What Does Early Retirement Feel Like? The Positives And Negatives Of Not Working For A Living

Retirement Travel In SantoriniFinancial independence and retirement are used interchangeably, but there are some subtle differences. Financial independence is usually applicable to people across their entire lifespan. Those who cashed out $5 million dollars worth of Facebook stock at the age of 30 are financially independent just like those who saved $5 million in their retirement funds by the age of 65.

Retirement, on the other hand, is a term often used to describe someone in the last quarter of their lives e.g. ages 65 and up. This is why some folks get so hot and bothered if you aren’t in the upper ages but say you are retired. They don’t think you deserve retirement because you’re not old enough! If you don’t want unwanted attention as an early retiree, just say you are unemployed, on sabbatical, or an entrepreneur.

The reality is all of us would rather be financially independent earlier, so we have more time to enjoy our wealth. When the director of admissions at Berkeley asked why I was applying so early (25), I told her it was because I knew what I wanted to do and felt it best to leverage an MBA degree sooner, for a longer period of time. Little did I know I’d be done 10 years later.

The older we get the more we are willing to trade money for time since we have less of it. Given I’ve already described what financial independence feels like, I’d like to now describe what life is like once you no longer have to report for duty. I’ll be as candid as possible so you can get a realistic understanding.


* No longer have to wait for the damn bus. It’s funny that not riding the bus was the first positive that came to mind as opposed to workplace politics, stress, or more common answers. I used to leave the house around 7:20am every morning to catch the 7:23am bus around the corner. Despite my punctuality, the bus would either not arrive on time or be so full of people I’d have to walk another 5 blocks just to get on. Now when I see folks crammed in buses I can’t help but smile.

* Running errands is easy. I do all my errands around 10:45am or 2:30pm, because that is when most people are still at work. There’s no traffic or lines at the store during these hours and I’m much more efficient in getting things done. I continue to wonder why everybody wants to come to work at 8am and leave at 5pm. It took me 1.5 hours to drive 20 miles to pick up my parents at Oakland Airport due to traffic the other month. It only takes 35 minutes during off peak hours. Come into work earlier and leave a little earlier. Your stress level will go way down.

* Lots of free entertainment. There is an incredible amount of free entertainment during the week. Part of it is because organizations want to show their community support and free access on weekdays provides the lowest amount of damage to their bottom lines. For example, I visit at least two $15 cover museums a month for free. There are also free cooking classes by Williams Sonoma, free interior design parties by AirBnb, free rock climbing lessons by REI, and so on. I’ve subscribed to a site called sf.funcheap.com which highlights the various free concerts around the city. Big names such as Alanis, Ed Sheeran, and Matt Nathanson all came to the Golden Gate Park last year. Early bird specials for half off rocks as well!

* House is much cleaner. I’ve never had cleaners and now I know I never will. I enjoy spending 10 minutes a day, or 50 minutes once a week cleaning the kitchen, bathroom, and common areas of the house. There’s something soothing about this process that also feels very rewarding. If you have a working partner, s/he’ll love you for it too. Stay at home men of the world, unite!

* You learn to do things yourself. When I was busy working, I didn’t have time to figure out how to fix the leaky toilet. I would call the plumber and pay him $150-$250 at a time. Nowadays, I simply search on YouTube for a home maintenance tutorial and voila! Call me handyman Sam. If I can’t fix something I’ll chat up the local hardware store attendee and see if he can tell me what’s wrong. Having a smartphone to videotape the issues helps tremendously.

* Better nightlife. Because I used to start work by 7:30-7:45am every morning, I was tired by 10pm. I just wanted to stay in and watch some Tivo or a new DVD after work. Now I’m always down to go out for dinner or drinks with friends during the weekdays. I’ve attended multiple events that last until 11pm and am ecstatic to not have to go to work the next day.

* Better friendships. I spend more time cultivating my offline relationships now that I don’t work. Those thin relationships one has on Facebook become stronger as you actually send them personal messages to see what’s up and hang out. The more you go out, the more friends you’ll meet. This is especially helpful for single folks. Friendships are vital to my happiness and I’m sure to many of yours as well.

* Better family relationships. I spend much more time speaking to and visiting my family now that I have more time. Spending more time with family is probably the most rewarding part about retirement. The younger you are, the more you appreciate it because you likely have more family still around. It was so fun to go car window shopping with my dad when he came to visit over the winter holidays. I also enjoyed taking my parents for a nature walk along the San Francisco cliffs at Land’s End. It’s a blessing to be able to share some physical activities with them.

* More comprehensive posts. My post length average has doubled to roughly 1,500 words from 750 words when I was working. Longer is not necessarily better, but it is more thorough for those readers who come here via search engines such as Google and Bing. A lot of people want informational posts about the ideal mortgage amountnegotiating a severance package, investing in real estate, rebalancing portfolios, evaluating a financial adviser and so forth. Most of my traffic comes from Google, and Google loves meaty content so I oblige. This post is 3,457 words as a reference.

* More purpose in life. Most people I know don’t believe their purpose in life is whatever they do at their jobs. In fact, plenty of folks start getting depressed when they talk about spending all their time at a job that doesn’t really make a positive impact. They see a job as a stepping stone for something greater and can’t wait to get out. Once you no longer have to work for a living, you sidestep such a means and get to go directly to the source. I’d like to think my purpose in life is to be a good son and leave some nuggets of financial wisdom to others that will last long after I’m gone. I’m looking at new avenues in public service such as working in the foreign service to continue my family heritage of serving our country.

