Meet Diane Wilbur · Founder, Retirement Fitness™
You’ve built a successful career. What do you want to build next?
I help accomplished professionals prepare for life after work—with a clearer sense of who they are, what matters, and how they want to spend their time.
My perspective brings together financial services, executive leadership development, and personal experience navigating an unexpected career ending.
Let’s Talk About What’s Next ↗
The perspective I bring
Experience that connects the financial plan to the person.
My background helps me understand both the preparation behind retirement and the personal questions that come with leaving work.
Leadership & Change
Understanding the person behind the title.
Former Head of Leadership Development, Fidelity Investments
More than 20 years coaching senior leaders through change, growth, and reinvention. I understand why leaving work can mean rethinking how you contribute, connect, and measure a good day.
Financial Perspective
Understanding what the plan makes possible.
Former CPA & Financial Advisor
I understand the discipline behind financial preparation. My coaching helps you clarify the life you want your resources to support, complementing the work you do with your financial advisor.
Retirement & Strengths
Turning self-understanding into direction.
Certified Professional Retirement Coach
Gallup-Certified Strengths Coach
Practical tools to help you identify what matters, build on your strengths, and create direction beyond work. Together, we turn reflection into steps you can begin taking now.
Why this work matters to me
I knew how to help people navigate change. Then it became personal.
“I’d spent years helping people navigate change. I was less enthusiastic when it became my assignment.”
I’ve worked since I was 12. Over the years, I moved from accounting and financial advice into sales leadership and leadership development. Work gave me challenge, connection, and a strong sense of contribution.
When my role ended unexpectedly, I was reminded just how much of daily life a career holds together.
The Monday after my departure, I opened my Outlook calendar. It was empty. No Zoom meetings. No deliverables. No one expecting me somewhere.
I had more freedom—and new questions about what I wanted to do with it.
That experience deepened my commitment to helping people prepare for the personal side of leaving work: who you are beyond your title, where you find connection, and what gives your days meaning.
Retirement Fitness™ brings my professional experience and personal perspective together to help you take practical steps toward what’s next.
Working together
Thoughtful reflection. Practical next steps.
You don’t need to arrive with a vision for the rest of your life. We start with where you are, explore what matters, and turn those insights into decisions and experiments.
Identify the abilities, values, and sources of satisfaction you want to carry forward. Your experience remains an asset.
Explore purpose, relationships, physical vitality, and a weekly rhythm that gives you both freedom and something to look forward to.
Use small experiments to explore interests, contribution, and connection—without turning retirement into another demanding job.
Talk through what you’re excited about, what you may miss, and where your expectations differ from those of the people closest to you.
Beyond the résumé
Making room for the life around work.
Time with my husband and our two adult children. Travel. Being on the water. A little adventure on an ordinary weekday.
These are some of the things I’m making more room for in my own next chapter.
I still love meaningful work. I also appreciate the freedom to decide when it fits—and when it’s time to get on the boat.
What would you like to make more room for?
Your next chapter
You don’t need every answer to begin.
Whether you’re approaching retirement, navigating an unexpected career change, or already wondering what comes next, let’s talk about where you are and the support that could help.
Schedule a Conversation ↗