Money Match-Up: Should You Retire Early or Not?

Here’s the latest post in the Rockstar Finance Money Match-Up series where two money bloggers argue opposite sides of an issue.

Today’s issue features another interesting debate — whether early retirement is a good choice or not.

We’ll begin with Dash 2 Retire who is in favor of early retirement…

The Case for Early Retirement

Early retirement doesn’t mean you don’t work. Early retirement means you don’t NEED to work. And that, my friends, is a big difference.

“Everybody’s working for the weekend.” – Loverboy

According to a recent Gallup poll, 70% of Americans HATE their jobs. Not dislike. Not strongly dislike. But HATE.

I get it.

Most of us start our careers giddy with enthusiasm. We have great hopes and dreams that through our work we can make a difference. And we’ll get paid while we’re at it. Win, win.

We can make the world a better place in which to live – whether we’re in military service, medical care, arts, entertainment, business, construction, technology, home services, legal assistance, you name it. Maybe we started our career in a trade straight out of high school or we obtained an associate, bachelor or advanced degree.

For the first few years everything is going great. But then reality sets in. We realize that we are going to be on this hamster wheel for the next 40 years.

Forty years is a long time to dedicate to anything. And it’s especially long if you’re like 70% of the population and you HATE your job. Just like those hamsters spinning on the wheel, we want to get off. As soon as possible.

While some people do find their careers to be completely rewarding and fulfilling for 4 or more decades, most of us desire something else.

“At the end of your life you will never regret not having passed one more test, not winning one more verdict, or not closing one more deal. You will regret time not spent with a husband, a friend, a child or a parent.” – Barbara Bush

We long for the day when time is our own. When we report to no one. No boss, no customers, no patients, no shareholders, no subscribers, no well, you get the idea.

Welcome to the world of early retirement.

“Early retirement is a remarkable feeling of control, each and every day.” – Steve via @ThinkSaveRetire on Twitter

And this ain’t your grandpa’s retirement, people. Gone are the days when retirement meant biding time sitting on the porch in a rocking chair.

We all need a reason to get out of bed in the morning. As Americans, we tend to tie our self-worth to success in our careers. When we retire, our purpose must be defined by more than just our old job.

Early retirement allows you to dedicate your attention to what really matters in life.

1) Spend more time with your family.
2) Care for ailing or aging family members.
3) If you have small children, spend QUANTITY time with them, not just QUALITY time.
4) If you have school-age children, volunteer at school, chaperone field trips, assist in the office or substitute teach (if your district allows).

Early retirement allows you to find your passion. And not your work passion. Your real passion. Maybe it’s your Second Act.

5) Work part-time.
6) Work full-time. But just for fun. Not because you need the money.
7) Start a business.
8) Take a class.
9) Teach a class.
10) Run for office.
11) Start blogging. Start gardening. Start dancing.
12) Turn your hobby into a business.

Early retirement allows you to eradicate the stuff that causes you stress.

13) Deadlines.
14) Bosses.
15) Meetings.
16) Customers.
17) Morning and evening commute.

Early retirement allows you to decide how you spend your time. And not be dictated by a work schedule.

18) Go to the gym when it’s not crowded.
19) Enjoy a matinee.
20) Travel anytime you want. Not just when work allows.
21) Go on a mission trip. Or immerse yourself in a language you’ve always wanted to learn.
22) Give back to your community through volunteering.
23) Find out who else shops in the middle of the day when the stores aren’t packed with stressed-out workers.

Early retirement allows you to cut expenses.

24) Prepare a nutritious lunch at home to avoid the grab-n-go lunch.
25) Stop dry cleaning clothes.
26) Stop buying “work” clothes, because every day is Casual Friday.

Early retirement allows you to lead the life you’ve always dreamed of.

27) [Fill in the blank] I can’t wait to _________________.

“There is no time like the PRESENT to retire and START enjoying life.” – Paul Merriman

Of course, Merriman makes a caveat to his quote – “If you have saved enough.”

