Retirement: it’s the dream we all chase, a distant horizon filled with leisurely mornings, no commutes, and endless personal freedom. But what happens when the initial thrill wears off and you’re left wondering, “Now what?” That very question is what drove Dr. Riley Moynes—educator, author, financial advisor, and now retirement researcher—to dive deep into the psychological terrain of post-work life. What he discovered could change how you think about retirement forever.

Having enjoyed a distinguished career spanning over four decades in both the public and private sectors, Dr. Moynes thought he was well-prepared for retirement. After all, he had been a teacher, superintendent, textbook author, and later, a founding partner of a wealth management firm. He even wrote a bestseller, The Money Coach, selling over 200,000 copies. Still, despite financial readiness, he admits, “I wish I knew then what I know now about the psychological challenges that accompany retirement.”

What Dr. Moynes didn’t anticipate were the emotional pitfalls of stepping away from the structured demands of a full-time career. Retirement wasn’t just a change in schedule—it was a change in identity. This realization prompted him to interview hundreds of retirees, all of whom had unique experiences but shared common patterns. His findings became the foundation of his Canadian bestseller, The Four Phases of Retirement, and a powerful TEDx Talk that’s resonating with thousands.

According to Dr. Moynes, retirement unfolds in four psychological phases. Understanding them can help retirees not only cope but thrive.

Phase One: The Vacation Phase

This is what most people envision when they think of retirement. Freedom. No alarm clocks. Long breakfasts. Golf, travel, hobbies, and rest. You do what you want, when you want. For most, this honeymoon phase lasts about a year. But eventually, something strange happens—boredom. Without a structured routine or purposeful activity, even paradise can feel dull. Many begin to wonder: Is this all there is?

Phase Two: The Loss Phase

When the novelty of leisure wears off, retirees often enter a darker phase marked by a profound sense of loss. Dr. Moynes identifies five key losses: routine, identity, relationships, purpose, and power. These often hit all at once. The emotional impact can be jarring. The three “D”s—divorce, depression, and decline (both mental and physical)—often rear their heads during this stage. It’s a tough, sobering reality that many aren’t prepared for, mostly because we focus so heavily on financial planning and ignore the psychological transition.

Phase Three: The Trial and Error Phase

Eventually, most people hit a breaking point in Phase Two and realize they can’t go on feeling aimless. That moment of clarity propels them into Phase Three—a time of experimentation. This is where retirees search for new meaning, trying out various activities to see what sticks. Dr. Moynes himself tried condo boards, writing workshops, even considered law school, and discovered how rocky the road to fulfillment can be.

Yet, this trial-and-error process is crucial. Whether it’s joining clubs, mentoring, writing, or gardening, the key is to keep moving, keep trying. The danger lies in doing nothing, because stagnation can pull you back into Phase Two.

Phase Four: The Reinvention Phase

Not everyone makes it to Phase Four—but those who do are some of the happiest people Dr. Moynes has encountered. This phase is about rewiring, not retiring. It’s where retirees rediscover purpose, identity, relationships, and yes, even power. It’s a time of meaningful contribution, often through service to others.

Dr. Moynes shares stories of retirees who reinvented themselves by giving back. One man, Bill, began organizing brain-exercise classes for seniors. From a modest nine courses and 200 participants, the initiative grew to 90 programs with over 2,100 participants. Others volunteered, mentored students, taught languages, or shared hobbies. The energy was palpable, the outcomes—transformative.

It’s in Phase Four that the five key losses of Phase Two are not just restored, but revitalized. A new routine emerges, built on passion. Identity reshapes itself around values rather than job titles. Relationships deepen, not around a water cooler but shared purpose. Power shifts from influence in the workplace to the power of making a difference.

Dr. Moynes’ core message is simple but profound: Retirement is not a single event, but a complex psychological journey. If you’re not yet retired, understanding these four phases can help you prepare in more than just financial terms. If you are retired, recognizing your current phase can provide hope and direction.

So, enjoy the rest and relaxation of Phase One, brace yourself for the turbulence of Phase Two, courageously explore in Phase Three, and aim to reinvent yourself in Phase Four. That’s how you truly squeeze all the juice out of retirement.

Credits: Inspired by Dr. Riley Moynes’ TEDx Talk and his book, The Four Phases of Retirement.