It’s Impossible To Stay Retired Once You Retire Early

Once you retire, it's impossible to stay retiredIn the spring of 2012, I hung up my sword after working in finance since 1999. 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. 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 where law students and professors helped 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 regarding questions about divorce, employment, accidents, theft, trusts, and more.

My question to a professor and to a law student was simply, “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 that can be advantageously used against their old employer if they join a competitor. 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.

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, and accepted my e-mail apology for the mistake. Once 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.

When my contact from Personal Capital called in the fall of 2013, asking me whether 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 never really thought much about actually going back to work at the time, even part-time. I deliberated back and forth with loved ones until we finally 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 has passed, and I've learned a ton about the startup world, financial technology companies, and digital marketing. Two bucket list items of working at a startup and 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, you just 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, 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.

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.

Financial Samurai Passive Income Report 2018

Now that it's 2018 and we have a one year old toddler, 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!

Related Post: The Dark Side To Early Retirement

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Updated for 2018 and beyond.

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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. 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.

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  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?

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  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.

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