* In better shape. Without having to sit in a chair for hours at a time, I’m burning more calories now. I used to struggle maintaining a weight of between 162-165, now it requires less effort. My static work weight was 167-170, which is a noticeable difference for someone with my frame. I now play tennis, bike, walk, or hike at least four times a week compared to just once or twice a week while working. Being in better shape is a great feeling. It might even extend my life, who knows! It mostly depends on genetics.

* You can always be busy. One of the biggest fears working people have before retirement is figuring out what they are going to do with all their free time. I worried how I was going to go from working 70 hours a week to just “working” 20 hours a week and playing sports in the afternoon. I put working in parentheses because I don’t consider writing online and interacting with folks over e-mail and social media work at all. After almost a year of not having to work, I can certainly say that I’ve had no problems staying busy. In fact, it’s hard for me to only restrict myself to around 4 hours of work a day because I’m so used to working 3X more! My mind is always racing to write a new article or try something new. If you have a hobby you are passionate about, you don’t have to worry about not being able to fill the void in retirement.

* No fear of getting fired. Nobody is safe in this economy. You could be a star performer but if your bosses hates you for whatever reason, you’re done. The internet and social media has also elevated your risk of getting fired because nothing you Tweet or write is ever fully private. There’s a recent case where two developers joked about dongles, forking, and repos (real tech terms) and a woman sitting near them overheard, got offended, posted their pictures, tweeted it to her 10,000 followers and one of the guys got fired! The woman who tweeted the picture also got fired so that equals a lose-lose situation. It is a wonderful feeling not having to always watch what you say or do in this free country. If you depend on your job to survive, do not mess around with social media. You will get forked.

* Always smiling. Every time I walk down the sidewalk, guys and girls are constantly smiling back at me. It was strange to have random folks constantly smile at me until I looked at my reflection in a store window and saw my own big stupid grin smiling back at me! I had no idea I was smiling at every stranger I walked by. I’ve got a big teethy smile that I guess makes people want to smile back. Maybe smiling when you don’t even know it is the true meaning of happiness?


* Become more impatient with waste. Traffic and long lunch lines used to annoy me, but now they really annoy me because I hardly ever experience them anymore. I get annoyed with myself for going anywhere during peak rush hour. In fact, I really try not to meet anybody if I have to commute during the hours of 7am-10am and 4pm-7pm. I have to remind myself when it’s bumper to bumper thank goodness I no longer have to deal with such jams on a regular basis. 

* Gets lonely sometimes. While your friends and acquaintances are busy working, you’re sometimes busy doing nothing. If you don’t have a partner or family, then you might end up having breakfast, lunch, and dinner alone. I really enjoy meeting people once a day. As a result, I’ve built a small network of work-from-home, unemployed, and early retiree types to spend time with throughout the day. I also try and play tennis or go for a bike ride after an early afternoon nap. It’s easy to feel disconnected if you’re always working from home.

* Easy to get lazy. I can’t remember feeling lazy since college. I knew I had a window of opportunity to make the most of my career and my finances so I did everything possible to achieve financial freedom. The work hours were extra long, and things got brutal when I spent 3 years getting my MBA part-time. But now I’ve got so much time that sometimes I’ll just take a nice hour nap in the middle of the day when nobody is watching. Sometimes I end up spending two hours in the hot tub without evening realizing the time. As a result of wandering time, I’ve adhered to a morning productivity schedule of writing from at least 7:30am to 11am. Once I’ve put in my 3-3.5 hours, I’m free to do whatever I want.

* Less money. This one is obvious, but maybe not. You only voluntarily retire and stay retired if you have enough money to support your desired lifestyle. It’s a different situation if you are forced into retirement. But, even those who are forced into retirement are enjoying life more. It does sting a little bit to no longer have a healthy W2 income. However, just like how we adapt quickly to a nice bonus or raise, we also adapt quickly to a loss of income. Adaption is one of our greatest attributes. I’ve discovered that we overestimate how much money we need to be happy.

* Vacations aren’t as exciting anymore. I used to love taking five to six weeks of vacation every year. If my old job could grant 10 weeks of vacation a year, I would have stayed on for at least another five years. Now that I’m literally on vacation everyday, planning a vacation sometimes feels like a chore. I went to Hawaii three times in 2012 along with a two week trip to various parts of Europe and Russia. I had a great time, but I’m also beginning to lose my enthusiasm for travel. Spending lots of money to go on vacation also doesn’t feel as rewarding. Pain makes pleasure more pleasurable. When you’ve got all you can eat oysters on the half shell, sometimes you just want a glass of champagne with ice cream instead.


* Spend less time on social media. For some reason, I spend probably 50% less time on Twitter than when I was working. Perhaps it’s because Twitter was a great way to pass the time during commutes. I also continue to spend very little time on Facebook except for my tennis team group page. It’s good to check in once a week to see what’s going on, but that’s about it. The automatic notifications for all my social media apps have been turned off so I can check when convenient not when pushed. I spend more time with offline friends at sporting events, dinners, or parties now.

* Know a lot of unemployed people. No matter what time during the day I go out between Monday and Friday, there are tons of people out on the street or hanging out at the tennis courts. When you’re working, you think everybody is holed up in an office building and only comes out during lunch or when the clock strikes 5pm. In reality, plenty of people are unemployed, but at least they look happy. These are the people the media talks about when they refer to the “real unemployment rate,” or the underemployed. If you can’t find full-time work, then you might as well enjoy the time off to relax in a park or sip coffee outside a cafe on a warm, sunny day.

* Discover so many different ways to live. When I was working I just figured most people live their lives the same way. Of course as I started to grow this blog, I realized many people also earn viable online incomes. Now that I’m meeting people during the middle of the day I realize there is a plethora of ways to make money and live a good life! I’ve met dog walkers, nannies, professional athletes, teachers during their summer vacations, government works with great pensions, bartenders, strippers, bouncers, tennis teachers, coffee shop owners, and a host of small business owners who enjoy a lot of freedom during the day.

