Career Pivot at 40? Here’s How to Find Courage! [W&S 79 ft Co-Founder Courage Chapter]

Embracing Courage: The Path to a Fulfilling Second Chapter

We delve into the profound topic of finding courage during life’s transitions and discuss the challenges and strategies around finding the courage to transition to a new phase of life.

The conversation centered around the concept of a “second chapter” – a major life or career shift that often occurs in the later stages of one’s professional journey. As Kai Ning explained, this transition is less about a specific age range and more about a shift in one’s career values and priorities.

“Second chapter is usually if you undergo a major life transition or like career transition, and usually it happens in a little bit of a later part in life. So after you have finished kind of like the bulk of your main career, you’re moving on to something else,” Kai Ning said. “And usually it’s, it, it encompasses a shift in career values as well.”


Kai Ning, the co-founder of The Courage Chapter, an organization dedicated to helping senior professionals navigate their second chapters through meaningful projects.

The Courage to Transition

Kai shares her perspective gaining from working with those seeking new purpose after lengthy careers. “I help seniors, though second chapter really refers more to a major life transition than age alone. If you’re moving to extend your career longevity, we can assist.”

This transition can take many forms, such as retirement, caring for aging parents or grandchildren, or simply a desire to explore new avenues after a successful career. Kai Ning emphasizes that the decision to embark on a second chapter requires immense courage, as it involves stepping into the unknown and potentially redefining one’s identity.

The Three Forms of Courage

According to Kai Ning, courage manifests itself in three distinct forms within the context of The Courage Chapter:

1. The courage of senior professionals: Overcoming the fear of venturing into uncharted territory after decades in the same industry or role.
2. The courage of companies: Embracing new employment models that meaningfully engage senior professionals, challenging age discrimination and outdated mindsets.
3. Personal courage: As a young professional herself, Kai Ning acknowledges the courage required to leave the traditional career path and pursue a purpose-driven venture.

Reggie astutely observes that courage is about “digging deeper into the strengths in you to overcome the fear of what you are seeing in front.” It’s about finding the inner resolve to confront challenges that initially seem daunting or overwhelming.

Lessons from a Trailblazer

Kai Ning shares an inspiring story about her mentor, a former Chief Marketing Officer (CMO) who made a bold career move at the peak of her success. “At around 50 years old, she was at the peak of her career, like she was the CMO and all that,” Kai Ning recounts. “But she realized that with every peak, right, it means that the next step is a fall.”

Rather than risk a gradual decline, this trailblazer chose to step back and reinvent herself, starting a coaching practice called “Reinvention Coaching.” Kai Ning admires her mentor’s clarity of thought and courage to pursue a new path while still maintaining her existing career.

The Power of Small Victories

Kai Ning introduces the concept of “micro-courage,” which involves intentionally seeking out and conquering small challenges throughout one’s life. These incremental victories can build resilience and self-belief, making it easier to tackle more significant obstacles down the road.

She cites the example of a former HR director who fearlessly embraced diverse gig opportunities, from freelance recruitment to museum work, displaying an admirable lack of ego and a willingness to adapt. “If it’s me, would I be able to do it?” Kai Ning ponders, acknowledging the inspiring resilience of individuals who can let go of their preconceived notions and societal expectations.

The Courage to Let Go

One recurring theme throughout the conversation is the courage required to let go of one’s identity and embrace change. Reggie shares her own experience of sacrificing her physical well-being to protect her child during a bike accident, highlighting the ability to act courageously even in split-second scenarios.

Ultimately, the guests conclude that cultivating an open-minded, adaptable mindset is crucial for navigating life’s transitions with grace and courage. By embracing a willingness to explore, learn, and grow, individuals can discover newfound purpose and fulfillment in their second chapters.

As Kai Ning aptly summarises, “If they succeed in their next chapter, right, it’s usually because they are very agile and very open-minded.”

This episode is for you if you are:

1. Individuals who have been retrenched or laid off and are looking to reinvent themselves.
2. Those who want to transition into caregiving roles, such as caring for aging parents or grandchildren.
3. Professionals who are burnt out or dissatisfied with their current careers and seek a more fulfilling path.

You can check their full interview on Wise & Shine, Episode 79 on Spotify, YouTube, Apple podcast for a thought-provoking exploration of the courage required to embark on a second chapter, even when one may not feel particularly courageous. The discussion offered a glimpse into the challenges and opportunities that can arise when professionals seek to redefine their purpose and create a lasting impact beyond their primary careers.

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