Retirement was supposed to be the reward for decades of hard work. The freedom you’d been dreaming about. The chance to finally do all those things you never had time for.
So why does it feel so empty?
If you’re secretly miserable in retirement but feel like you can’t admit it, you’re not alone. I’ve been retired for several years now, and I can tell you the adjustment was harder than I ever anticipated.
Here are eight insights that might explain what went wrong, and more importantly, what you might be able to do about it.
1. You retired from something instead of to something
This is probably the biggest mistake people make, and I’ll admit I almost made it myself.
You spend years counting down to retirement, focused entirely on escaping the alarm clock, the commute, the meetings, the stress. You’re retiring from work, from obligation, from all the things you’re tired of.
But here’s the problem: you never really thought about what you’re retiring to.
The first few weeks feel amazing. Sleeping in, no schedule, no boss, no deadlines. Pure relief.
But relief isn’t a sustainable emotion. It wears off. And when it does, you’re left with a vacuum where purpose used to be.
I had a friend who couldn’t wait to retire from his job in middle management. He talked endlessly about being done with corporate nonsense.
Then he retired, and within six months, he was the most depressed I’d ever seen him. He’d been so focused on getting away from something that he never developed a vision for what came next.
Retirement needs a destination, not just an exit. What are you retiring to? What will give your days meaning?
2. You underestimated how much of your identity was tied to your career
For better or worse, our work becomes a huge part of who we are. It gives us status, purpose, a role in the world.
When someone asks “what do you do?” they’re really asking “who are you?” Your answer to that question shaped how you saw yourself for decades.
Then you retire, and suddenly that identity evaporates. You’re not the teacher, the engineer, the manager anymore. You’re just… retired.
That word doesn’t carry the same weight.
As shamanic teacher Rudá Iandê writes in his book Laughing in the Face of Chaos: A Politically Incorrect Shamanic Guide for Modern Life, “We live immersed in an ocean of stories, from the collective narratives that shape our societies to the personal tales that define our sense of self.”
When your career story ends, you need a new narrative to define yourself by. Without one, you can feel invisible, irrelevant, like you’ve lost your place in the world.
You might find yourself bringing up your old job in conversations even though it’s no longer relevant. You’re clinging to an identity that doesn’t exist anymore because you haven’t built a new one yet.
3. You assumed you’d automatically know how to fill your time
Freedom sounds incredible when you’re stuck in meetings all day. All that time to do whatever you want!
Except when you finally have it, the reality is more complicated.
Too many options and no structure can be paralyzing. You thought you’d fill your days with hobbies and projects, but instead you find yourself wasting hours scrolling through news sites or watching television you don’t even enjoy.
The hobbies you imagined would sustain you turn out to be less fulfilling than expected.
Golf three times a week gets old. Woodworking is harder than you thought. These activities are fine, but they’re not enough to replace the structure and purpose that work provided.
What made work satisfying wasn’t just the tasks themselves. It was the deadlines, the collaboration, the sense that what you did mattered to someone.
Your hobbies don’t have those elements. Nobody’s waiting on you to finish that puzzle. There are no stakes, no accountability, no external validation.
Learning how to create your own structure and meaning takes time and intention. This is something I’m still figuring out myself, and some weeks are definitely better than others.
4. You lost the social connections that work provided
Work gave you built-in social interaction whether you fully appreciated it or not.
Colleagues to grab lunch with, chat with by the coffee machine, complain about management with. Even if you weren’t best friends with your coworkers, they provided daily human connection and a sense of belonging.
Retirement strips that away. Those work friendships often don’t survive once you’re not seeing each other every day. They’re still in that world, and you’re not.
Making new friends at this age is genuinely difficult. Social groups for retirees can feel forced or awkward. Your spouse or partner can’t fulfill all your social needs.
The loneliness of retirement catches people off guard. You thought you’d enjoy the peace and quiet, the freedom from office politics. But humans need connection, and if you haven’t intentionally built new sources of it, there’s a good chance you’ll feel isolated.
