Why People REGRET Financial Independence Retire Early (FIRE)

Why do people regret early retirement? I thought that if I could find the answer, it might help me plan for my own future. But instead, what I found had much more impact on how I live my life right now. To find the real gems, I went into a subreddit that was biased towards early retirement and looked for consensus against the FIRE movement.

Why do people regret early retirement?

As someone on the outside, it’s hard to believe. Isn’t everyone striving to escape the rat race? But after hearing stories of depression, divorce, and even death, I decided to scour the internet for some insight.

I thought that if I could find the answer, it would help me plan for my future, but instead what I found had much more impact on how I live my life right now.

To find the real gems, I dug deep into Reddit and looked into a subreddit that was biased towards early retirement and looked for the consensus against retirement. I scoured hundreds of comments, looked for the common threads and found some surprising patterns.

There are 5 lessons that I learned from the mistakes of others who were kind enough to share their story.

On the go? Watch the video HERE.

Lesson 1: Journey

The Financial Independence subreddit is closely tied to the FIRE movement. FIRE stands for Financial Independence Retire Early, F I R E. In this subreddit, there are 2.2 million members, and so there is a lot of wisdom to be gained.

This community is solely focused on acquiring enough wealth such that your investments fund your lifestyle completely. Generally, this is done as fast as possible within reason.

After achieving financial independence, some people decide to keep working, but most decide to retire early.

It should come as no surprise that the overwhelming majority of comments were for early retirement.

When a post asked the question directly, nearly 87% of comments were positive. But, in that 13%, there were some common threads and some lessons to be learned.

The first common thread, which is perfectly described in this poetic comment:

 “An object in possession seldom retains the same charm that it had in the pursuit.” 

Pliny the Elder

In other words, When somebody solely strives for financial independence, the fulfillment they get from achieving that goal does not measure up to the effort it took to get there.

For many, it takes decades of sacrifice in the form of frugal living, coupled with hard work and dedication in one’s professional life to move up the ladder and get higher compensation.

After all, that’s the formula for early retirement. Decrease spending as much as possible and increase your income.

Many people find themselves after 20 or 30 years ready to retire, but that means leaving a job that they put all of their energy into and ready to spend money, but all they practiced was frugal living.

Arriving at their goal means an end to all their pursuits.

This is one common thread that links a lot of these early retirement’s forums. It’s the arrival fallacy, where people think arriving at their goal is going to carry the same charm as the pursuit of that goal.

In this post directly asking people if anyone regrets retirement, we had 16 people say there was no regrets at all but there were 2 comments that said they missed certain things like a sense of accomplishment at their job or being surrounded by like minded people working towards a common goal.

In this comment by Paverbrick, they talk about missing being part of a bigger goal.

“I miss belonging to a workplace. Perhaps more broadly, I miss being part of something bigger. When I was working at a tech startup a decade ago, there was an energy and enthusiasm that I am nostalgic for. Working with passionate people in the same direction was a lot of fun.” 


The first lesson that I learned is that satisfaction comes from the pursuit of meaningful goals, not in the completion.

For me, I am incredibly lucky to work alongside driven and passionate people in the pursuit of a worthwhile goal, but I’m not going to work there for the rest of my life. I’m reminded to have other meaningful pursuits outside of my 9 to 5.

Lesson 2: Friends

The second lesson I learned is very similar to the first. It is a hole left behind by leaving a career. We saw a taste of this in the previous comment, belonging to a workplace.

When we spend 40 plus hours per week in a work setting, it’s easy to pick up some skills, but it’s also easy to lose other skills. I spend a lot of time at work. Therefore I spend a lot of time with my coworkers.

I am lucky to have really cool co-workers, but the downside is I’m not as motivated to find new friendships and maintain current friendships outside of work.

It feels like grind culture is becoming the norm, at least in the U. S.

People are going into monk mode when they get home from work and working on their side hustle instead of going out with friends or making new friends.

A lot of the grind is in pursuit of financial independence. But once financial independence is reached, you find yourself in a place where you’ve spent years not making new friends and you’ve lost the skill.

This is a common problem for many people, but it is really felt by people who retire early.

A Redditor with the tag RetiredAndLost made this post.

“I FIREd at 30 and now I’m lost, depressed, and don’t know what to do. I realized how small my social circle is and how little time my social interactions actually fill and haven’t the slightest clue how to expand my social circle.” 


This is a common problem for many people but it is especially felt by people who retire early. The co workers that they’ve built up relationships with are, I don’t know working or something, but the same thing goes with their old friends.

The second lesson is friendship.

This is a reminder in my life to continue flexing my friend making muscles because if I don’t use it, I’ll lose it.

Lesson 3: Family

I’m realizing at this point that many of the problems that people are reporting with early retirement are in some way related to the excessive pursuit of early retirement.

The neglect of one aspect of someone’s life that is then amplified when they are faced with 100% free time.

I found one especially sad comment from a throwaway account.

“ I didn’t spend money with her to do the things she really valued. I didn’t buy plane tickets to go visit her family with her when she desperately wanted me to come. My whole life I said I wanted kids then discovered financial independence and changed my mind because they were too expensive.

I refused to buy nicer furniture for our apartment and made her embarrassed about our place and not comfortable in our own home. Over and over I made this mistake and we drifted apart. I realize this now, but it’s too late.” 


