Plan the life you are retiring into
Retirement Fitness™ helps prepare high-performing professionals for the personal side of retirement-the shift in identity, purpose, relationships, daily structure, and well-being that begins when a career ends.
Why we exist
Financially ready does not always mean “retirement ready”.
A career provides more than income. It creates identity, structure, relationships, recognition, and purpose. When work ends, those foundations can shift at once—even for people who are financially secure.
Retirement Fitness™ helps individuals prepare for the life ahead—and equips financial advisors to guide the human conversations that financial planning alone cannot address.
Because retirement requires more than enough money. It requires a life you are ready to live.
Our approach
Financially ready is only part of the plan
While advisors focus on financial readiness, we prepare clients for what comes next- the psychological, emotional, and lifestyle transition that follows.
High achievers often underestimate the impact of stepping away from long-held roles, structure, and professional identity. Success has provided rhythm, purpose, and recognition. Without intention, this shift can create uncertainty, disengagement, and a quiet loss of direction.
Our work creates space for honest reflection and forward-looking structure. We help clients redefine identity beyond title, strengthen relationships, build healthy daily rhythms, and develop a roadmap for a purposeful next chapter.
Retirement is not simply a financial milestone.
It is a life redesign- and it deserves preparation.
Outcomes: Providing you with tools to transition smoothly
Our work helps retirees plan the life they are retiring into by focusing on the mental, physical, social, and spiritual dimensions of a fulfilling retirement lifestyle. The result is a smoother transition, greater clarity, and clients who are more confident, grounded, and engaged—benefiting both the retiree and the advisor relationship.
Individual & Couples Coaching
Personalized Strategy for Life Beyond Work
Our private 1:1 coaching engagements provide confidential, strategic partnership for accomplished professionals who want to approach retirement with intention, clarity, and confidence. This is not casual conversation. It is structured, forward-focused work designed to help you transition thoughtfully into your next chapter.
About
A perspective shaped by both sides of retirement planning.
I’ve spent more than two decades working with senior leaders at moments of significant transition: promotions, restructures, reinvention, and change. What experience has shown me is this- the most complex transitions are rarely professional. They are personal.
Retirement is one of them.
While retirement is often framed as a financial milestone, it is equally a psychological and identity shift. Stepping away from long-held roles, structure, and recognition can create uncertainty that few high achievers anticipate.
Earlier in my career, I worked as both a CPA and financial advisor. I have deep respect for financial preparation — and a clear understanding of its limits.
Retirement Fitness™ supports accomplished professionals through the non-financial side of retirement — the part no one talks about. We create space for honest reflection, challenge limiting patterns, and build a clear roadmap so this transition becomes intentional- strengthening health, relationships, and purpose for what comes next.
I work exclusively with high achievers who are ready to approach this chapter with the same thoughtfulness and discipline that defined their careers. My role is not to reinvent you - it is to help you redeploy your strengths, redefine identity beyond title, and design a life structure that sustains clarity, engagement, and meaning.
Retirement isn’t an ending.
It is a life redesign - and it deserves preparation.
Diane Wilbur
Founder, Retirement Fitness™
Former Head of Leadership Development, Fidelity Investments
Over 20 years coaching senior executives
Former Registered Financial Advisor & CPA
Certified Professional Retirement Coach-CPRC
Certified Clifton Strengths Gallup Coach
Who we work with
Individuals & Couples
We help pre-retirees prepare for retirement beyond the numbers. Through personalized coaching and structured programs, we guide you in redefining purpose, identity, relationships, and daily life after work — so you move into retirement with clarity, confidence, and a plan for a fulfilling next chapter.
Financial Advisors
By working together, we deliver a truly comprehensive retirement experience. We help clients prepare emotionally, socially, and psychologically for life after work — leading to more confident decisions, stronger client relationships, and greater long-term retention.
Human Resources
We partner with HR professionals to deliver structured, human-centered retirement transition coaching. Through workshops, group programs, and individual coaching, we help employees prepare for retirement not just financially, but emotionally and socially — ensuring a confident, well-prepared transition