How much is enough? It’s different for everyone. Some people choose to live on a small fraction of their income to speed the process of becoming financially independent (having the income to support your lifestyle without relying on a full-time job).

How can anyone save enough? Most people can, regardless of income. It starts with living well below what your income allows. It requires planning, patience and perseverance. But the sacrifices are worth it.

Retirement is not the end. Retirement is the beginning of the life you’ve always dreamed of. Where YOU decide how to spend your time, your money and your talents.


Now let’s switch to Misty from Simple Organized Lifestyle who thinks early retirement in not a good idea…

8 Cups of Why You Should Not Retire Early

7:30 a.m. My grandfather rolls out of bed and heads straight to the coffee pot. He fills the first cup out of 8 (yes, EIGHT) for the day. Shortly after he’s got on a pair of carpenter jeans, boots and a short sleeve pocket t-shirt. He puts a small notepad and pen in his shirt pocket and clips his measuring tape on his right jeans pocket.

8:00 a.m. Cup of coffee #2 in hand (a reused McDonald’s cup, never a lid and one teaspoon of a creamer) he’s heading out the door. At age 74, his services and experience with fixing plumbing, electrical, heating and air problems are in high demand.

He’s past the age of traditional retirement and would have never even thought to consider early retirement.

Retirement is what you make it…

Early retirement for those of us in our prime income earning years is very appealing. It comes with the image of every day being a Saturday. Time on our terms. No one telling us what to do and how to do it. Freedom. Fun.

But the truth is taking a different path of retirement as we know it requires a lot of research and pre-calculated decisions. It is possible, but not probable without a unique money mindset. It’s not a fit for everyone, and it’s okay. It’s not appealing to everyone, and that’s okay too.

Retirement, early or not, is like most things…it is what you make it. With that in mind, let’s chat over 8 cups of coffee about why you may want to choose the traditional retirement path, or perhaps not retire at all.

1- One cup of interesting

Jobs come with people and people are interesting. Interesting- funny. Interesting- brilliant. Interesting- crazy. Just interesting. How often do you come home from work and talk about what one of your coworkers, customers or supervisors did or said? I would guess every single day. It may not have been anything professional or even pleasant, but it was most likely interesting!

People need people. Perhaps retiring early could lead to a major onset of FOMO (fear of missing out), creating a feeling you didn’t even realize was possible. You could very well find that retiring early pushes you into a space that’s much less interesting.

If you retire while those around you do not, it’s like closing a door even though many of your friends are still on the other side. It changes the dynamics of your friendships and your conversations. If you haven’t thought about a new way to engage with people, you may be disappointed to find out that retirement is just not that interesting.

2- One cup of saving

More working years are more opportunities to save and let the savings’ soldiers (aka interest) keep working too! While you may still be working, so are your investments. It could mean more interest, more dividends and not risking a huge penalty should you have to tap into savings sooner than you planned.

Visualize a big jar where you empty your pocket change every day. The jar keeps growing. Your income is the pocket change and the jar is your savings and investments. When the income all of a sudden becomes a zero, you’re left with picking up the jar and pouring it out. That’s a scary thought if you have not taken enough time to make sure those investments keep growing!

Social security benefits can be more and tax penalties less by delaying the age you draw benefits. Otherwise, that’s money gone that should be rightfully yours.

3- One cup of happiness

If you equate happiness to being without a job, you could be in for a big disappointment. Early retirement is not a cure for unhappiness. It may relieve some kinds of stress but it will create others. People who suddenly feel less productive or needed can actually become depressed.

If you have a job that makes you miserable and see retirement as a ticket out, maybe the answer instead is finding a job that makes you feel motivated! We’re also living at a time when traditional job norms are starting to shift towards more flexibility and options. It could just be that a change is needed.

