What Happens When Career Achievement Stops Feeling Fulfilling
After nearly a decade helping build a fintech company from the ground up, I reached a point few people talk about—the quiet moment when achievement starts to feel like autopilot.
I loved the work.
I loved the people.
And by most measures, I was at the height of my career.
But underneath all the success, a new question started to surface—not “What’s next on the ladder?” But “What’s next for me?”
That single shift changed everything.
The Comfortable Plateau
At Best Egg, I had the privilege of helping lead an incredible team through startup grit, scale, and transformation. We earned national recognition for customer experience and culture. We built products that mattered. We built a brand.
For a long time, that fueled me. But slowly, something shifted.
The spark was still there but it flickered differently. The energy that once propelled me forward started pulling me inward. It wasn’t about leaving something behind. It was about moving toward something new.
That realization can be unsettling, especially for high achievers. When you've spent 20+ years building and doing, it takes real courage to pause, to question, and to listen to what you actually want.
The Turning Point
The seeds of change were planted years before I acted on them.
I watched my mom reinvent herself at 62, leaving behind a 40-year business to run for public office. Not because she had to—but because she wanted to make a difference. And she did. Those years turned out to be the most fulfilling of her life.
Her story stayed with me.
So when my kids neared the end of their college journeys and my financial obligations started to ease, I realized I finally had something I hadn’t in years: Freedom.
Freedom to take more risk.
Freedom to explore new ideas.
Freedom to ask: What if there’s more?
I had startups I wanted to explore, causes I cared about, and a growing fascination with the intersection of AI, strategy, and purpose. But I didn’t have a roadmap.
So I did what I always do when I’m curious.
I researched. I reflected. I journaled. I talked to peers. I hired a coach.
And while helpful, I kept running into the same challenge: the tools out there were either too generic or too expensive. I couldn’t find anything that blended clarity, strategy, and affordability in one place.
That gap—that missing piece—became the spark behind Find My Chapter 3.
Understanding the Three Chapters of a Career
I reflected a lot on my career journey, the highs and lows and everything in between. I thought about my mom’s journey and I started to frame a general story that now shapes how I think about career evolution—Chapter 1, 2, and 3.
Chapter 1: The Learning Years.
You’re building your skillset, testing what fits, and discovering where you can thrive. It’s a season of exploration—sometimes exhilarating, sometimes exhausting—but it’s how you find your footing.Chapter 2: The Earning Years.
You’ve narrowed in on what you do best and where you drive value. You take on more responsibility, make more money, and climb whatever ladder you’ve chosen. For many, this chapter spans decades.Chapter 3: The Returning Years.
You’ve accumulated experience, credibility, and a measure of financial freedom. But now, the question isn’t “What’s next on the ladder?” It’s “What matters most?”
I believe this is when you begin to return—return to passions, purpose, or the impact you’ve always wanted to make but never had the space to pursue.
Redefining Success
When you’ve built your identity around achievement, it’s easy to confuse success with pace:
How fast you move. How much you produce. How high you climb.
But clarity taught me something different.
Success isn’t acceleration.
It’s alignment.
I didn’t want to run faster, I wanted to run truer.
I wanted flexibility. Creativity. Purpose on my terms.
I wanted work that sparked curiosity, not just responsibility.
That mindset shift led me to unexpected places—like spending hours each week experimenting with new AI models, fascinated by how technology can amplify human potential rather than replace it.
Building My Chapter 3
Eventually, I stepped away from corporate life and built something new:
Find My Chapter 3, a platform that blends AI and expert coaching to help mid and late-career professionals find clarity, confidence, and reinvention.
At the same time, I joined 2nd Careers, continued advising startups, and leaned into board work, strategy, and service. My weeks now reflect the alignment I craved—where creativity, impact, and energy converge.
I’m still working hard—just differently.
And for the first time in a long time, I wake up curious about what’s next—not anxious about it.
Looking Ahead
When I talk to mid-career professionals today, I see that familiar look—the quiet restlessness that comes after years of success.
They’re not lost.
They’re just ready.
Ready to reconnect with purpose.
Ready to design work that fits who they’ve become.
Ready to write a new chapter—intentionally.
If that’s you, know this:
You don’t need the full plan.
You just need to pay attention.
Clarity doesn’t come all at once—it builds through reflection, curiosity, and the courage to ask hard questions before life forces you to.
That’s why I created Find My Chapter 3—a space to explore what’s next with more intention and a lot more heart.
Because your next chapter isn’t behind you.
It’s waiting to be written.