The Negatives Of Early Retirement Life Nobody Likes Talking About

Early retirement sounds great and it is great for the most part. But there are negatives of early retirement life that also needs to be discussed. I retired early in 2012, at the age of 34. But the years that followed felt unnatural, so I decided to keep busy doing some part-time consulting from 2013-2015 and write on Financial Samurai.

Since leaving my day job in 2012, I've redefined what early retirement means to me. As a result, I now call myself a “fake retiree.” I say “fake” because I'm still writing on Financial Samurai three times a week. I'm also recording a podcast twice a month as well. Even though these activities are enjoyable and intellectually stimulating, they require about 15-20 years of work a week.

Over the past 12+ years, I ended up actively doing a lot of things that provided meaning and purpose, including writing Buy This Not That, an instant WSJ bestseller. And such things ended up making me money, hence my fake retirement.

The Desire To Really Retire Again

Today, however, I want to re-retire because I’m so tired after the pandemic! I've been a stay-at-home father of two young children, 4 and 6.5 their entire lives so far. Fatherhood during a pandemic was at least 50% harder than even the hardest years I had in banking.

Taxes are going up, reducing the return on our effort. With the economy also slowing, grinding harder if you don't need to grind harder is a suboptimal choice. Finally, spending two years writing and six months marketing my new bestselling personal finance book took a lot out of me.

You won't really know what early retirement life feels like until you actually walk away from a steady paycheck. It's easy to pontificate what you should and shouldn't do in retirement. Further, you can assume a high safe withdrawal rate when you are gainfully employed.

However, I promise you your expectations about retirement and the reality once you are in retirement will be different. Don't be fooled by early retirees who only crow how amazing early retirement life is. Be wary instead. The Instagram life is not reality.

For all the positives of living an early retirement lifestyle, there are plenty of negatives as well. I know why we revert back to our baseline state of happiness, no matter how much freedom and money you have.

Negatives Of Early Retirement

Now that I'm a grizzled early retirement veteran, here are the six main negatives of early retirement few people like talking about.

1) You will suffer an identity crisis for an unknown period of time.

When you’ve spent at least a decade working in a profession, you’ll find it incredibly jolting to no longer be identified as the person who is a marketing expert, an investment professional, or the management consultant who can figure out how to optimize a business. It’s only after you leave your job do you truly realize how wound up you were in your profession.

Your identity crisis may last as short as three months or it might last for years. It all depends on how wrapped up you were in your job and what you plan to do next. It also depends on long you spent getting educated after high school and whether you have a clear plan post-retirement.

Doctors are some of the people who suffer the most identity crises after leaving their occupations. Conversely, high school graduates who somehow struck it rich with a product or an invention seem to adjust much easier in post-retirement life.

Job titles can be incredibly addictive. Why else do people get so depressed when passed over for promotion? Why else do people try so hard to get promoted sooner and faster than everybody else? Do not underestimate the importance of being a manager, director, vice president, or even a C-level executive.

After all, the most common question people ask when they first meet each other is: What do you do for a living? And if you tell them you don’t do anything for a living, well then you might just feel like a sheepish loser. You’ll want to try to explain yourself, but by then, your three-second first impression will no longer hold the other person’s attention.

Negatives Of Early Retirement #1: What happened to me

After working in the Asian equities business for 13 years, it felt hollow to no longer have my Executive Director title or be identified with my investment firm. I felt sad that I could no longer go to Asia for conferences or travel with clients. For so long, taking a business class trip to Hong Kong, India, China or Taiwan was part of my quarterly routine. Shallow as it may sound, it felt special to have priority boarding. I felt important when clients would entrust me to show them around in a foreign land. 

For the first year after leaving my job, I wondered how the business was doing without me. Could they really survive without my expertise? After all, I was there for 11 years. Surely, they needed my relationships. But after months went by with no email or phone call from my old firm saying they wanted me back, I had to come to terms that I was no longer important to them.

I wanted to believe that my position meant something to the firm and to the people that I serviced. But at the end of the day, the person I trained to replace me as part of my severance agreement, was good enough. And because he was good enough, I concluded that I was no longer any good.

This ego hit took me a full year to get over.

2) You will be stuck in your head. 

When you suddenly have an extra 10 – 14 hours a day of free time, it can be very difficult to optimize your time wisely. Just like how bedrooms naturally get messy, your mind naturally gets lazy the more time you have to do anything.

Your productivity will suffer in retirement. You will no longer feel motivated to achieve great wins. As a result, you may slowly start to get depressed. Only after some really deep soul-searching and some, what the hell am I doing with my life questioning will you begin to organize your time better and become more productive.

Your mind can be very dangerous because it can always second-guess your actions. Did I retire too soon? What if I run out of money? Will people think I'm a loser? What if I can't ever get back into the workforce if things go wrong? When you have a lot of time to think, your doubts go on and on.

Perhaps one analogy is to compare being stuck in your head with Locked-in syndrome. LIS is a condition in which a patient is aware but cannot move or communicate verbally due to complete paralysis of nearly all voluntary muscles in the body except for vertical eye movements and blinking. This could be one of my worst nightmares. Retiring early may render you inoperable for a while.

Negatives Of Early Retirement #2: What happened to me

Because I left work at the age of 34, I was worried for about the first two years whether or not I had made the right choice. No rational person leaves a well-paying job to be unemployed in their mid-30s. Your late-30s is when you start to finally make good money. And by the time you reach your 40s, you should be at your maximum earnings power. 

During my first year of early retirement, to the outside world I proudly proclaimed I was retired from a career in finance. But on the inside, I was second-guessing my decision to leave. Because of my uncertainty, I decided to do some part-time consulting with a financial technology startup for ~20 hours a week. It was a great way to distract my mind from all my fears.

I also earned some side income and got to replug myself into society. I also kept in touch with multiple banks until my Series 7 and 63 licenses expired.

Finally, I dived deep into my writing on Financial Samurai. Writing has always been my most cathartic way to deal with any uncertainty or problems I might have. For example, now that I have a son and daughter, I've been worried about whether our passive income is enough to support a family of four if they don’t win the SF public school lottery system. It's taken almost 20 years for me to generate this passive income level, and it still doesn't seem like enough.

Given this worry, I did a deep dive budget analysis for a family earning $300,000 a year. It it sure seems like we need to earn $100,000 more to maintain our lifestyle in San Francisco. Alternatively, we can always move to a lower cost area of the country. 

3) People will treat you like a weird misfit.

Whether it's because retiring early is unconventional or because people are secretly jealous you aren't grinding away at a day job, people won't give you the same amount of respect as working class citizens. After all, if they can't describe what you do for a living, then they can't pigeonhole you into an archetype that is comfortable for them.

Having a job means you are a productive member of society. If you retire at a young age, people will assume you are simply slacking off and not paying any taxes. They'll sometimes look at you as a leech they want to flick off.

Further, if you are an outcast, then you won't be invited to parties or events that other working people always get to attend pre-pandemic. You're simply not top of mind to them and you will feel more lonely as a result. If you are an extrovert, early retirement will be much more difficult than if you are an introvert.

Negatives Of Early Retirement #3: What happened to me

After the first year of early retirement, I no longer told anybody I retired early. Instead, I told anybody who asked that I was a writer, a tennis teacher, or a fintech consultant. Prior to that, I think a lot of people just assumed I was a trust fund baby who did not have to work. And the last thing this middle-class guy who went to public school wants to be known as is a trust fund baby. 

My favorite time of the year was during the winter holidays. I loved going to all the holiday parties and getting tipsy with fellow revelers. Now, I get invited to zero holiday parties because I don't work for anyone. Nor do I get invited to client holiday parties either.

Even though I have several partners who are based in the SF Bay Area. It may sound silly, but having a drink with good people with shared interests really means a lot to me. 

It takes a lot of effort to build new social networks if you aren't part of a larger organization. There is no weekend BBQ party a colleague is hosting on Labor Day Weekend to attend. I've had to participate in various meet-up events in order to find new people to hang out with.

So far, my social network only revolves around tennis and softball. But even then, it's not like I've found buddies who will come over and just chill in the hot tub over a beer or anything. 

I know. Cry me a river. but those parties to be merry with others were amazing! Maybe more people will empathize with the need for more social connections thanks to the pandemic.

The negatives of early retirement life

4) You'll be disappointed you aren't much happier.

So many people think that once they achieve financial freedom or leave a job they dislike, they'll suddenly be permanently happier. The truth of the matter is, your elevated happiness will only last at most three to six months. Eventually, you'll revert to your natural state of being.

Think back to your high school or college days when you didn't have any money compared to now. I'd venture to guess you were just as happy, if not happier when you were a broke college student. I felt rich even though I was poor.

Having the freedom to do what you want is priceless. But you will eventually take your freedom for granted like the air you breathe. On the days you feel angry or sad, you will start questioning what the hell is wrong with you since you've got more than the average person. You might even feel stupid for feeling unhappy when there are literally hundreds of millions of people in the world wondering whether they'll have enough to eat the next day.

You think, if I can't be happy when I'm financially independent, surely there must be something seriously wrong with me. And you could be right! Can you imagine being unhappy as a Norwegian? Norway is perpetually ranked as one of the top five happiest countries in the world.

What happens after grinding so hard for so long is that once the grind is done, you may experience a trough of sorrow. You sometimes feel this emptiness inside where you long for more. It’s a baffling feeling!

best reason to retire early, greater happiness, biggest benefit of retiring early

Negatives Of Early Retirement #4: What happened to me

I thought I'd be much happier not having to report to a micromanager boss I did not respect. But my increased happiness was fleeting. It only lasted for about a week before I was back to my regular self. Instead, my happiness was weighed down by months of uncertainty on whether I had made the right move to leave my job.  It was only after about two years did my doubt finally start to dissipate.

Although corporate politics no longer piss me off, other things end up filling the void. For example, drivers who decide to double park on a busy street in rush hour traffic really piss me off now. So do dog owners who let their dogs poop in front of my house and don't pick up after them. In the past, I could only allocate a small amount of annoyance to such incidences. 

I also thought I'd be happier once Buy This, Not That (Amazon), made the Wall Street Journal bestseller list. After all, less than 0.5% of nonfiction authors make the list. Alas, the happiness only lasted for about five days. Without anything else to look forward to, an emptiness developed inside.

Despite not being permanently happier after publishing, I'm still proud Buy This, Not That will help readers develop more wealth and make more optimal decisions. You can pick up a copy on Amazon today.

Buy This, Not That: How To Spend Your Way To Wealth And Freedom Bestseller

Instead of being permanently at a happier level, I'm simply no longer as annoyed at things as frequently. Further, the volatility around my steady state of happiness is lower. In other words, I’ve mellowed out. That said, don’t offend me because I still enjoy a really good fight!

Related: If I Could Retire All Over Again, These Are The Things I'd Do Differently

5) You constantly wonder whether this is all there is to life. 

Retiring early is like finishing up your favorite longstanding TV show. You’re glad there’s a conclusion, but you’re also sad that it’s over. You hope to find a show that’s as good or better, but there are no guarantees.

Most of us spend 13 years going to grade school so we can spend four years in college in order to get a decent job. Then we spend decades trying to earn and save money in order to provide for our family. Then one day we hope to retire by 65. With good luck, we'll live for another 20 years to enjoy all the fruits of our labor.

When you retire at a much earlier age, you are constantly left wondering what's next. A potentially 50-year retirement is a very long time! You are mentally twiddling your thumbs waiting for the next big thing while your close friends are all at work. Early retirement can get extremely mundane and boring because you have nobody to spend time with.

As a result, you're repeatedly forced to will yourself into action. This constant self-starting attitude can become extremely trying. It may get to the point where you long to rejoin the workforce and be told what to do.

Negatives Of Early Retirement #5: What happened to me

I probably drove my wife nuts during the first two years of early retirement. I constantly told her I was bored. Only boring people get bored right? Wrong. Everybody gets bored at some point.

When you're working, you don't have time to get bored because you're working. There's only so much tennis, golf, and softball I can play before my knees break apart. There are only so many churches to visit in Europe before they all start looking the same. In fact, I decided to apply to some AI-related jobs after retiring for so many years. So far, no luck getting a job!

She used to have vacations from me because I would be away traveling for work every month. Now she was seeing my cherubic face every single day! It's a good thing we had three bedrooms at the time. Otherwise, I'm pretty sure we'd both have gone crazy from seeing each other so often. 

It was only after our son was born in early 2017 that I felt a renewed sense of purpose. Before my boy, I felt my purpose was to help educate as many readers as possible about personal finance.

After my boy was born, my purpose has expanded to keeping Financial Samurai running long enough to teach him about operating an online business. I fear he may have a tough time getting ahead. In addition, I now need to live long enough until both my kids find someone who loves them as much as I love my wife. 

I don't think I'd be able to die in peace if there's nobody to replace his mom or me. As a result, I'm exercising more, eating healthier, and meditating longer. 

6) Your relationship with your significant other might suffer.

As more people retire, I'm noticing an increase in breakups and divorces post retirement because there is a mismatch in retirement philosophies. The most obvious one is where one spouse retires first and the other spouse keeps working for years.

Resentment naturally builds up by the working spouse who doesn't absolutely love his or her job. And nobody loves their job so much that they'd rather work than be free to do whatever.

There is also an interesting anthropological trend where the man retires early and the wife still works. Instead of the man saying he is a stay at home dad taking care of his children, mostly due to ego, he tells everyone he retired early.

Meanwhile, he is frantically behind the scenes trying to make supplemental retirement income. Sadly, they don't truly have enough money for both to comfortably retire. We men have fragile egos.

To minimize relationship problems, it's important to have the same philosophies. It's also important for couples to have enough passive income to cover the couple's desired living expenses. It would be a shame to let money get in the way of a happy retirement!

Negatives Of Early Retirement #6: What happened to me

When I retired in 2012 at age 34, my wife and I made an agreement when she was 32 that she could retire early before she turned 35 in 2015 as well. We shot for equality. With almost a three year deadline, we created some cash flow and financial goals.

When she finally retired, it was great b/c financial and career objectives were met, and she also negotiated a severance package much better than expected. We traveled together a bunch and it was nice.

However, I did have some resentment for the first couple of years because she was able to sleep in while I couldn’t after 13 years of getting up at 5 am. In other words, I was jealous she was enjoying her initial years of retirement so much! During my first year of early retirement I was always wondering: hmmm did I do the right thing leaving my job so young.

To solve this jealousy and resentment, we agreed that she would spend more time working on the back end work for Financial Samurai. Once we had our son in 2017, there was no more jealous and resentment at all. Being a full-time mom is the hardest job in the world! Now that we have a 3-year-old daughter, I'm super grateful for any support she can provide with FS.

7) You will feel more stressed in a bear market.

One of the best times to retire is in a bear market. If you can, your finances will have been properly battle tested. Your downside is limited. When a bull market ultimately returns, everything will feel like gravy as both your net worth and passive investment income increase once more.

However, the downside of retiring in a bear market is the increased stress you will likely feel. Because when things are going bad it's easy to extrapolate how bad things will continue to get. As a result, your worry will naturally go up even though the average bear market only lasts around 14 months.

Negatives Of Early Retirement #7: What happened to me

Until 2022, I had not experienced a prolonged bear market since I first left work in 2012. Sure, risk assets turned down slightly in 2018, but the downturn wasn't very deep nor did it last very long. The March 2020 crash was scary, but the stock market rebounded within two months. Real estate, my favorite asset class to build wealth took off.

