After decades of alarm clocks, meetings, and deadlines, I figured the hard part was over. Turns out I was wrong. Letting go of work proved far easier than releasing all the habits and obligations I’d dragged through my working years.
The difference between people who thrive in retirement and those who struggle? It’s not about how much money you’ve saved or where you travel. It’s about what you’re willing to leave behind.
1. Keeping relationships alive that died years ago
We all have them—friendships that exist purely out of habit.
You meet for coffee once a year, exchange awkward small talk, and leave feeling drained rather than energized. Maybe it’s a college buddy you have nothing in common with anymore, or a neighbor you’ve been pretending to enjoy for two decades.
Retirement gives you permission to be selective. Your time is genuinely precious now, and spending it with people who don’t add joy to your life is a choice you’re making.
Letting go doesn’t mean being cruel. It means allowing natural distance to happen instead of fighting it.
2. Apologizing for having boundaries
I spent forty years saying yes when I meant no.
Yes, I’ll take on that extra project. Yes, I’ll help you move. Yes, I’ll attend that event I have zero interest in.
The folks at BetterUp have noted that people-pleasing often stems from a fear of conflict or rejection, but it comes at a tremendous cost to your own wellbeing. Retirement is your chance to unlearn this.
You don’t owe anyone an explanation for how you spend your time. “No” is a complete sentence, though “No, thank you” works fine too.
3. Living by someone else’s retirement script
Society has a very specific idea of what retirement should look like.
Golf. Cruises. Volunteering at the library. Moving to Florida.
None of these things are wrong, but they’re also not mandatory. I recently came across Jeanette Brown’s course Your Retirement Your Way, and one thing that really struck me was her reminder that your beliefs about what retirement “should” look like literally shape your experience.
The course helped me see that I’d been carrying around inherited programming about retirement—ideas that came from my parents, from TV, from everywhere except my own desires. Jeanette’s guidance inspired me to question all of it.
What if your perfect retirement looks nothing like the brochures? That’s not just okay—it’s exactly the point.
4. Holding onto grudges that only hurt you
You know that person who wronged you fifteen years ago?
They’ve moved on. But you’re still carrying it around, turning it over in your mind whenever things get quiet.
Forgiveness isn’t about them. It’s about refusing to let someone who hurt you continue controlling your thoughts and mood.
This gets easier with age, but it still requires a conscious choice. Every time that old resentment surfaces, you can either feed it or let it pass.
5. Trying to stay relevant in a world that’s moved on
This one stings a bit to write about.
The world doesn’t work the way it used to, and younger people aren’t particularly interested in hearing how things were done in your day.
Your experience matters. But constantly explaining “how we used to do it” or complaining about modern ways makes you exhausting to be around.
The happiest retirees I know stay curious rather than critical. They ask questions instead of delivering lectures.
6. Maintaining appearances you no longer care about
The expensive car lease. The house that’s way too big. The country club membership you haven’t used in three years.
We accumulate these status symbols throughout our working lives, often to impress people we don’t even like. Retirement is your chance to ask: what do I actually want versus what have I been conditioned to want?
Downsizing isn’t about deprivation. It’s about freedom.
The less stuff you’re maintaining, the more energy you have for what actually matters. And nobody is paying as much attention to your lifestyle as you think they are.
7. Putting off what brings you genuine joy
“Someday I’ll learn piano.” “When I have more time, I’ll start painting again.” “Eventually I’ll take that trip.”
Someday is now. Yet many retirees still postpone their own happiness.
I’m no know-it-all, but I’ve noticed something about the people who seem most content in retirement: they gave themselves permission to be beginners again. They didn’t wait until conditions were perfect or until they felt “ready.”
They just started.
8. Tolerating family dynamics that make you miserable
Blood relation doesn’t obligate you to emotional suffering.
If family gatherings leave you feeling terrible, you get to rethink your participation. If a sibling treats you poorly, you can set limits or step back entirely.
I’m not talking about cutting everyone off at the first sign of difficulty. I’m talking about recognizing that you’ve earned the right to protect your peace.
The people who truly love you will understand. The ones who don’t? Well, that tells you something important too.
9. Worrying about what other people think
Most people are too busy worrying about themselves to spend much time judging you.
That realization is remarkably freeing.
Want to wear comfortable shoes instead of fashionable ones? Do it. Want to skip the reunion? Skip it. Want to spend your savings on experiences instead of leaving a bigger inheritance? That’s your call.
This is well backed by the experts at Harvard Health Publishing, who point out that seeking social approval activates the brain’s reward system, but over-dependence on external validation undermines authentic self-expression.
Your job now is to figure out what makes you happy and do more of that, regardless of whether it makes sense to anyone else.
10. Staying in your comfort zone out of fear
And here’s one I really don’t want you to miss.
The biggest regret I hear from people in their seventies and eighties isn’t about things they tried and failed at. It’s about things they never attempted because fear held them back.
Fear of looking foolish. Fear of failure. Fear of being too old, too out of shape, too whatever.
But retirement is your last chance to take some risks while you still have your health and energy. That doesn’t mean skydiving if you’re terrified of heights—it means stretching beyond the familiar in ways that excite you.
Taking a class. Traveling solo. Starting a business. Finally writing that book. The time to begin is now.
Not next year. Not when you feel more confident. Now.
Final thoughts
Walking away from these ten things won’t happen overnight, and that’s okay.
Start with one. Pick the item on this list that resonates most strongly and make a small change this week.
Try this:
• Identify one relationship, obligation, or fear that’s been weighing you down for years
• Take one small action to create distance, set a boundary, or face that fear
• Notice how it feels to reclaim even a small piece of your freedom
Retirement doesn’t automatically make you joyfully carefree. But consciously letting go of what no longer serves you? That’s how you create the space for joy to move in.
And trust me—you’ve earned it.
