It’s Impossible To Stay Retired Once You Retire Early

Once you retire, it's impossible to stay retired

In the spring of 2012, I hung up my sword after working in finance since 1999. But I've discovered it's impossible to stay retired once you retire early.

There was actually a hiccup the very last day of work, a Friday. When I was e-mailing some personal files from my work account to my personal account (pictures, tax docs, etc), I inadvertently e-mailed a five year old client file that was caught by compliance. The e-mail almost derailed my retirement plans!

I was warned this was a violation of company policy. And that I would be hearing from them about any repercussions the next week. I apologized for the mistake and waited nervously about the fate of my severance check.

To allay my worries, I actually went to a free Hastings School Of Law community service event. Law students and professors volunteer to help those with legal questions. They just so happened to host the event on what I thought was the first free weekend of the rest of my life. It was great to see the school give back to literally hundreds of people. Some of the topics were about divorce, employment, accidents, theft, trusts, and more.

My question to a professor and to a law student was pretty simple. “Can my firm take away the agreed upon severance contract due to a five year old company file that I inadvertently sent to myself?” Financial companies are notoriously strict about ex-employees transferring sensitive client documents. Employers don't want client info taken to competitors after all. I told my company that I was retiring from the finance business altogether. But, how could they know I was really telling the truth? In our business, few people voluntarily walk away from such paychecks.

After getting comforting council saying that I should be fine, I promised that day to NEVER go back to work in finance if I could still get my severance and deferred compensation.

My new manager was in from New York City that day and was already busting my balls for the incident. I went a step further and promised to never go back to working for anybody. Hundreds of thousands of dollars were at stake and I was worried.

Dodged A Bullet!

HR called me the following Tuesday and told me everything was fine in the end. They agreed the client file was irrelevant given it was five years old. In addition, they accepted my e-mail apology for the mistake.

When I got my severance check several weeks later I felt like I had sheepishly won the lottery. Instead of spending it all, I sat on it like I would any financial windfall.

By the summer of 2012, the market had taken a little dive. And I finally invested the entire amount in the stock market so as to make it disappear. I wanted to stay hungry and pretend I received nothing. 

Despite The Promise, I Couldn't Stay Retired

For almost two years, I spent several hours a day writing online, playing tennis in the early afternoon, hanging out with the people I love, and spending 12 weeks a year traveling abroad. It was wonderful seeing Stockholm, Helsinki, St. Petersburg, Mallorca, London, Paris, Amsterdam, Malta, Bruges, Zurich and more. Spending time with family for two-to-five weeks at a time in Honolulu was also wonderful. I was in the best shape of my life.

The time spent writing on Financial Samurai paid off. Traffic and revenue doubled in 2012, and then doubled again in 2013. I didn't have to live the frugal lifestyle I had anticipated with my then ~$80,000 a year passive income. Things were good because I had enough money + all the time in the world.

But towards the end of 2013, I really started getting a little bored of the lifestyle. One unemployed friend I'd hit the card rooms with midday couldn't understand my situation. He said he would never be bored if he were in my shoes. But, he's never been in my shoes, so he has no idea! My closest friends all had to work full-time jobs. And there were only a couple unemployed folks I actually wanted to hang out with who were available to go on random adventures last minute. Random adventures tend to cost money.

Ventured Into Private Fintech Consulting At Empower

Then my contact from Empower called in the fall of 2013. He asked if I was interested in taking up a social media / content manager job. I was very hesitant in the beginning.

I actually went down to interview Bill Harris, the CEO during the summer. But I never really thought much about actually going back to work at the time, even part-time. I deliberated back and forth with loved ones. Finally, we came up with an agreeable solution to work 25 hours a week, with only two days a week on average in the office.

A year of consulting passed, and I learned a ton about the startup world, financial technology companies, and digital marketing. I also crossed off two bucket list items. 1. Working at a startup and 2. pivoting into a new role outside of finance were crossed off.

What's interesting is that people in internet/tech land actually e-mail me back now, whereas in the past, the responses would be few and far between. I guess the industry is sort of a club. But, now I'm wondering, what else does the future hold?

Let me provide a candid assessment of why I couldn't stay retired and why I don't think any early retiree will ever be able to stay fully retired. Once you read the reasons, you should seriously ask yourself whether all your savings, hustle, and risk-taking is worth it. Perhaps a 40 year career is a much better way to go.

Why It's So Difficult To Stay Retired

1) You're used to years of excessive stimulation.

In order to retire early, you've got to save aggressively, take a lot of calculated risks, and probably work your ass off more than the average person. You don't have to be smarter. But, you have to be more productive than the next person with the same amount of time.