2022 was a year of endless down days. With the Fed aggressively raising rates, they seem determined to ruin the world. Most of my tech stocks that performed so well in 2021 gave up all their gains and then some. Facebook, Amazon, Google, Netflix have all been crushed. Then there is the cryptocurrency debacle with FTX.

When you depend more on your investment portfolio to survive, as we do, you will be more concerned about the state of the world. But one of the biggest ironies of a bear market due to high inflation is that it's actually easier to generate more passive income!

Thanks to rising rates, I've actually been able to boost our overall passive income by ~10%. Therefore, I should feel even more secure in early retirement because cash flow is more important than net worth. Cash flow is real, whereas net worth is more subjective. Below is my latest passive income estimates for 2023.

After buying a forever home in 4Q2023, I blew up my passive income and now it’s estimated at only $230,000.

Financial Samurai passive income investments 2023

Early Retirement Is Great, But It Doesn't Solve Everything

It might sound like after reading this article that I’m depressed. But I’m not. There are some nice surprising benefits of retiring early as well.

I’m simply highlighting some of the negatives of early retirement you will probably go through if you decide to leave the workforce early. The more extroverted you are and the higher your position, the more you will have difficulties making the early retirement adjustment.

Having the freedom to do what you want cannot be overstated. However, your mind will play games with your spirit during the first few years after leaving work. Some of you won't be able to handle early retirement life and will go back to work.

Just know that with enough conditioning, you will eventually embrace your freedom. Nobody I know who retired from corporate life early has stayed retired. You will find your purpose. Once you do, you will take steps, such as building passive income, to ensure you remain free forever.

Saving rate chart to help you reach financial freedom and retire early

Here's another chart to help get you motivated to save more in order to retire earlier.

How to retire early: save as much as possible - The negatives of early retirement

Having Enough Money Is Important For Happiness

Since 2012, I have not spent a single dollar of my investment principal. Instead, I've been living off the income my investments generate. This is due to the rise in the stock market, real estate market, and the growth of Financial Samurai.

With the return of a recession and a murkier future. I recommend everyone build more capital before retiring and lower their safe withdrawal rate in retirement. You won't regret being more conservative with your money during times of uncertainty.

Hopefully you can appreciate all the negatives of early retirement I've shared with you in this post. It is one thing to run the models and pontificate about what early retirement is like when you are still gainfully employed. It's another thing to actually experience early retirement when you no longer have a steady paycheck.

In the end, I believe the positives of early retirement outweigh the negatives of early retirement by a 3:1 ratio. Further, after 11 years of fake retirement, the best reason to retire early is greater happiness for longer!

Therefore, you might as well shoot for early retirement and discover what all the fuss is about for yourself!

Recommendation To Retire Earlier

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The Negatives Of Early Retirement is a Financial Samurai original post. I've been writing about FIRE since 2009. The journey to financial independence has been full of twists and turns. Make sure you enjoy your journey!

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192 thoughts on “The Negatives Of Early Retirement Life Nobody Likes Talking About”

  1. Hi Sam,

    Thank you for this article. It really helped me emotionally this morning.

    Molecular biologist at a biotech who retired at age 32 in 2002. Grew up poor. After 2 years of early retirement, I went to law school because I was bored. No business lunches, etc. – exactly what you wrote. I didn’t care about titles. I had academic freedom.

    Boredom and loneliness because your friends have to work and socialize with their co-workers and clients.

    Thank you for sharing. Great to know I’m not alone in feeling isolated. I’m glad you have transition well.

  2. Interesting. When my partner took early retirement @58 yrs., we moved from Ontario to VAncouver. He had planned all that, including home. I left a management position and had no job in hand in new location. So I did sell my place and relocated across the country for love.

    He threw himself in local cycling advocacy volunteer work for several organizations, wrote reports, served on boards and grew his network of locals/distant friends. Meanwhile I worked full-time after landing a job 9 months later. I did have 2 other unemployment periods which thankfully during each time while applying for jobs, we did longer bike trips together. He also created 3 different public blogs. For about 8 yrs. he, also did the accounting online and set up Shopify ecommerce site for son’s Toronto butcher shop. To make a long story shorter: he died 2 yrs. ago while I’m still workng at tail end of my career.

    Though I’m sad not to spend my retirement with him for at least a few years, I’m so grateful he had a happy 20 yrs. retirement that was highly productive. (By the way, I’ve been happy to work full-time, since I grew more in my jobs.) I worked more….it pushes me forward while also earning more money. Admittedly I nearly worry for my own retirement — after living with a beloved who had a exemplary retirement.

  3. Definitely got me thinking about a few of those topics as I am planning ahead for early retirement in 10-15 years (currently 38yr old).

    One point you keep returning to is the happiness metric and how retiring early, the variety of aspects to this, don’t necessarily make you long term happy. This is great insight and something I’ll continue to keep in mind!

    I’ve found that I return to my Christian faith as the ultimate barometer of happiness or joy. If I have a right relationship with God, then all else becomes gravy, as you say :)

    Just wanted to offer this perspective as I’ve found it to be the greatest source of peace, even though I do look forward to the freedom of allocating time differently during early retirement.

    Thanks for all you do and write about!

  4. I could hardly believe how closely your thoughts on retirement matched mine. I found myself devouring every word! I too, retired at a young age (45) and experienced everything you discussed in this article. I am 67 now and I still suffer pangs of regret for selling my company. You are correct, the sad feelings dissipate with time, but oh my, how it still stings sometimes.
    I have reinvented myself over the last 20 or so years and it has been wonderful to be able to use my talents to help others.
    Thank you for this…a much needed emotional check for many of us.

    1. Thank you for reading Tina! And I’m glad you reinvented yourself over the past 20+ years. You actually retired at the age I think is ideal. Check out this post: https://www.financialsamurai.com/ideal-age-to-retire/

      But it sounds like you have a different perspective. I’m 45 years old now and there is no way in hell I would ever go back to working for someone else. But I also will never sell Financial Samurai so long as I have a joy in writing.

      1. How quickly things change! Less than a year and a half after writing “there is no way in hell I would ever go back to working for someone else” you’ve changed your tune. I guess it’s a great example of never say never. Life has a funny way of twisting in unexpected ways. Best to always be ready and flexible for the unpredictable.

        I’m a 55-year-old software dev who stepped away from work 7 years ago. Still think it’s one of the best decisions I’ve made even though there have been some ups and downs. Was close to having to work again during the COVID market crash; happily, the market turned around and I’m feeling pretty safe now (knock on wood!).

        1. Man plans, God laughs as they say!

          Yeah, I didn’t anticipate finding my forever home for a reasonable price in 2023. And I’m so tired from being a stay at home dad for almost 7 years now. I need a vacation and doing some consulting to fill the void will be a good solution IMO.

          It’s been a good 12-year run of financial freedom. Consulting part-time for 20 hours a week this year could be the ideal balance once both kids are in school. There’s just so much excitement in SF now.

          My new worth is also up, but it’s boom times again in SF. I’m excited to see what’s out there.

  5. Hi Sam. This really hit home for me. I retired at 42 in 2000. I was the CEO of a bank that was sold abruptly and I joined my stay at home husband in unemployment. I haven’t worked for pay since but have served on a number of non-profit boards. The section on social interactions really resonated as we moved shortly after retiring. I too get antsy during a downturn and 2007 was tough as our real estate also lost 50%. Having lived through that I’m a bit calmer this time. Knowing that tomorrow isn’t promised we are now traveling more and spending more on experiences. If we eventually run out of money, we still haven’t touched principal, we have told the kids we will move in with them!

  6. This is one of your masterpieces, it is so true!
    And one will realy feel this only when you retired early. If you read this when you are still on your journey, maybe you think about it rationaly, but feeling and knowing it is different.
    Best thing about early retirement is, that you have so much more time to work on becoming a happier person. Because when you retire you are still the same person as before.

  7. Hey Sam, great read! Your comment that physicians (dentists and pharmacists and nurses included) have so much difficulty defining themselves outside of medicine. I saw this first hand with my father. He retired in his 70s from dentistry and he has wasted away in retirement. He never found a way to define himself as anything other than a dentist. As such he mostly just watches television, mows the lawn, and opens a glass of wine for himself around 4PM. Rinse and repeat. He enjoyed this for about a month, then he became depressed. He is now 3 years into retirement and nothing has changed. With dementia setting it, breaking this familiar cycle has proven to be difficult. I write all this to say, reaching financial independence and retiring early are incredible goals. Im pursuing the same! But I think it is critical to really explore your interests and build hobbies well before you retire. This way you can have something to transition into when you retire. I think ‘fake retireing’ for a few years after retirement may actually be helpful for many approaching retirement. I would imagine it can be confusing to go from ’60 to 0.’

    Thanks for another great article. Cheers!

  8. Sorry Sam, you are NOT a “grizzled veteran” of early retirement, you went back to work a year later and have been grinding it out since. I ACTUALLY retired at 40 years old (end of 2014) and have been quite content in BEING RETIRED. Am I happy ALL OF THE TIME? Of course not, no one is. But, I am content. VERY contend as a matter of fact. See, here’s the thing…I don’t even call myself retired…instead, I am FREE. I can do whatever, whenever I feel like…I don’t have anyone (outside of the government) telling me what to do. And sorry, I don’t do social media including Instagram, so I am not sharing my adventures of freedom with the world. So stop talking down early retirement. Folks are different for you and me.

    1. Yes! I thought the same thing. Sam didn’t retire, he just found himself working outside the traditional office politics. Retirement will be defined differently for each, just as success is.

  9. Hey Sam, so glad you shared this with your readers. It hit home for me and it was very reassuring to see someone else go through the same journey. After 20 years of selling my business I still struggle with some of these same emotions. My happiest days were when I was building a business and achieving success.

    1. Planning for retirement typically includes saving enough to cover your expenses, reducing costs and maybe downsizing your home. All of this is done in anticipation of the day when you will finally be “free of working”! But will not working really bring you the happiness you are anticipating?

      Or is what you are seeking a way to spend your time doing something that you are passionate about? Being constantly under time pressure and on the hook for various nonsense and then constantly worrying about restructuring and being laid off does create a lot of stress. This can sap the enjoyment out of life, but suddenly going from the rat race to idle time with no commitments does not seem to lead to ultimate happiness. In fact, my observations have been that suddenly having nothing you must do can lead to feelings of boredom, isolation, depression and having no purpose. I have witnessed this happening within my own family.
      Family gatherings have gone from discussing:
      · How stressful work is, how bad management is, how unfair the policies are and what a bad boss they have and how they cannot wait to retire and get out.
      To
      · Aches and pains, complaints about the government and society, dealing with limitations due to medical issues, losing touch with other people, regrets about opportunities not taken when they had the chance and never getting to enjoy retirement before it was too late.

      The point is, long term happiness is not as simple as ditching your job and then being totally stress free. The human mind is always active and you need something to focus your thoughts and energy on to keep you engaged and maintain your mental and physical health. This must be something compelling and meaningful to you. What we are really seeking is not to stop “working” but to spend our time “working” on something that brings us joy and satisfaction. Haven’t you heard people quoted as saying something like “do something you love and you will never work a day in your life”? The fact is that the people who are working in jobs they really enjoy don’t feel stressed and burned out, even if they are putting in many hours and lots of effort into their work. Think about people who could easily retire with the wealth they have built over many years, like Warren Buffet or Oprah Winfrey or Paul McCartney. But they keep “working” why? They choose to keep on with their work because this drives them, it is not a chore at all. And this is the one to the big keys to enjoying our “retirement years”.

      How many times have you heard some say “Once I retire, I will finally have time to …………”? So the questions is – why wait to retire? Why not start now? There are many part time ventures which can be started on the side while still working a full time job, and these can be scaled up or grown as appropriate. Pick something that you enjoy doing and could make you some extra money. I have a friend who has started a side business making furniture and has set a woodworking shop. Someone else I know makes jewelry and sells it online, another person I met makes stained glass window ornaments and sells them at flea markets on her website, and another friend write fiction novels and edits movie scripts on the side…

      ​For me my passion project is information publishing; writing instructional ebooks, how-to guides, business plans and printable items. This satisfies my creative side while utilizing my technical experience and I can see myself continuing to do this once I “retire”. It makes me enough money to fund itself and extra to invest and enjoy on fancy dinners and weekend getaways. Who knows, it might grow to make me enough money to retire earlier that planned. This is not just a sketchy get rich quick scheme. I view my side business as an investment in my long term happiness and health, just like investing in retirement funds, I am, investing in myself. You never know where this may lead you and you never know what will happen with your current company that says they are doing so well, as I’ve learned several times the hard way. Now is the time to start! Remember, it is never too late…until you decide to give up.

      1. Thanks for sharing your thoughts and perspectives Erik Kopp. I totally agree with them and even saved what you posted. I am FI and can retire at any time, however I haven’t because I have been struggling with what to do when I retire: how to remain productive and challenged after I retire. The easy choice is to actually just continue working.

      2. greenbalrog

        Thanks for your comment. After reading and thinking about a lot about what I should do after I retire (since I could reach FI in a few years), I believe your comment was the best I’ve read, I mean, everywhere so far. It did resonate with me.

        Thanks Sam also for sharing your story.

        Live long and prosper.

  10. I retired from the Foreign Service at 53 and consider it the best decision I have ever made. I have always loved traveling and retirement gave me the opportunity to truly be free and see the world without having my life controlled by the State Department.
    However, I do agree that for the overwhelming majority of retirees that your concerns are very true. My biggest concern is that with increasing age I may no longer have the physical ability to do what I most enjoy

  11. All the negative things about Early Retirement are stated as if they WILL happen. But actually, it is more true to say they MAY happen. Most of these negatives are predicated on the idea that work is much of how you identify and value yourself. Since work (and colleagues) go away once you retire then the negatives the author listed seem inevitable. The author must be a very self-actualized man (remember Mazlov”s “Hierarchy of Needs” anyone?). But for many of us work is just our J-O-B and once you see that most of his negatives melt away. Also, although it took a great deal of planning to be able to retire early, it seems the author totally forgot that retirement requires much more than finances to be successful. It can take years of planning to be successful in retirement; such as finding value in other things besides work and colleagues, since they are by definition actually quite transient.

    1. Kennie P. Coco

      Retirement sucks. Especially when you r forced out due to a hostile take over, State Government interference. 45 years of service with needed2 more years to actually retire safely. I feel for us and many like us. We now face poverty. We have always lived on a budget to prepare but so much for that. U truly find out who ur friends r when this happens. It will kill us before our time. God’s hands is all we have.

  12. Hi Sam,

    I’m reaching out to say how much I liked your article a lot.

    I’m in a bit of a similar situation, where I was able to stop working at 35 and move down to South America with the goal of learning Spanish and experiencing a different culture.

    I think you really hit the nail on the head with the article and I totally resonate with the downsides you’ve mentioned. It’s been the best decision of my life, but when people ask I tell them you still have good and bad days and your problems don’t all go away once you take work out of the equation and change locations. It was really interesting to see someone write an article talking about the same thing!

    I count myself as really lucky to have been hit with those realizations at 35, though. I think they’re bound to come at some point in life, so better to learn these things about yourself and about life at this age than to work your whole life at something you hate and then be hit with that feeling of purposelessness and regret at 65.

    Anyway, great piece! I’ve sent it to a number of friends who are in the same boat and who I’ve had similar discussions with.

    All the best,

    John

  13. This post really helped. I retired early and I’m now second guessing all my career choices, realizing my identity was defined by my work and I have an empty feeling that isn’t going away. I’m also driving my wife nutzs! The fact that we are isolated during a pandemic isn’t helping much. Thank you.