* No desire to play golf. I used to love golf but at $58 and five hours a round, I’ve kind of lost interest. If I had a close golfing buddy who could play from 11am to 4pm on the weekdays, I’d probably enjoy it more. The other thing is that I’m no longer rapidly improving given I’ve got a 9.8 handicap. In order for me to regularly break 80, I’ve got to spend massive more time practicing with not much incremental progress. I’d rather play tennis or write instead. For those of you who are golfing fanatics, the handicap sweet spot is 15. Don’t try and get better!

* Feel inspired by older workers. Every time I go grocery shopping, I bump into cashiers and baggers who are over 60 years old. They probably only make around $10 an hour. Their hard work inspires me to not take things for granted and work harder. Everybody starts off with different opportunities in life. We’ve got to make the most of what we’ve got.

* Just want to feel useful. When you don’t work, you may feel you have too much time on your hands somedays. I’m often done with all online related activity by 9am given I wake up at 6am. Running errands or fixing things in the house makes me feel good because it makes me feel useful. If I don’t feel useful, then I feel listless. I can see how feeling useless can lead to depression. Hence, I try and stay busy after writing online by doing more household chores and volunteering. There will be times where I’ll think, Is this it?

* Constantly wonder what else is there in life. When I was busy working, I didn’t have much time left to think about philosophy. Now I’m constantly wondering what else can provide more meaning to life. I feel a little bit like Neo in The Matrix who discovers the world is a meaningless reality made up of billions of entities doing what they are told and not what they want. Then I think how it’s a good thing they don’t know what freedom is like, otherwise there would be a worldwide revolt. We need people to work for as long as possible to pay taxes and support society. I’ve begun reading passages from the I-Ching, The Dhamapada, The Bible, The Koran and other religious works for inspiration.

* It gets harder to stay retired over time. The first six months of retirement were full of excitement, fear, and joy. As time went on, I adapted to my newfound freedom by creating a routine that best suited my desires. Once I mastered my routine life got incredibly easy. When life gets easy, life also starts getting a little boring. I hunger for challenges to keep me motivated. Now that the bull market has returned I’m finding it increasingly difficult to sit on the sidelines as old colleagues maximize their incomes. A growing part of me wants to get back to work so I can leverage the upswing for the next several years.


There are studies that show death comes quicker after retirement due to a lack of purpose. With the internet and so much good we can do once we have our free time back, I can’t see how anybody would ever feel permanently lost in retirement. Try volunteering at a charity or mentoring a child if you start feeling aimless. Everybody could use a helping hand. The way I like to contribute is through this site.

Retiring early is a blessing because our bodies still allow us to climb the steepest Mayan steps and start the most daunting businesses when we are younger. Hopefully this post gives you some inspiration to get up a little earlier, save more after-tax income, and take calculated risks to retire early as well. The feeling of being able to do whatever you want is priceless. Just know that once you’re retired you may very well want to go back to work!

Recommendation To Build Wealth

As an early retiree, I stay on top of my finances with Personal Capital. They are a free online wealth management tool that keeps me within budget, tracks my net worth, and allows me to manage my risk by providing an easy way to visualize my asset allocation. I also run my 401k and investment portfolios through Personal Capital’s 401k Fee Analyzer every time I make a major rebalance to make sure I’m not paying unnecessary expenses. I saved over $1,700 a year in portfolio fees I had no idea I was paying. When you no longer have W2 income rolling in, it’s more important than ever to know where your money is going. The most important person you can trust to do what’s best for your money is you.

They’ve also come out with their incredible Retirement Planning Calculator that uses your linked accounts to run a Monte Carlo simulation to figure out your financial future. You can input various income and expense variables to see the outcomes. Definitely check to see how your finances are shaping up as it’s free.

Retirement Planning Calculator

Retirement Update In 2015

It’s been three years since I retired from Corporate America to focus my time traveling, spending time with family, and working on Financial Samurai. Financial Samurai is actually earning a good passive and active income stream online now. If you enjoy writing, creating, connecting with people online, and enjoying more freedom, see how you can set up a WordPress blog in 15 minutes with BluehostYou never know where the journey will take you.

It’s fun to keep active in retirement. I’m consulting with a couple financial tech companies in the San Francisco Bay Area part-time as well.

Photo: It was 77 degrees in Santorini when I visited in October, 2011. After spending three hours exploring every little church and side street, I stopped at a bar to enjoy a Mythos beer. The bar had wi-fi and in streamed my e-mails regarding various opportunities. That’s when I realized maybe, just maybe it was finally time to make a move



Sam started Financial Samurai in 2009 during the depths of the financial crisis as a way to make sense of chaos. After 13 years working on Wall Street, Sam decided to retire in 2012 to utilize everything he learned in business school to focus on online entrepreneurship. Sam focuses on helping readers build more income in real estate, investing, entrepreneurship, and alternative investments in order to achieve financial independence sooner, rather than later.

You can sign up to receive his articles via email or by RSS. Sam also sends out a private quarterly newsletter with information on where he's investing his money and more sensitive information.

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  1. says

    I like working…for now. I just want to become financially independent so that I can have more choices. I don’t necessarily want to quit working completely. There are things that I like doing that happen to make money as well. I really just want to quit my 9-5 job sooner rather than later =)

  2. says

    I love your positives and negatives of early retirement. You make some really good points, and I don’t think many people think about the negatives.

