Who’d have thought there’d be so many reasons to retire? But our world has changed. Instead of being straightforward, you’re likely faced with thing you never before contemplated.
Traditionally, it used to be based on your:
The 21 best reasons you should retire expands on this usual stuff. There’s lots more to consider in making this important decision. Some of these are positive influences while others may be events beyond your control.
Let’s also be clear, there are valid reasons you shouldn’t stop working. For instance, keep working if you enjoy your career or are behind in your financial preparation.
1. The Most Common Reason for Retiring - Your Age
The most common reason for retiring is turning a certain age. For instance, slightly over 18% of Americans leave the workforce at age 62. Interestingly, this coincides with Social Security eligibility.

Further to this, over half of people leave between the ages of 61 and 65. Thus, for many, age appears to be a milestone signaling when it’s time to leave work behind. For more information, see Should You Retire at 62.
2. Sufficient Retirement Income
A second milestone would appear to be achieving financial independence. It’s also one of the best reasons you should retire. This will vary for each person, yet the question is “how much is enough”?
That largely depends upon the lifestyle you desire. Unless you love your job, you’re probably already evaluating the trade-off between working a few more years and all the things you could be doing.
If an inheritance were to come your way, this might further clarify your finances.
An interesting comment from a retiree in a forum, he calculated an extra year of work didn’t make much difference in his retirement income. He referred to it as a measly twenty bucks a month which helped him realize it wasn’t worth it to him.
3. You're Debt-Free
Congratulations on becoming debt-free! Your home is paid off, no more car payments and you’re financially prepared. Why put in more years of work? For many folks, this is about crossing the finish line.
Some may have downsized or plan on relocating to an area with a lower cost of living. Somewhere warmer or closer to where they want to be.
4. Slow Down and Enjoy Life
One of the best motives for retiring is the almost a universal desire is to slow down and enjoy life more. After four decades (or more) of busy work lives, the chance to finally slow down is very appealing.
No more alarm clocks and the freedom to do what you want.
5. Time with Family and Friends
The negative impact of the lockdowns and public health directives left most of us feeling isolated and lonely. We weren’t able to share time with the people important in our lives.
Special occasions such as birthday celebrations, Thanksgiving meals and even getting together with friends were restricted. Our perspectives have changed, especially for those who've lost loved ones.
Sticking it out for another year or two may not be as important anymore.
6. Travel
After being locked down for the past year, travel is something most of us have dearly missed. Maybe you want to travel while you’re still young enough to enjoy it.
According to the Transamerica Retirement Survey, 67% of American workers plan on traveling after leaving work. Further to this, Investopedia found the average retiree spent $11,077 a year on travel.
7. Starting a New Career
Out with the old and in with the new! Retirement is a crossroads and might be the opportunity to begin something you’re passionate about. Perhaps getting involved with a non-profit and volunteering your time to a worthy cause.
Or, maybe becoming an entrepreneur and starting your own business. With all of our years of experience and business contacts, we’re poised for much greater chances of success.
A study by the Kauffman Foundation, reveals over a quarter (25.8%) of all new businesses were started by those between the ages of 55 to 64.
8. Your Spouse / Partner Has Retired
Often, after one partner leaves their job the other might question if they want to remain working. They might love their career. If not, this can raise the question if they’re in the position to think about retiring.
Why Should Spouses Retire Together sheds more insight into this topic.
9. Affordable Health Insurance
One of the greatest deterrents to retiring early (before 65) has been the high cost of healthcare insurance. With recent changes to the Affordable Healthcare Act, you might be surprised to find more reasonable costs.
Healthcare costs are one fear that may be a little bit more manageable. The 8 Greatest Retirement Fears expands upon the many unknowns in retirement.
10. Maxing Out Your Pension
If you’re fortunate enough to have a pension, at some point you’ll have maxed out your contribution. Hopefully, with enough to live comfortably. This can also become a trigger point to move on.
11. Incentive for Retiring Early
Most organizations actively look for ways to reduce employee expenses. Younger workers generally cost less and they may incent older employees to leave. This might consist of cash bonuses and / or extended benefits.