  14. Christopher Gan

    I have no problem with the free time that comes with early
    retirement. I never get bored and instead feel there’s not enough time in a day and how quickly time passes. It’s up to you to give yourself a job. If you have the cash you can go to as many conferences and vacations you want and even make a YouTube out of them! The only worry about retirement is money – to ensure you don’t outlive your savings. Yes, money DOES bring happiness!

  15. Searched up this topic after a visit to the dentist yesterday. He shot me up with novocaine and then asked me “what do I do for a living” and proceeded to pitifully explain “early” “savings” “consulting” “used to lead” all while my mouth slowly stopped working. Realized I need to get my arms around retiring early and not being ashamed of it. I retired at 52 and now focus on my three young children. This article really hit home. Thank you for writing it and capturing all this here for it to help others.

  16. Thank you, I retired 2 years ago At the age of 50 and got depressed that I had to go back to school to work on my doctorate degree. I’m still retired and a stay at home dad of two boys in elementary. I just wanted to research all my feelings and see if anyone was struggling with outside achievements like I was. these past 2 years.

    “Thank you for this article.”

    1. No problem! Glad you found something to do.

      Before people retire, I always encourage them to retire towards something, not just retire away from their job.

      Being able to write for and connect on Financial Samurai has been my main activity post retirement. However, since 2017, my main focus has been my children :)

      GL!

    2. I am planning to retie in 6 months and then having worked 41 1/2 years of federal service. I am 67 now. I am having a little trouble figuring out what my purpose will be in retirement. You have helped me realize that retiring early doesn’t solve this problem of finding your purpose. I still need to find my purpose. I shall pray and focus on finding my purpose and will see if i can negotiate a way to stay at my job and find my purpose if I go or stay. I don’t think it matters if I work or retire. It really comes down to finding my purpose. Thank very much for your perspective. ED

  17. Ron Richter

    Good article but only relatable for people who retired early as well.
    I’m one of them. Retired in my mid 30’s and moved from Europe to Thailand. It was great first but I hated the question “What do you do?” when meeting new people.

    Most of the time, I was traveling, working out, reading books, volunteering (that one helped feeling useful and productive). Then, I started to envy people who are working. It felt like they have a purpose.

    I retired early because it was my dream to live in a warm place and being able to travel full time. But once I achieved it, I got bored very quickly and I ticked it off my list now.

    Some suggestions what we can do, after retiring early:
    1. Work part time somewhere to have a routine
    2. Start a business (online or offline)

    We need work and a regular routine to stay mentally healthy.

    1. Yes, you can find a purpose in life. Look & observe – dirty, dreadful places. Next, go to a beautiful park – with flowers blooming, fruit trees, & different variety of plants. Indulge all your senses, look and think.

      After that, find the most accurately translated Bible. READ, imagine and meditate. Start reading the book of Ecclesiastes. May you find answers to those questions that you have entertained for a long time.

  18. Wholesome Wallet

    Many people get bored and develop all kinds of sicknesses when they retire. I think semi-retirement is the way to go

  19. Righteousnova

    Imagine someone telling you consistently about their retirement 10 years prior and 10 years after.

    – Are these people invested in your life. No mostly they are people who are nice enough to say hello to you but, the constant 2 dimensional mindset of your upcoming retirement and after retirement is only important to you. No one is jealous. No one finds you interesting. You don’t even find yourself interesting. You live for retirement and your looking for someone to impress with the fact that you are going to retire.

    Usually none of these people know you. We do not share finances. Most of all we wouldn’t be attending your funeral.

    But, here we go again it’s morning and here you come with your fixed income speech looking for approval from someone who is busy..

    Nobody cares. Most of all YOUR FAMILY.

  20. Great article. I agree with all five of your points. I chuckled at your point about people thinking you are a slacker because you retire early. I get weird looks from people when I tell them I retire early too. That’s why I now tell people I’m a business consultant even though I’m no longer working.

  21. Hi Sam, fantastic article and I pretty much related on every point you made. I was asked to leave my senior role at a biotech about a month ago, have been saving avidly for 5-7 years and am a little shy of the 15k a month target that you set for yourself and I incorporated into my own planning. I’m 34.5, out of shape from 12 years working a job that was okay during the best of years and miserable during about half of them. I’m happy to be removed from the last situation which was squarely miserable, but have the identity/whether the money will be enough/whether I shouldn’t be living out a purpose that I believed during working that my job was keeping me from.

    I don’t know if this is the end of my worklife or whether I’m just burned out and need to reset, or whether I should be taking the leap of becoming and entrepreneur or investor of some sort. I know I’m physically and mentally worn out though, so an extended pause at a minimum seems to make sense. You’re about 7 years ahead of me, I’m not sure if you would be open to some consulting/coaching arrangement as I navigate this new path, which clearly you have already walked. An experienced sounding board for some of my future plans would add a lot of value to my life, and hopefully would be enjoyable for you if you were open to that sort of thing. Even prior to leaving employ, I’ve been playing with the idea of an executive coach, which hopefully will help me level up in life, and we share a number of background/career/philosophical characteristics.

    Really love your content and particularly your method of thinking through problems and data.

    Cheers,
    Jason

  22. baldmetalnerd

    I never understood SJWs before I read this article. Okay I still don’t really but I do really understand some of the use of one of their favorite words “privilege”. This article to me basically reads “I got REALLY lucky and made a few million dollars and retired and things aren’t completely perfect boo hoo.” Give me a BREAK! As a currently unemployed person struggling to get another job this article made me sick! Shockingly I don’t have a few million bucks what a surprise! Now do I have some “privilege”? Sure of course I am getting unemployment and I’m lucky enough to have a fairly in demand skill so I’m hoping my unemployment is brief and I’ve averaged around 2 interviews a week. But this article would be the equivalent of me walking up to a homeless person and complaining that my Starbucks is only luke warm instead of piping hot! Get over yourself! Anyone with half a brain would never think money solves all problems but it sure does make things MUCH easier!

    1. You are right. Being born an Asian male and getting to live and work in america makes me extremely privileged. I absolutely attribute the large reason why I was able to retire early due to luck.

      I hope you find better luck in your life too.

      Here are some articles that might be worth reading:

      https://www.financialsamurai.com/solving-happiness-things-that-will-make-you-happier-and-wealthier/

      https://www.financialsamurai.com/income-by-race-why-is-asian-income-so-high/

  23. Investment Pancake

    $200k enough for Bay Area retiree. I retired at age 40, before early retirement was a thing. This was in 2010, shortly after the financial crisis. One of my closest friends retired at around the same time. I opted to expatriate to Lisbon, Portugal, whereas my friend chose Marin County, where he and his family now live. This week, my friend and his wife flew out to visit me and my wife and our one child. We’ve had a great visit with them, but they’ve been sort of shocked by how inexpensive things are in Lisbon compared to Marin County. My friend and I sat down for a few minutes last night and I showed him our annual budget for non-discretionary items: private school, health insurance, maintenance charges on our apartment, local taxes. That number comes in at about $56k per year (although we spend roughly the same amount each year in travel expenses). My friend told me that he spends over $60k a year in property taxes alone – and once you throw in California income tax, private school for his kid, health insurance, gas/food/electric/groceries, their number for nondiscretionary expenses comes in at many, many, many times what my family and I spend in Lisbon. Our lifestyles and tastes are comparable, and we’re probably roughly in the same range in terms of our investment income. They are now thinking about selling their home in Marin and moving to Lisbon. The weather is comparable, access to nature is comparable. They really see it as a potential opportunity to replicate their CA existence in Europe at a small fraction of the cost – as well as an opportunity to expose their kid to a new culture and to have closer and lower cost access to other European countries to visit.
    If you are thinking about chopping your bills and having some adventure, it might be worth considering a visit to Portugal. I write about living as an expat in Portugal frequently on SeekingAlpha.com – both in articles and more frequently on my blog. Some of those articles could answer any questions you might have about the nuts and bolts of moving here. You can also send me an email to my account at SA as well if you have specific questions that I might be able to answer.
    Thanks – loved your article, too.

  24. Hi Sam,

    My guess is that you get hundreds of messages a day but I wanted to comment on your Retirement aerly article. I saw it published under Market Watch.

    I am semi retired at 64 and sometimes still feel like you did that if I don’t keep up on my work then I will the be out of the conversation with those that do work.

    When I left full time status a few years ago I spent a lot of time learning some new accounting systems and looking for work so I wasn’t technically not working anymore. I think this made the transition much easier. Now I have eased into the mode of not really caring one way or another. I believe this is easier than fully leaving the workforce.

    I did laugh at your comment that you can only play so much golf, tennis and softball. Those are the exact words I use to keep myself working.

    I am guessing it is harder to retire at an earlier age. The old idea that those that retired later died earlier probably doesn’t hold up as much anymore. I don’t sit around watching tv and none of my retired friends do either. But in your 30’s it has to be an odd feeling. Most of us need purpose and without that you rot away. It looks like you found a passion and that is great. Don’t lose that and if you do I am sure you will find something else.

    Take care and all the best.
    R

  25. 1) You will suffer an identity crisis for an unknown period.
    My take: nope – if you are en egotist, you will suffer an identity crisis. if you are a normal person, you will enjoy not being badgered day in and day out by people whose mentality is “what have you done for me lately”. I retired as a Managing Director and didn’t miss the title for a second!
    2) You will be stuck in your head. When you suddenly have an extra 10 to 14 hours a day of free time, it’s very difficult to optimize your time wisely.
    my take: you don’t have to optimize your time wisely – you’re retired. I wake up at 10 AM
    3) People will treat you like a weird misfit.
    my take: they’re just jealous. close friends will treat you the same way they always treated you – the others aren’t friends so who cares!!!!!!
    4) You’ll be disappointed that you aren’t much happier.
    my take: I still get the Long Island Railroad updates and I am getting email alerts every day about big delays (and of course the delays are always coming home, never going to work) This alone makes me happy.
    5) You constantly wonder whether this is all there is to life. Retiring early is like finishing up your favorite longstanding TV show. You’re glad there’s a conclusion, but you’re also sad that it’s over. You hope to find a show that’s as good or better, but there are no guarantees.
    my take: I revel in and spend time with my aging dad and mother in law as well as my kids.

      1. Money, money and mo money. I never found money inside an MRI tube. I didn’t find it in the lab where my blood was drawn. I didn’t find it in the operating room where my wife’s breasts were removed. And there was no money to be found on the cancer floor of the hospital. There was no money stuffed in the wheelchair. Money, money and mo money.

    1. I so agree with you, Mike. I do not have an identity crisis as I was a receptionist. I do not feel left out of anything because I have always been by myself in the front of a building where no one said anything than hi, bye and I need help. The biggest thing I do not miss is the politics, the bitterness and the unproductive reviews that were just a cover for ‘what are you going to do for your job now while we do nothing for you’. I am an independent person with outside friends, volunteer for organizations and love my time off. I also spent 24 years in real estate so I saved for this happiness.

  26. Claudia Garrett

    The discussion around August 28 was interesting but seems to equate “giving” with writing a check.

    There is so much truly desperate need for volunteers, not just a check, and the opportunity to form friendships with other volunteers, in the fields of animal rescue, wildlife rescue.

    While contributing to medical research is worthy, fields of animal rescue cannot even dream to get grant support or research funding such as that given to ‘human’ fields such as nystagamus research.

    Animal rescue depends solely on donations of time and money, and the reward of truly making a difference, directly and immediately saving a life whether it is a bird or turtle egg, a kitten or puppy dumped by an unfeeling person, cannot be overestimated.

    I am just saying, if you have time, and would like to really make a difference, and meet people who are committed to making a difference, there are opportunities besides monetary charitable donations.

  27. Shasta Jones

    I’m quite different from you. I never made a lot of money but I did other things. I went car free. I raised a garden. I rarely went out to eat. I did the work instead of working longs hours to make money so I could pay someone else to do it. I probably worked 60 hours a week but didn’t get a paycheck for it. Instead my pay was the loaf of homemade bread sitting on my table or the fresh vegetables I went outside to pull when I was preparing dinner. The only thing I hired out for was mowing my lawn. I was dumb enough to major in Broadcast Journalism. I went to night school but eventually became a data entry clerk. I certainly don’t identify with that. Certainly I’m more than what I do for a living. At 61 things weren’t going well for me at work and I realized that working to 67 was a dream. I got out of debt and stayed out of debt. Just after I turned 62 I retired living only on social security and pension. In September I became a substitute teacher. I had always wanted to be a teacher. Finally, my degree in broadcast journalism was paying off because as a college graduate I make more than a high school graduate. I save the money that I earn teaching and I don’t plan to pull out my savings until I’m 67. The problem I have is that people know I’m retired and expected me to do a lot of things I’ve had to turn them down and tell the I started a new career. Oh, yes I made a big goof as an 18-year-old in college but I am still young enough to have another career.

  28. People buying lottery tickets

    When I read content like this, I reflect on people buying lottery tickets. People have this idea that winning a lot of money, will allow them to retire & live happy ever after. I would love to know some of the stories behind those who win money suddenly.

    I have considered early retirement & people mostly think I am crazy to do this. I must say I was alarmed to read some of the negatives above. People are not really happy for you & think you are a misfit? How sad when you have the money to retire. I would like to think that the positives strongly outweigh the negatives.

  29. Torbjørn Enger

    If you think 200000$ a year is not enough, you should come to Norway. half of it and an downplayed house would be more than enough. Dont have to care about the medicare thing and such ;-).

  30. I am currently retired and was in a ‘senior” mgmt position. I totally relate to the fact that I miss those perks (even though I can pay for them myself now). I am no longer the go-to person so I volunteer to help out where I can to have some people contact. I am glad that you wrote this so that others in a similar position can relate.

    A separate q: why is your equity allocation so low (you have enough to live on so you can afford to put more in the market and get a better return. You are also young enough to ride out the recessions as long as you are not dependent on the equity allocation.

    keep up the great work

    1. Hi Bill, I don’t have a higher equity allocation because I’m happy with what I have. Given I was happy with what I had In 2012, and my net worth has more than tripled since then, I’m OK earning percent a 5-6% return.

      I found my balance, and I sleep well at night.That’s one of the most important things about early retirement.

      1. Hi Sam, I had a corporate sales job for about 10 yrs and retired in 2012 when I was 31. I did it through the stock market. I haven’t found a better place to produce income as well as store and manage wealth. The stock market allowed me to achieve not only financial freedom but time freedom; there is a huge difference. I spend most of my time raising my 2 yr old daughter and a little bit of my time now to help others achieve time freedom. A good friend of mine (Chris Hanson) invited me to join him in doing a podcast to spread the message about time freedom and discuss the mindset it takes to achieve time freedom. I was curious to see what was discussed online regarding time freedom and early retirement. I did a search and stumbled upon your site. I’m not a social media guy so I’m just now finding out about you. Congrats on your early retirement and the brand you’ve built online. When I read your response about in the comment section about 5-6% return, I felt so compelled to grab you by the collar and tell you that “you just need more information”! I have studied the stock market for the last 20 years and can tell you that with a little more information and work put in, you’ll laugh 5 yrs from now at the thought of being “happy” with 5-6%. You can find more about me and Chris Hanson from InvestingFromTheBeach podcast. Feel free to reach out to Chris Hanson or me. I have no intention to solicit or advertise anything with this post. I found you by accident online and connect with your story and know I can help you. By your success and the work you’ve done so far, I know you have the strong work ethic and the proper mindset to do much better in the stock market!

  31. Hi Sam,

    I can relate to your article very much and I am based in Singapore! I am still looking as I have yet to find my “Financial Samurai”!

    still wandering..

