The Four Phases of Retirement with Dr. Riley Moynes

In this powerful and insightful episode, I sit down with Dr. Riley Moynes, author, speaker, and creator of the viral TED Talk on "The Four Phases of Retirement," which has amassed nearly 5 million views. Together, we unpack why retirement is far more of a human problem than a financial one, and why so many retirees struggle despite having "enough" money.

Riley shares the emotional, psychological, and personal transitions that retirees face and offers an actionable framework to help listeners navigate their post-work lives more meaningfully.

• The Four Phases of Retirement and why most people will experience them.

• Why retirement is not just a financial challenge but a deeply human one.

• The common emotional and psychological struggles retirees face.

• How retirees can proactively prepare for the non-financial aspects of retirement.

• The importance of purpose, identity, relationships, and service to others in retirement.

• How to avoid becoming a "statistic" in retirement dissatisfaction.

• Dr. Riley Moynes' personal career journey and how he developed the Four Phases of Retirement.

• Why traditional financial services fail to prepare people for the real challenges of retirement.

• A deep dive into each of the Four Phases:

  1. The Vacation Phase – The early, carefree, "holiday" phase of retirement.

  2. The Loss and Lost Phase – The period of disillusionment marked by loss of purpose, identity, relationships, and routine.

  3. The Trial and Error Phase – The experimental stage of trying new activities, facing failures, and re-finding purpose.

  4. The Reinvent and Rewire Phase – The fulfilling phase where retirees give back, often through service, and thrive with renewed purpose.

• The emotional impact of retirement and why depression, divorce, and dissatisfaction spike for many retirees.

• The predictable pattern of retirement struggles and why awareness is key.

• Why simple joys and purposeful service are at the heart of a successful retirement.

• The Four Phases of Retirement: What to Expect When You're Retiring by Dr. Riley Moynes

• Dr. Riley Moynes’ viral TED Talk — "The 4 Phases of Retirement"

• Mention of Fritz Gilbert’s blog, The Retirement Manifesto

• Kübler-Ross Change Curve (Grief & Loss framework referenced in discussion)

Your Unique Ability Reflection Dr. Moynes recommends this simple but powerful exercise:

1. Write down the top 5 things you love to do and know you do really well.

2. Reflect on 5 key wins, successes, or achievements in your life so far.

3. Look for patterns and connections between the two lists. Ask yourself:

• Can I apply these skills, passions, or experiences to new areas in retirement?

• How can I use these to serve others and find fulfillment?

This introspection can help you transition into the most meaningful phase of retirement.

Retirement is not a finish line, it’s a transition into one of the most complex and potentially fulfilling stages of life. But it requires intentionality, emotional awareness, and often hard inner work. As Dr. Moynes reminds us, it’s not about endless vacations or financial spreadsheets; it’s about redefining purpose, reconnecting with joy, and ultimately serving something bigger than yourself.

Retirement is a human challenge, not a maths problem. The sooner you embrace that, the smoother and more fulfilling your transition will be.

• The Super Sunday Retirement Roundup Newsletter

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• The Humans vs Retirement Sketchstore

• Book in a Time For us to Chat About Your Retirement

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