5. You retired at the wrong time
There’s this idea that retirement should happen at a certain age, usually somewhere between 62 and 67.
But the right time to retire is deeply personal and depends on more than just your age or your bank account balance.
Some people retire too early, before they’re emotionally ready, because they hit a financial milestone. They still have energy and drive, but nowhere to direct it.
Others wait too long, pushing through until their health or energy is diminished, robbing themselves of the active retirement they’d imagined.
The right time to retire is when you have something meaningful to retire to, when your health still allows you to enjoy it, and when you’re genuinely ready for that transition.
Sometimes that aligns with a particular age. Often it doesn’t.
6. You’re comparing your retirement to others’ highlight reels
Everyone else seems to be thriving in retirement. They’re traveling to exotic places, picking up new hobbies, spending time with grandchildren, volunteering.
You see it on social media, in holiday cards, at gatherings. Their retirement looks vibrant and purposeful.
Meanwhile, your days feel small and repetitive. You’re not traveling the world or learning Italian. You’re just existing. Getting through the days. Your retirement looks nothing like what you see from others.
But here’s the truth: you’re comparing your everyday reality to everyone else’s carefully curated highlights.
Nobody posts about the boring days when they can’t figure out what to do with themselves. They show you the vacation, the grandkids’ visit, the successful garden.
I’ll be honest, I fell into this trap hard during my first year of retirement. I kept seeing former colleagues posting about their amazing retired lives while I was struggling to find meaning in my days.
It took me a while to realize I was comparing my behind-the-scenes to their highlight reel.
7. You haven’t adjusted to the shift in financial mindset
You spent decades saving money, being careful, planning for the future. That mindset served you well.
But now you’re actually in retirement, and you’re supposed to spend that money. Except you can’t quite let yourself do it.
Every purchase feels wrong somehow, like you’re depleting your safety net. You worry constantly about running out of money, even if your financial advisor tells you you’re fine.
You find yourself still living like you’re saving for retirement even though you’re already there.
Or maybe you went the opposite direction. You spent freely in the early years, finally allowing yourself the things you’d deferred. But now you’re looking at your accounts and feeling trapped, realizing you need to pull back significantly.
The financial psychology of retirement is tricky. You need to find a balance between enjoying your money and not being reckless with it. If you haven’t figured out what feels right for you, the financial stress alone can make retirement miserable.
8. You expected retirement to fix problems it can’t solve
Maybe your marriage had been strained for years, but you told yourself it was just the stress of work. Retirement would fix it.
Or you’d been vaguely dissatisfied with life, but surely that was because you were too busy.
Except retirement doesn’t fix relationship problems. If anything, it amplifies them.
Now you’re spending all day, every day with someone you’d grown apart from, and there’s nowhere to hide. The cracks you’d been ignoring become impossible to miss.
Retirement doesn’t cure depression or anxiety or dissatisfaction with yourself. It doesn’t heal old wounds or resolve conflicts.
If you had personal issues before retirement, you still have them after. But now you have more time to dwell on them and fewer distractions.
One of the toughest periods of my retirement came when I realized that the restlessness I’d blamed on my demanding job was actually just part of who I am. Retirement didn’t cure it.
I had to do the actual work of addressing it instead of waiting for my circumstances to magically make it better.
Finding your way forward
If you’re recognizing yourself in several of these insights, take some comfort in knowing that identifying what went wrong is the first step toward making it better. Retirement is a major life transition, and transitions are hard.
The retirement you’re living right now doesn’t have to be the retirement you’re stuck with forever. You can redesign this phase of your life.
Build new routines that give you structure. Develop a new identity beyond your former career. Seek out social connections intentionally. Create purpose where it’s lacking.
It’s okay to admit that retirement isn’t what you expected. That honesty is actually the starting point for building something better. Your retirement doesn’t have to look like anyone else’s, and it definitely doesn’t have to stay the way it is now.
