Kate Billing

Leaving The First Mountain

For many high-achieving midlife women, the early chapters of life have been dedicated to climbing what author David Brooks calls the “first mountain”: a path defined by external success – titles, income, influence, and recognition. It’s a journey often driven by necessity, resilience, and the pursuit of validation.​

However, as we reach midlife, a profound shift often occurs. The accomplishments that once brought pride may now feel hollow. The roles we’ve mastered no longer align with our evolving selves. As one senior women leader shared at our recent Pathmaker Community pre-launch event:​

“I spent 20 years building a career that looked perfect on paper. But inside, I felt like I was living someone else’s life.”

This sentiment is increasingly common. According to research by Phoenix Insights, one-third of professionals aged 45–54 anticipate making a significant career change before retirement. Yet, only 15% have received career advice in the past three years, highlighting a gap in support during this critical transition.​

The first mountain often serves as a survival strategy, a means to prove our worth and secure our place in the world. But as we evolve, so do our definitions of success. The climb that once felt purposeful may now seem misaligned with our true selves.​

This realisation isn’t a failure; it’s an invitation. An invitation to explore the “second mountain” – a path defined by authenticity, purpose, and inner fulfilment. It’s about shifting from external validation to internal alignment.​

If you’re feeling the stirrings of this transition, know that you’re not alone. Many women are navigating this journey, seeking deeper meaning beyond traditional and socially normed metrics of success.​

With our soon-to-be-launched Pathmaker Community, we will be extending our support of midlife women leaders in this transformative phase, offering guidance, development and community as you explore new horizons.

Because the second mountain isn’t just about climbing higher, it’s about finding a path that truly resonates with who you are becoming now.

QUESTIONS FOR YOU TO REFLECT ON:Over the Easter weekend I invite you to create 15–20 minutes of uninterrupted space to reflect on the following series of questions:

1. What did success look like to me in the first half of my life?
2. Who or what shaped that definition?
3. What has success cost me, and what has it given me?
4. What signals have I been receiving that it might be time to step off this mountain?
5. If I weren’t afraid, what would I explore next?

You don’t need to know what the second mountain looks like just yet.
That will become clearer as you move consciously and deliberately toward it.
This reflection is simply about honouring the truth of where you are now : )

Our Pathmaker Foundation Membership will be launching at the end of May. Learn more and join the waitlist HERE.

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