I knew from the very first month on the job after college that I couldn't work for three decades like my parents did. As a result, I saved 50%+ of my after tax income every year for 13 years, aggressively invested 70% of my money (30% was in risk-free CDs just in case I blew myself up), and developed a rental property portfolio.

When you're working 60 hours a week, spending an hour trading the markets, another hour or two reading research reports, managing properties on the weekends, and spending another 20+ hours writing online, you begin to get used to all the activity you must do. Downshifting to a 4-5 hour work day feels like you're not doing anything at all. You naturally try and fill the other 10 hours of your day with something to do.

2) You constantly want to learn new things.

After my 10th year in the equities business, I knew 85% of what there was to know. It was the same old stuff over and over again given the markets are cyclical and there aren't a plethora of new companies going public every year that matter. I've discovered that work stops becoming fun for me after there's not much left to learn.

After you learn most of what you need to know, work becomes repetitious to the point where you can't really take it anymore. One of the strangest, and perhaps worst feelings is the depressing feeling of having to work for money, not out of love for what you are doing.

After two years of growth on Financial Samurai, I proved to myself there is a correlation with hard work and progress in the online world. A book on achieving freedom was written. And the site was picked up by several large media organizations, and you, the community blossomed. I'm challenging myself with creating monologue podcasts now, but I'm not sure if that's going to be my thing. I'll give 12 episodes a go, and then decide from there.

Desire To Learn More About Digital Marketing

I wanted to learn about digital marketing and how startup culture differed from traditional corporate culture. On the one end, there's Financial Samurai, a completely homegrown site that spends hardly anything getting recognized. On the other end, there are plenty of companies who've raised millions of dollars who are using such financing to increase brand awareness through advertising spend. 

My experience at a Silicon Valley company is not very different from my experience at my old firm in finance because I was the boss of my own business in a satellite office. I only realized how much freedom I truly had at my old job of 11 years after I started consulting.3) There's a desire for order and direction.

When you have nobody to report to, you start taking your freedom for granted after a while. Sleeping loses its allure when you can sleep in every single day. Freedom doesn't feel as free when nobody is checking up on you. Days start blurring together when there are no concrete daily objectives.

My simple objective is to always be happy. Financial Samurai is actually secretly a blog about achieving happiness. But being happy is a little too amorphous. So I challenged myself to make X amount of revenue in three years online. That was a good goal that kept me focused, but I blew past the revenue goal after the second year.

So I sought to join an organization that had their own objectives I believed in. I didn't mind getting told what to do because being told what to do provides structure. Besides, I knew I always had the option to quit if I didn't like the structure, which is one of the most amazing feelings ever.

4) You love the security money provides.

Early retirees likely watch their money much more carefully than the average person. It's not uncommon for an early retiree to check his or her bank account multiple times a day. It's a no brainer for early retirees to leverage as many free tools as they can to help track their net worth, reduce expenses, and manage their cash flow. Early retirees love money because they recognize money buys freedom.

To go from a nice steady paycheck every two weeks for 13 years to nothing was a shock to my system for the first couple of months. But I got used to the lack of cash flow after the third month. It's true that we easily adapt to our money circumstances, so don't worry if you feel that you won't have enough to live a comfortable retirement.

Despite the growth of my online revenue and passive income streams, I still felt I lacked another financial buffer to feel absolutely secure. One change in a Google algorithm and there could be a 75% hit to my online revenue for years. I realized I love receiving a steady paycheck in the mail every single month, even if it is never spent.

5) You start really harnessing the power of money to do what you want.

Every single early retiree I've talked to has wondered what it would be like if they had a different career. Several I know have gone back to school to get a degree in something they once loved, but found impractical to learn from a money making/survival standpoint. Many pursue far less lucrative careers, but potentially more rewarding careers that offer more excitement. For fun, ask yourself what you'd do if you were a billionaire.

I've had a tough time getting out of the mindset that whatever I do should have the highest ROI possible for my time and effort. It was a big step for me to take the consulting job because the pay is much less than what I used to make, which is why it is really important for me to constantly be learning something new on the job. The moment I feel like I've stopped learning is the moment when I will start considering doing something else.

Early Retirement Becomes A Challenging Game

If you manage to retire early, like sub 40 early, I bet you a steak dinner at the finest steak house in the world that you won't be able to stay retired for more than three years. I made a Herculean effort to not get back into the workforce after almost two years, but like a velvety chocolate cake sitting in front of me, I couldn't resist stuffing my face with glee!

I think trying to retire early and live without a paycheck for an extended period of time is like trying to hit a million net worth; they are temporary challenges that once met, are shelved away to make room for the next challenge. Progress is my one word definition of happiness.

If you can have progress in your career, finances, family, spirituality, and your love life, no matter where you start, you will always be happy.