  32. “I understand your anxiety about making $200,000 a year passively, but wondering if it’s enough for SF living.”

    Once you have paid off your mortgage, $200K/year is more than enough to live on, by far. Prop13 keeps property taxes very low in California, and if a good portion of your portfolio is tax deferred, the tax bite is also much lower than when working. Also, remember, there is no Social Security or Medicare to pay for once you retire.

    1. If I kept my rental house, my property tax would be $23,000 this year. I don’t consider that very low at all. Tell me about your experience retiring early in an expensive city. I’d love to see some expense numbers and such. Thanks!

  33. I understand your anxiety about making $200,000 a year passively, but wondering if it’s enough for SF living. I would guess that every retiree wonders about income during retirement at some point. I would.
    We’re not retired. My husband decided to start his own business so he could be his own boss, make a big salary and retire. Unfortunately, not much happened in that realm. Banks won’t loan money to anyone unless they have money, so the biz never took off. Consulting a bit here and there from past working relationships didn’t amount to much either. At the age of 50, his income has dropped by 60%. He works overtime as much as he can. For me, I finally took a management position. I gross $37,000 a year. We have rental properties, 401k, IRA’s…..But I don’t see retirement happening soon. Which brings me to my next point
    If I didn’t work, would I still get the “Yay factor?” As in, “Hey, I worked more and can get some prime rib for dinner! Yay!” Or, Christmas is coming and I’m hoping to be able to get my family a (fill in the blank). Yay!” There is something to say about working and feeling satisfied that it was difficult, but you got through it and can afford something. ya know?
    Retirement is another chapter in the book of Life. Was the journey worth the destination? Only you can decide.
    As for those holiday parties/employee appreciation outings, most corporations have gotten rid of those things. So don’t feel too badly about not going.

    1. Yeah, there’s a lot of mental gymnastics that goes into being comfortable with money once you don’t have a steady paycheck for sure.

      I have a $300,000 passive income goal because more is generally better, but also having goals to strive for feels great overall. I love me a challenge.

  34. Hi Sam, you are very spot on about the confusing feelings after early retirement. I tried it once at 54, and resigned from a career of working for one employer for 20+ years. After 2 months of early retirement, I panicked and got a new job. I see how my, yes, micromanaging supervisor, is neurotically losing his temper here and there, and have submitted my resignation after just a year and a bit, now at 55.5. But the immediate feelings are intense. Maybe I will not make it to full retirement even this time, but I do hope so. Now with just few days to go in the office, I see these people’s faces distorted with pity for me, silently wondering whether he molested me…some with sympathy, others with vindication. Its severely messed up. As soon as I walk outside from the office and feel the breeze, I know I am on the right track; and was so happy to see your message in my inbox. Will persevere.

  35. I think your third negative happens a lot more to people who FIRE than to people who retire at or closer to normal retirement age.

    I early retired three years ago at 53 (I would not call this FIRE by current definitions). Never felt like a misfit, but reactions from others were generally of surprise (I look younger than I am), but never made me feel uncomfortable. Reactions were almost always, “wow, how were you able to do that?”. These days (now 56) reactions are less of surprise (especially once I tell them my age).

    No issues whatsoever with the transition. Never been happier. Dear wife and I travel a lot and go to the gym together when home. Days are full – she is always commenting “where did the day go”. I remember other retired people telling me they don’t know how they got stuff done while they worked and thought it was a joke. Well, it is not. You find a way to fill your days with lots of fun and interesting things to do.

    Work is necessary to build the nest egg to allow you to live the rest of your life. Once retired go and live your life. I never, ever think about work or what I would be doing if I were working. It’s almost as if never worked a day in my life.

    1. Agree. The later you retire in the early retirement spectrum, the less weird you will feel simply because you are moving closer to the norm.

      Hmm, now to get my wife to join me in regular exercise. That would be fun! Gotta go hiking together again.

  36. Joseph Donnaway

    “Nobody I know who retired from corporate life early stayed retired.”
    Your research is obviously limited. You need to meet more people.
    I know several who, like me, retired early and have enjoyed a fulfilling life. I retired at 56 from an engineering carreer at a global corporation, and never seriously condidered re-employment. Ten years have passed and my life is full and happy. The key is to have a strong self-identity not dependent upon a job title, a plan for financial independence, and diverse interests and commitments. Solely playing golf won’t cut it. Of course there is an adjustment, just as all major life events require adjustments. Plan for it.

    1. Thanks for sharing. You are the first person I met who ended up relaxing and doing nothing after retiring. Expanding my perspective is one of the key reasons why I write.

      What are some of your secrets for being able to not pursue new hobbies, interest, dreams, etc?

      Perhaps the older you retire in the early retirement spectrum, the easier it is to just chill.

      I’ve discovered so many new things I’ve wanted to do after retiring e.g. HS tennis coaching, fintech consulting, blogging, foster care volunteering.

  37. For one, I’m very much the opposite of Sam in this regard.

    IMHO, the white collar workforce offers the least gratification of any activity out there, except for the ‘Oo Ahs’ from ppl who don’t have a titled position in finance, management consulting, medicine, or engineering. Sorry, but that stuff gets old when one’s not in one’s 20s/30s anymore.

    So when someone responded … “When anyone asked what I did, I would just say Consultant.”

    My answer to the above is … long before you cut the cord, start your own company, XYZ Alliance Contractors (as an example), get others to freelance for you, paying them (but not yourself) and build a profile of activities which you can talk about in public. And then, when you leave the mothership ‘Corporation’, you’re not a so-called Consultant w/o a job but a ‘Director of XYZ’, even though you don’t actually do the work.

    And thus, even though you’re on the computer, perhaps couple of hours per day, collaborating with others on what they did, that’s not real work. It’s more a social hour but with friends from other geographic locations. And then, what do you do with the remaining 12 hours per day?

    Here’s what I did …

    Tai Chi Sword & BaGua (internal martial arts)
    Masters level courses in Math & Chemistry
    Teach basketball
    Write articles for various online journals
    and finally, go out for drinks with graduates students living in my area

    All and all, I had no trouble finding things to do.

  38. I went though all the negatives of retiring early. I even wondered what the neighbors would think when they saw me at home all day long until I realized that half the neighbors had work-at-home jobs, even though they worked for major employers. When anyone asked what I did, I would just say Consultant.

  39. Sam, you’ve clearly touched a lot of people with this article and your blog. I completely agree with the negatives of early retirement. I discovered your site in 2014, a year after being laid off/retiring from a plushy corporate job at 41. Like you, my financial journey has gone amazingly well and has completely exceeded my “middle class” expectations.

    Although I had a handle on my finances, your site provided validation and a sense of community for what I was doing. It has otherwise been a lonely journey because:

    1. My wife clings to her plushy corporate job like a life raft; she has little interest in enabling financial independence. I sometimes send her one of your articles to convey what I’ve been doing or what I’ve been going through.
    2. No one else knows that we’re independently wealthy because, well, stealth wealth. We live well beneath our means because we are used to it and we don’t want our two young kids growing up with a sense of entitlement.

  40. As for me, I enjoy retirement totally and am writing my third retirement book called “The Joy of Being Retired: 365 Reasons Why Retirement Rocks — and Work Sucks!” In fact, I have come with 50 Bonus Reasons to make it a total of 415 Reasons Why Retirement Rocks — and Work Sucks.

    Elan in his comment mentioned my book “The Joy of Not Working” and in my reply to him I mentioned my other retirement book “How to Retire Happy, Wild, and Free.”

    Yesterday Daniel Richards of Andover, Massachusetts posted this on my Facebook Timeline.

    “So Ernie Zelinski I read your book “How to retire happy wild and free” several times prior to my early retirement at age 59. Based on your suggestions, i did a lot of pre-planning for my retirement making sure i had plenty of activities to keep me busy. One of my interests was genealogy which i have been doing for several years. Recently however i wanted to some how to give back because i have had such a great life. I started to volunteer at a non-profit called Searchangels.org. It’s a company that finds the biological parents of adoptees. My first case was a 51 year old women who has been searching for her parents for 30 years. After 3 short weeks, I identified her mother via DNA search techniques and she made contact with her. They are going to meet next week for the first time in 51 years. Thanks to you for encouraging me to retire early, I have the time to profoundly change people’s lives forever.
    Your book profoundly changed mine forever.”

  41. There have been many insightful comments regarding retirement but I haven’t read one about what might be the most important aspect of enjoying a good retirement, being healthy enough to enjoy it. One might have all the money in the world but without your health (physical & mental), it will be difficult to enjoy all the fruits of your labor. There are so many things to do on my bucket list and they all require fairly good health.

    I’ve been very fortunate to have good health by watching what I eat and exercising regularly while reducing stress as much as possible, but as I get older, the aches & pains (mostly from playing tennis) are starting to catch up. I have enjoyed operating my business for almost 30 years but after hearing of acquaintances who passed away shortly after retirement, I am more inclined to reprioritize and live a more balanced and joyful life.

  42. Interesting article. I think I am currently suffering in some of these anxieties.

    I’ve always been frugal and planned on taking it easy – if not retiring early by 55.

    Well…my older sister died last year at 54 years old. She left me her $50K/year CPI adjustable state pension for life, almost $1M in cash and retirement funds, a modest fully paid for 1B/1B condo in Honolulu, a big boxful of jewelries, and 4 truckloads of stuff (she was a hoarder) I had to get rid off because I don’t need nor want 90% of it.

    In the meantime in LV, I have a 3B/2B house, a 2B/2B condo (both fully paid off), an SUV (paid off), my own $500+K 401K/IRA/ROTH, and a job that can pay $100K-$150K/yr if I work “full-time” 8 months out of a year (but physically demanding and mentally boring).

    I just turned 51 last year. My only child is 21 years old, don’t want to go to college, and doing her own thing. My mother who is 81 years is sickly but still lives independently. I ended an 8 years relationship 2+years ago. I already have 3 college degrees, a real estate license, and a side business as a travel consultant.

    On spreadsheet, I could retire today. My retirement and brokerage accounts invested mostly in index ETFs are currently returning an average of 9% annually. My fixed expenses are barely $2000/month.

    I have been hanging out here in Honolulu when Vegas heat hits over 100 or dips below 65. I don’t think I should really stay in Vegas too much since I find myself donating too much to the casinos since I can tell myself – “You can afford it.”

    Right now, I feel lost. There’s only so many gym time, classes, museums, volunteer work, hobbies, hikes, travel, etc…you can do before you realize you’re just filling time.

    Often, I have to do stuff alone because most normal people I know are busy working 50+ hours per week working 2-3 jobs to support and parent their 2-4 school aged kids on top of keeping their spouses happy in addition to keeping an eye on their aging parents and parents-in-law.

    I do get the “must be nice” comments too. I am yet to find a short-hand version of explaining myself to people whenever they ask what I do or how I can afford to have so much time in my hands. Maybe, I will just say “I am a trust fund baby” and laugh.

    I like traveling and checking out exotic places – but I hate long flights, driving long distances, and dragging luggages around. I thought of buying a $1M+ house, my dream car 2019 corvette stingray corvette convertible, a Harley, a boat, an RV, a closet full of designer swags, etc, etc – but then I will probably end up having to work just to pay for the maintenance of all that “stuff” that might impress other people but doesn’t really mean anything to me once the high of new acquisition wears off. Besides, I will have to constantly worry about all that expensive stuff breaking down or getting stolen.

    So…..eventhough I love the freedom of doing what I want when I want with who I want – you’re right. Too much of anything is never a good thing. Once you – theoretically – have the power to make yourself happy, you still have to figure out exactly what it is that will sustain your happiness beyond buying more stuff and doing more things.

    I am gonna try semi-retirement for now. I will do another self-assessment in 5 years.

    Now that I am financially independent, I wonder about all these people who make $1+M/year and worth $1+B in equities. Why the hell do you need all that stuff?

    I guess that is the reason why some people with all that money start dabbling in politics and start playing with other people’s lives – it is because they are bored and because they can.

    Oh, one thing you might want to add as a downside of early retirement:

    Some of the people who give you that “must be nice” snides are also the same people who now think that you should be giving them interest free loans (and not pay you back because you don’t need the money); you should be picking up the entire tab when you eat out; expect you to take them on trips and pay for all/most of it since they are providing you with company; and expect you to be in their beck on call whenever they need a ride, a baby or dog sitter, or other emergencies – because “Hey! You got all that time in your hands!”

    1. I’m a recent Vegas transplant from the Bay Area and its odd how our struggles parallel each other to a degree. I feel a little relief knowing there’s someone pretty close by that has the same petty problems. :P

      I too haven’t figured out what to tell people what I do for a living and that seems to be my biggest problem in life. LOLz.

      I’m 10 years your junior though and I stopped seriously working since 34. I don’t think much will change if you decide to retire based on my experience. These are the same lingering problems I had years ago. I imagine finding another SO will take priority now. Curious to what that would be like coming from you.

      Things keep getting easier as I get older except making friends have been really hard. Lucky my wife is here and not sick of me yet. And my kids are still young.

      The comments about being lost, doing stuff alone cuz everyone is working and just doing things to fill time really struck a chord with me. Oh well, good problems to have I suppose. Fortunate to be naturally happy despite it.

  43. Excellent. While I retired more traditionally at age 63, I have experienced many of the issues you cite from your experience.

  44. Even as I am building my own chess blog and chess coaching business, unconventionalchess.com, I get a lot of blank stares in terms of how I am trying to transition to being a full time entrepreneur. Most people today have a narrow conception of what life is all about because of either classical conditioning or societal peer pressure. I can’t give a damn at this point about what they do because my future can only be decided by me. So that is why the idea of making a living by doing something other than a W-2 confuses people. You have to stay true to your values. The only reason why someone would get bored in “early retirement” is because they haven’t had shock therapy. I remember reading a book by Ernie Zelinski called The Joy of Not Working, and there are so many things one can do in life that if someone is still “bored” after that, then what a shame. Being bored is a mindset problem not that life is inherently boring.

    1. Elan: Great comment. Also, thanks for mentioning my book “The Joy of Not Working.” I also wrote a book called “How to Retire Happy, Wild, and Free” which has now sold over 375,000 copies and has resulted in many people emailing me and writing to me about how the book has helped them retire happy. If you go to my website, you will find my email address there. Send me your address and I will send you a complimentary autographed copy of “How to Retire Happy, Wild, and Free”. Alternatively, I can send you a copy of “Career Success Without a Real Job.”

      1. Hey Ernie,

        I hope you got my e-mail and would love a copy of your book “Career Success Without a Real Job”. I sent my e-mail to two e-mail addresses as I am not sure which one is better. Can’t wait to hear from you! I can’t even remember how many times I have read “The Joy of Not Working” but will read it again tomorrow just to remember my roots when reading that wonderful book.

        Elan

      2. Erie Zelinski, I always recommend “How to Retire Happy, Wild and Free” to friends contemplating retirement. “What will I do to keep busy” is a hot topic with the “in our 50’s” crowd. Your book helped me a lot and I refer back to it often if I’m feeling a little bored.

        Everyone looking at this blog sound read Ernies book!

  45. Good stuff, Sam. I retired at 55, which was considered ‘early’ by my peers, but not by FIRE standards. My experience isn’t quite as ‘jarring’ as yours in that I generally look the part of a 55-65 year old guy. I fill a lot of time with selfish ‘giving’; I volunteer as a High Performance Driver Education (HPDE) Instructor. I have fun, I get to engage with a wide variety of people (teens to retirees) and it adds some structure to my retirement. My wife (also retired) has churned through a few activities to fill her time, and she made the observation that I’m lucky to have found something that I enjoy and where people appreciate what I do. She is in search of her next big thing.