    Like Holly, I like working as well, but on my own terms. Thankfully I don’t have a 9-5 I want to escape from.

    • says

      I really tried hard to think about more negatives, but this is all I could come up with. It does stink that the excitement of going somewhere new has waned. However, that may be a natural evolutionary mechanism to help keep folks grounded to raise a family perhaps?

      Everything is relative when it comes to negatives.

  3. says

    Thanks for sharing all of these insights. I can imagine how the first six months were a lot more emotional because it was such a big change. Now you are finding new ways to adapt further and make your retirement more rewarding in new ways. I imagine mixing up your routine must help so every day feels different. That’s what makes some of my work weeks better than others- when I’m working on a new project or doing things on a different schedule or in a new way.

    I think I’d volunteer at the zoo, the food bank, or a local school a few days a week if I retired to get myself out of the house and give back in ways that I can’t do now. I hope you enjoy your retirement for many years to come. It must be nice not to be on the bus each day! ;) Im commuting as I write this.

    • says

      That’s quite a long comment to type while commuting! Thanks for sharing. It’s interesting how I’ve discovered it takes effort to make retirement more fulfilling. Reward doesn’t just keep coming because we all adapt to what we’ve got, good or bad. So in that sense, it’s great to go through the bad b/c we really won’t find the bad so miserable. Sacrifice now and reap the rewards for years to come.

  4. Darwin's Money says

    Sam, curious, with how things have worked out thus far, if you had to guess – would you EVER be back in a traditional W-2 income type job for the rest of your life? Or do you think you’ll never go back? There’s financial, social, professional considerations involved; I’m just curious what odds you’d put on ever going back to the grind.

    • says

      It’s a good question that I’m thinking about more and more b/c I still have so much energy and time on my hands. For example, it’s 4:48am right now and I know I’ll be done with everything online by 7am and it’s going to rain all day today, so tennis or any outdoor activity is out.

      If I were a betting man, which I am, I’d say the chance is 65%. “Ever” is a long time.

  5. says

    I think a MASSIVE positive and negative for me would be the ability to see my child all day, everyday. Positive because he is awesome but negative I would never get any work done lol.
    The wife works from home and she has expressed those exact same pros and cons, for her the real tough one is the loneliness she finds when everyone she knows is working.

  6. Glenn Millar says

    Great article Sam. Although that golf thing has me puzzled. Of course, I don’t have a single digit handicap. Let’s hit the tennis court sometime though. I’m playing a couple of times a week now.

    • says

      You should join a USTA league Glenn. It’s a lot of fun! Season starts in April.

      There’s nothing better than hitting that perfect approach shot in golf that lands right where you want it to on the green. The problem once you get to a 10 handicap or below is that those shots are EXPECTED. So when you don’t hit them, which is frequently the case for someone who doesn’t shoot in the 70s, then it gets frustrating. It’s all an expectations game! 15 handi is the sweet spot of golfing fun.

  7. says

    Sounds like you are enjoying it for the most part! I know if I were to retire from a traditional job at this moment I would spend time building a business anyway. Also my commute is only 3 minutes so I’m just working on building my career experience right now, and working the business on the side. Maybe in 10 years I will consider early retirement!

    • says

      A 3 minute commute rocks! I cannot imagine having to spend much more than 30 minutes one way, five days a week going to work.

      It’s exciting to be on the rise in one’s career. Enjoy every moment of it!

  8. Mike says

    I found it’s fairly easy to fall into ruts if you are self-employed. And it might be fairly easily to stay there if you are not motivated at all to make changes. But overall it is more enjoyable I found than working for someone else. It is infinitely easier to be able to live life on my own terms than someone else’s.

  9. Jeff Kosola says

    Congrats on one year Sam. I haven’t paid a visit here in a long time but I just wrote down a wonderful quote from the post. “Adaption is one of our greatest attributes”. I couldn’t agree more. Take care and don’t forget to drink your Ensure every morning.
    Your old pizza delivery buddy – deliverawaydebt

  10. says

    Having been employed, underemployed, and unemployed, each for long periods of time, I can say, without a doubt, that I’d rather been employed and have no interest in retirement. I feel more purpose in my life working a boring job for somebody else than I do having my days free to do as I please. Maybe I’m lazy, but I prefer to be busy and prefer somebody else come up with stuff to keep me busy.
    I’ve probably said this a hundred times in comments to posts about retirement, but my grandfather was my hero when it came to work. He “retired” 5 times over 15 years. Others would convince him that it was time to slow down and enjoy life, but he would find that he just couldn’t bear not having something to do and would find a new job. When his doctor told him he just wasn’t healthy enough to work anymore, he finally retired, and passed on 11 months later.

  11. says

    My biggest hurdle to overcome if I retired early would be getting lazy and wasting my days. I was extremely good at it in college & can still waste a weekend or vacation day doing absolutely nothing. It would be imperative for me to find a lot of things to occupy my time with each day.

    I’ve seen you mention going back to work a few times now. What would it take for you to do so? Would it be a certain salary, or just a challenge that you found really exciting?

    • says

      I don’t know why, but I have a hard time doing nothing. The sweet spot is when I can do two things at one e.g. go hiking and get exercise while spending some QT with my parents.

      There would have to be a great cultural fit, a minimum salary, and a product or movement I really care about in order to go back. Step one is probably having someone reach out to me and pitch me why I need to join, instead of me pitching them why they need to hire me. I sometimes cringe thinking about getting back on the bus again, but work can be a lot of fun with the right product and people.

  12. says

    Wow, has it been a year already? Time flies when you’re retired. :) I should write a post like this too when my year is up. The biggest positive is that I spend a lot less time on the computer. Sitting in front of the computer all day and night is incredibly bad for you. I don’t really have many negatives, I’ll have to think about it more.

