Joe’s Retirement Fantasy
Joe got his dream.
Then he wondered if he’d made the biggest mistake of his life.
For years, Joe had dreamed about the day he’d quit work and retire.
He met with his financial advisor well in advance, and together they worked out a financial plan to ensure he could retire when he wanted to.
He daydreamed about what retirement would be like: getting up when he wanted to, no routine or structure, playing golf every day.
Joe’s retirement was terrific for the first year, but then it started to sour.
When friends asked him how retirement was going, he answered, “Great!” because he felt that’s what he was supposed to say, but he didn’t feel that way.
Joe was surprised to realize he had lost the sense of purpose and meaning he had found in his work.
He missed the friends he had at work, and he missed the structure and routine he had when he was working.
He was starting to wonder if he’d made a big mistake retiring.
Maybe you’ve felt this too — the quiet “Is this it?” that creeps in once the novelty wears off.
Retirement Isn’t What You Imagined
You won’t know what retirement is like for you until you live it.
It’s good to plan, but don’t expect that plan to actually work for you. Retirement is a major life transition, and something that you’ve never done before.
Even if you worked with a retirement coach to plan your retirement, aspects of your plan may not survive the first few months.
Retirement coach Tony Hixon pointed out this dynamic in his book, Retirement Stepping Stones:
“Regardless of how much effort you put into planning your dream retirement, you may still find that you don’t love it once you’re living it every day.”
In a condensed quote attributed to Prussian field marshal Helmuth von Moltke the Elder, he wrote, “No plan survives first contact with the enemy.”
This is true for retirement as well.
Financial plans matter.
Life plans evolve.
The Biggest Losses You Don’t See Coming
When we close the office door for the last time, we lose our identity, purpose, meaning, status, and social relationships.
We spent decades earning our identity through work. Overnight, it disappears.
Before retirement, we tend to fantasize by playing the retirement highlights we see in commercials.
As Tony Hickson notes in his book Retirement Stepping Stones:
“Retirement in the media and in most advertising targeted toward pre-retirees depicts retirement as a golden paradise.”
Even if you have educated yourself about the losses that you’re going to experience when you retire, it’s all academic until you’re actually experiencing them.
They don’t seem real.
They won’t apply to you.
But the transition to retirement can be much more impactful than you’d imagined.
You likely won’t realize this until you’re over the honeymoon phase of retirement (usually about a year) and reality sets in.
Retirement podcaster and blogger Dan Haylett reported in The Retirement Fix of November 23, 2025,
“A 2021 study in Psychology and Aging found that retirees experience their highest spike in anxiety not in the run-up to retirement… but in the first year after leaving full-time work.”
Anxiety spikes because the familiar scaffoldings of life — relationships, routine, relevance, meaning — are suddenly gone.
It’s unsettling to lose purpose. It’s lonely to lose friends. It’s disorienting when every day has no shape.
Explore, Experiment, Reinvent
Work told us who you were. Retirement asks you to answer that for yourself.
In retirement, you need to discover who you want to be and the kind of life you want to live.
You need to bring routine, structure, purpose, and meaning back into your life.
To do this, you have to be flexible and willing to experiment.
You don’t need it all figured out before you retire. As a matter of fact, in many ways, you can’t do that.
• Decide to Reinvent Your Retirement. It’s very possible to reinvent yourself, even after you’ve been retired for some time.
The first step is to intend to change, then take actions to change.
• Become an explorer and experimenter. Follow your curiosity and try some new activities. Make a “curiosity list” of the things you’re interested in now or things you were interested in.
During the exploration phase, you try out different options, including things that may interest you or have been of interest in the past.
Try some “Tiny Experiments.” Decide what you’d like to try out, and make a simple pact with yourself: “For X days I will do Y.”
Example: “For 14 days, I’ll volunteer at the library for two hours each week.”
When you reach the end of your experiment, evaluate. Do you want to continue doing this, modify it, or stop?
You can’t fail when you do tiny experiments. If you try something and decide it’s not for you, that’s a win because now you know it’s a dead end.
If you try something and it works out, that’s a win because you’ve found something that can give you a new sense of meaning and purpose.
• Don’t Make Commitments While Exploring. As you try things on for size, don’t make any significant commitments. Remember that you’re just testing and trying things out to see how they fit.
You’re exploring and experimenting. So at this point, don’t block yourself in.
• Find New Purpose. When you find those things that work for you, and you practice them, you reinvent yourself and regain your sense of meaning and purpose.
Start Small, Start Now
You don’t need a five-year plan to make retirement fulfilling. You just need a first step.
Pick one thing you’re curious about — something that might add purpose or joy — and commit to a tiny experiment. Try it for a week or two. Then adjust.
Your future identity doesn’t arrive fully formed. You create it, one small action at a time.
So here’s your challenge: What tiny experiment will you try this month?
AI 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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