    My students often ask me “what I do”. I have to admit that saying I worked thirty years in engineering for Boeing and then retired is probably my way of saying, “I earned this” and avoiding the “trust fund” status. Still, I do get a few rueful “must be nice” responses.

    Keep on keeping on.

  46. Completely understand where your coming from. I retired twice (20 & 30’s) and got stir crazy after a year so went back to work at a full time job and full time investments.

  47. Great article. Thank you for giving us an unvarnished look at extreme early retirement.

    I’d like to counter your statement that introverts would have an easier time with early retirement. Extroverts have the tools and reward centers to go out and make new friends in early retirement.

    Introverts don’t have these reward and many may not have developed the tools to make relationships. Indeed, having the structure of work and coworkers may have facilitated introverts’ ability to form relationships in a familiar environment. When the work is gone, what does an introvert do?

    I make this point because introversion is not about being alone. That is a loner.

    While an introvert doesn’t get the same payoff from socializing, an introvert in early retirement still wants close relationships and could have a hard time developing those. Of course, being part of a family would help.

    Thanks again for presenting both sides of early retirements.

  48. John Forsythe

    Hi Sam, thanks for being open and honest, it’s hard to share struggles, even past ones, it is for for me anyway. I wouldn’t want people to realize I don’t live a perfect life What struck me most about this post is what you said about visiting a bunch of European Churches and meditating. I’ve sought a lot of things in life to bring me a sense of purpose and joy but found nothing on Earth gave me an everlasting joy or happiness, so I looked for it elsewhere and have found it in church (some churches anyway). I was wondering what you found, or didn’t find, in church and meditation?

    Thanks for talking about the parts of FIRE that aren’t so glorious and being real with us!

  49. I think the secret should be to have a plan for what you are going to do when you retire early. To quote Timothy Ferris in his 4-Hour WorkWeek book, liberation should have some sort of a plan. If it is being an activist, then use your time on that. If it is to travel, then travel. The key is to find something that you can do and perhaps not interact as much with other people.

  50. From our youth to adulthood, the caravan club of mainstream culture treats jobs like a chapter that gets us to “the end”- work until you can afford to retire and then life will be a dream (sh-boom). Yet, anyone who actually achieves retirement quickly realizes that financial freedom alone does not create happiness or contentment. Financial freedom just gives us the opportunity to experience life on our terms.

    Converting our financial assets to make us richer in life is a skill we rarely cultivate until retirement; many, unfortunately, never do. Relatively few people invest in themselves to learn the skills that can make a difference in their level of happiness.

    To me, the most beneficial aspect of early-retirement is being able to slow down. Slowing down can help us reduce stress and enjoy more happiness in life. When we slow down, we feel more comfortable exploring new things and taking risks. Our brains have more downtime to rejuvenate. Our attention is shifted from defending against information overload to proactively making adjustments that improve our wellbeing. I might do less, but I create more.

    Your writing continues to be a huge help in sorting through the different angles of retirement- thanks!

  51. Sam,

    Thank you for sharing such an insightful thoughts on early retirement. I have been contemplating early retirement because I have reached my financial goals, which is $20,000 cash flows per month from real estates. I still have a day job, that I make over $100k per year. The job is easy, it does have benefits, and it is not stressful at all. I have a larger family, 4 kids, they are still in school (6, 7, 9, and 11 grade). While I think that my financial is secure, I am worry about the aspects that you mentioned here such as next stage of life, the day to day tasks when I retire. My most concern is about the job, because it is easy, I am not challenge myself enough…so should I retire and focus on something that I like to do which is helping investor achieving financial freedom through real estates…

    1. Hi Tom – If you’ve got $240K a year in cash flow from real estate versus $100K per year from your job, I’d definitely consider taking a sabbatical or an extended vacation. That ratio of 2.4X higher semi-passive income to active income is rare, and would have made 90%+ of people leave their jobs already if they don’t like their jobs.

      With 4 kids, I think you’ll find you can easily fill up your free time getting more involved with them. Those ages are the time when kids want to hang out with their parents the most.

      Related: Overcoming The One More Year Syndrome To Do Something New

      Best, Sam

        1. Reshma Nazir

          Hi Tom, I would love to learn from you about investing in real estate.

          I am contemplating semi-retirement but am afraid to do so due to not having enough passive income.

          1. Hi Nazir, I would to share my real estates investment. I am in the Orlando area, let me know if you ever come this way. I have a gathering at Starbucks often to talk about real estates investment…meanwhile you can reach met at lntrentalsfl@gmail.com.

            Thanks, Tom.

  52. I’ve been following ur posts for a while, and i was about to submit my retirement application today but for some reason did not.
    I come from a different part if the world, so our whole retirement and financial system is different. However, I can totally relate to all the emotions, needs, frustrations and hopes.
    Im few days before being 39, and have worked hard for 15 yrs. Im a mother of 2 kids, and will get a decent monthly pension, besides we have no mortgage to pay and I shouldn’t worry about healthcare or education since its covered.
    I just lost the spark and motivation, and i tried many means to revive it, but i know for sure its dead for any 9-5 job.

    I do feel I need a break, my kids r at an age I would like to enjoy their company. I want more time to relax and take care of my female self instead of running around the whole day. Btw, female pampering needs time:) Applying a face mask seems like an additional exhausting task on a working day. My parents are growing older and I wish to have relaxed breakfasts or days out with them. I feel that me staying at home will add a lot to my family’s quality of life, which is something I’m willingly wanting to do.
    The only thing that Im not sure about is the next steps, I have several thoughts in my mind, but Im not sure if I’ll have the drive to work on any. I believe that once I detox from corporate life I’ll have the options to decide, but this uncertainty and self-doubt is still in the back of my head. Esp. that early retirement is not the norm. I’m also considering having a baby. A baby to enjoy, not to just consider an additional task or responsibility.
    I’m not worried a lot about social networks because we tend to have more inter-connected social networks in our culture. Im also not worried about identity because I’ve never identified myself through my title only, it has always been more related to myself. I just worry that I have always had this drive to success,,, is it dead? Or I’m just done with corporate world and i need to move on? Or I need to divert it to a new route of success, which im not yet sure what will it be.

    Keep ur posts going. Its useful to people even from the other side of the world.

    1. The worry in our heads is worse than reality.

      Before you submit your “application,” I would formalize an exit strategy that provides a severance. It was my severance and the ability to keep all my deferred stock and cash that was the catalyst to say sayonara to my old firm. You will feel like you are winning when you walk away, versus feeling empty handed.

  53. Robert Graham

    Something I’ve noticed with my friends that have lifestyle businesses on the Internet is that they’ve achieved a level of freedom that few to none of their local friends possess. It’s less fun to ski 90 days a year if it’s by yourself even if you built a business and a lifestyle intentionally with that in mind.

    It’s a real consideration in achieving your own freedom. How will you use it and with whom?

  54. Sam,

    If you ever don’t have a buddy to have lunch with or go to happy hour with, I’m sure us Bay area folks would love to have you as a lunch buddy!! :)

  55. I appreciate you sharing this. I wonder if the reason I don’t feel as bad about being partially out of the workforce is because, as a woman, it’s less expected for me to work. Or perhaps it’s because the last few years have been going back to FT work while have 4 babies in 6 years, and I’m just done with the whole 9-5 routine, pumping in airports, and struggling with childcare while we both work crazy hours.

    We’ve been through a brutal last few years, but my husband and I kept at it. I now work 20-24 hours/week, but make my equivalent income, plus investment income. I kept my nanny (4 kids, 11 month to 7 years) 4-5 days a week. And – I LOVE the freedom. I love seeing my kids, but being able to leave them to speak on panels (IF I want), manage our house renovation, etc, is refreshing. I couldn’t care less that people think we are wealthy or lucky or just inherited money. If you don’t want wealth and work for it, you’ll never understand anyway. If people think I’m lazy or lucky, I just laugh.

  56. Fantastic observations, FS. Two quotes come to mind…

    “I actually think happiness is the absence of suffering. It comes from peace. That comes from being careful about desire, judgment, and reaction.” – Naval Ravikant

    “I asked my therapist, ‘what is the best way to feel happy and improve self-esteem’? He replied, ‘finish the things you start.’ I thought that was brilliant, so I came home and noticed on the shelf, a half bottle of scotch…'” – Ron White

    Sam, wishing you and all Financial Samurais happiness!

  57. I’ve owned and operated my business for 30 years (I’m 57 now) and about 5 years ago someone asked me if I was retired. I was totally taken aback because the question implied to me that I was getting old and approaching my “senior years”. At that time, I still considered myself relatively young and had a passion for my business and retiring never crossed my mind.

    Recently, the local government decided to ban the product I sell. Some friends and family are worried and asked me what I will do but I have no worries. Looking back, there were many events that seemed to fall in place without me having much input, including meeting the right people at the right time. Many other people my age have also experienced these serendipitous life events and we learn to just trust in the process. I’ve also come to realize that after our basic needs our met, happiness really comes from within, not without. It seems the more I appreciate what I have, the more opportunities comes my way. I really enjoy traveling, and I see me next venture having something to do with that.

  58. Reverse the Crush

    Great post, Sam! This is something that not many people are talking about and you raise some great points.

    I’ve always felt the opposite about the identity crisis part though. I guess since I’ve always been interested in having a small business, I try to relate more to being a small business owner.

    I think the rest of your points are spot on. Especially the points about being in your own head and being treated like a misfit. I am more of an introverted person and am in my head a lot anyways. And as for being treated like a misfit, I have already started to notice how regular folks react to financial independence. Thanks for sharing.

  59. Hi Sam

    Besides going to meetups on shared interests do you have any other suggestions for a retired 30-year-old individual to meet higher level hustlers/entrepreneurs who actually understand the mindset of early FI? I can’t relate to people at FI meetups as I am already at the end of the road.

  60. Hi Sam,

    So good to read your articles again. I just came back from the Balkans. Agree with all points and feel very related. I really hope to see you have a whole new profession. Man supposed to be out of the house. Family, kids are not the reason for staying. Working for schools and kids would also not be considered to be working. They are cute and lovely but not at the intellectual levels to be on par with yours. You will not get enough satisfaction. Action counts. US economy is doing so well I wish I were there.

  61. I retired at 50 and am now 55. Because of Financial Samurai, I never say the “r” word in case someone gets jealous or takes my early retirement in the wrong way like I’m a sloth or something. In my experience, all of the negatives of early retirement in the article are true. I am alone a lot with no spouse or kids. It does get lonely at times. I miss the office camaraderie like joking around with my team or going out to eat together. I’d rather go to a restaurant for lunch with a buddy but people are working when I want to eat these days! So that kinda sucks.
    Now my social circle consists of my dogs, friends and extended family.

    Thanks, Sam, for making me aware that because I’m an introvert I’m more suited to being retired than an extrovert. That, too, is very true. Would I consider going back to work full time in the corporate world if I great job fell into my lap? No. Although there are negatives to early retirement, I do love being in charge of my own day. No corporate politics, insane pressure, backstabbing colleagues, and impossible deadlines. I lived that life, I used to love that life, and now I’ve left that life — for good.

    1. I can relate to Ropefish. I’m 55 and plan to resign myself from the corporate world in ~ 16 months. I’m an introvert as well and after 33+ years my job as an Executive in Information Technology within the Financial Industry (Investments/Banking) no longer appeals to me as I long to be in charge of my own day as well … and get away from the corporate politics, pressure and yes the impossible deadlines … It has literally worn me down … I’m hoping to make it 16 months as this will allow me to vest 100% in a small pension but there are days that I just want to throw in the towel! So all of the negatives you outlined Sam … appreciate the realism! I’m not ready to retire … just pursue other interests and experiences!

  62. I identify a lot with this post, thanks Sam!

    I was a poker pro for 10 years and transitioned fully into investing my profits over the years. Always worked/studied 60+ hours/week and now that my long/short stock portfolio only requires 30 hours a week to maintain, I often wonder what to do with my extra time. I loved video games and strategy games as a kid but 10 years of poker is enough to kill whatever passion I have in this hobby.

    Don’t get me wrong, I do enjoy the total freedom now but maybe it’s time for the next project. Luckily my wife is also doing invstment research so we both get to work at home. We are planning to live around the world (mainly to low cost of living cities to reduce the withdrawal rate to below 3%), maybe starting a family, or starting a business (hedge fund would be my far-fetched dream…).

    Most of my friends and families simply do not identify with this mindset and it does make me feel lonely and like a misfit at times. I guess I take comfort that there are others who are financially free and doing some self-employed work and facing similar struggle as me.

    1. Leo – would you mind sharing what are some of the books, sites or YouTube video where I can develop a more in depth skills and technicals to manage a stock portfolio? I have discovered investment research is my true passion. I am working toward to save up enough that I can leave my day and move to managing my own stock portfolio in the next few years. Thanks.

      1. Since my strategies are “low-tech” quant based, I learned a lot reading what the quant finance academia has to say and try to find billionaire hedge funders that are willing to teach. I learned a lot from Cliff Asness, Ray Dalio, Charlie Munger, Warren Buffett etc.

        Avoid paying for educational material since there is so much garbage out there and you would not be able to judge what’s good or not. Avoid charting. Avoid options. Avoid mainstream financial media. Avoid going long in hot industries. Those are likely to lead to a deadend.

        The more important thing is actually putting money in and start investing to gain experience (amount that you are comfortable losing). It is important to learn to be humble when you are doing well, and remain confident when you are not doing well.

  63. “Early retirees have higher rate of skin cancer from playing out in the sun all day”

    All joking aside, retiring early ages people. Better off finding a career that you don’t hate.

    And my wife and I would kill each other if I was home all day.

  64. I think that ultimately financial freedom isn’t about doing nothing or being fully retired. Clearly, we all need work or business in our lives to keep us motivated and happy. As such, FI is much more about a flexible approach to work and life and the ability to structure your day/week/month/year/life as you see fit. Thanks for sharing such an honest account

    1. Agree with GDB. I reached FI in my early 40s but enjoy what I do for a living (one of the reasons I reached FI). Working each day because you WANT to, not because you have to, changes one’s mindset. It makes it easy. I have never been a backer of FIRE. FI yes but RE not so much (but one must define retiring young as I plan to retire in my mid 50s, now 47). I believe in FIRM: Financial Independence, Reap More. I think I am working harder (and smarter) now in my FI days and reaping more rewards both financially, professionally, and personally.

  65. TheRunningMan

    I’ve spent most of my adult life developing toward the goal of not really caring what other people think. Early retirement seems like a great opportunity to perfect that notion. Being forced to care for the two years that I must continue working will be the challenge.

  66. This is great Sam and gives lots of food for thought. I’m still tussling with the decision. I keep turning my spreadsheets over and over and trying to convince myself another two/three years of working is the right decision. It keeps coming back to the fact that I can step away from corporate life now, but my identity as a CFO is strongly rooted. I’m still on the fence. Financially I can make it work but the mental shift is strong.

    1. Hey CFO, I resemble your remarks. I’m also a CFO who is planning to exit in February 2019. I’m currently serving my OMY as I had originally planned to exit this year but I do enjoy my job and my team but one more year of vesting finally convinced me. I also think that my numbers are good. My issue is burnout. My gig entails extensive weekly travel plus I’m 57 so I’ve been at this a long time and my exit would not be considered that early. I’ve been a CFO for 6 years and the thought of going out on top is appealing to me but many of the issues that Sam cites in the post plus the identity issue that you mention concern me. On the plus side I am an introvert. That, plus my age makes me hope that many of the issues posted here hit me easier than someone retiring much earlier. While I do enjoy my job, I think the ongoing stress is what is pushing me over the fence.