  13. says

    Great post Sam! I can relate to many of these things since we run our own business. I love being able to go run errands in the middle of the day and not have lines to deal with. The easy to get lazy point is so true! Without a set structure it can be incredibly easy to find yourself just not being productive. Thankfully my wife and I are pretty driven, otherwise we’d not be able to put food on the table.

  14. Chris says

    These are my favorite kinds of articles by PB’ers. I always enjoy a glimpse of life “out of the Matrix.” Good for you Sam, what a cool perspective this experience must have given you, regardless of if/when you go back to work. The coolest thing is-it’s on your terms now. I find the closer I get to FI, the more free I feel at work, the less stress I feel and the more enjoyment I feel. Go Bold and do the Foreign Service gig! I’ve been thinking lately that when I become FI, my real purpose in life will begin.

    “I’ve discovered that we overestimate how much money we need to be happy.” Live simple and be fulfilled!

    • says

      Thanks Chris. It really is about going out and getting back in on your own terms. It felt amazing to initiate and then negotiate an exit, especially since I was thinking about it for at least a year and a half.

      I also have to imagine it to be great to work without needing to work. I really want to experience that at some point if only to be able to write a post about it.

  15. says

    You’ve retired from your corporate job, but you’re still a part time online entrepreneur. When I think about retirement, I consider it strictly living off my investments – no outside employment, blogging, corporate or otherwise.

    Given that I’m on track to be able to retire in 10 years or so, I’d have to say that I don’t really know what I would do in retirement. I think it might get boring. Of course, my bar for retirement is simply having enough investment income to meet my expenses. I think I’d need 50-100% more passive income in order to have a more exciting and fulfilling retirement.

    Early retirement for me would mean a lot of changes. While I like my job, I don’t care at all for the area I live in. It’s too expensive for too little. I’d either have to move to a much more expensive area like NYC or a much cheaper area, like a college town in the South. Either way, my expenses would be much more in line with the perks of the location.

    After relocation, then the hard part kicks in. Trying to fill all that available time. I would really love to take art and music lessons. I feel like I missed out on these as a kid. But they cost a bunch, so I’d have to have the income to cover it.

    If I didn’t have pets, I would try to find someway to do a slow, meandering, world tour of traveling.

  16. says

    Wow, so many great lines in here, I don’t know where to start:

    “This is why some folks get so hot and bothered if you aren’t in the upper ages but say you are retired.”

    I’m not even retired yet, but people give me tons of crap when tell them my plans to retire early. Some even get angry. Similar to what you mentioned, one person told me I’d die early because I won’t have a purpose in life. Another accused me of being engaged in illegal activity because ‘you have to work until you’re at least 60 to be able to retire.’

    “The older we get the more we are willing to trade money for time since we have less of it.”
    YES, most of us don’t realize that until its too late.

    “Early retirement is a wonderland”
    Now that just makes me smile.

    • JayCeezy says

      “I’m not even retired yet, but people give me tons of crap when tell them my plans to retire early. Some even get angry.”

      These words, and FS’s *hot and bothered* description, really hit home. I no longer discuss it with anyone other than a very few people who share my goals or are at least supportive of mine as I am of theirs. My thought on this phenomenon of ‘anger’ towards the plans/goals of early retirement, is that they feel competitive and see themselves as “losing”. Too bad, they have made other choices and probably enjoy a fully-realized cashflow (or even greater than 100%!:-)), lots of “career” based decisions and hopefully results, etc. Their goals are just different.

      I guess everyone wants validation for their choices. Anyway, one of the reasons I enjoy the Yakezie network is that there are like-minded bloggers and posters who share my goals and aspirations, so it is OK to discuss it with people who won’t get ‘angry’. Continued success to you, Mr. 1500!

      • says

        Spending lots of one’s paycheck every month is fine so long as they love to work for a very long time. It’s when one spends all the paycheck and then complains about their own retirement situation which makes thins a little perplexing!

    • says

      Good to hear from you mate. If you don’t want the hate, best to not mention it too much or at all in real life. When you get there, saying “unemployed,” “on sabbatical,” or “entrepreneur” is a great way to deflect!

  17. nbsdmp says

    Being able to comfortably retire at 42 yet choosing to work since I still love it, I bet I find myself lusting after those things that are your positives about as much as you spend thinking about your negatives. Instead of the traditional “retirement”, I kind of have a hybrid situation where I’ve hired more staff to take the workload off…I have enough money that I’m never going to allow some rude/idiotic customer to ruin my day or weekend. I love the thrill of closing the big deal, but still being able to skip out at 1:30 to go boating on a beautiful tuesday afternoon. It’s all about moderation…sometimes I wonder what the world would be like if everybody who could have retired early would have, everything would look a lot different. Steve Jobs would not have created the iPad, JP Morgan wouldn’t have founded General Electric, Jordan wouldn’t have won 6 rings, Tiger wouldn’t have broken Jack’s record for Majors…oops on that last one, but you get the point…some people path is to keep doing what they are great at and continue with their passion in life.

  18. says

    The biggest positive is you get to look ahead because you are not tied up with the day to day struggle of earning money. The biggest negative is it is all up to you what you do with your time. Another positive yo have the time to explore anything and everything because you have the most precious of things, time!

  19. says

    Awesome post Sam. Thanks for the insights, can’t believe it’s been a year!

    For me, financial independence is something I will strive for. Retirement doesn’t mean I’m going to quit working, just means I am no longer *required* to work. heck, I feel like I’l live MUCH longer if I keep working in somehting that I believe in.

