Retirement Fitness™ · Plan Beyond the Portfolio
Plan the life you’re retiring into.
You’ve given your career years of thought and effort. Your next chapter deserves preparation, too.
Retirement coaching helps you explore identity, purpose, relationships, and daily life after work—so you can move forward with clearer priorities and practical next steps.
Take the Free Retirement Readiness Scorecard ↗Financial advisor? Explore ways to partner →
Find your starting point
What brings you here?
For Individuals
What comes after a successful career?
Explore what you want to carry forward, what you’re ready to release, and how you want to spend your time.
Whether you’re planning your departure or finding direction after leaving work, coaching gives you space and support to consider what comes next.
For Financial Advisors
Help clients plan beyond the portfolio.
Support the personal side of retirement through specialized client coaching, educational events, and advisor training.
Connect the financial plan with the identity, purpose, relationships, and daily life your clients want to build.
The Retirement Fitness™ Framework
Financial readiness is the foundation. There’s more to prepare for.
Work provides more than income. It creates structure, connection, recognition, and a sense of contribution.
The Retirement Fitness™ Wheel brings five connected dimensions of life after work into focus.
Physical Vitality · Daily Structure
What we work toward
A next chapter you can begin shaping now.
Clearer direction.
Identify what matters, what you want to carry forward, and what you’re curious to explore.
More intentional days.
Create a rhythm with room for connection, contribution, learning, movement, and the freedom to choose.
Practical next steps.
Test ideas, learn from experience, and move forward without needing every answer in advance.
Meet Diane Wilbur
Finance. Leadership. Lived experience.
I’m a former CPA, financial advisor, and Head of Leadership Development at Fidelity Investments.
I bring more than 20 years of coaching experience and a personal understanding of what happens when a career ends sooner than expected.
Today, as a Certified Professional Retirement Coach and Gallup-Certified Strengths Coach, I help accomplished professionals prepare for life beyond work.
Meet Diane →Resources for Financial Advisors
Better Conversations™
Practical retirement questions, listening cues, and follow-up prompts for understanding the person behind the plan.
Browse the Conversation Guides →“What are you retiring to?”
Start with a clearer picture
How ready are you for the life you’re retiring into?
Begin with the free Retirement Readiness Scorecard™ and identify what deserves your attention next.
Take the Free Scorecard ↗Ready to talk? Schedule a conversation ↗