An important consideration is the offer may not be made again. If you plan on retiring in a year or two anyways, you might be better off accepting the offer. Likewise, there’s no guarantee as you might also be let go down the road.
12. Stay Healthier Longer
Your job may, quite literally, be killing you. High stress, exposure to unsafe working conditions, or physically demanding activity could be taking a toll.
Coupled with any health concerns, such as an underlying condition, leaving could improve your quality of life and extend your healthy years.
13. Health Issues
The truth of the matter, money doesn’t matter much when our health is failing. For instance, surviving a heart attack or cancer changes how you view life. Trying to squeeze in a few more years of work doesn’t seem as important anymore.
14. Need to Care for a Family Member
The aftermath of the pandemic heightened a lot of medical issues. You might find yourself torn with assisting a family member. This could include an elderly parent, spouse or child requiring a little more help or even becoming their primary care giver.
15. Lack of Fulfillment at Work
You might be in a situation where your job has become tedious and boring. After all these years, you can almost do it in your sleep and it no longer offers any challenges. If you’ve financially prepared, this might be the time to consider moving forward.
16. New Management Direction
Our world changed in 2020 with almost every organization forced to adapt. Many are moving to a greater online presence and / or call centers. Existing divisions and regional offices may be closing. Perhaps services are being outsourced.
Some of these changes might force you into a new role or even relocation. From your perspective, you might be questioning if it’s time to leave.
17. Not Seeing Eye-to-Eye with the Boss
One of the best reasons you should retire is not seeing eye to eye with your manager. Not all bosses are created equal! Your supervisor might be an incompetent or arrogant ass.
Instead of recognizing and rewarding stellar performance in their employees, their goal is to make themselves appear important.
Not a great position to be in and might have you wondering if it's time to pull the plug, so to speak.
Both my wife and I have been there. There’s nothing more demeaning than having your performance and contributions being marginalized and diminished. Debbie discusses more of her experience in her Bad Boss post.
18. Ageism
Although no company will ever admit it, ageism is alive and well in America. Management believes in “fresh blood” and promoting their rising young stars.
Meanwhile, years of loyalty are discounted and experienced employees are viewed as expensive liabilities. Your boss and most of your co-workers are likely half your age.
We’re viewed like dinosaurs with our input not appreciated. If you’re in this position, your days may be numbered as management figures out a way to get rid of you.
19. Working Conditions
Another one of the best reasons you should retire is working conditions. On average, you spend about 40 hours a week at work.
When it becomes a soul sucking experience, it’s hard to feel happy, upbeat and positive. Some conditions can make this massive chunk of your life unbearable include:
20. Working from Home
The pandemic created an unusual situation where almost all knowledge workers began working from home. Perhaps you were one of the ones who appreciated that flexibility.
If you’re now expected to show up each day, you likely aren’t pleased with the “return to normal”. Especially when this requires a long commute each day.
Conversely, you might've missed not being able to go into a defined office space. Company policy may have shifted to encourage working from home. This could allow them to slash office and real-estate expenses.
In either situation, you may not be happy with the changes and questioning if it’s time to finally “pull the plug”.
21. Job Loss
The ultimate reason to leave is when it's not your choice and you experience job loss. The sad truth, it’s far more difficult to find good paying employment opportunities once you’re 50 or older.
Further to this, we observed a massive increase in unemployment in 2020. Besides hurting younger people, it disproportionally affected older workers.
Unless you have exceptional skills and knowledge in your industry, this might be the time to consider retirement. How to Deal with Forced Retirement provides insights into coping with job loss.
Closing Thoughts on Best Reasons You Should Retire
This list of 21 reasons to retire captures how much our world has changed and takes a fresh view of all the factors. While it used to be somewhat clear cut, now there are many more considerations.
For instance, why would you stay at a job you don’t enjoy if you can afford to leave? Traditionally, we worked until a certain age and became eligible for Social Security or Medicare.
I’m not saying that isn't important but should it be your primary criteria? Likewise, fear of outliving your savings leads some individuals to extend their working years longer than they need to.
In some situations, instead of enjoying their golden years they’re losing out on the greatest time of their lives.