Ambition Meets Contentment: Redefining Fulfillment

For decades, the path was clear. You climbed the ladder, chased the title, and defined your worth by your proximity to the corner office. But what happens when the ladder disappears?

As high-achieving women transition into their "encore years", whether that means consulting, entrepreneurship, or non-profit leadership, they often face a startling question: Who am I without the title?

In a recent episode of Executive Encore, I sat down with motivational speaker and career coach LaPora Lindsay to tackle this identity shift head-on. We explored how to balance gratitude with growth and why leaving the corporate world doesn’t mean leaving your ambition behind.

Here are three transformative insights to help you navigate your next chapter without self-doubt.

1. You Can Be Both Content and Ambitious

One of the most persistent myths women executives face is the idea that contentment is the enemy of ambition. We fear that if we pause to appreciate where we are, we’ll lose our edge or "settle."
LaPora challenges this polarization. She argues that contentment isn't about stopping; it's about gratitude. Ambition, on the other hand, is about openness to what’s next.

Think of Oprah Winfrey. Before she became a global mogul, she practised deep gratitude for her early roles while remaining open to future alignment. Rather than resenting her present to fuel her future, she utilized it as her foundation.

Key Takeaway: 

• Embrace the "Gap and the Gain." Instead of obsessing over how far you have to go (the gap), look backward to measure how far you’ve come (the gain).
• Gratitude fuels growth. You can love your current life and still strive for a new legacy. They are partners, not competitors.

2. Owning Your Value Beyond the Ladder

In the corporate world, value is often external - the budget you manage, the team size you lead, or the title on your business card. When you step into your encore life, those external markers vanish. This can lead to a crisis of self-doubt.

It is crucial to distinguish between Self-Worth and Workplace Value.

Self-Worth is internal and constant. You are worthy simply because you exist.

Workplace Value is about contribution and translation. It’s not just about working hard; it’s about translating your unique skills into something your new environment (or client) values. Workplace value can become relevant in your new venture if you are transitioning into a new career path, volunteer work, or venturing into entrepreneurship in your encore.

LaPora shared a story of a client who was highly productive but felt undervalued. The disconnect? The client was focused on output, while the organization valued relationship building. Once she aligned her actions with what the environment valued, her sense of worth in that role skyrocketed.

Key Takeaway:

• Detach identity from titles. Your value lies in your wisdom, resilience, and unique perspective, not your rank. 
• Translate your skills. In your new venture, focus on what your clients or partners value most, not just what you are used to producing.

3. The "How" of Comparison: From Envy to Inspiration

"Don't compare yourself to others." I am constantly reinforcing this mantra with clients, colleagues, and friends. But let’s be honest, in the age of social media, it’s impossible not to notice when a peer launches a successful consultancy or travels the world while you’re still figuring out your next step in life, or your next move in establishing a new professional life.

Comparison itself isn't the problem; it’s how we compare that trips us up.
LaPora admits that early in her business, she was told not to follow certain strategies for growing it. She compared her path to the "experts" and felt she was doing it wrong. But when she followed her gut - and succeeded - she realized that everyone’s "behind the scenes" looks different.
Instead of letting comparison breed envy, use it as an observation and research tool.

Key Takeaway:  

• Use LaPora's signature "PADA" method. Analyze what others are doing. Don't imitate; emulate. Ask yourself: What do I like about their approach? What can I adapt for my own journey? 
• Turn envy into data. Observe and research. If you feel a twinge of jealousy, it’s just data telling you what you truly want. Use it to fuel your own transformation.

Your Encore is Just Beginning

Transitioning from a high-powered corporate role to a life of flexible, meaningful work is not a step down; it is a step toward alignment. You have the freedom to redefine success on your own terms, blending your vast experience with a renewed sense of purpose.

Are you ready to stop climbing the proverbial ladder and start thriving on your own path?

Join the Conversation:
I’d love to hear how you are redefining success in your encore years. Are you finding it hard to balance contentment and ambition? Let’s thrive with purpose, together.