How to Design Your Career Chapter 3 While Still Thriving in Chapter 2
Strategic career planning for mid-to-late career professionals looking ahead to their next meaningful role
The Question Everyone Asks: "What's Next?"
When I announced I was leaving Best Egg after nearly a decade, one question kept coming up: "So... what's next?"
The honest answer? I didn't know exactly.
But here's what I did know: I had been thoughtfully planning for Chapter 3 for years—while still fully engaged in Chapter 2.
Two years before making my move, I hired a career coach to help me navigate this question. It was a significant investment of both time and money, but it provided clarity on what I wanted and what I didn't. More importantly, it gave me a decision-making framework I could trust when the pivotal moment arrived.
That's what I want to share today: Why shaping your next professional chapter before you need it can transform your career trajectory—and how to begin this process with intention.
The Power of Proactive Career Reinvention
Too often, career reinvention happens reactively: following a job loss, reorganization, burnout, or persistent restlessness. But reinvention becomes significantly more powerful—and far less chaotic—when approached intentionally.
Your "Chapter 2" (those peak years of leadership, operating, and building) offers a unique window to start crafting what's next because:
You have credibility earned through demonstrated success
You have access to networks and opportunities
You have a platform from which to explore new interests
You likely have the financial resources to invest in your future
What you may not have yet is clarity. That requires mental space, deliberate experimentation, and a fundamental mindset shift.
The Strategic Chapter 2 → Chapter 3 Framework
This isn't a rigid process—it's a mindset and approach. Here's how I recommend thinking about it, drawn from my own experience and from mentoring other mid-career professionals navigating the same transition.
1. Clarify Your True Drivers
Get grounded before you get going by examining:
Your proven strengths — Use performance reviews, peer feedback, 360s, and assessments like DiSC or StrengthsFinders to gain perspective.
Your core values — What matters to you now that might not have five years ago?
Your ideal working style — Full-time executive? Fractional leader? Advisor? Creative independence?
Your personal interests — Is there space for them to play a more central role?
Your energy patterns — What energizes you now that didn't before? What drains you that once fueled you?
Start a living document to track these insights and patterns. This becomes the foundation for finding truly fulfilling work in your next chapter.
2. Experiment While You Have Stability
Try on potential future roles before committing fully:
Host a roundtable discussion on a topic that genuinely interests you
Mentor someone in a field you're curious about exploring
Accept speaking invitations or advisory roles in adjacent spaces
Join boards or committees that align with emerging interests
These small "test runs" provide invaluable data about what truly fits—and what doesn't—without requiring a complete career pivot.
For example, in the photo you see, I am participating on a panel discussing being a woman leader in financial services at an AWS event. This was one of my “test runs.”
3. Build the Capabilities and Network You'll Need Later
Want to become a board member? Start learning governance language and principles now. Considering executive coaching or angel investing? Begin participating in those communities today.
Your Chapter 2 position provides the perfect platform to plant seeds for future growth—and discover which ones naturally flourish.
4. Define Success on Your Own Terms
This is simultaneously the most personal and challenging aspect. Success in Chapter 3 may look entirely different from Chapter 2.
It might mean:
Greater autonomy and flexibility
More meaningful impact in specific areas
Better alignment with your evolved values
Integration of multiple interests and skills
The key is: define success for yourself before external expectations define it for you.
Why This Matters Now More Than Ever
The professional landscape is transforming rapidly—and so are our relationships with work. The linear career path has disappeared. What replaces it are series of meaningful chapters, each shaped by our evolving values, priorities, and aspirations.
If you're currently in Chapter 2, you're not behind—you're perfectly positioned to design what's next with intention rather than reacting to circumstances.
Let's Navigate This Journey Together
If you're contemplating your own next chapter, I'd welcome the opportunity to connect. I've walked this path—and continue to navigate it myself.
I'm currently exploring how AI tools can support mid-to-late career professionals through this transformation process. There's tremendous potential to combine human insight with technological capabilities to make career transitions more intentional and fulfilling.
Ready to start planning your Chapter 3?