Strategic Retirement Coaching

Your GPS to the Future

Every great journey needs a plan: let’s map yours together to navigate the personal, social, and day-to-day changes of leaving work, making life after your career a purposeful, rewarding adventure.

Updating our roadmap to serve your journey better.
Full site coming soon!
Older couple enjoying an active retirement in the mountains
A whole-life approach to retirement

Preparing for what comes after work

Transition Expert — Phyllis Diamond, LCSW

With 16 years as a Certified Retirement Coach and 30+ as a psychotherapist, I help you build a successful retirement plan focused on you—not just your portfolio. Together, we navigate the non-financial side: reclaiming your identity, finding purpose, and structuring fulfilling days.

We Work For You

Using a reflective, conversational style, I work with high achieving individuals and couples to turn retirement goals into concrete action. Plus, I partner with businesses to deliver interactive workshops for employees and clients preparing for their next chapter.

Tools and Resources

My priority is empowering you with the right information. You can explore my free guides, retirement assessments, and planning tools—or check out my co-authored book, The Retirement Challenge: A Non-Financial Guide from Top Retirement Experts.

Phyllis Diamond
About

Phyllis Diamond

I have over 30 years of experience helping clients break through the barriers that keep them from achieving their life goals. I bring my wide range of experience in counseling, business and education to my coaching practice.

Trained as a licensed clinical social worker, I have been in private practice as a psychotherapist for 30 years, specializing in work with individuals and couples on relationships and family issues. My particular interest has been to help clients handle major life transitions.

Coaching Services

A safe place to think through retirement

Retirement coaching can help make the transition from work life to home life more intentional. Sessions are customized to the individual, couple or group and may include reflection, assignments, practical action steps and progress toward personal goals.

  • Explore possibilities, fears and concerns.
  • Clarify what you want daily life in retirement to look like.
  • Strengthen social connection, relationships and sense of purpose.
  • Create practical next steps rather than leaving retirement plans abstract.
Two women enjoying an active retirement

Individual Coaching

One-on-one support for specific concerns or broader goals such as building a social network, finding meaning, overcoming obstacles and creating a satisfying next chapter.

Couples Coaching

Support for discussing expectations, retirement timing, changing roles, shared and individual goals, and strategies for staying connected as life patterns change.

Group Coaching

Non-financial retirement planning for corporations, organizations and associations, with an interactive format that allows participants to learn from one another.

The Retirement Challenge book cover
My Book

The Retirement Challenge

The Retirement Challenge: A Non-Financial Guide From Top Retirement Experts brings together retirement professionals to address the often-overlooked personal side of retirement.

The book explores purpose, transition, thoughts and feelings about retirement, and why planning beyond dollars and cents matters. I contributed a chapter about facing forced retirement and finding your footing when plans change unexpectedly.

Resources

Learn, reflect and prepare

Education has always been a core part of my approach to retirement planning. I help people think beyond finances and consider the personal areas that shape a satisfying transition into retirement.

Topics I commonly address include:

  • Determining when is the right time to retire
  • Adjusting when retirement happens unexpectedly or earlier than planned
  • Understanding the emotional and practical sides of retirement
  • Replacing a 40+ hour workweek with an intentional daily schedule
  • Preparing your relationship or marriage for the challenges of retirement
  • Maintaining purpose, identity and social connection after work
  • Uncovering new passions, volunteer opportunities, or creative pursuits
  • Establishing healthy habits around leisure, rest, personal growth, and physical activity.

For information about current resources, coaching or assessments, please contact me directly.

Get in Touch

Let’s Connect

For questions about coaching, assessments or retirement planning, please call or email me directly.