      1. Leaving at the top is a smart way to go. It is probably one other reason that I want to hold on a big longer. I’m looking at a gig to move to a 5bn$ market cap company and that may keep me hooked in a little longer. But then again, what if I then get a gig at a 50bn market cap. When do you call it quits, I suppose.

  67. I think your post relates a bit to what I’m going through. I am 29 years old and just left my job voluntarily to drive for Uber. Life is hard as making money from this is not that easy as everyone seems it to be. In fact, the reason I left my job was because my ex-girlfriend asks me to (bad decision there) and I thought I could earn more (doesnt make much difference).

    While I appreciate the new-found freedom that I have, you can get lonely at times whereas previously you have working colleagues to spend time with. I try to spend time with a fellow Uber driver at times and my family but you will have to spend most of your time alone. My high school friends are mostly married and are too engrossed in their work/family and have almost no time to see you, except on rare occasions when we do get together.

    Then there is the public perception that we are useless to society. I think that is not true as we all are contributing to society in our own ways, even you with this website and how it is helping other people. It has been two months since I left my job and I still haven’t found my true purpose in life. A close friend and my sister has told me to search what it is I’m rrally passionate about but I haven’t seem to figure it out. I am not married and finding a girlfriend has been much harder after I left my job, probably due to the negative connotations it has.

    I’ve been thinking about applying for a proper job but I’m not sure if I want to sacrifice my freedom for a similar amount of money that I’m making right now. I’m not saying Uber does not have its cons (nearly got cheated by a passenger the other day). It’s just that I have not found my true calling, whatever it is. I hope I will find it soon.

  68. Hey Sam,

    You can come to my Companies Holiday Party!

    Good honest stuff. Society is so full of this made up process that we all have to work until we die and that our identity is our job/career. It is a flaw sense of mind. I have a few years left before I FIRE but will remember this post to prepare for life after work.

    Keep up the good writing it helps all of us readers prepare and not have regrets.

    Give us an update on your little one soon as they grow up so fast!

    1. Thanks for the invitation! Maybe it’s the celebration with colleagues in the trenches after a years worth of hard work. It’s fun to celebrate achievements with other people.

      I don’t celebrate enough, and it’s probably because my birthdays in the summer, and as a kid, I was never able to celebrate it with friends.

      But gosh darn it, I’ve had the best month ever for the business in August 2018, and maybe the month has been the best ever in my life with my son’s milestones, and some other random wins.

      We will be celebrating big-time in Samurai September! I hope you join me.

  69. DaretoDream

    Sam you write such thoughtful and true reflections. The notion that early retirement and financial independence are going to make you happy when you weren’t before (after the fleeting good feelings from the accomplishment) is a good remainder to find joy and contentment with the present and love what you have vs desire the have what you love.

    After reading Dan’s post above critiquing you about not giving more (wasn’t even close to the point of your post and from someone who thinks rewarding tenants that pay on time with a latte is somehow giving back) I have a suggestion that may help you write for a long time without get burned out by the occasional nasty post – just let the community respond to the posts like Dans or from that woman a few posts ago who critisized your terminology of helping your wife with child care duties. One thing I’ve learned about social media in my business is your fans will jump in and defend you better than you could yourself and you avoid having to put energy into or reacting to the one off, maybe even baiting, post. Selfishly I want you to write for a long time!!

    1. It’s a good suggestion! And that would be awesome. The thing is, I’m the one who approves the comments, so I see it first and then I approve it and respond to it if it motivates me to do so. The readers would have to read the post, then read the comment, and then make some of their own rebuttles.

      I’m so used to just knocking things out extremely quickly they’re waiting for any type of support can be difficult. Finally, I’m often up until 1 AM and wake up around 6:15 AM.

      What I’ve got to learn as patience and letting go. Stop checking the Internet as much would help too.

      But I’ve come up with a solution that I’ll introduce before the year is over! Thanks for your support.

    2. I think a lot of people were reading some kind of attack into that comment that wasn’t really there. It’s not wrong to say that if you are financially free but lacking meaning/social connection, finding a way to give can really help. It can replace the drive to earn with the drive to help and someone like Sam is in a unique position to influence a ton of people in the same position to also help, by writing posts about how to do so and how great it feels.

      I don’t think the point of the post was that Sam (or anyone else) is being selfish and ought to give it all away and how dare they not go build schools in Africa. The point was that it feels good to give and would help solve a lot of the problems Sam is mentioning here. Problems specific to people who are suddenly in a really valuable position of being able to donate a lot of time and/or money and really make a difference. It’s a good match.

  70. Interesting read, as I spent most of the day binge watching old episodes of NYPD Blue on Amazon Prime. Just couldn’t seem to get motivated to do much more. I’m a veterinarian who is semi-retired, down to 1-2 days a week depending on the season. Haven’t fully retired, since I own the practice,which provides me good semi-passive income. My oldest son just left for college, my youngest is starting his sophomore year of high school. So we’ll be empty nesters in a few years. Might cash out then.

    I’m lucky to have some very close friends in the neighborhood that work flexible hours, so I can find a lunch or happy hour partner regularly, and we try for a weekly “board meeting “ when schedules permit.

    But I’ve definitely hit the boredom/what’s my purpose wall, and have been considering different potential things to focus on- basketball leagues, seriously focusing on writing a book I’ve started, habitat for Humanity, etc Definitely need to find some consistent thing to have to get up and moving towards…

  71. Paper Tiger

    Sam, like many others, I loved this message and its honesty. I was “retired” by my corporation at 57 which gave me an excuse to join some former colleagues and start our own business that we have been working on for the last 3 years. I think having this new “hobby” allowed me to ease into some of the challenges of “downshifting” later in one’s career. I can still answer the question of what I do for a living with my involvement in our startup business while at the same time having a lot of gaps in my days to enjoy other pursuits.

    I did experience many of the other transitional challenges you mentioned. Full retirement will probably be a harder pill to swallow than I ever imagined which is why I believe I will always have some side projects taking up a few hours a week as I fill up the rest of my time with real retirement pursuits. I’m not mentally there yet to fully retire and I guess a lot depends on if our business develops enough traction to sustain itself and for how long.

  72. Comrade Sam! Great article and I really like the personal connection to how it’s impacted you since “retirement.” I think this is very much part of the Life journey and everyone’s is different. As noted above, there are similarities to other events like kids moving out for full-time parents or the person dealing with a layoff.

    In my case, I’m three months into being FIRE’d up at 57 — something that took some planning in that I “retired” twice for the life-long passive income. In both cases, I mentally prepared 3 years out from the target date and I think that made all the difference (there’s a whole discussion on what that takes!). One military mentor’s words have always stuck with me, “If we’re lucky and don’t get killed we can stay with it till retirement. Then someone else can fill our shoes for Uncle Sam. Don’t think you’re so important that you die at you desk.”

    Agreed that the social connections have to be worked. I’ve found meetup groups for motorcycle riding and there’s a herd of us “retired folks” in Austin that ride to breakfast every Wednesday. That’s lead to more interactions and social opportunities.

    1. Good to hear comrade Rudy! Yes, absolutely, we must realize that although we wrap our identities in our careers, we really aren’t that important because companies move on without us, whether we like it or not.

      I LOVED riding my motorbike in the past. Nothing like the winy open road up the mountains and in wine country. But alas, I’m trying to minimize risk with a son. Need to be alive until he gets a job at least!

  73. Hi Sam, you know me – I retired 11 years ago from a job most people would kill to have, and I haven’t worked a minute since then.

    The most challenging part of retirement after 11 years is to fully understand how much you left on the table as you see friends and family who were way behind you financially, pass you up on their way to 10 million dollar mansions, 9 figure net worths, and commercial property portfolios. ;-)

    Also despite trying to challenge your mind in retirement, nothing will ever keep your mind as sharp as that profession that paid you millions to work your magic.

    Oh ya and health insurance premiums are murder.

  74. Martial arts Mama

    OMG! I can’t believe some of the comments you have to endure from some of your readers! Your articles are really insightful, and I’m so thankful to have come across your blog and all of your awesome (and free) content.

    Truly, if you did want to charge for some of your services, you should consider offering an online financial review/assessment of individual portfolios. I know my husband and I would be interested in getting your input. We currently have another financial advisor who is great, but also quite conservative. I’m not sure they are also aware of some of the investments you support like real estate crowdfunding or P2P lending.

    1. Thanks! Writing and putting yourself out there can be tough work, but someone’s going to do it right?

      I’ll likely never charge anything. It’s fun to tell stories and to provide some financial perspective so that other people can learn. I truly believe in the democratization of education through the Internet. I love reading work from people who have experienced Something you’re looking to achieve.

      The problem is, too many people who have already got theirs, don’t want to or don’t have the time to share their experiences on a regular basis. So from that perspective, I absolutely do believe that writing for free to help people improve their financial situation and answer any problems they may have is a form of giving back.

      And given that giving is very addictive, I plan to writr until my fingers fall off.

  75. This is your best post yet. I retired at age 44 from a job in financial services four years ago. I have experienced pretty much everything you described. I still have days when I question it, but I keep busy enough with elementary age kids for the moment. Some of the comments here are also gold. Sam – thank you for continuing to share your work!

  76. Damn Millennial

    Saving for FI by itself makes you an outlier. People always think I’m nutty when I talk about money.

    Or bare minimum they wonder why I don’t spend more when we earn a great living compared to many peers.

    I think life is always changing so therefore there are always going to be the ups and downs.

    For me a big part of investing to FI is just to give myself stability and options because so many people I care about were robbed of this in their lives due to money.

    As I move forward I realize more and more it’s about balance. Even having a strong head start and solid footing now makes me feel like I have options going forward.

    Having a quality relationship with a significant other is also important. I think hopefully they balance you out. I’m happy my wife pushes me to spend more and invest less. We have built some awesome memories over he years because of this. I have also challenged her to not spend on things we don’t need and we both meet in the middle.

    As far as holiday parties I have never been a big fan. If you ever come through Denver and want to have a beer let me know!

    1. “Having a quality relationship with a significant other is also important.”

      I think this is key. Having a like-minded person to share life with makes early retirement wonderful.

  77. Sam, Thanks for your candid assessment on the RE part of FI. I’ve benefited greatly from the FI movement which I began to follow in 2010. FIRE gave me the framework, the tools, and most importantly, the community, to achieve FI (@51, ~$8M liquid assets, excluding $2M home, no mortgage), but i’m not so sure about the RE part…

    When I tried to take a leap to RE by taking a 3 month sabbatical from work, I ran into pretty much the same problems in your posts: wife don’t need/want me at home during the day, she’s been a stay-home mom and have her own schedule and social calendar, your life loose structures, etc… To keep myself from getting bored, I end up doing all the online courses and began to develop a renewed interest in my profession, and end up switch to a more interesting field with more interesting work and more positive people.

    The negative part of work is still there, but amazingly, once you have FI, you realize you *don’t* have to go to lunch with coworkers you don’t like, you can choose projects that are interesting, you no longer care about raises or promotions, and if anything, you can always go to another team or company and not worrying about paying bills. The equanimity that is bought by FI is tremendous.

    At this point, I’m still working and pulling in ~$450K per year, and donate unspent salary to charity. When consulting with the head of charity we donated to (a retired Cal professor who runs a free after-school tutoring program for rural children) whether I should retire and volunteer for his organization instead, he told me i’m over-qualified as a tutor and he’d much rather I donate $$$ so he can hire more out-of-work people as tutors who really need $$$, so he can solve 2 problems at once: reduce unemployment & provide free tutoring). His advice is the main reason for me to continue working even we don’t need the $$$.

    As part of my RE research, I also read “Escape from Freedom”,
    https://www.amazon.com/Escape-Freedom-Erich-Fromm/dp/0805031499 – it basically says human are social specie by evolution, and we (unconsciously) crave for the social structures (unless you have autism). The book has been very helpful in giving me the mental framework to stay working. We still aim to retire @55, but will see :)

  78. Sarah Nguyen

    Sam, have you ever heard of cognitive behavorial therapy? Look up helpful and harmful thoughts; I think it would be very helpful to you!

    1. I haven’t. Any cliff notes you want to share?

      Does this post make me seem like I’m down and out? If so, perhaps I’m too good at arguing one Perspective, because overall, not having to go to a day job is one of the best things ever. But I just don’t want to talk about how good it is because that’s pretty annoying.

  79. Sam,

    Thanks for putting these thoughts to words. After reading, I can see how each of those downsides can define an early retiree’s day-to-day life.

    As with all major changes in life, stress (or dread) come along for the ride- even for good life changes. I try to remind myself that positive change can still create stress and this is my body/mind’s way of reacting to change.

    By way of personal example I can relate to your second item, though not from early retirement, but from some life changes. I’ve recently had a lot of time free up as a result of a job change and passing my final CPA exam. Before, my normal work load and studying would combine for ~80 hours per week on average, with some weeks being much heavier (i.e., during quarterly earnings). This was the case for the past 3-4 years and my schedule normalized to these obligations occupying most of my time.

    However, in the past few months since I’ve transitioned to a much more reasonable work/life balance, I was initially at a loss for what to do to occupy my time. This was time I hadn’t a need to account for because I was either at my work desk running through spreadsheets or my kitchen table with my nose in a book or taking practice exams on an iPad. I quickly decided I needed to do something besides loafing around and watching Netflix with my wife each evening after work. My first thought was to build more skills to help me advance my career. As such, I enrolled in an online class to learn different software packages routinely used by a data scientist, thinking this would be useful. While I enjoyed developing those skills, my heart wasn’t in it. I needed something else.

    After noticing my wife’s mentioning of a financial blog she was reading (your’s), I thought it would be a great idea to repurpose my time not to helping myself, but to helping others. I would regularly field questions from friends and family about personal finance topics and I thought it would be useful to put pen to paper (or maybe fingers to keyboard?) and document some of my discussions to guide others in my generation who may have the same questions. Selfishly, I’ve really enjoyed the entrepreneurial experience that has come from starting a blog. But it’s been equally rewarding hearing about specific topics people want to know more about and then writing a piece and sharing it with them.

    This is all a long way of saying that I don’t know if I’ll ever be an early retiree, but your points resonated with me in a similar way. My changing schedule did feel like I walked into part-time work despite my new job still accounting for 40 hours per week. And you’re likely right that my annoyances will change with more time available to pay them mind. However, I think with all major changes, the stress is best dealt with when you have a strategy and structure in your life. That mindset along with a routine have really gone a long way toward me overcoming the downsides of my life changes. Thanks for sharing your thoughts!

    1. Congratulations on passing the CPA exam! That is quite an accomplishment you should be very proud of. Nobody can take that away from you. I can’t believe it’s been over 12 years since I graduated from business school. I have my diploma in the guest room/playroom and it’s fun to look at every so often.

      Enjoy the blog and journey! Half the battle is just survival.

  80. I lived much of what you explained in this honest take, Sam and it was great to hear it from someone operating at a higher financial level than I am. Thank you!

    Anyone who can relate to the challenges in this post would likely get a lot from Jordan Peterson’s talks on meaning and responsibility. He’s a clinical psychologist and now a modern philosopher of sorts exploding in the male world of psychology.

    A quick search on YouTube and you’ll feel smarter just from listening to him — like this blog! His theories changed my life.

      1. Yikes, that Jordan guy was not what I was expecting. Maybe I found the wrong guy, but I don’t think so. What’s your opinion if you watched his talk?