The Challenge To Earn More Continues

Now that it's 2023 and we have two young kids, I've also come to realize there is greater pressure to provide for your family than ever before. When there is a helpless little one to also support, the natural instinct is to try and earn and save more money to support a family.

That said, I've been fortunate enough to build enough passive income before he was born so I'm not stressing too much. All I wish I could buy with my money is energy now. Who knew taking care of a baby/toddler 24/7 was this tiring!

Financial Samurai passive income investments 2023

Related Post: The Dark Side To Early Retirement

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93 thoughts on “It’s Impossible To Stay Retired Once You Retire Early”

  1. Being single without a wife, and retiring early, is entirely different than retiring with a wife and young kids in the picture. I can’t picture myself becoming bored. My spouse already stays at home, and she’s bored, in part, because I am not there.

    She volunteers instead and spends more time at the kids’ school than working mothers do for sure. With me back in the picture, she will have a lot more options to do things she can’t now. I love TV and netflix, so that will be exciting for me. I also like to hike and have a blog as a hobby. I love to write about finance as well.

    I guess I could become bored, but early retirement was always a desire of mine. I always pictured myself retiring early, and then retiring even earlier.

  2. Tortoise Banker

    excellent perspective, different from Mmm, ere, and several other writers I’ve grown interested in. Thank you!

  3. I retired in 2003. I have traveled all over and love my life. I am now 55 and do not plan on working again :)

  4. Man, you made me laugh because what you said made us feel what you were going through. Nice and clearly honest.
    I’m passed 40, just turning 57. Plan to retire next year or two.
    Here in Australia they keep lifting the retirement age.
    My plan is to Retire, live permanently in Caravan travelling around possibly work.
    It’s the Freedom to Live and Work and learn from other people you met on the way.

  5. Pingback: Which States Are Best For Retirement? | Financial Samurai

  6. I think this is why I’m more focused on “financial freedom” as opposed to “early retirement”. I want to accumulate wealth so I can choose to work whenever, wherever, and on whatever. I don’t think I can stay “retired” for too long.

  7. I feel people are hard wired to work (our previous generations has it tough and lived through wars and hardship) – so the thought of clocking off early is a real test due to guilt and expectations from society. It takes a strong minded, determined person to make early retirement happen. My goal is not about money as such (although you need enough of it to get over your “line”)… is about achieving personal freedom and having choice. The real life challenge is doing something positive and purposeful with that earned freedom.

  8. Some people just need to stay busy to feel their best. I think you’re one of those people. :) I think it’s rewarding to feel like we’re making an impact every day and learning new things; I think that’s why it’s hard to just kick back and not do anything work related for a long period of time. Sounds like you have quite a good balance right now and although you like to have flexibility and do your own thing, you also like being continually engaged and always producing something.

  9. DAMN IT SAM! So I go ahead and retire early a couple weeks ago and now you come out with this post!?! LOL, just kidding…just got back from 2 weeks in Costa Rica and catching up on your old posts, pretty funny this is the first one I read and have a chance to comment on. So having had the first month or so off in a row for the first time since I graduated high school many moons ago, I can say without a doubt I am not sick or retirement just yet…it is great actually. But I can see myself already formulating a plan for the next start-up or adventure. Hopefully I’m a little smarter this next time and will dive into something that is as rewarding, but less consuming of my time and energy. Its fun to have a goal and a purpose…but also really nice to take a well deserved break. Your current state of mind really sort of reflects how I’ve felt about retirement in general all along, if you do something you enjoy it really doesn’t feel a whole lot like work…and if it is fun and you like the people along the way, how else are you going to better spend your time?

  10. Pingback: The Dark Side Of Early Retirement | Financial Samurai

  11. This article as well as the comments have inspired me to say screw it! for 2 weeks anyways. I’m in a position to retire now at 43, but I’m to scared to pull the trigger. For all the reasons listed above, plus some more I conjured up, I stay in a job that I despise. Today I make a change! I’m taking a 2 week retirement trial starting today. It may not be enough but its more time than I”ve ever taken off before.

    Thank you Sam, and thank you commentators

  12. Vawt @ Early Retirement Ahead

    I am always paranoid when I send personal stuff from my work computer to my home computer (something I scanned in or an article I wrote over my lunch break).

    I am a homebody and think I will be just fine milling around the house and taking our two kids to their activities (and maybe be their basketball coach). I was thinking of consulting a bit or vounteering with Habit for Humanity on a regular basis (or some other local charity).

    That is what i like about early retirement, I will have tons of choices to keep me busy. Hopefully some golf as well…

  13. James@StartingNegative

    I’d always feel the need to obtain some sort of goal, but I might still be able to do it in retirement. My goals would all be learning or fitness related, I’m sure. Maybe some travel ones in there.