And it doesn’t matter how much money you have in the bank. In this comment, this person said they had around 3 million: cars, toys, and a nice home.

“I had built a business over the course of 7 years and sold it to have a better family life. My wife didn’t work and life was easier. Then 2 months after I sold my business, she wanted a divorce and wanted half.”

Clearly, this person put certain things on the back burner in exchange for building more wealth and now they consider themselves to be a miserable millionaire.

Even Warren Buffett is famous for saying that the most important decision that you make in life will have nothing to do with your career or your money. It is who you choose as your spouse.

Warren Buffett says the most important decision you’ll ever make has nothing to do with your money or career

These stories are sobering reminders that my spouse is my most important investment. My life partner, who I want to enjoy the fruits of our labor with. Or maybe I could just get like 10 cats. That would probably replace my wife, right?

Just kidding.

Lesson 4: Health

Once again, the reckless pursuit of financial independence and early retirement is the culprit for the fourth pitfall that I read about in these comments.

One happy life shares a story about her father’s journey.

“The backstory is that my dad scrimped and saved to be able to retire at 62 and had triple bypass and dementia by 64. So he never got to enjoy all of the years he’d saved for.”


Then I saw this comment from Silly Goose.

“ I had a boss who hated his job, would always say if I stay another year I can get a higher paying job when I leave. Another year goes by, he says, one more year for a better exit opportunity, still hates the job. He passed away on a boating trip when he took a vacation.

He spent his last years doing a job he hated, hoping for a payoff later, presumably in the goal of financial independence.” 


Silly Goose reminds me to have fun along the way and One Happy Life reminds me that health is right up there with family in terms of the most important investment of my life.

Working myself ragged to achieve early retirement isn’t worth it if I don’t have the health or the lifespan to enjoy what I’ve achieved.

I’m reminded to take a step back from monk mode, take some time to cook a healthy meal, decompress and de stress with my wife, friends and family and stay physically active.

No matter where I am in life, I want to have the health to enjoy it.

Lesson Five: Happiness

The reckless pursuit of financial independence or early retirement we have seen is a common thread through all of these stories, but I think it is just a symptom.

What pushes people to strive so hard to arrive in paradise only to be depressed, divorced or dead?

I think I found the answer when I was reading through this post titled “Was anyone 100% confidently sure that fire was the answer, but after retiring early realized it was a mistake?

Lukin88 said:

“Not quite the same thing as early retirement, but I was completely miserable and was convinced that if I could just quit my job, I would be okay again.

Then I had an opportunity to do it. I gave myself 2 years to fix everything about my finances and life to put myself in a good position to quit. I was so excited about quitting that I literally changed my whole life. I lost a bunch of weight, started exercising regularly, got out of debt, became financially independent and started dating again, went back to school to pick up some related skills, etc.

After 2 years, I was a changed person in every way and was really happy.

The whole 2 years was about quitting my miserable job that was making my life hell. The 2 years was up and I realized that my job was actually not that bad. I actually liked it. My misery wasn’t coming from there. My misery was coming from my toxic attitude, from not taking care of myself, and from feeling financially trapped.” 


It seems like the people who regret retiring early are the people who have not yet found internal happiness and the people who do find internal happiness, no longer desperately feel the need to retire early.

Thinking through this reminds me of a very inspiring podcast called Diary of a CEO where the host, Steven Bartlett brings on an expert in happiness named Dr. Robert Wallinger.

There are many parallels between the missing links from the commenter’s stories and the elements of happiness according to Dr. Wallinger. But getting happier starts with this understanding that really what it is.

He says that happiness is analogous to your diet. You have to have proper proportions of the three macronutrients, protein, fat, and carbs. The three macronutrients of happiness are enjoyment, satisfaction, and meaning.

Happiness illustration by author

  1. Enjoyment is not just the pleasure that you feel, but pleasure combined with people and memories.

  2. Satisfaction is the joy that you get from progressing towards a goal, not the achieving of the goal.

  3. Why People REGRET Financial Independence Retire Early (FIRE)

Actually executing on these big words is of course the hard part that even millionaires struggle with along with the rest of us. If you have figured it out please let me know in the comments.

So What Now?

Tying that podcast and the stories from comments together really made me reflect on my own life.

My wife and I both work full time jobs and most nights we come home and we work together on this YouTube project.

One day, we realized we were arguing about YouTube.

We had been eating junk food that whole week because we had no time. We hadn’t seen our friends or family in a while. We were working our asses off. And we would be stressed out because we weren’t hitting the metrics on YouTube that we thought we needed to hit.

We definitely don’t have it all figured out yet, but we wanted to share our progress. The goal is to take time to appreciate each other, our friends, our family, our health, and enjoy the process of making YouTube videos regardless of how many people like, subscribe, or watch.

Don’t get me wrong. We do appreciate you watching the videos and reading my articles and doing all of those things. And we do strive to improve our videos every time so that one day, maybe we can monetize. But what’s important is that we enjoy the process along the way. And if you like the video, it’s just a nice bonus and we would appreciate it.

One small way that we have had some success is by finding a way to live a frugal life without feeling like we’re sacrificing health or happiness. 

In this video HERE, I’m sharing my wife and I’s frugal living strategies

Catch you on the flip side.

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