  81. intrinsic value

    Is this a post about the meaning of life or early retirement? A close friend of mine wrote a book about his journey riding a bicycle around the world. Somehow it was repackaged into a pursuit into the meaning of life. He certainly had some interesting life experiences money cannot buy (especially in a “5 star hotel”) and several near-death experiences ending with the shocking conclusion that, “the meaning of life is whatever meaning you give to your life”. I know his trip was not about searching for the meaning of life at least initially, but here is a glimpse into truth that people like to twist for their own conveniences. He was my roommate in DC, and on the same day I was moving away (lost his best friend). His girlfriend broke up with him (lost his GF), and his boss told him he was the worst art director he ever worked with (lost his job). I told him well what does he like? Knowing him well I said the 3 B’s: Beer, Bicycles and Babes. We were still in our early 20’s is my best defense. Why not combine all three by bicycling across the country? He took my advice.

    But he didn’t have to bicycle around the world to find the meaning of life, because for the most part the meaning of life is in our back yard. He was simply running away from the realities of life that life is hard and to have success you must make sacrifices and even if sacrifices are made not everyone will receive success. Our ancestors knew this tenet well but described it in terms that modern life has trouble relating to. Our ancestors sacrificed goats and sheep (hard work), and they received blessings (success) but not always (Cain). My friend’s true intent on bicycling around the world was a way to coupe with his inability to sacrifice long hours at work in a competitive field. He couldn’t hack it and that’s okay, but why not be honest about it and move on. We don’t have to bicycle around the world. With maturity how could the idea of pursuing the 3 B’s be offered as the catalyst for bicycling around the world when searching for the meaning of life gives so much more status? LOL, I could really use that “$10 Starbucks card” now, do I qualify writing this free reply? If only I was one of those lucky renters.

    1. Good stuff! It’s whatever you want to make it out to be.

      I’m sure Daniel Cohen in the comments would be happy to mail you a $10 Starbucks card if you ask nicely. Give it a go!

      1. That guy Daniel Cohen is something. Lecturing others on giving without having a clue what giving they do, not that it is anybody’s business. Lots of very good reasons for not disclosing that besides the Bible saying it has to be anonymous to get credit for it (or something like that). Bragging about his cheapskate “giving” yet. His tenants must burst out laughing after his 3-month inspections.

        Anyway, Sam, you give yourself big time all over the place, which is the best giving of all, and I am betting your financial giving is thoughtful and generous.

        Good post — All of those retirement realities are very true and as always you describe them well. There are transitions in life, retirement being a big one. Lots of adjustments. But when something is lost, new things come to take its place. Exciting to see what those will be.

        I have watched friends retire abruptly at 65, and stumble for the first year before finding a groove. Those that have plenty of interests and activities while they are working hardly skip a beat. Those that have done very little other than work don’t know how to go about filling a life.

  82. Sam, Although this post is about retiring from “paid work”, a lot of what you write about and your emotional mindset applies to nonworking parents when their children become independent and leave home.

    I only worked for a few years, and then chose to stay home raising our 3 children. I had a lot of “mommy” friends, and was very busy taking care of the children, taking them to activities, cooking, etc. In fact, I used to wonder how the heck I could have held down a full time or even part time job. There were man-days my kids were home sick, I volunteered in school, etc.

    Then over time, the “crazy busy” life tapers down, and you look around and wonder what the heck you will do now. When people ask you what you do, you can no longer say “stay- at- home mom”. It is as if you have been fired or retired from your job. The difference I had was that my friends were all in the same boat, and we still socialized, volunteered around town, etc. But on some level I feel like I have been waiting for the rest of the world to retire and join me in my life.

    Not sure if this makes sense, but I bet many many stay- at- home parents have experienced a lot of what you talk about in this post.

    1. Oh wow! What you write makes complete sense! Further, being a stay at home parent is crazy hard! So much time is invested in being a parent as a stay at home, that I can imagine when the kids are gone, there is this sunken feeling.

      I hope my son remembers how much time I spent with him and how much I loved him for his first 18 years. I hope he doesn’t forget about me and remembers to call. Just a few minutes a week to tell me how his life is would make me so happy. And even if he doesn’t at the time, I know he’ll appreciate all the podcasts I will have recorded for him when I’m gone.

      It takes so much work to build and maintain a social/support network. But I’m determined.

      Hope your children are doing well!

  83. This post hit me at my core. Little background. I semi-retired at roughly 31 (38 now). I say semi because I still work about 15 to 20 hours a week (although by choice). I’m a litigator with an extreme specialty. I usually pull between $500k to a little over $1m a year. After law school I went to one of the best firms in the world, but only for four years. I made a good enough impression that I was able to take work with me when I left to open my own firm. I leveraged that opportunity into a very small niche practice. No kids. No debt. No responsibilities in this world other than my wife.

    Unlike many of the responsible folks that read this blog, I’ve gone in the other direction for the past several years. I bought a $200k car. I live in one of the nicest buildings in my city. I’ve saved, but not nearly as much as I should have. I decided instead to travel the world while I was young. But, not just travel–instead, travel in style. Always business or first class, five-star hotels, driver, etc. Exactly like you see in the movies. In the last three years alone I’ve been to well over a dozen countries, including the Maldives, UAE, South Africa, etc. Two years ago I spent $100k wrapping the globe. Bucket list stuff for sure. I just got back from almost two full months in Europe. The point isn’t to humble brag, but rather set the scene.

    So last night I was up to 4:00 a.m. unable to sleep–something all too common for someone so “lucky.” The thought that passes through my head over and over and over is “now what?” As you mentioned, I have very few friends or clients left from my work years. I stay in touch, but mostly I just get “must be nice” comments because folks are still working harsh hours at a firm. I certainly don’t get invited to the Christmas parties anymore. I grew up modest–so my family offers very little in the way of support. Again, mostly “must be nice” snipes. Plus, when family sits around and talks about jobs, trying to pay bills, etc.–I can’t relate anymore. I end up writing a check for $10,000 and making up an excuse to leave.

    Anyway, the purpose of all this is two things. First, thank you for this post. It was actually quite nice to hear that others experience the same issues. It takes guts to be so “lucky” and talk about these issues (particularly on the internet). Second, for others, in my humble opinion, you shouldn’t be trying to “retire.” You should find something you love to do and then keep doing it. My grandfather used to tell me if you love your job you will never work a day in your life. Don’t slog away for 25 years to squirrel away enough to sit on the couch all day. Squirrel away a few hundred thousand and go open up a business doing something you love. And keep doing it–forever! If you are really lucky, you will find some good people to go into business with and share the journey.

    I was absolutely convinced if I had enough money to never work again and travel the world I would be happy. I was wrong. There is much more to life. I used to hear people say that all the time, but I always thought it wouldn’t apply to me because I didn’t grow up rich. It is absolutely amazing what you can get used to and start taking for granted.

    1. This was a great story and comment, thanks for sharing. Like Sam’s post this is inspirational or uplifting for those of us not doing the typical career routine.

      While I’m not as financially successful as you it helps me not to worry about that as much now.

      And for what it’s worth using your money to help others now that you crossed off bucket list items is a smart move. Even if it’s hard to relate you’re still helping and contributing to society.

    2. I do litigation with a narrow specialty as well. I’m curious to know what area you are in, if it’s not too intrusive.

      1. I’d rather not say exactly, but it involves science. I have a somewhat unique educational background. That results in a specialty within a specialty. Plus most folks with a dorky educational background like mine hate showing up in court. I enjoy it, so that helps a lot. As you likely already figured out, I’m not being paid at an hourly rate either. That’s why the yearly swing in salary is so much.

        1. I understand, and thanks for the info. I don’t get paid an hourly rate either – caps your income.

    3. Thanks for this comment. I agree with you about retirement. The longer I work and the more I make – especially now that I’m at a firm full of people I like and clients I enjoy socializing with – the less I am interested in retiring. At the same time, that leaves me with a net worth that could afford me early retirement combined with a big salary and savings rate. I’ve consciously loosened the purse strings as a result over the last year or so (not that I’ve ever been truly frugal), and it’s fun and comfortable but also rings hollow and doesn’t really feel good at the end of the day. Putting a wedge between me and my spouse and our families, us becoming uncomfortable in all but the most luxurious situations, inability to relate to “regular” money problems and people.

      At the end of the day none of that is fulfilling, even work in many cases. We don’t particularly want kids, but family is the only thing that has ever given me purpose (besides religion which I gave up years ago). That said, my career gives me a routine and schedule, an identity, a social and professional network, a team that relies on me, and a reason to get out of bed and put on some nice clothes and use my brain on a daily basis. Frankly even if I hit the 9 figure lottery I think giving all that up would cause more harm than good.

    4. Must be nice. (Sorry, couldn’t help myself!)

      In all seriousness what about taking your own advice? You have more than enough space to start a business doing something you really care about. What about a non-profit, or helping kids that need it?

      I’m still on my path to a modicum of financial freedom but I currently imagine my days would be filled with hobbies and meaningful pursuits. There are lots of things I still want to do that don’t require a lot of money, but require time and attention. I guess a lot of them are a means of addressing my inadequacies. I’ve never been good at sports or music or art, so I’d like to work on learning BJJ, drums and painting with a good teacher to guide me.

      I don’t think I was always a good brother so I’d like to help my sister out, and be more involved in her life, and I want to be a bigger brother (i.e. apply to the bigger brother foundation). I’d like to code things that would help people without feeling like I have to think about monetization or return on my time. Similarly for business, it would be nice to help some people without worrying about whether there are affiliates in the space or courses I can make. I’d try and write some short stories or even a proper book — it wouldn’t matter if it was awful.

      Am I wrong here? I imagine that even without work I’d fill my schedule quite easily, and that’s without dating/a spouse and kids on top. What’s your experience been?

      1. The honest answer to your question is a little weird. I absolutely love efficiency–probably to a fault. Financially at least, I don’t start a new business or invest in time consuming projects because I’ve never come across something that can pay more than what I do for as little effort. Even though I have the time, it bothers me to “waste” it. I also really enjoy what I do. I think I’m good at it (or so I’m told) and that is always a good feeling. However, once I hit between $500k and $1 mil a year I shut down. My brain just says: “what’s the point in doing more?” If there is something in this world you can’t buy with a salary like that then you have issues. At least that is what I tell myself. Could be a justification to be lazy, but lazy isn’t how most people would describe me.

        I do give to charity, but had to pull back from doing legal aid type work. Long story. It can be emotionally too much for some people (particularly when it involves kids). I’m designed better to litigate for or against large corporations.

        Hobbies are fun. I like to travel. I’ve lost a ton of weight over the last few years and I am in the best shape of my life. I run, bike, swim, do yoga, etc. Goes back to that efficiency thing though. I see the point and benefit in exercise. It makes sense to me. I’m not evolved enough yet I guess to enjoy art or music. I’ve never been interested in anything even as a hobby unless it results in a tangible and productive result. My reading list would seem like torture to most people. Played around with politics for a bit as a “hobby,” but it was way too toxic for me. It was fun (I love a good debate/argument), but it brought out the worst qualities in me so I had to stop.

        I too imagined it would be easy to fill the day. But, if you minus off kids, most family, a “real” job, money issues, health issues … there is a ton of time in a day to fill. 18 hours a day is a lot of time if you like staying productive. My wife is a lot of fun to goof off with, but a few hours a day of me is enough for her. After that I stress her out with my constant need to do something useful or productive. She can sit on a beach for 12 hours a day doing absolutely nothing and be totally happy. I’m jealous!

        1. I can empathize with the focus on productivity or efficiency — but why not point it at a metric other than money? Viewers on a youtube channel, people helped by a non-profit, reviews on a product/book, streams of your music…

          I’m not really in any position that allows me to advise you, but I personally would use those things as a weapon rather than letting myself feel like they are flaws. I’d try and turn them on a new challenge. It’s not rewarding to do something and feel like you’re just idling time away or spinning your wheels, so I think you have to bring the efficiency and need for achievement to anything. I feel it’s always about the bottom line, but the bottom line doesn’t have to be money, especially since you’re effectively done with that game. What do you think?

    5. Thanks for sharing! Such great insight. Do you have a spouse and family? I’ve found these people help fill the happiness void and make freedom, money, and effort more meaningful.

      Before my son came, all I was doing was traveling and making money for my financial freedom and my wife’s. After a while, it felt kind of pointless, or at least less meaningful. Now, I’m so amped up every single day to Take care of my family that I feel my life took a step up in purpose.

      1. I’m married. Which is great. Once we both quit working our relationship really blossomed into something I never expected. It was like setting down a ton of bricks and leaving it behind. Your post was about the negatives, so my comments are geared toward the “downsides.” I could fill paragraphs for sure with the positives. The positives are just not what I thought they would be ironically. You would think the ability to travel the world would be the main upside (and it is nice for sure). But, after awhile, the little things end up being even more special somehow. Like the ability to step in and help someone at the drop of a hat since you have complete flexibility in your schedule. I can’t tell you how many times someone has genuinely felt like they were “saved” from a disaster when all I donated was time. This one is stupid, but I also love accepting last minute invitations from people that are only being polite because they assume you could never get the “time off” to join with no notice. Immature to be sure, but often hilarious and sometimes you actually have an amazing time with someone you don’t know very well. I spent a week in Miami in December with a group of total strangers because one of them said they had two extra tickets to Art Basel and my wife and I should come. We were at a bar in New York City and the tickets were for the next day. The point was to teach the guy a lesson on “bragging,” but it turned out him and his friends were really nice. We just spent a week with two of the guys at their house in Germany. Again, the little things like having the time to meet new people is something that was not on my radar initially.

        Sounds like your little one was not the primary motivation for leaving your job, but rather a very pleasant surprise benefit. I love kids, but prefer spoiling other people’s to having my own.

        1. I hear you about all the churches in Europe all starting to look the same. That is cool to have the spontaneity to do whatever.

          We weren’t sure that we really wanted kids, but we also decided it would be a wonderful addition and a exciting new journey to our lives.

    6. Firstly Sam, your article is awesome. This comment is great too because it so clearly illustrates someone who can easily enhance their happiness just by adding one additional, vital objective to their list.

      Since social capital is proven to be the clearest predictor of happiness, we all should be keeping an eye on our strategy for building and maintaining social capital.

      Your social capital is the web of relationships you have that give you connection with others, a sense of belonging and hopefully some amusement or support (and often irritations too but that’s part of the fun of it). These relationships can range from the little ones (the doorman, your dentist) to the very intense(spouse, children parents). Its all important.

      The workplace conveniently packages up a large part of our social need for relationships, community and a sense of belonging. Ensuring those needs are met outside the workplace is a skill which people as brainy as us can crack pretty easily so long as we keep unrealistic expectations in check.

      Sam writes well about his strategies for connecting with other people. He is very thoughtful about his social capital.

  84. Most are these are a concern I have for my husband. He’s still working and he thinks / believes it will be great after he leave work but I’ve warned him that meaning and purpose is going to smack him in the face double time. I worry he’s not going to find that thing that sparks him like I found my thing. One can only play so many video games until it gets numbing.

    Great to hear your son has given you a renewed purpose! I think we are planning kids first and then retiring after they start walking and talking and all health signs are green. Then my husband can go into stay at home dad mode and feel purpose in that way… Otherwise I’m not sure if he’s going to find his spark.

    1. It’s a good plan you guys have. Just know that nothing ever goes 100% according to plan, and it’s important to stay flexible. What we imagine what things are like in our heads is often different from reality. Sometimes better, sometimes worse.

      I had some pretty clear goals w/ FS after leaving work, but still felt uneasy for a couple years. Make sure your husband writes out his plan and tests it out before leaving!