    Of course, maybe I’d get bored of that in a few years and would want to try different career paths. Scratch that — I’d definitely want to try a few different career paths. Probably something in the wiring, with a strong desire to learn.

    I’m saying all this while being nowhere near retirement, so it’s not like I can speak from experience.

  14. I’m right in the middle of this right now. Early last year, I stepped down from running my company but my wife is still working in corporate America, albeit part time. I definitely wish she was here with me because no one else my age (33) is in my position. There aren’t very many people out there who you can call to play golf with at 11am on Tuesday, other than the silver hairs. My wife is pregnant with our first, due April, so I’m hoping that will get me out of this rut.

    I spend a lot of time watching investments, reading blogs/books on finance and self help stuff but there is only so much that you can read about this stuff. Sam, your site is really one of the only blogs that I actually get excited for anymore. MMM is gotten stale to me and Bogleheads gets pretty stale as well after spending time everyday on it.

    I would love to be able to find a local group of people that are in the same position but they are just few and far between.

    1. Thanks for the kudos. I definitely try and make things as interesting as possible here, b/c if I’m bored writing, I know others will be bored reading. It’s hard writing about topic to try and make more money, but that’s where the fun and challenge really is.

      Congrats on your first and good luck!

  15. I mostly agree with you Sam. I should ER in 2-4yrs and I don’t plan on doing nothing, I’d be curious to see if anyone who has the foresight to ER sit around and do nothing. Most of us still have tons of creative energy that needs an outlet, but it doesn’t necessarily need to come in the form of paid work. It’s about the power of choice. I recently made a big directional change with my job and, as a result, I’m no longer playing in the promotion game. Meaning, it doesn’t really matter what my next performance report says and that feels great. Already, getting up for work is more enjoyable because I focus more on learning and progressing for the sake of learning, instead of competing and getting promoted and it feels great! I’d imagine this is what ER will feel like-learning and growing for their own sake, doing for doing’s sake and saying to FU to the constant pressure of performing, producing and competing. Great post Sam!

    1. Congrats on removing yourself off the treadmill! Amazing how much more relaxing and enjoyable work is yeah? The feeling of learning and growing trumps making more money, most of the time. Unless it’s really big money… then….

  16. “If you manage to retire early, like sub 40 early, I bet you a steak dinner at the finest steak house in the world that you won’t be able to stay retired for more than three years.”

    I’ll take this bet :) The finest steak house in the world is probably our own kitchen, so it won’t even cost you that much. I’ll check back in when I hit the 3 year mark in October :)

    I too enjoy learning, and have done a lot of it in the past 2+ years. I’m currently taking 3 hours of Mandarin classes a day.

    But tying income to it adds performance and time frame commitments that I’m not interested in. I even turned down a scholarship because it came with grade requirements. I could have had my tuition paid, but would have had to do all of my homework. That’s not going to happen

    It’s great pursuing travel, hobbies, learning, etc… in a way disconnected from time and $. I don’t see myself ever having a job again

      1. I’m studying Chinese at the Mandarin Training Center for NTNU

        The city of Taipei and the school itself give several scholarship each semester to existing students, and they seem to have more money than students some semesters

        The scholarship is roughly $300/month, which covers the cost of tuition. The requirement to continue receiving payment is grades must average above 85% or so and attendance must be near perfect.

        There are also options to apply from outside Taiwan, but I haven’t looked into those options

          1. I would say in Taiwan they teach fan ti zi. I spent sometime both in Beijing and Taipei learning Mandarin. When I took classes at NTNU, I think it was 1.5 – 2 hours daily. I thought to make my day more productive, I took additional classes near NTNU. There are quite a few Mandarin Training centers nearby. Or you can do language exchange with the students there. They teach you Mandarin and you teach them English.
            While when I was at Beijing, 1 session = 4 hours and they use jian ti zi.
            If you really want to brush-up your Mandarin skill, maybe you can watch Chinese drama online (streaming), they have the subtitle and it helps me to catch-up new vocabulary or just to refresh the character…I do that, but it is addicting :-)

            1. Yeah, it is fan ti zi / Traditional characters / 繁體字

              Of course Taiwan is probably the only country left using traditional, but I’ve heard it is easier to learn traditional and then go simplified than the other way around

              I’m in the intensive classes, 3 hours a day every weekday. 1 quarter/3 months we do about 150 hours of class

  17. Retired 2 yrs ago at 46. Happiest day off my life, leaving a corporate job that I despised, despite the exceptional pay. My response to why retirement wouldn’t stick would always root back to not really really really having saved enough. You can try a a bunch of ways to convince your conscious self you have enough, but if you’re unconscious mind doesn’t buy it, you’ll never find peace. This is the only reason to go back to activities that make money, period.