    I’ll have to say that I don’t resemble anything you’ve described above, as my net worth is nothing, and I have a lot of working years ahead of me, unless something miraculous happens. That being said, I’m trying to make my own luck, so we’ll see :)

    Thanks for the inspiration.

    • says

      No problem Jacob. Your greatest attribute is time and enthusiasm. As soon as you start feeling “the fade,” do everything possible to plan for something else. My fade happened after around 10 consecutive years of work and going to school. I could have done 8 more years, but instead I figure out a way three years later. It came quicker than I thought… but everything does the older you get. Good luck!

  20. says

    I remember when I started my site and was publishing guest posts to get noticed. You asked me in the comments how I could be “retired” and be interested in building a web based financial education business. Seeing your list of positives and negatives, it looks like you’ve answered the question for yourself. Congratulations on your independence. Now comes the fun of living up to the responsibility that comes with it.

    • says

      I forgot what I wrote Todd, but I don’t doubt it. I hope I can live up to the responsibility of having a good time. Curious to know if there is a retirement code of responsibility one has to live up to you can point me to? Thx!

  21. says

    Great list. One big pro for me is to be able to listen to my body. I don’t have to eat because it is time for a lunch break, but because I am hungry. I can have a sleepy morning during the week and be productive on weekends. Like you I have lost interest in being on holiday, I am happy at home. But did two 6 months trips in 2011 and 2012 so that was a lot.

    • says

      Good point on listening to your body! Drink when thirsty, eat when hungry, wake when energized. I think I do so anyway, but it’s a good reminder. Even while I was working, I haven’t had to set an alarm clock since I started FS in 2009 b/c I’m so excited to wake up everyday that my body ready to go at 6am. This morning, it was ready to go at 4:45am, but that’s b/c I passed out at 11pm last night :)

  22. says

    I retired at 52 about 8 months ago and would say your list is fairly accurate except “It gets harder to stay retired over time.”

    For me, it has gotten much easier to be retired. I really love being able to control my own time and I care less about making more money. Also, I’m really excited about the new blog I just started, taking classes, reading interesting books, etc.

    • says

      Just starting your blog and growing it is one of the greatest joys I’ve found. I’m excited for you! Hope you can overcome the hump and continue on.

      Retirement is getting harder for me b/c it is becoming so easy and routine. I’m always looking for a challenge, so a challenge is what I will find. I really don’t want to spend more than 4 hours online a day b/c even online stuff gets dull after a while. New post coming!

  23. First Gen American says

    I really loved this article. Although I am not retired I can definitely relate to that need to leave a mark on this world. I’ve recently realized how important that sense of community is in people’s lives. Being a catalyst to bring people together is in itself a gift you give others that is lasting and positive. People love being part of something bigger but they often don’t have the time or aptitude to be that change agent. I look forward to hearing more.

    • says

      Long time no hear! Great to hear from you. Community really is important. The quest is to find that right community given there aren’t many early retirees here in SF. Everybody is busy doing something. Takes effort to connect!

  24. says

    Sam, liked this one very much. Have to say that John has been working from home for the last 15 years and he agrees with most of the positives and all negatives; apart from the ‘ running errands’ one – he says that because it is easy I tend to dump it all on him :). How do you cope with the loneliness? Also I think I’ll find it hard without some structure to my life.

    • says

      I cope with loneliness through interaction on this site and through tennis. I’m part of a club and a tennis league that battles for 4 months a year. It’s a great time. Now I’ve got to fill out the other 6+ months of the year with other activity.

      My original structure was 7:30am-12noon. But I’ve found I’m often done with 90% of what I want to do online by 9am.

  25. says

    I am by no means retired or financially independent at this point, but just cutting back to 2-3 days per week in my main job has made a tremendous improvement in my overall attitude and ability to plan for the future. I think if I didn’t have to work at all, I could come up with all kinds of things to fill my time. Of course with a small child, lots of that time gets filled with their activities. Congrats on the one year mark. That’s very motivating.

    • says

      I think working 2-3 days a week would be wonderful! In fact, if I could find a job that could allow me to work 2-3 days a week and get 4-5 days of vacation every week, I’d probably work until I was 70! Congrats to you on finding such a sweetspot!

  26. says

    I’m convinced that having ten-twelve more hours a day because of no job would open up a massive amount of new opportunities for me. I still love what I’m doing, but I can’t wait to be the architect of my day everyday. Great post!

  27. says

    I think the greatest hurdle that most retirees would be faced up with is losing their sense of purpose, so it’s always good to see retirement in this kind of perspective weighing the good with the bad and seeing things the options still open to them.

    • says

      Well, I know a lot of folks who realize their work is not their purpose, so it might not be that bad. Perhaps it’s more finding new purpose which is more worrisome. What if nobody believes in them?

  28. says

    Great post – nicely sums up issues.

    I am looking forward to experiencing the positives later this year.

    The greatest fears I have about early retirement are the potential for boredom and a decline in mental and physical health. Keeping myself occupied in retirement could end up being a full time job.

  29. says

    Sam, I love that you post on this subject once every few months…don’t stop doing this! It is what drew me to your site in the first place, and it is what keeps me motivated as we all move on with life.

    “Retirement” to me means doing only what I want to do; and that for me is meaningful work that helps people. No dying early here! It’s pretty obvious that the positives outweigh the negatives, but I get bored easily, so that worries me a bit.

    Thanks for continuing to be a huge inspiration to me!

    • says

      Cool Tony. I agree with your meaningful work that helps people. The worst is working that doesn’t really help anybody!

      I find writing online to be helpful to those who want to improve their finances. It is VERY gratifying to help strangers who stumble upon this site and watch them succeed.