  85. When someone asks me what I am, I say that I am an engineer. Its more of my identity than anything else, insomuch that it is also my profession. I built my first pc from parts at age 11.

    Saying that, I fear the laziness birds will land on my back. I have many hobbies and interests, but what happens when I don’t have the clock against me. Who knows.

    One big thing I have not done yet is worked backwards. What I mean by that is that I have not found the savings rate that will enable me to retire when I want to. My hope is maybe 10 to 15 years more work at tops. That is what this post got me thinking about.

  86. Super insightful! And all true. I remember thinking “I’ll have so much time to do xyz” like finally organize all the kitchen cabinets and closets once I stop working. I did some of that but definitely not as much as I imagined. I felt so happy to be free of a stressful job and while I did have more time, there were other things that came up and I didn’t manage my time as well as I could have before I got pregnant and had a baby. I also felt like goofing off more than I anticipated when I should have used that freedom to do more fun and productive things, see more friends and family, places, write more, etc. I love being a full time mom now though and I certainly keep busy around the clock now!

    1. I am glad you are a full-time mom :-) you’ll look back with on this I believe once he goes to school full-time or leaves the nest. What treasure we have the able to spend time with our son.

  87. Ten Bucks a Week

    Austin is cheaper, but you’d definitely send your kid to private school. I’m happy I moved here, can save much more than when I was living in California.

  88. Great post! I have definitely experienced everything you’ve mentioned as an early retiree. I completely agree with what you said about introverts. I believe being an introvert has helped me with my transition. I don’t really mind that I don’t see that many people every day, though it does get lonely sometimes. It’s interesting to see how much we all depend on our jobs to give us community, purpose, and direction. Our jobs also dictated our to do list and how we managed our time. And it has been somewhat of a transition to take on all those responsibilities myself. However, now that I’m retired, I know for a fact I will NEVER go back to work full time (and I just turned down a part-time gig recently). I value my freedom too much to do that.
    Thanks for the honest and well written post!

  89. Daniel Cohen

    Hi Sam.. Great Article!!

    However, I think one major part is missing that can make early retirement worthwhile.

    Life is all about what we GIVE and NOT what we GET.

    Nowhere in your article did you mention how you have been a giver in retirement? What makes you think you can be accepted, appreciated, and invited to parties when you don’t spend part of your retired life giving to others? When is the last time you met someone and just gave them a 10$ starbucks gift card immediately? Would they care you are unemployed after that?

    Are you thinking you are giving by training people on Financial Samurai about finances? Why do you think making money from your articles is giving?

    I challenge you to start making your life about going out of your way to do positive good things for other people and expect nothing in return.

    1. Actually, you bring up a good point. Do you think I should charge for my articles on Financial Samurai? I’ve received a lot of thank you e-mails and comments over the years from readers who’ve said I’ve helped turn their lives around. I’ve long wondered about the benefits of a subscription business, because writing these articles take a loooooooong time to write and edit. I was up until 2am for this one, for example.

      I feel embarrassed to write about my giving. I’m the type of guy who will give anonymously, or under the name of someone I want to honor instead of my own name. I have hosted content regarding educating my readership on foster care, for example, because I’m a foster care mentor.

      Do you think I should be more open about how much I give? I’m sure I could do more to help other people. If it pleases you, I did donate money last week to the American Nystagmus Network to help spread awareness and do research on this visual impairment. One strategy for spreading awareness is to incorporate things I care about into my articles e.g. The Chens who have a son with nystagmus.

      How about yourself? What are some of the things you do to help others? I’d love to read your work as well, because goodness knows it can sometimes be a thankless job to write for free. It sounds like you are doing a lot to help others, and I’d love to learn from you and hear what I should do.

      Thanks for your guidance! Hope Seattle is treating you well. And say Mahalo to your man in Hawaii for me.

      1. I’m the same way and keep my giving private. When someone brags about their giving or gives in order to have their name on a building, you’ve got to wonder whether they are giving because they want to give or because they want the attention. There was this whole story recently about a hedge fund manager who said he’d only give to the school if his name was on it, so they declined. Haha.

        For the record, I’ve never sent you any money to read your work, and it has helped me think about issues more deeply. So thank you! I don’t know what Daniel Cohen is talking about.

        Maybe he’s Mother Theresa in disguise? It’s always fascinating when others judge others about how much they give without disclosing what type of giving they do to make them so holy.

        1. Daniel Cohen

          Hi Andrew,

          Maybe he’s Mother Theresa in disguise? It’s always fascinating when others judge others about how much they give without disclosing what type of giving they do to make them so holy.

          Response: Why are you being so hard on yourself? And what makes you believe I am judging others? Why do you think it matters how much someone gives? I’m more interested in whether people give without expecting anything in return. Otherwise, people are buying.

          My intentions are pure and I work to live a life add value to others around me.

          I am very appreciative of the articles Sam puts together for free. If I thought Sam needed the funds, I would contribute. However, Sam is doing better than I am financially and I have other friends and people in more need right now.

          1. If you call giving your tenants $10 a Starbucks gift card charity, then I think you are a little bit delusional. But then to take it a step further and ask why Sam is not donating more, when this is not the topic of the post, shows that you really lack emotional intelligence.

            Do you have a wife and family? If so, maybe they can provide some perspective. Because it feels like something is really wrong. Like there is a void of happiness in you somewhere.

            1. Daniel Cohen

              Hi Andrew,

              But then to take it a step further and ask why Sam is not donating more,
              Response: If I said, why he is not donating more, then I miswrote. I thought I was just pointing out that he did not mention anything about donating in the article. And I was pointing out some of the best parts of life are about giving. You should read the book “The Go Giver” by Bob Burg.. Great book.

              when this is not the topic of the post, shows that you really lack emotional intelligence.
              Response: I’m confused. There was nothing emotional about what I wrote.

              Emotional Intelligence is defined as:
              The capacity to be aware of, control, and express one’s emotions, and to handle interpersonal relationships judiciously and empathetically.

              Do you have a wife and family?
              Response: Yup.

              Because it feels like something is really wrong. Like there is a void of happiness in you somewhere.
              Response: You are correct.. This is why I see a therapist.

      2. Daniel Cohen

        Hi Sam,

        Do you think I should charge for my articles on Financial Samurai?

        Response: You can charge whatever you want for your articles. However, if you are making enough money to cover your expenses, then what will the extra money bring you? Are you looking to charge so you can be a bigger giver? I thought I read that you are happy with how Financial Samarai is going. So, charging for your articles might not be necessary.

        Do you think I should be more open about how much I give?

        Response: Yes, I think you should be more open about how much you give in order to inspire others to give.

        How about yourself? What are some of the things you do to help others?

        Response: I’d love to be able to do more than I can right now. So far, I currently give to my tenants. When I come to check out my properties every three months, I show up with 10$ gift cards to Starbucks for each renter and tell them how much I appreciate that they pay on time and take care of the place. I don’t expect anything for it but I seem to find myself with really good tenants.

        I also give to random people in the streets. One time, I paid for someone’s lunch because they didn’t have a wallet. Another time I gave a starbucks gift card to someone who looked like they were having a bad day.

        I also contribute to some company sponsored campaigns like giving tree.

        However, the most important giving I do right now is to a friend of mine who recently got hit by a drunk uninsured driver going the wrong way on the freeway. You can find out more going here: https://www.gofundme.com/cassell-family-emergency-relief

        Thanks for your guidance! Hope Seattle is treating you well. And say Mahalo to your therapist for me in Hawaii.

        Response: You are welcome. If you are ever up here in my neck of the woods, feel free to reach out, I’d be happy to host you if you need a place to stay. BTW. I pay $135 a session.

  90. Nice summary Sam. For people like me that started late (>35 years) in this business of investing, our FIRE strategy will not be to retire before 50. Hopefully we will not experience some of the things you talked about here. But certainly the most important thing is discovering your true passions so that when you are free and retired, you can pursue those passions forever

  91. I don’t think most people realize how much their identity is tied up in their work. They may complain, but given a ton of free time I’d think that depression would set in. This is especially true for someone like you Sam.

    If you’re the kind of person that has the drive to work hard and smart so you’re able to leave the corporate world in your 30s, it’s also highly likely that you’ll need to find another challenging way to occupy your time.

    Driven people always need some new mountain to climb. Financial Samurai has become what it is because you parlayed what you did in the securities industry into professional blogging. I appreciate that you’re sharing that early retirement isn’t all sunshine and roses.

    I’ve worked from home for the past 9 years so I’m hoping that my transition to early *retirement* will be a bit easier. Time will tell I guess.

  92. I went through some of the same things but to a lesser degree.

    Identity crisis – I think everyone has to make this transition when they retire. You’ll try to hang on to your profession, but eventually, you have to move on. When I first retired, I told people I’m early retired. Now, I just tell them I work from home. It makes more sense to them.

    Happiness – I’m surprised you had to struggle with this. I’ve been following FS for a long time and you never really mentioned it. My happiness level is much higher now than I was working and it seems sustainable after 6 years. I was miserable at my old job, though. That makes a big difference.

    Purpose – Our son was 18 months old when I retired. That’s plenty of purpose until he’s gone off to college. After that, we’ll figure something out.

    Other downsides – For me, it is having less friends. Once all the work friends are removed, there are a lot less people in my life. I’m also not good at making new friends so that part has been tough for me.

    1. Yep, tough to make new friends, or at least good friends for sure.

      I wasn’t miserable at my job, I just found it to be extremely boring and pointless after my 13th year.

      I’m generally a happy-go-lucky type of guy. But I probably joke a little too much to my detriment because there are plenty of stiff people who easily take offense. With social media, it seems like getting outraged has become a national pastime!

      For example, I had a bunch of people on Twitter get pissed off when I wrote, “Would you suffer through the indignity of going to public school for $1,000,000?” They basically told me I was an elitist a-hole for jokingly using the word “indignity” when if they read the post, they would realize I was all for going to public school and accepting a big fat check upon graduation.

      So of course, I had to write my April Fool’s Day post entitled, Creating The Next Best Frugal Website: Frugal Wonderful, to make some lemonade out of the situation. The post has some serious undertones, but the people who were outraged by my Tweet have never come back to FS. Maybe it’s because they all decided to join a stiffy convention.

  93. Wow, this was a fantastic and honest read. This yields strong motivation to build surplus funds in FIRE, having the freedom to explore numerous activities and pursue varying interests and at whatever cost. Thankfully I generally enjoy my career, its challenges, social aspects, etc. I can OMY and build that extra cushion, but in the meantime, we’ll start to mentally prepare for some of these negatives ahead of time. Might be time to reread The Guide to the Good Life (Stoic Joy).

  94. Simple Money Man

    All of those are reasons why I don’t plan to retire until at least 60 no matter what my financial situation, all else being equal. In addition, I’ve read that many have health problems from retiring early too. There probably isn’t anything scientific to back that up, but I know myself. I won’t be motivated to go out to the gym and exercise on a regular basis. At least now there is a gym at my work so it’s hard to avoid it and not go, especially since it’s free! :-)

    1. Oh, don’t let my post discourage you from living in early retirement lifestyle. I wouldn’t trade it for going back to work full-time any day.

      The negatives that I talk about is really about maybe 20% of the pie. The other 80% is very positive, so the positives outweigh the negatives by 4:1.

      1. You ever thought of joining Brazilian Jiu-Jitsu?
        Becoming a student again, it’s challenging to learn, good for self-defense and your son will eventually benefit from it. On and on but it’s helped me keep my sanity for about a decade plus now.

      2. I spent many years to become a lawyer. Then I spent many years learning my job. I have helped many people. They needed me. When I retire, clients who want me to help them, won’t have access to me. You had skills people needed. Why did you decide to remove your skills from the world? I wonder how many people you could have helped. Retirement isn’t only about you or me..

        1. Congratulations! Make sure you stay a lawyer for as long as possible and make the big bucks.

          As for me, I like to help people for free and give them some financial guidance. Over the years, I have received many emails and letters thanking me for helping them and it is the greatest feeling.

          1. You are right. I enjoy your site. But you are the exception. I read 10,000 baby boomers retire a day. That’s 1.2 million a year. They aren’t you. If you don’t believe me, tomorrow see how many people 60 and older are fat and how many don’t smile. I think people don’t retire, they decay. Then again, who am I?

      3. One last thought. If I was an interesting person, I would have become that guy already. I would have found what excites me long before I retire. Who I am is the guy who will retire. Retirement will not make me more than I already am.

      4. My accountant mailed more money to the IRS. I don’t need to make more money. I need to keep more money. Your thoughts are about making more money. Save more money. Spend less money. All is well and good til tax time. If your readers could save what they pay in taxes, they would have the money they want.

  95. These are some great thoughts and observations based on your own experience. I just retired at 40 a few weeks ago, and already some of the things you mention have come up. I’m sure this article will be a good reminder for me as time goes on.

  96. Joshua Myers

    The people that I’ve seen who are most successful at this transition have a goal that they’re running towards. If you’re entire path to early retirement is centered around running away from a crappy life, the transition will be brutal. You still need something to do with your life. Sitting on a beach drinking fruity cocktails is a vacation, not a life plan.

    That said, the longer that you’ve spent in the trenches the harder it can be know what you will actually enjoy doing once you’re “free.”

  97. I’m glad you mentioned doctors who retire early in your post Sam. It is a common issue I have found with docs that have retired, early or not.

    When you have trained so long to become a doctor and then spend X amount of years being referred to one, it will be quite a different feeling when you no longer have that type of interaction when you pull from the workforce.

    You also hit another point that I am glad I have started creating now as I plan to retire early in the upcoming years and that is to do something that keeps your mind going. For me starting a blog has been a wonderful experience and I feel will keep my mind sharp as well as create social interactions to make up for the ones I will lose when I do retire.

    The FIRE crowd is pretty conservative and it is more likely that we suffer from one more year syndrome rather than leaving too early and thus have a greater chance of running out of money, but even so, I know that will be a thought running through my head when I pull the plug. We create disaster scenarios in our minds such as the sequence of return risk from hell that keep us up late at night. I think this will take a few years of actually being retired before you really feel comfortable that you will be financially ok.

    1. I would think suffering from the one more year syndrome would minimize your chances of running out of money because you continue to work and save no?

      If doctors can go part time and earn $100,000-$200,000, I think that would be pretty good.

      1. Yes, part-time has been a great way to go for me. I really like my time at work. But I have more time for the rest of my life and to blog, help at home, plan investments, sleep, exercise etc. And I’m still able to make more than the numbers you quote without withdrawing from “retirement” funds.

      2. Hey Sam. Sorry for my confusing sentence. Yes one more year syndrome will reduce the chance of running out of money. The greater chance of running out of money was referring to the leaving too early part portion in that confusing sentence.

        For me I think part time may be a great compromise. Still can bring home a great salary but more importantly if I can cut down the hours to the minimum that qualifies me for Healthcare I can take the xpensive option of private individual coverage off the table

  98. Wealthy Content

    Wow, great insights Sam. Should not be underestimated. I think most believe they do not care a lot of what society thinks, but it can be daunting if you are a misfit and stuck in your own mind. Thanks, some food for future thought.

  99. Accidental FIRE

    People will treat you like a weird misfit.

    I’m only semi-retired and I’m getting quite a bit of this. Neighbor: “I’ve noticed you’re home a lot during the day, did you get laid off?” Me: “Ugh, no.” Neighbor “Hmmm….”

    Some of my friends pretend to be happy for me but are obviously skeptical and think I’m odd. But that’s been most of my life :)

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