    1. “You can try a a bunch of ways to convince your conscious self you have enough, but if you’re unconscious mind doesn’t buy it, you’ll never find peace. This is the only reason to go back to activities that make money, period.” – very accurate statement..

      I totally agree. I am planning to quit in 2 weeks. I feel that there is enough to survive and enjoy. At the same time mind is still not accepting it and it constantly needs reinforcement. It seems like one has to retrain their brain for this change. Money attachment is crazy..I need to tell myself that more money I will make, i will not be able to spend it…Fear takes over all the time!!.

  18. Being able to “retire” just gives people the time and freedom to figure out how they really want to live their lives. Nobody has to spend it on a couch watching tv. I’d love to be in that position now. Kuddos to those who are.

  19. Investingfortime

    Well written! Lately I’ve given quite a bit of thought to what I think I’d do once I’d be able to retire if I felt like it. I’ve come to the conclusion that I would not completely stop working. Instead I would like to try being an entrepreneur because that would give me the most freedom regarding how many hours and when I would work. Also it would provide me with some cash flow along with my passive income.

    I’ve had a ‘real’ job for about a year and a half and have managed to negotiate to only work 30 hours a week. So I’ve made a conscious decision to work a shorter week even at the beginning of my career even though it means less money. It has worked really well for me and I think it’s a logical move to enjoy your free time also in the beginning of your career especially if you never plan to fully retire. This way I get to reap some of the rewards of partial freedom already now! I hope I can maintain the shorter hours and at some point start scaling back even from the 30 hours a week.

    1. Very interesting that you have decided to take up kinda the opposite approach that I had, which was to work my ass off for 70+ hours a week for around a decade in order to break free.

      Your approach is just as good if you can work the 30 hour work week and spend the other time being free. The French and Greek are very happy with a 35 hour work week and retirement pensions for life starting in their early 50s, so why not!

  20. People who can successfully pull off early retirement are very goal oriented and driven in the first place. That doesn’t go away once you hit the numbers and are financially independent. You are still you. I retired early intending day one to retire often. I knew after some time off I would want to still be open to pursue opportunities. Retirement should be the absence of needing to work not just the absence of working. I think your article is right-on and whether early retirees take on a new career working for someone else or start their own thing they have earned that freedom of choices through their financial independence. My drivers are more about learning new things and some of the social aspects. The money earned is just added to my net-worth. Although some of the factors to return to work you detailed don’t fall into my mindset, everyone will have their own drivers. Early retirees have earned that freedom. Some traditionalist will call working in retirement a retirement failure but they are wrong. Just ask me.

    1. I like that tagline, “retire early and often.” Something to think about. Maybe after 5-10 years in the tech/internet startup land, I will retire and move on. Who knows.

  21. After 20 years as an investment banker I retired at the age of 48. That was nearly 11 years ago and I have not regretted a day. I Loved being a banker but have discovered I love (and am quite good at) doing nothing. For 20 years I pretended I was a banker, but at heart I was and still am a surfer. A serious battle with cancer at 44 allowed me to refocus my attention back to my family and the ocean. I appreciate that I am very fortunate to be in a position to have this life style and encourage anyone who can to at least make the effort. We all have friends who wished they had more time only to discover that time is the one thing we have so precious little of. Thanks for your article.

  22. Although the population of early retirees is small, I guess there are as many opinions as the number of retirees. Everyone is different, but financial independence provides choices which is the only basic thread. Some will start businesses, others volunteer, form foundations or do absolutely nothing (minority). some will return to work or even find a new career (teacher). When you get to the top of the pyramid, you find things that help you self actualize. The best part of independence is doing the things you want to do vs. what you have to do. You start to look at information differently because you now have the time and resources to do something about it. Aside from teaching, I still have a great deal of joy looking after my investments although it does not take much time. I still want an active retirement where I can find stimulation to keep me actively engaged. I know choices is an overused word, but an important one.

  23. I’ve always thought that I’d want to have something to work on when I ‘retire’, albeit it would be on my own terms, own hours and level of commitment – and would no doubt vary over time.

    This is why I haven’t felt the need to reach a portfolio based on the 3% or 4% rule – I don’t intend to work solely to build a portfolio I can live off forever, all I need is a little more financial flexibility, then I’ll start making some bigger changes in my life.

      1. I’ve set myself a stock portfolio target of $1 million, but if anything I might end up revising that down if I just get sick of the work I’m doing, and want to make a change in career without worrying about the money, or perhaps just cut down my hours.

