Retirement isn’t just the end of one chapter; it’s the start of an entirely new book—one where you finally get to be the author of your own schedule and priorities.
But from what I’ve learned (and keep learning every day), truly enjoying retirement often means releasing certain expectations we’ve carried for decades.
I spent much of my adult life in an office job before hanging up my proverbial tie and switching gears to writing full-time.
And in my early days of retirement, I discovered that some of the assumptions I brought with me—about how life “should” look or feel—were actually holding me back.
Over time, by letting go of them, I’ve found more peace, satisfaction, and, dare I say, fun in these golden years.
So what are these assumptions, exactly? From my perspective, there are seven big ones.
If you’re having a grand time in your post-work life, chances are you’ve already set these unrealistic ideas aside (or you’re at least in the process of doing so).
Let’s dive into each one.
1. The belief that retirement means constant relaxation
I’ll admit it: for the first few months, I had this rosy expectation that retirement would be one big vacation—lounging around the house, watching movies, and taking Lottie (my rambunctious dog) on extra-long walks whenever I pleased.
That’s the popular image we see in ads, right?
But truth be told, real life doesn’t pause just because you stop working.
There are still bills to pay, errands to run, and responsibilities to juggle—even if they’re fewer or different than before.
If I clung to the fantasy that every day would be a carefree day at the beach, I’d end up disappointed whenever “real life” knocked on my door.
By letting go of the idea that retirement should be a 24/7 spa session, I opened myself up to finding joy in ordinary tasks.
These days, a simple routine (like cooking a new recipe for my grandchildren) can be surprisingly satisfying.
After all, Winston Churchill once said, “To improve is to change; to be perfect is to change often.”
Retirement might offer a slower pace, but there’s still plenty of growth—and occasional stress—along the way. And that’s perfectly okay.
2. The expectation that your identity still hinges on your old job title
I meet a lot of folks in retirement who struggle with the question “So, what do you do?”
When they used to answer with “I’m a teacher,” “I’m a banker,” or “I’m an engineer,” they felt a sense of importance or relevance.
But after retirement, that neat label isn’t there anymore, and it can leave a gap that feels unsettling.
If you’re enjoying your retirement, you’ve probably recognized that you’re more than just your former position.
Letting go of that expectation that your identity is 100% tied to your career can be incredibly liberating.
Instead of saying, “I used to be a manager,” now I tell people, “I write about personal development, spend time with my family, and try to keep up with Lottie.”
I’m not living in the past; I’m living in the now.
Research backs this up. A study has found that retirees who cultivate new roles or activities after leaving their jobs report higher satisfaction levels.
So, if you’re finding real joy in retirement, you’ve probably embraced the understanding that your value isn’t dictated by a business card.
3. The assumption that family and friends will revolve around your schedule
This one hit me after a few months of retirement. Suddenly, I was free to do what I wanted, when I wanted.
But guess what? My adult children still had jobs, my friends had their own commitments, and my grandkids were busy with school and sports.
I’d think, “Well, I can pop by for a visit anytime!” only to realize that they were juggling their own daily grind.
Letting go of the expectation that everyone else’s availability matches yours is key to enjoying these years.
Once I realized that my pace of life doesn’t automatically align with my friends’ or family’s pace, it saved me a lot of frustration.
Instead, I plan activities that I can do solo—like reading an old favorite book on stoicism or exploring a new park with Lottie—and then I relish those moments when our schedules do converge.
If you’re retired and genuinely loving it, you’ve likely come to appreciate that your circle isn’t on your personal clock.
Life flows a bit better when we respect each other’s timelines rather than insisting everything cater to ours.
4. The idea that you must stay perpetually busy to be “successful” at retirement
Ever heard someone say, “I’m busier now than when I worked”?
There’s a strange badge of honor some folks wear, boasting about how overbooked they are with volunteer work, hobbies, or traveling.
Now, there’s absolutely nothing wrong with staying active—I love my side writing projects and volunteering occasionally—but there’s a difference between pursuing genuine interests and cramming your schedule to prove you’re making the most of retirement.
In a previous post, I once touched upon the importance of finding meaningful activities rather than just busywork.