  30. says

    Fantastic post. The positives far outweigh the negatives! The negatives you wrote about are just minor inconveniences in reality. I think the biggest takeaway from this is time. Your time is the valuable thing on this earth and it’s a finite amount. A few years ago I wrote down what I wanted to do and quitting the rat race and was at the top of the list. Thank you for the inspiration.

    • says

      Thanks Kevin. You’re right. If boredom and loneliness are the biggest negatives then things really aren’t so bad.

      I look forward to reading your post when you’ve quit! But don’t quit, get laid.

  31. Jacob@CashCowCouple says

    We definitely want to exit the rat race. What will we do then? I’m not sure, but hopefully something that will benefit others.

    Thanks for the honest assessment. I don’t think many people would survive 50 years of “retirement.” But then again, I doubt they are the ones frequenting this blog.

    • says

      Figure out something you love to do on the side and try and do it for at least one hour a weekday for a year. There’s a lot of different things we can do, but once we start doing it, we might not find them as fun. Good luck!

  32. says

    “Now that the bull market has returned I’m finding it increasingly difficult to sit on the sidelines as old colleagues maximize their incomes. A growing part of me wants to get back to work so I can leverage the upswing for the next several years.”

    What is the reason to get more money than you already have? Bigger house, or maybe a Lamborghini? :)

    My biggest fear is to get lazy which I’m really good at. I love movies, and reading non-science stuff. I have big problem to read less and do more for my (small so far) online business.

    • says

      Just being in the action really. It’s fun to work when times are good. It’s no fun to work when times are bad and friends are losing their jobs and compensation is getting compressed even if you hit it out of the park.

      Oh, and a Lambo would be nice, if it had jetblack tint so nobody could see me in it!

    • says

      When times are good, as they are now, it’s hard not to have the itch. With one year under my belt, I will have no regrets looking back when I’m old that I gave things a go on my own. One of my biggest fears is not doing the things I’ve always hoped to do out of fear.

      Congrats on completing you A-Z Savings book btw!

      • Glen @ Monster Piggy Bank says

        I just don’t think times are good for the right reasons and I can see the market falling back down again if the fundamentals don’t catch up to the euphoria.

        I actually really admire how you have gone about your business and are doing what you want. You are currently living my dream by doing what you love.

        The book has been a lot more effort than I thought it would be originally, but I am glad that we did it as I have learned so much from the experience.

        • says

          Book producing is definitely an eye opening experience. The biggest thing I’ve found it does is help you with branding and authority on a particular topic.

          It’s also very gratifying to have a product out there which can help others. You’re not likely to get rich off a book, but we don’t write to get rich in the first place!

  33. says


    Don’t you sleep?! Answering comments back at 5:51 your time. We did sell the other place and bought another one. Mansion no? but probably double the living space which has been nice. Still doesn’t mean I can stay home with The Wife everyday. I’ll take the high road and say she’d want to get rid of me way before me of her.

    • says

      Haha, nice. I’ve been responding to comments since 4:40am this morning… which is another reason why I’m itching to do something more. I’m going to be done with all my online duties by 7am!

      Doubling the size of your house is a huge move man. All is relative! Congrats on selling your old place. That must feel GREAT!

  34. says

    I won’t retire for a long, long time but I will need to develop more friendships to sustain me when I get there and before I get there. As a single person I am excluded from a lot of couple activities with my small circle of friends and it gets harder to make connections as you get older.

    I can’t ever see myself enjoying cleaning and if there was some giant windfall of cash I would hire a biweekly cleaning person to do the big jobs. Wasteful? Yes, but I don’t drink, travel, gamble or wear expensive clothes and everyone should have some sort of a treat in life.

    • says

      That does get tough when other friends who are couples have their couples retreats and family dates. Enjoy your house cleaner! I don’t know why, but I find it gratifying to clean myself and will never have a housekeeper. I like to garden and paint as well.

    • says

      Good luck! Many people are getting very wealthy nowadays with their startups. Just got to be in the right place and keep on executing. There is way more money out there than you think!

  35. Eric Shun says

    My employer allows workers to reduce their weekly work schedule, with a correspondent reduction in salary. I just reduced my work schedule & salary by 10% by taking every other Friday off! I’m going to enjoy those two 3-day weekends every month!

    • says

      Nice! I’d love to do that as well. Just make sure your employer knows you are still serious about work if you plan to work for a while. Flex hour employees get less love and are at more risk than full-time, balls to the wall employees as Marisa Mayer at Yahoo! has demonstrated.

  36. says

    What a great honest and objective review Sam! You seem very sociable so this lifestyle suits you. But for those who aren’t, I can see loneliness a huge con that isn’t apparent at first. Funny take about waiting in lines and great point about vacations not as fun as well. Thanks for the eye opening post! Has it already been a year? Time flies when you’re having fun!