        I had set myself the goal of just increasing my income, and perhaps taking on a new job that pays more (and no doubt even longer hours than I already do), but I’ve always worried about the stability of this when it comes to my own well being, especially after what you said about the depressing feeling of having to work solely for the money. Perhaps a better option is to just focus on finding better work from day one…

  24. I think the key to staying retired will be making sure you have enough activities and structure to keep you interested. For example, I would like to continue my current board positions for not-for-profit community organisations, help my wife make her business more efficient/productive, and, if we can manage it, go and live in Germany to learn the language properly. I could work in a finance job that is way below my current level just for the exposure that it would provide.

    I think if you don’t have enough interests outside work then the allure of earning another year of income at a good salary will stop you from retiring or drag you back into employmeet.

    The only other thing that could keep you retired could be hating your old industry with a passion, which doesn’t seem to be that uncommon on many PF blogs. Of course, you could just get a role in a different industry… maybe blogging or in Silicon Valley!

  25. I think this article is right on! Now that we’re in a more comfortable financial position, my husband wants to take a year or two off from working. So, he’s going to go for it, but I see him finding another job or starting a business within 4 or 5 months, tops. He’s an engineer and loves his field too much!

    1. Ooooooh, how fun! Good luck! What will you do when he retires? Take a break too? Or do you have lots of flex?

      When both spouses can have the flexibility that’s when the real fun begins!

  26. We didn’t retire as early as you, I was 41 and my husband was 46 — but we are military retirees that have had NO problem staying retired . . .

    We both thought (and kept being told by friends/colleagues) that we would HAVE to start second careers.

    Call us boring, but we both value time over money. It has made us (we think!) better parents, better offspring, more healthy/fit and happier than pursuing second careers.

    1. Justin Williams

      Agreed. Add a toddler to the mix and the thought of having spare time vanishes rather quickly. Spending time with kids is magical and goes so fast. Maybe I’ll work again someday on my terms.

  27. Love your insight and personal experience on this topic. For me I think I’d never fully “retire.” I have a lot of projects in mind that I’d love to do once I achieve early retirement. Besides with a son and possibly more kid(s) to come, I’m sure I’ll be busy at home with early retirement. :)

  28. I can see why the goal-oriented, high-achieving people who tend to achieve early retirement wouldn’t be able to stay retired! Instead of FIRE we are thinking about it as financial flexibility, or having freedom to choose how to spend time, whether at work, play, contracting, or volunteering.

  29. The Alchemist

    One helluva quality problem ya got there, Sam. :)

    You write, “One of the …worst feelings is the depressing feeling of having to work for money, not out of love for what you are doing.”

    Yep. Unfortunately, I fear this is the reality for 90% of humanity. It takes tremendous courage to buck convention and just “do what you love”. Because 9 times out of 10, that won’t pay the bills. Most people have to buckle the hell down and work their asses off (as you already have done) to reach sufficient financial independence to be able to do something they love rather than something that will make bank.

    Many have noted here that “retirement” really is just the opportunity to finally pursue some constructive endeavor that calls to their heart. Boy, does that sound wonderful! I envy every one of you in that position. For myself, I’ll be keeping my head down and working toward my own eventual financial emancipation. Still seems depressingly far off, but I’ll keep plugging away….

    1. If you are interested in a career in copy writing, you can really pursue it. But you’ve got to hustle and start at crap pay for a couple years!

      We all got to reset in a new endeavor. Our years of savings to provide the buffer is what will help push us through.

  30. I felt the same way when I was working from home. The problem is there aren’t a lot of like minded people to hang out with because they’re off working a job.

    Sounds to me like you need a kid or two, that will definitely satiate all of what ails you :)

  31. I don’t agree with this one – You desire order and direction. I love not having a boss. I can do whatever I want, whenever I want. I really don’t think I can go back to working for someone else unless it’s a good friend who let me do whatever I want.

    I don’t think anyone can stay fully retire early. It’s too boring if you don’t have goals. Being a stay at home dad is taking a lot of time, but it will get easier. I’ll probably work a bit more (for myself) when the kid goes off to school.

    I bet I can stay part time self employed for at least 10 years. :)

  32. Our goal is financial independence, not necessarily early retirement. I don’t know if I could ever see myself completely not working, as I like a good challenge.

  33. I couldn’t agree more, Sam. Even the thought of taking a break from everything for a few months makes me feel restless. I also agree with you on the financial industry. My first job was in financial planning and insurance, and it was INSANE.

  34. Even if I retired at a more “traditional” age of say, 65, I envision it as more of being financially independent and having options than an idea of lazy days just golfing and sleeping in. I’ve always imagined my “retirement” as a time of my life where I get to explore other things without having to worry about providing a means of support for myself or my family. Best news is I get to begin trial runs on lots of interests prior to retirement and while still earning as the kids graduate college and move on. From my perspective it’s more about going back to a lifestyle pre kids, both in terms of cash flow and time available and focus on what I want to do. I don’t have to worry anymore about driving them to an afterschool activity or ensuring they get from soccer practice to karate to a study group, etc. where as a parent you tend to decrease your social activities to pump up theirs. Sure, there is likely to be additional money and support spent and there could be boomerangs back to the house and new challenges. But heck, just not having to save for their college anymore will be a significant plus to cash flow in my case.