Because if we’re just piling commitments onto our calendar to avoid being seen as “lazy,” we might miss out on the actual joys of free time.
Letting go of the need to appear constantly occupied can help you discover that balance of relaxation and purposeful activity we all crave.
Stoic philosopher Seneca famously stated, “Leisure without study is death.” Of course, we can adapt that a bit and say, “Leisure without purpose can feel empty.”
But that purpose should be self-defined, not imposed by an old notion that we must be busy at every moment to be worthwhile.
If you’re finding contentment in your retirement, you probably realized that it’s okay to take a day—or several—to just be.
5. The expectation that it’s too late to learn something new
I’ve lost count of how many times I’ve heard retirees say, “I’m too old for that.”
Too old to learn a new language, try a new instrument, or, in my own case, pick up writing.
But the truth is, if you keep telling yourself you can’t, you’ll never prove yourself wrong.
Once I dropped the notion that my sixties were a barrier to new beginnings, my world opened up.
I’m not claiming it’s always easy—I’ve found myself frustrated more than once trying to navigate new software for my blog.
But the sheer pride I feel when I finally get the hang of it is hard to beat.
Bill Gates has said, “Most people overestimate what they can do in one year and underestimate what they can do in ten years.”
In retirement, we might not have a decade’s worth of career hustle left, but we do have time—and a lot of it can be channeled into new skills, interests, and passions.
When I see other retirees wholeheartedly enjoying their new pursuits, I know they’ve shed the belief that they’re too old to learn anything fresh.
6. The illusion that financial stability is set in stone
If there’s one expectation that can really zap the joy out of retirement, it’s clinging to the idea that your finances will remain exactly as you predicted.
Investments fluctuate, unexpected medical bills pop up, and sometimes you decide to take that dream trip you hadn’t budgeted for.
Now, I’m not a financial advisor, so I won’t pretend to have it all figured out.
But I’ve learned enough to recognize the importance of flexibility. When you release the belief that your retirement fund (or your expenses) will never change, you give yourself breathing room to handle life’s twists and turns.
And that makes day-to-day living a lot less stressful.
It might be something as small as downsizing a few everyday luxuries or being open to part-time work or consulting.
Whatever the solution, retirees who adapt are the ones who remain happiest.
“Someone’s sitting in the shade today because someone planted a tree a long time ago,” Warren Buffett once quipped.
Translation: your earlier planning is a huge benefit, but you may still need to prune the branches as life evolves.
7. The notion that retirement is supposed to be perfect all the time
We’ve all encountered that idea: once you retire, you finally “have it made.”
But realistically, life still has hiccups—health concerns crop up, relationships shift, or maybe you find yourself feeling restless.
If you assume retirement will be smooth sailing 24/7, any bump in the road can feel disproportionately big.
Enjoying retirement often comes down to accepting that imperfections don’t spell failure.
A friend of mine once had his dream RV trip spoiled by constant breakdowns and poor weather, but if you ask him, he’ll say it was still the trip of a lifetime—because he embraced the adventure, not the fantasy that everything should be flawless.
Letting go of perfection is an ongoing practice, of course, but each day I remind myself that not every plan needs to unfold exactly as I imagined.
The real gold of this stage of life is learning to adapt and find joy anyway.
Brené Brown has a quote I love: “Let go of who you think you’re supposed to be; embrace who you are.”
Even in retirement, that means dropping the need for a picture-perfect existence and simply rolling with what each day brings.
The result? Far less pressure and a lot more peace.
Wrapping it all up
Retirement can feel like both a reward and a blank canvas.
But holding onto fixed expectations—about finances, identity, endless relaxation, or constant perfection—can hinder your ability to fully enjoy this phase.
Letting go of these seven specific expectations has been a game-changer for me, and I see the same in others who radiate contentment in their post-work lives.
So, as you mull over your own journey, which old assumptions are you ready to release?
If you ask me, there’s no time like right now to free yourself from old scripts and truly savor the days ahead.
After all, these are the years to embrace the life you’ve been building toward, one step at a time.
What do you think—are you hanging on to any expectations that no longer serve you?
