Part 1: Recognizing When Success Starts Feeling Hollow
🌿 THE NEXT CHAPTER JOURNEY: A three-part series for accomplished leaders redefining what success looks like next
Nine years ago, I left the company I founded.
On purpose. At the peak. While everyone told me to stay.
My social enterprise was thriving. $5 million in annual revenue (top 1% of women-owned businesses in the U.S.). Eighty countries. Millions of lives impacted. We'd created the Global Youth Economic Opportunities Summit, the go-to convening for 250+ institutions from 55 countries.
The team was strong. The work was meaningful.
And I walked away.
My colleagues thought I was making a mistake. My CFO asked me three times if I was sure. Friends and clients wondered if I was having a crisis.
Not because I was burned out. Not because we were failing.
I left because we were succeeding.
Here's what I've learned about strategic exits: The best time to leave is often when no one thinks you should. When you're still building momentum, not trying to recover it. When you can hand over something valuable, not something that needs saving.
Leaving at the peak gave me the freedom to ask: What's next? What else am I meant to build?
That question led me to create the WILD Network (Women for Impactful Leadership Development), which now connects 25,000 purpose-driven leaders across 100 countries. To teach at Georgetown University McDonough School of Business, where I get to shape how the next generation thinks about leadership and social innovation. To launch the Next Chapter Accelerator, helping accomplished women navigate their own pivotal career transitions. And to write a book (coming March 2026) about how accomplished professionals navigate professional setbacks and reinvention.
Everything I'm doing now only exists because I chose to leave when I could have stayed.
The greatest act of leadership isn't holding on. It's knowing when your next contribution lies somewhere else.
WHEN SUCCESS STOPS FEELING LIKE SUCCESS
Since I shared that story publicly, hundreds of leaders have written to me. The patterns are remarkably consistent:
"I'm in that same place. Successful on paper, but feeling the pull toward something different."
"I thought I'd feel more fulfilled once I reached this level."
"I'm not burned out. I'm just... done with this version of success."
Some wonder if that feeling means they're restless. Ungrateful. Losing their edge.
That pull you're feeling isn't a problem. It's evolution.
TWO SIGNS YOU'RE READY FOR WHAT'S NEXT
Not everyone experiences transition the same way, but these patterns show up consistently among accomplished women ready for what's next:
1. You're asking different questions
You find yourself asking "How do I want to spend my energy now?" instead of "What's the next thing I can conquer?"
After building Making Cents for eighteen years, I became obsessed with a different question: How do women leaders persevere when they face not just standard CEO criticism, but an entirely additional layer of scrutiny?
Male CEOs get criticized for strategic decisions, financial performance, market positioning. But women leaders face all of that, plus commentary on how they dress, whether they have childcare help, if they're too aggressive or not assertive enough, too emotional or too cold.
This double standard fascinated and frustrated me in equal measure. I watched accomplished women in my network navigate this impossible calculation: how to lead effectively while managing criticism that had nothing to do with their actual competence.
That's what pulled me toward creating WILD. I wanted to build a space where women leaders could share the real challenges of leadership without pretending the gendered criticism doesn't exist, and without letting it define them.
2. You're looking for something different
"Different" varies. Here are the five patterns I see most often:
At a career high point: Thinking about "one more big role" before shifting pace or focus.
In a life transition: Having stepped back for health, caregiving, or other priorities, and now seeking clarity on what's next.
Leading with purpose: Currently in influential roles and wanting to take their leadership (and impact) to the next level.
Reimagining their work: Ready to pivot toward a portfolio career or entrepreneurial venture that offers more variety and autonomy.
Redefining retirement: Entering a new phase of life and wanting to design it around their true aspirations and practical realities.
These patterns emerge at mid and late career for a reason. You've proven yourself. You've achieved the markers of success you were chasing. Now you have the luxury of asking deeper questions: What do I actually want? What impact do I want to leave? How do I want to spend the decades ahead?
These aren't mutually exclusive. Many leaders I work with are navigating two or three of these simultaneously. What they share is intentionality about what comes next, even when the specifics aren't yet clear.
The common thread? You're not running from something. You're designing toward something.
YOU'RE NOT ALONE IN THIS
If you're at a crossroads like this, you're in good company. The most successful leaders I work with are asking these same questions, often for the first time in their careers.
The difference between women who thrive through transition and those who stay stuck? Clarity to recognize what's happening. Courage to move without a complete map. Community to remind you that reinvention is possible.
🌿AN INVITATION
If this reflection resonates, you might appreciate the Next Chapter Accelerator. It's not another leadership program. It's a space where accomplished professionals (men and women) get clarity through a structured process that brings clarity, courage, and community.