  35. I don’t think any of your points are…or need to be…mutually exclusive with retiring early.

    Perhaps you should retitle the headline in the first person. It feels like you are projecting you on everyone else.

    Does the steak dinner bet apply to folks who ER’d at 52?

    P.S. I love that your simple objective is to always be happy. That alone, as a purpose in life, as long as you don’t harm (and in fact strive to help) others physically or psychologically, is actually a noble purpose.

    1. 52? Nah. After 30 years of investing and saving after graduating college at 22, one should be able to amass a good enough amount, no?

      Steve, since u live close by, I’m hoping to collect on the steak dinner!

  36. Retiring early is great for those who want to die early. Significant studies reflect as much. I think the point is to retire and keep working on things you want to work on, not to play cards with the senior citizens and lounge.

    1. A study in Japan found that early retirement resulted in a longer life span. I’m imterested in reading the studies you’re referring to.

  37. I imagine that the problem is, at a minimum, a good one to have. I think the distinction must be made between work and productivity. Work has a well-deserved negative connotation–you’re working generally because you have to. There’s a negative reinforcement kind of pressure; you have to play the game. Productivity is something we all need in our lives–retired or not. It’s why most retirees I speak to (older retirees) place a big emphasis on “keepin’ busy.”

    We need to produce something–even if that something is just our own knowledge, or money, or whatever. However, distinguishing the unforced production of something is rewarding, it’s delivers happiness. These acts are at confluence of freedom, meaning, compensation, and enjoyment.

    1. The biggest thing I realized in 2014 is how TERRIBLE it feels to work for the desire for money, and how exciting and great it feels to work because of new learnings and experiences.

      I never really experienced this in finance b/c the work was almost always interesting, and when it wasn’t, the pay was always very high, so there was nothing really to complain about.

      So to turn things around, for those who hate their jobs and make let’s say $50,000 a year or less… it might be a much easier, and freer situation to leave, take some risks and do something you really love to do. Worst case is making $20,000 a year minimum wage. But if you make say $200,000 a year, the worst case is still similar at $20,000 minimum wage, but a drastic change in lifestyle must be made.

  38. Mick Jagger, 71.
    Steve Wynn, 72.
    Warren Buffett, 84.
    Rupert Murdoch, 83.
    Sumner Redstone, 91.

    All of them have cool jobs, and have held them for a long time. For most of the rest of us, we are/were cogs. Just slugging it out, trying to keep our health, dignity, and a small piece of our souls uncrushed. Like Cyclesafe noted, very little value is placed on one’s time by those who do not have to pay for it. Bottom line, if you have a cool job or a cool opportunity comes up, of course you won’t stay retired. But 93 million Americans are now out of the workforce, and I’m not sure the marketplace can absorb 93 million new blogs.:)

    1. Haha, my venue is blogging. But other people’s outlets can be singing at 70+.

      All them folks you mention are creatives or entrepreneurs. They can “choose” their destiny.

  39. As we have discussed before, to me the benefit of early retirement is that it gives you flexibility to do other things. I doubt many people actually retire early if retirement means doing nothing. Even for older people who retire at the “normal” age, many do not actually “retire.” They consult, volunteer, manage private investments, work seasonally, etc. But since they are “retired” they have the flexibility to travel, to do nothing, to go to school, to spend time with family, to do all those things that many of us would like to do right now.

    Striving to retire early is good in that it makes you strive to save early and often. If you strive to retire early by age 40, 45, 50 – whatever – and get to where you can. Whether you do or do not, you have probably set yourself up to be very financially successful.

    I can work in my professional field for a very long time, and probably earning a very good living. But I certainly do not want to feel forced to do so. I suppose at some point, I will want to try something completely different. But I need to have the financial security to do so.

  40. Retirement time must be managed time. Nothing new here.

    In 2000 I became one of the discouraged unemployed. Just filling my days, not to speak of finding fulfillment, was now a seemingly unsurmountable challenge. I had enjoyed playing golf, but at 45, I was too young to make this my life.

    I went to law school, passed the bar, and interned at a legal clinic for a short while, but I soon realized that no one valued my time spent under fluorescent bulbs doing legal research – even if I was doing it for free. So, in 2004 I changed my bar status to “inactive”.

    So for something completely different, I got into bicycling and physical fitness. I rode more than 10,000 miles per year and competed in numerous triathlons. I maintained my BMI at 21, straightened my teeth, and lasiked my eyes.

