Individual Retirement Coaching
You’ve built a successful career. What comes next deserves a plan, too.
Retirement coaching for accomplished professionals who want to move into life after work with direction, connection, and a sense of purpose.
Start with the Retirement Readiness Scorecard™ to reflect on the personal side of retirement and identify where you want to focus.
Start with the Free Scorecard ↗The questions behind the decision
“I’m ready for more freedom. Am I ready to leave the role?”
“Where will I find challenge, connection, and contribution?”
“What does success look like when it’s mine to define?”
Redefining success
Define success when work no longer defines the score.
For years, progress may have been measured through responsibility, results, recognition, and the people who relied on you.
Retirement gives you more freedom to choose. It also asks you to decide what makes your time feel worthwhile.
Identify the challenge, learning, relationships, and contribution you want to carry forward.
Consider which demands, expectations, and measures of success you’re ready to leave behind.
Explore meaningful commitments alongside adventure, relationships, and rest— without filling every space on the calendar.
The Retirement Fitness™ Framework
Five dimensions of life beyond work.
A fulfilling retirement involves more than a financial decision. The Retirement Fitness™ Wheel brings five connected dimensions into focus, supported by the foundation of financial security.
Recognize who you are beyond your career and what you want to carry forward.
Explore what gives you meaning, direction, and a sense of contribution.
Strengthen important connections and make room for new ones.
Make room for movement, energy, and the activities you want to enjoy.
Create a flexible rhythm that gives your time intention without overscheduling it.
Coaching helps clarify the life you want your resources to support, complementing your work with a financial advisor.
Your first step
Start by taking stock.
The Retirement Readiness Scorecard™ offers a starting point for thinking about the life you’re preparing to retire into.
Use it to notice what feels clear, where you have questions, and what you want to explore further.
Take the Free Retirement Readiness Scorecard ↗Reflect on your readiness for the personal side of retirement.
Identify what you want to strengthen, understand, or begin changing.
If you’d like support, bring your reflections to a conversation with Diane. We’ll discuss whether coaching is a fit.
Schedule a conversation ↗What we work toward
Turn reflection into decisions and action.
A clearer direction.
Identify what you want to keep, release, and create beyond work. Develop priorities grounded in your values and strengths.
A workable weekly rhythm.
Build a flexible framework for connection, contribution, learning, movement, and rest. Try it, then adjust it to fit your life.
Possibilities you’ve tested.
Explore mentoring, volunteering, learning, projects, or continued work through small experiments before committing.
Conversations you’re ready to have.
Clarify expectations about time, relationships, and independence. Prepare to discuss what matters with your partner and financial advisor.
Why Retirement Fitness™?
A coach who understands the person behind the career.
Diane Wilbur brings together financial services experience, leadership development expertise, and firsthand understanding of an unexpected career ending.
A former CPA and financial advisor, Diane understands the preparation behind the financial plan—and helps you clarify the life you want it to support.
As the former Head of Leadership Development at Fidelity Investments, she brings more than 20 years of experience coaching senior leaders through change.
A Certified Professional Retirement Coach and Gallup-Certified Strengths Coach, Diane combines thoughtful questions with tools, experiments, and accountability.
Questions you may have
Before you begin.
What is retirement coaching?
Retirement coaching helps you prepare for the personal side of life after work: identity, purpose, relationships, daily structure, and practical next steps.
Who is individual coaching for?
Retirement Fitness™ provides retirement coaching for executives and accomplished professionals approaching retirement, facing an unexpected career ending, or finding direction after leaving work.
Do I need a retirement date?
No. You can begin while you’re considering your options. Coaching helps you explore what you want from work and life without pushing you toward a particular decision.
What happens after I take the Scorecard?
Use your reflections to identify priorities. If you’d like help exploring them, schedule a conversation with Diane to discuss your goals and the available coaching options. Taking the Scorecard does not commit you to coaching.
Does coaching include financial advice?
Coaching helps clarify the priorities your financial plan should support. Investment, tax, and legal advice remain with your qualified advisors.
What does individual coaching cost?
We’ll discuss coaching options, scope, and investment during our introductory conversation so you can consider the right support before committing.
Start with a clearer picture
How ready are you for the life you’re retiring into?
Take the Retirement Readiness Scorecard™ and begin identifying what deserves your attention next.
Start with the Free Scorecard ↗Already completed it? Let’s discuss your next step ↗