4- One cup of health insurance

Have you or any of your coworkers ever complained about health insurance? Especially in the U.S., I bet you can answer that with a resounding yes! It’s crazy that people in a steady, stable job are struggling to cover these costs that are inappropriately named “benefits!” Now, can you imagine what that would cost or look like without those benefits? As dismal as they may be, not having a plan for health insurance until Medicare kicks in is not a risk worth taking.

Can you sleep well at night if you are not sure that your retirement funds will cover everything that comes with maintaining your health? Without your health, retirement doesn’t even matter.

5- One cup of financial stability

One thing you can do with your budget while you’re working is adjust it to pay off debt sooner. You can spend or save along with the ebb and flow of inflation and economic ups and downs.

If you have an early retirement budget and the numbers must match, then you could find yourself upside down at some point with nowhere to turn for additional income. It leaves you hoping that you can hit that number every month or year, and “hope” is not a plan!

Continuing to work gives you the numbers to make a plan. It literally “buys” you more time to make sure you’re setting yourself and your family up for success when/if you do decide to retire.

6- One cup of mental and physical well being

Our jobs put our brains and bodies to work. There are problems to solve, projects to complete, and new concepts to learn. Each day presents challenges, wins, and lessons learned. It keeps our minds at work and active.

Retirement will put all of those muscles into neutral. That’s what we envision right? That may be fine for a while, but if we’re not finding new ways to exercise our brains and bodies, it will have a domino effect on our overall mental and physical well-being.

7- One cup of play

Our six year old son loves being outdoors and there is nothing that makes him happier than going to a playground. But as much as he loves any type of playground, if there are not any other kids around, he always turns it down.

Think about how you spend your hours after work now. Now flip that to the working hours and look around. Is your spouse there? Your children? Is there anyone to go on a day trip or meet for a bite of lunch?

Early retirement could leave you feeling a little like being the only kid on a playground. All of the fun things to do are there, but there’s no one to play with so you end up feeling lonely and a bit lost.

8- One cup of purpose

Our jobs give us a place to put our skills and services in action. It gives us a purpose. When we’re no longer providing those skills and services, it could change how we see ourselves. While a job shouldn’t define you, it does refine you.

Purpose, especially when combined with passion, gives us our “why” and is a whole lot more important than the paycheck that comes with it. Regardless of traditional, early, or non-retirement, purpose wins.

One teaspoon of conclusion

I adore my papa. And that is the reason I hope he doesn’t retire anytime soon. Because I feel certain that if he had retired according to societal norms, he would have lost much more than a job. He would have lost what gives him purpose, profit, and fills much more than his cups of coffee.

Anyone who would question my papa’s decision to work well past the age when the world says “stop” would be doing him and the people who receive value from his services a huge disservice. By not doing so, his cup is overflowing and it spills over to the generations after.


So, those are the two sides of the issue. What do you think?

10 replies on “Money Match-Up: Should You Retire Early or Not?”

Two misses on the pro side:
1. By retiring early, you are more likely to be physically able to enjoy many activities. I am planing to spend the first 10-15 years of retirement living aboard a sailboat in the Caribbean. Not a bad plan at 53. But at 65-70? – not so much.
2. Working until 70+ just isn’t an option for everyone. Many people are forced out of the workforce due to injury or disease. So even if you plan TO work until you die, you better plan FOR the possibility you will have to retire early.

My wife and I are in our sixties and we hike, play tennis and distance run with many people in their late sixties, seventies and eighties. For people who have a lifetime commitment to fitness sailing the world at 60-75 should be duck soup, I have a friend in his nineties that is still winning at tennis tournaments. I would humbly submit that your view of old age decline is out of date for people who take care of themselves. And it is a dangerous way for you to view the world in terms of your own health. If you really think you’ll be limited at 60 then you may well be. Me, I’m in my sixties and I can still beat all the high school tennis team players and some of the small college ones as well. But part of it is mentally not accepting that age has to limit my life!

