Retirement often starts like a dream vacation you never have to end—but sooner or later, the scenery changes.
But what happens when the vacation feeling wears off?
The Vacation You Never Have to End
Most people experience a ‘honeymoon period’ when they first retire.
In his TED Talk and his book, Dr. Riley Moynes describes the four stages of retirement that many retirees experience. The first stage is called “Vacation Time.”
It’s like being on vacation 24/7. You have little or no structure or routine in your life. You can either splurge on new toys or travel.
There’s a reason this stage is so welcome. When many people retire, they are exhausted and burned out from decades of work. They need an extended vacation to rest and regroup.
It feels wonderful at first to have no schedule, no expectations, no routine. You can do whatever you feel like.
Sleep in if you want. Spend your mornings on the golf course, afternoons by the lake, or binge-watching your favorite shows. This vacation period lasts from about six months to two years, typically about a year.
When Freedom Starts to Feel Empty
But eventually, the thrill of unlimited freedom can fade. Dr. Moynes calls the second stage “Feeling Loss and Feeling Lost.” You get tired of the lack of structure, and full-time hobbies get boring.
The same wide-open days that once felt liberating can start to feel empty.
The same things that you initially celebrated as giving you freedom become the cause of feeling a loss of purpose and meaning.
As professional retirement coaches Roberta Taylor and Dorian Mintzer wrote in The Couple’s Retirement Puzzle,
“Relaxation and leisure are wonderful, but too much of a good thing can lead to boredom and leave you wondering, ‘What am I supposed to do now?’”
You realize that when you retired, you lost your routine, your work relationships, your status, your power, and your responsibility.
And along with them, you lost your sense of purpose and identity. As a result, you feel insignificant and irrelevant, and that you don’t have a purpose in life.
Getting Stuck in Stage 2: Entertainment, Alcohol, and Drugs
Unfortunately, I have seen many of my fellow retirees get stuck in the “feeling loss and feeling lost” stage.
Without a new sense of purpose, it’s easy to drift—filling days with distractions, entertainment, or even unhealthy habits like alcohol and drug abuse that can spiral into depression.
Sometimes retirees attempt to mask the sense of loss by staying busy all the time: going on road trips, taking overseas trips to exotic locations, and booking multiple cruises.
None of these are bad in themselves, but if they are being used to keep you from dealing with the sense of loss of identity and purpose you feel, it’s not healthy.
But distraction is not a destination. So what does moving forward actually look like?
How to Start Finding Your Way
Retirees are sometimes able to advance to the third phase of retirement, which Dr. Moynes calls “Trial and Error.”
In this stage, you think, “How can I still contribute?”
You conduct some Tiny Experiments in which you try something for a specified period, then evaluate. Maybe you test the waters with a woodworking class, tutor high school students, or launch a small online shop. You might keep some, drop others—but each experiment teaches you more about what energizes you.
The key in this stage is to stay flexible. Some things will work out in the long term, and some things won’t, and that’s okay. It’s a period of discovery and experimentation.
Stage 4: Reinventing Yourself
So what comes after trial and error? The fourth stage is called “Reinvent and Repurpose.”
In this stage, as a retiree, you are asking, “What’s my purpose and what do I want to become?” Retirees in stage four are open to new ideas and direction.
You’ve experimented with many new ideas and activities and have decided what works for you.
You discover who you are and craft a new identity and purpose. You know who you are and feel like you’re making a contribution.
When the Honeymoon Fades, Growth Begins
The honeymoon won’t last forever—but that’s not a problem to solve. It’s a transition to navigate.
The retirees who land well in Stage 4 aren’t the ones who had it all figured out. They’re the ones who stayed curious long enough to find what fit.
Pick one small experiment this month. A class, a project, a conversation you’ve been putting off. You don’t need to know where it leads. You just need to start.
Note: I wrote this blog post myself using my own words and thoughts for the initial draft. I used AI only to suggest headlines, section headings, images and text improvements.
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