  37. Steve H says

    I recently (8 months ago) retired from a career in law enforcement. Back when I hired on, one didn’t get into that field to get rich or have plenty of money in retirement. As chance or happenstance would have it, Las Vegas remained the fastest growing city in America for the decades and years that I worked as a cop. Pay raises and opportunity for advancement were phenomenal, as were the union contracts and the pension system for police and firefighters. As a result, I retired at 51 and the pension is a nice cherry at the top of a long career. It’s comfortably generous. The deferred compensation program I participated in combined with personal savings from lbym is added insurance. I DON’T MISS WORKING. Even after 8 months I cannot see this sentiment changing. Freedom is something everyone should experience. I do have survivor guilt though. I feel like I walked away from a catastrophic event completely intact. I see people hurrying to work, stressed out, tired and self neglected. Been there, done that. The guilt ends. It’s 70 degrees in Vegas and I’m wearing a t-shirst, cargo shorts and sandals while doing a little shopping at a leisurely pace in a sparsely populated Costco a few short minutes ago. Life is indeed good. Also, you ARE retired. I read some posts arguing otherwise. You are also contributing to the lives of people in positive ways. Would your return to the rat race contribute to people in the same way? You ain’t missing out on anything, bull market or not. If I have learned anything, It is that we make our own life. For those who feel they can’t be happy in retirement because they won’t have anything to do, I feel sorry for them. They needed to unplug From the matrix and control their own destiny. Are we all lab rats pecking away a the bait for a reward of predetermined importance? It can be hard to commit to controlling your own destiny. It can be scary. Here is the challenge. Go out and do something you’ve always wanted to do but never had the time for. Make time for it and do it. Once you do, you will know what is waiting on the other side for you. You’ll learn that it is you who decides your happiness, boredom, satisfaction or elation at the business of being free.


    Las Vegas

    • says

      Hey Steve! Congrats man! Your pension must definitely be a nice cherry on top.

      I can relate to your “survivor’s guilt” comment as I have the same feelings as well sometimes. It’s like we played a game and won. But then I think “now what?” Life is relatively easy in America compared to the other places I’ve seen and lived in.

      “Make time for it and do it.” You are right. One of my goals I’ve put on for a while is being SCUBA certified. Small goal, but a fun one so that I can start planning my vacations around the dives.

  38. says

    Great post!

    I think it’s easy to come up with the list of positives, but listing the negatives of early retirement is much more interesting as they are the day-to-day challenges we’ll be facing.

    I find the laziness factor interesting as well. Of course, I’m looking forward to a good 6-month sabbatical where I just Netflix out on movies and shows before I really get in gear and figure out “what’s next”.

    Best wishes!

    • says

      Thanks man. I wanted to list more negatives, but I couldn’t really think of any more. Trust me, I’m trying. I guess the “Other Observations” posts could have some negatives, but not really.

      I think you will find Netflixing out to movies very boring after 3 weeks! But, do let me know when the time comes. Cheers

  39. says

    That would be a very interesting comparison indeed!

    Every single one of the researchers who’s goal is to highlight retiring leads one closer to death are all working. There’s a bias there :)

  40. says

    I enjoyed this post. I don’t think I could ever retire truthfully. Not because of financial reasons, but because I get too antsy if I don’t have something to do. I know you mentioned it before, but have you thought of volunteering at a worthwhile charity to help you find more fulfillment? I think thats what I would be doing if I didn’t have to work. I could’t imagine feeling more fulfilled than when I am helping others

    • says

      I have. A little bit of time here and there. I’m finding utilizing this platform and the Yakezie Network to share stories and help folks with their finances to be very fulfilling. It is so awesome to see fellow Yakezie Members quit their jobs and do what they love. I think we’ve got over 10 Members who’ve managed to do so. And then to get personal e-mails from readers who mention how so and so post helped them with their finances is also gratifying. I think the internet is the most efficient way to reach and help folks.

  41. says

    I can’t wait for the day when I can quit my day job. Mainly because I want to become an independent investment advisor. Working for myself, instead of a large brokerage house, is such an attractive venture. I have a specific dollar amount in mind and once it’s reached, I’ll be ready to manage portfolios on the beach…

  42. says

    Wow Sam, you really hit it dead on! I have only been out of the “rat race” for a month and a half now, but so much of what you write about is what I have experienced thus far! For instance, I’ve caught myself running errands at commuter times…very annoying, and have since learned to not do so (it’s just an old habit to run errands at certain times of day!). I am spending a lot less time on social media, which is not necessarily a good thing, and have found that many things I used to do because I didn’t want to do my job. That was a hard realization (for example, checking my financial accounts once a day or so to pass the time at work). The good news is that I’ve had an incredible time expansion because of working for myself, as well as not feeling the need to do these things I used to do to pass some day time. Life has really opened up for me! Not that I was miserable before, but wow, I am just SO happy.

    Anyway, that is just a month and a half in. I’ve been pretty productive and focused, though I have my days as well. The good news though is that I work on the weekends as well and wake up without an alarm at 6:00ish each morning (I have always been a morning person), so if I have an unproducctive Thursday I just make up for it when I am at my peak. In fact, having the freedom to work when I am feeling focused and into it has really helped with productivity as well.

    • says

      Sounds good Amanda. The first several months is always a thrill. The thrill of being able to sleep in and set your own schedule kind of faded after 6 months as I didn’t need an alarm clock for the past 3 years anyway. I hope the thrill lasts longer for you than it did for me.

      I still enjoy early retirement after one year. I’m just looking for more excitement since there’s so much more time. Good luck on your journey!

  43. says

    Very inspiring Sam!

    let me ask you a personal question: do you feel that you had to postpone the project of having a family because you were so focus on working and seeking financial freedom?

    I’m asking because I almost lost my wife and “perfect family picture” at one point while I was doing my MBA at the same time that I was pursuing a great career and creating my online company. I use to work a lot and understood that it would bring me a lot of materials but I would lose my family in the process. Any thoughts on the difficulty to combine both early retirement and founding a family?

    • says

      Not at all Mike. I had no desire to start a family in my 20s. I was excited to work, learn, travel and be mobile to go where the opportunities were greatest. I didn’t want to be grounded so soon.

      I got my MBA partly due to the downturn then, and partially due to having a lot of spare time. I remember even in 2000 waking up by 6am on weekends, bored as the world slept. So I decided to go to school on the weekends instead. I should have started this site the ! Now that I have the time and financial means, a family is a possibility.


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