to contribute to the collective vision.

Confronting Obstacles with Lisa’s FACT System

Entrepreneurs often encounter internal barriers, hindered by fear, doubt, and the looming shadow of past setbacks. The fear of rejection, often rooted in past experiences, can be a significant roadblock, preventing individuals from taking the necessary steps toward growth. Moreover, the tendency to forget past successes can diminish self-confidence and hinder progress.

In response to these common challenges, Lisa shares a defining moment in her own journey after facing the daunting bar exam multiple times. This experience led her to formulate the FACT system — encompassing faith, action, courage, and tenacity.


At the core of the FACT system is faith — a foundational belief in oneself and the journey ahead. Lisa emphasizes the importance of cultivating unwavering faith as a precursor to overcoming challenges.


Following faith, the FACT system advocates for decisive action, translating beliefs into concrete actions and moving beyond intentions to tangible steps forward.


Lisa identifies courage as an integral component. Entrepreneurs must summon the bravery to face fears, confront doubts, and tackle challenges head-on. Courage becomes the catalyst for change.


The final pillar of the FACT system is tenacity — the resilience to persist despite setbacks. The entrepreneurial journey is seldom linear, and tenacity ensures the stamina to endure and evolve.

Action tip: Integrate the FACT system into your mindset, using it as a framework to navigate obstacles and foster personal and professional growth. By acknowledging fear, embracing faith, taking decisive action, summoning courage, and maintaining tenacity, you can break free from self-imposed limitations and chart a course toward success.

Are You Ready to Be Courageous?

Courageous leaders are not bystanders; they are active participants in their evolution. As you absorb Lisa B’s tips and anticipate the road ahead, remember that the journey toward courageous leadership is a continual process — a series of bold steps that promise growth, impact, and the realization of your fullest potential.

Being an entrepreneur requires overcoming self-imposed limitations and claiming your rightful seat as an effective leader. If you’re ready to take the next steps, visit Lisa B’s website at for additional resources and guidance on developing a courageous leadership style.

Read: The Best Way to Practice Transformative Leadership in Your Business

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