As to retiring early, or slightly early in my case, I’m all for that. It can be awesome if you have an idea of what that life will look like for you. It has certainly been a great experience for me!

Great post! Having retired a few years ago at the age of 43, I can attest to all of those pros and cons.

For me, the biggest obstacle has been your #1 cup – Interesting. I worked in the Internet tech sector in SF for many years, and had the pleasure of working with many weird, interesting, intelligent people.

To make up for no longer having access to that, I try to reconnect with former colleagues and meet new people as often as possible. Although I’m more of an introvert, I almost always feel energized after a good conversation.

And the good news is that when you’re retired, you can more easily carve out time to meet with others. When I was working, I usually only time to connect with fellow co-workers. Now I find I spend time with all sorts of people — neighbors, local business people, family members, etc.

I am on the Early Retirement bandwagon for sure.

Although I agree with some of the counter-arguments with those 8 cups, I think someone who is dedicated enough to save and plan for early retirement is also dedicated enough to plan for avoiding pitfalls you mentioned.

Without relying on money, you can engage in activities you want to and still be connected with others. Teaching, writing (such as blogging) and other creative endeavors still allow you to keep social interactions in early retirement.

Those in early retirement have likely saved enough to not worry about saving any more (FIRE people are extremely conservative and tend to overshoot the “number” they need to FIRE by a lot and also have planned for health insurance, taking those 2 cups out of the equation.

In the end, the biggest thing is that you can enjoy life when you are physically able to rather than waiting till traditional retirement age and maybe have 5-7 good years left to travel etc. Plus the future is never guaranteed, who knows if you won’t keel over 1 week after you retire at 65? If you can retire early and enjoy as many years as you can, I say go for it.

My response is “get busy living or get busy dying”. If working feels like dying a little every day and there are other things you want to do, and you can afford to retire early, then do it! I agree with the people who said they want to do a lot of active things in retirement. My parents retired at 62 and by 75 were really slowing down quite a bit. That’s not much time to enjoy all the money they saved.
My second motto is I have a bucket list and a f—-it list, the latter list was too long and the former too short. Now they are reversed. Retired at 58 (a week ago).

Early retirement all the way!!! I think the 8 Cups argument is a case for early retirement as well – all these things can be achieved, but with the financial freedom to do all those things on your own terms. I like that Dash2Retire website – many funny but true stories! They are a great writer and very creative…bring us more Dash2Retire!

How about the middle path- a long career of very part time work? As a nurse, I work summers, as well as 3 weeks in the fall and 2 weeks in the spring. That lets me pay the bills and spend over 8 months a year playing and living like a retiree.

Working so little makes my job feel novel and exciting, but doing it full time would be such a drag. I’m nearly through my 9 weeks of summer work and I’m ready to get back to total freedom. I don’t think I’ll ever be able to buckle down and churn out 7-10 years of the full time work that early retirement would require.

Frugality, geographic arbitrage, a decent wage in a high demand profession, and a sizeable emergency fund make my lifestyle easily attainable. For the life of me, I can’t figure out why more people don’t do this?

I think there’s a dichotomy in the early retirement section. Let’s say you take up a second act in your retirement – like running for office or starting a business. That completely negates the part about getting rid of stress, deadlines, clothing bills, commutes. But the reason you include stuff like work on your passion as a retirement goal, is because a lot of people are afraid of losing meaning in their lives when they retire. But you can’t have all the good stuff and none of the bad. Either you throw yourself into something else – and all the stress and obstacles it incurs – or you lay on the beach and have other stresses.

While everything you said about retiring early is true (I mean the cons) I think most of us would still choose to retire as early as possible. Today there are so many more things to do and experience than 30-40 years ago. The possibilities are limitless – all we need is TIME and a bit of money (in some cases).

I’ve started my retirement process by saving money and also investing in stock and cryptocurrecies. Hopefully, in 10 years I will get there and be able to do anything I want to and not be dependent on anyone else or a job.

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