    I also resumed traveling about three months a year to the usual international places, actually living in Florence, Moscow, and Croatia. I trekked the Annapurna Circuit.

    My point is this. Retirement means that you have to provide your own structure for fulfillment. After being fired/laid off, I sought structure in another job and then in another career. But I only found myself when I eschewed the external and adopted the internal. I’ve fully accepted that it is my responsibility and mine alone to find fulfillment.

  41. Done by Forty

    Sheesh, way to throw water on my dreams!

    Just kidding: all your points are insightful, and I truly appreciate the view from someone who’s been to mecca and returned. I may not be able to stay retired, but early retirement at least gives me more options. I can return to work, and then leave just as easily. I can work jobs that I normally would not (if the compensation or benefits are crap, for example) if I find them otherwise fulfilling. The freedom of options provides immense value.

    But in a decade, maybe I’ll fly up to the Bay Area for that steak. :)

    1. Yeah, give up your goal now! Not worth it :)

      You might THINK u can just pick and choose and quit whenever you want. But your inner core and social customs will prevent U from going too out of the norm.

      It’ll be great for U to fly to SF to buy me a steak dinner. Cheers

  42. I don’t completely understand your claim. Are you saying that: even if you make enough money and quit your job at age 40, you will still find yourself doing useful things for 50 hours a week? When I think about “retirement”, I do not think of lying in bed watching Netflix all day. I imagine myself actively working towards learning new things, building skills, working on my hobbies etc. So your claim is true, but for a trivial reason.

    But perhaps your claim is that: even if you make enough money and quit your job at age 40, you will still want to devote 50 hours a week doing the thing *that has the highest ROI*. In that case, your claim is interesting and will make me seriously reconsider trying early retirement.

    1. Not sure where the 50 hours a week of work came from. Did I write that?

      If one manages to hit all the financial metrics to be a self sustainable early retiree (not living off the government or another person), then yes, I bet the person goes back to work in some capacity by the 3rd year.

  43. I always wondered this about those who retire early. I expect to be working at least well into my 50’s and sometimes I can’t even think of what I’d be doing at that point in life let alone at 40. My job is great and not too physically demanding so I hope to be working for a long time, but I do have some things in mind for when I finally get that free time. But with a full time job, blog, wife and kid, it’s hard to think about free time! Thanks for the great post.

  44. Happy Friday, Sam!

    You can tell by the opening that I’m still full-time employed. Your points are well-taken; much of this would have never occurred to me.

    I love what I do–but the hours are long, and pay only moderate, so your insights re: preparing for retirement and sound advice help a lot.

    I think I’d like to retire “early”, but for me, that might be 50 or 55 (as opposed to age 67 as the government directs). Hopefully still young and healthy enough to enjoy new challenges, but not so full of restless energy as to be bored.

    As always, really enjoy your site and thank you for the time you take to post.

  45. Hi Sam:

    Couldn’t agree more.

    I think there are a lot of people out there like myself who could make the numbers work for early retirement, but still find a lot of meaning in their jobs (along with the frustrations and all the rest.) The question is, how would you spend your day?

    Not everyone has the creative juice to maintain a money-making blog or the patience to manage a large portfolio of rental properties, for example. Until I find something more meaningful and challenging to do, ER is not in the cards.

    1. Ah, but how will you know you don’t have the creative juice until you try for a while?

      My biggest fear leaving corporate America was failure to create something on my own. But, I had to try!

  46. I had this problem in between careers. I had left from one career. Spent 6 months traveling europe, a year without a job, and I just could not fill up the day in a way that didn’t involve TV. Which I was trying to avoid. Who wants to lose their brain to the tubebox?

  47. John C @ Action Economics

    Although most of us (myself included!) plan and desire to retire, the concept of retirement is against mans’ nature. I think we are hardwired to be productive, especially while younger. Even during the periods of a few months when I am off work between projects I get bored as well. I have to find something, whether it is a project at home, helping out a friend with his business, or even working on my writing to keep my mind stimulated.

    1. Jay @ ThinkingWealthy

      Agreed. I felt funny not working over xmas break! I wanted work to do. I hated just laying around so when I had a 4 hour management call scheduled the day before Christmas Eve, I was actually excited! Perks of enjoying what you do, I suppose.


      1. Jay,

        I think this absolutely reflects the company situation you’re in. In a positive work environment, I just want to keep going. But I clearly remember, once, with one week remaining in my Christmas break, I was already dreading having to return to work.

        I’ve only realized recently just how awful my last company was, along with how great some of my earlier companies were.

        Glad you’re enjoying what you do. Relish this time!


  48. Personally, I never want to retire so to speak. One of the biggest joy of life is to learn something hard, and master it. I have so many ideas to try, I “just” need money for it.

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