Conquering the Career Cliff: How Female Executives Are Embracing Small Business Ownership

For many women senior executives and professionals, hitting a "career cliff” can be one of life’s most daunting experiences. Whether it’s an unexpected layoff, the unexpected package (retirement package), or the growing dissatisfaction with the corporate grind, this point of transition often leaves high-achieving women at a crossroads.

Instead of seeing the career cliff as an ending, what if you viewed it as an opportunity—a launching pad into a new and fulfilling chapter? For countless aspiring entrepreneurs, especially senior women executives, the career cliff serves as the perfect time to take stock of their transferable skills and take the leap into small business ownership.

This is part one of a blog series exploring why small business ownership is an excellent path for those transitioning from corporate careers. We’ll discuss how to evaluate entrepreneurial potential and discover viable business opportunities along the way.

Part two will offer inspiration and actionable steps for embarking on this exciting journey. It will share best practices for transitioning from employee to entrepreneur and valuable resources to support aspiring small business owners from start-up to scale-up.

The Career Cliff Phenomenon

Many professionals, especially women, encounter the "career cliff" at critical moments in their journey—often triggered by a significant milestone, life event, or the unsettling realization that their worth is being undervalued. The term conjures the image of a summit where traditional career paths begin to level off, stagnate, or even descend—be it a gradual plateau, a steady decline, or a sharp drop. The career cliff often stems from external factors like organizational downsizing or societal biases related to age, making it a significant challenge for many high-performing professionals and an assault on their identity and self-regard. Other times, it’s driven by personal awakening—internal restlessness—emotional self-awareness and the realization that the corporate world no longer aligns with personal values or ambitions.

For senior women executives, the career cliff often comes with added challenges. Research reveals that women in leadership roles often encounter intensified scrutiny and diminishing opportunities for advancement as they age—often in the prime phase of their careers. They also face unfair judgment regarding their ability to return to work after illness or recovery, grappling with the persistent stigma surrounding these challenges. The combined impact of gender and age discrimination often leaves high-achieving women, brimming with potential and experience, questioning, "What comes next?"

But here’s the empowering truth: The career cliff doesn’t mean it’s time to stop climbing. It simply means finding a new mountain—one where you define your own path, set your own pace, and reap the rewards for yourself rather than an organization. It is the time to remaster your life and work based on what's best for you without jeopardizing what you have built for yourself.

Understanding the Appeal of Small Business Ownership

Small business ownership is not a backup plan for displaced professionals—it’s a vibrant, meaningful option that offers a wealth of benefits, including:

Independence: Say goodbye to office politics, rigid corporate hierarchies, and mandatory return-to-work policies. The power to make decisions, define your vision, and design a personal and professional life that seamlessly blends your needs allows you to achieve your priority of harmony between life and work.

Purposeful Work: Running your own business allows you to build something truly meaningful. Whether you're solving a problem, pursuing a passion, or contributing to your community, the sense of purpose it brings is unmatched.

Financial Control: While entrepreneurship comes with risks, it also allows you to reap the rewards of your efforts. Say goodbye to salary caps, restrictive performance reviews, and tight company budgets. Those who claim they cannot risk leaving the stability of a secure job must recognize that true job security no longer exists in the second decade of the 21st century.

Limitless Growth Potential: Unlike corporate roles, which can stagnate over time or keep you stuck in a role that is unfulfilling, owning a business offers continuous growth opportunities. These include scaling operations, branching into new ventures, and expanding one's personal and professional network. You are in control of your own professional development plan.

For many individuals, the most compelling part of entrepreneurship is the ability to run a business that aligns with their personal values and passions. Many women entrepreneurs strongly desire to lead and innovate in unique, transformative ways. Their motto? "Defining a Different Way."

Assessing Your Skills and Passions for Entrepreneurship

Transitioning into small business ownership begins with self-reflection. To build a venture that’s both sustainable and fulfilling, start by assessing your strengths, interests, and motivations.

Ask yourself these questions: 

• What am I most passionate about?
• Which skills and expertise have I honed throughout my career?
• What problems do I genuinely want to solve for others?
• How do I envision my ideal day-to-day as a business owner? My ideal week? My ideal year?

Cheryl Scoffield, founder of Kickstart Business Academy, turned her career cliff into an opportunity to help other professionals transition. In her 50s, she left her corporate job. She came to a striking realization: traditional employment would likely fail to recognize the full value of her skills and contributions, leaving her both unfulfilled and financially vulnerable. Cheryl leveraged her sales and branding expertise to coach others through LinkedIn optimization, technology adoption, and creating their own businesses.

Take inspiration from Cheryl and use your corporate experience as rocket fuel for your entrepreneurial dreams. The resources below explain Cheryl's call to action.

Identifying Viable Business Opportunities

Once you’ve pinpointed your passions and skills, it's time to determine how they translate into a viable business. Here are some areas to explore:

Freelancing or Consulting: Share your industry expertise by offering specialized services. Many corporations are eager to hire consultants for specific projects. This opportunity is ideal for individuals who excel at problem-solving, take initiative, and embrace accountability, all while enjoying the rewards of their success.

E-commerce: Got a knack for crafting or curating products? Platforms like Shopify make it easier than ever to start an online store.

Service-Based Businesses: Think about what skills you excel in—marketing, coaching, project management—and offer them as services tailored to your niche. A word of caution: simply setting up shop is not enough in today's entrepreneurial landscape. To succeed, you need to stand out. Establishing social proof and a clear, compelling differentiator is essential. Pursuing formal training and accreditation is highly advisable; without it, you risk being overshadowed by competitors and imitators.

Niche Markets: Explore gaps in the market. I’ve interviewed numerous women business owners, asking them "how" and "why" they started their ventures. Almost all shared a common story: they loved their work but noticed gaps in services that their employers were unwilling to address. These women courageously left employment and created their businesses to fill those gaps. Ironically, some went on to become trusted vendors for their former employers, addressing gaps that were once overlooked or underestimated.

Seize the Opportunity and Conquer the Career Cliff

The career cliff may feel intimidating, but it’s not the end—it’s a new beginning. It’s your chance to create something extraordinary, combining your career expertise, passions, and vision.

Still unsure? Start small—pilot your idea part-time before fully committing. Part two of this blog will help you prepare to transition from employee to entrepreneur.

Every great entrepreneur started with a single step. What’s your next step?

Whether you're still mulling over ideas or ready to execute your dream business, the first step is committing to yourself. Cheryl Scoffield and countless other successful women entrepreneurs have proven that the career cliff is less of a fall and more of a launch.

Ready to take the leap? Schedule a call with me to discover how I support new women entrepreneurs in building successful, purpose-driven businesses. Connect with Cheryl at Kickstart Business Academy to learn more about her services. Cheryl and I provide the tools and guidance you need to transition from employment to entrepreneurship with belief in yourself, financial clarity, and the systems you need.

Let’s kickstart your journey to a thriving business today! Experience self-actualization.

Your next chapter is waiting. Stay tuned for Part Two, "Navigating the Transition from Employee to Entrepreneurship"

Resources and Call to Action

Schedule an Executive Encore Complimentary Call with Patricia Muir

Schedule a Strategic Coffee Chat with Cheryl to learn about how to start your online business. Learn more about Cheryl's services at Kickstart Business Academy.