Starting Early: A Retirement Roadmap for Midlife Women Leaders 5-10 Years Out

Retirement isn’t a finish line—it’s a doorway to what’s next. It’s the moment to step boldly into a new chapter, where your passions, purpose, and unrealized dreams finally take center stage.…Dr. Geneva

For years, I dreamed of becoming an entrepreneur.

I’d built a successful career as a nonprofit executive, raising millions and making an impact. Still, I had always had this unrealized dream of pivoting into the for-profit world and starting my own business.

When I finally reached a point where retirement seemed like an option, people would ask me, 'Are you retired now?' I’d laugh and say, 'I tried retirement for two weeks—didn’t like it.'

But the truth is, I’d been planning this pivot for a long time. Despite the challenges, I took the time to build a strategy and stayed determined to make this vision a reality. Now, as a business owner, I’m living out that dream—and it’s my best life chapter yet.

For many women leaders, retirement planning is less about ending a career and more about creating a new chapter. It’s a profoundly personal transition, often rooted in legacy and impact, and comes with its own challenges and dreams.

What if, instead of viewing retirement as “winding down,” we could see it as a chance to self-actualize—designing a life that fully expresses our passions and values?

“There is a whole new kind of life ahead, full of experiences just waiting to happen. Some call it 'retirement.' I call it bliss." – Betty Sullivan, pioneering chemical engineer

This article draws on real-life examples (with names changed) of women who took intentional, strategic steps to shape their futures. Some began planning five to ten years out; another started later, well into retirement. Each of these women pursued more than comfort—they embraced their desire for purpose, fulfillment, and a new sense of excitement in this next chapter.

Envisioning Your Ideal Retirement: More Than a Financial Goal

Retirement planning for women leaders goes far beyond financial readiness. It’s about asking: What will bring me joy? How will I leave a mark? How can I make these years not only meaningful but deeply satisfying? The stakes are high for women who’ve poured themselves into successful careers. Now, they’re asking, What’s next?

Coach and author Patrick Foley observed about retirement:

“It is a chance to redesign your life into something new and different.”

Client story: Consider Karen, a top healthcare executive in her early 60s, with five years left before retirement. Karen wanted financial security, yes, but also fulfillment. She’d always been interested in fashion and decided to explore it seriously, enrolling in a fashion design course. Did it turn out to be what she saw herself doing after retirement? No. But this experiment allowed Karen to clarify her interests, a powerful insight for anyone planning their next chapter.

The Strategy: It is critical to create a “game plan” early on. This is more than a vague outline; it’s a structured approach that includes identifying interests, experimenting with new roles, and exploring potential passions. For many women, building a meaningful retirement means exploring potential paths now, not later.

Financial Foundations: Preparing for Security and Flexibility

Financial planning may not be the most glamorous part of retirement preparation, but it’s one of the most essential. Women tend to live longer than men, and for midlife women leaders, the goal is to build a retirement that offers freedom—freedom to travel, explore new ventures, and live fully.

“Retirement is like a long vacation in Las Vegas. The goal is to enjoy it to the fullest, but not so fully that you run out of money.” – Jonathan Clements, financial journalist and author

Client story: Judy, another executive with a ten-year horizon, was thoughtful about her approach to retirement. She wanted to be a coach and mentor after retirement, drawing on her years of expertise. Together, we developed a strategy that helped her use her current high-level role as a foundation for her future. She began building her network, joining professional groups, and attending relevant courses, all with the future in mind. By leveraging her position now, Judy set herself up for the next phase while still earning an income.

The Strategy: Leveraging your existing circumstances... and money... for the future makes sense. So does developing a solid financial plan early on to help you feel more confident and secure. Consider crafting a “financial checklist” that includes everything from healthcare to potential future investments.

Start this forward-thinking approach now!

Discovering Your Passions and Building a Supportive Network in Retirement

Stepping away from a high-powered role can leave many women wondering who they are beyond their careers. Years of focusing on work and family often mean they haven’t paused to ask, What do I truly want?

Client story: Recently retired, Helen had poured herself into her career and family. But when work was no longer part of her life, she felt an unsettling emptiness.

She told me, “I wake up every morning wondering, What am I supposed to do now?”

Through our sessions, we worked together to help her uncover the passions she’d overlooked. We pinpointed what truly made her feel fulfilled, showing her how to shape her daily life around these new discoveries.

With her renewed love for art, Helen began volunteering at a local art program, where she found joy and expanded her social network, connecting with people who shared her interests.

The Strategy: It's never too late to identify and pursue your passions, whether pre-retirement or already there. Start by asking yourself:

• What activities or subjects have always intrigued me but I never made time for?
• If I could spend my days doing something I love, what would it be?
• What do I want my legacy to be, and how can I start building that now?
• What activities in my life right now bring me joy, fulfillment, or a sense of purpose—and how can I continue or expand these in retirement?

Together, Helen and I built a personalized plan that included actionable steps that make retirement an engaging, connected experience rather than an isolated one. Remember those networks you built while working? It's vital to keep connected with others in retirement. Find people who share your interests.

“The best time to plant a tree was 20 years ago. The second-best time is now.” – Chinese Proverb.

Conclusion: Make Your Next Chapter the Best One Yet

Retirement means more than leaving work behind. It’s the chance to step into a life full of new possibilities.

You’ve built a career—now it’s time to create a future with just as much meaning. Start planning today, not just with your finances but with your passions and dreams.

Don’t wait for the last day to think about what comes next.

Begin now.

Find what lights you up. Connect with others who share your interests. Make a plan that turns retirement into a time of joy, growth, and purpose.

This next chapter can be everything you want it to be—maybe even more.

What’s one unrealized dream you’d like to bring to life in your next chapter?

Vibrantly,

Dr. Geneva