Is Early Retirement Worth It? Thinking Of Quitting My Job

Are you exhausted from work and wondering is early retirement worth it? I'm here to give you some perspective after retiring in 2012 at age 34. Since 2012, I've done some part-time consulting. I've written over 1,000 personal finance articles on Financial Samurai. My wife and I traveled the world. And we had two children.

So if you are to ask me today in 2021+ is early retirement worth it? I have to say emphatically YES! Early retirement has been wonderful so far. I'm now on a mission to traditionally publish a book with Penguin Random House for 2022.

I first published this post in 2011, because I was anxiously looking for early retirement stories from other readers. I'll then share more about my thoughts post early retirement nine years later. Here's JayCeezy's early retirement story. Joe is a FS reader.

From No Net Worth To $500 After Four Years Of Work

A tired and exhausted goat resting on a bench - Is Early Retirement Worth It? Thinking Of Quitting My Job

This post will ponder is early retirement worth it. After almost 20 years of work, I feel like I’m on the road to an early retirement. According to my back-of-the-napkin calculations, I’ll be done in another 5 years, give or take, which will put me in my mid-40s. But, as much as it’s inspiring to have a game plan and see the progress, I feel it’s also sucked some of the happiness out of my life.

When I came out of college with a degree in Math in 1995, the economy was not the best and I had no idea if I was even remotely employable. It took me close to 6 months (sending out 10 resumes by mail each day) but I finally landed a beginning-level job in the IT industry.

The salary was over minimum wage, but not by much. I was very happy with getting the job, but I felt as though I could do better. I then asked myself “What’s next?”, a phrase that even now drives my wife crazy. Within 1 month, my resume was updated and I was fishing for the next thing.

In the following years, I worked like hell at my career. Working during the day, taking courses at night, learning all I could. I was now a software developer (a job I still do) and was switching jobs every 2-3 years, always negotiating a higher salary. During these years, I also moved to the US from Canada and became familiar with the harsh and often arbitrary immigration system.

It was very clear that if I were to become unemployed, there would be no safety net. Then, the large layoffs from the dot-com implosion started to happen in 2000 and the company I was working for closed. I managed to find something else, but it was not easy and I had to move across the country to do it. Even in a good economy, few companies want to spend extra money on immigration lawyers and paperwork.

Starting A Failed Online Business

At this point, I felt as though I was more on my own than ever, but at least I was working a good paying job. Still, a little voice inside my head kept reminding me that jobs are indeed temporary. I needed to escape somehow; more, I needed an alternative source of income. So I again asked myself, “What’s next?

I knew the internet (or at least I thought I did), so a friend of mine and I tried to start an online business. For over 2 years, we worked in the evenings and weekends, bootstrapping a company with a few zero-interest credit cards and our own money, trying to make a go of it. I even took a leave of absence from work to try to get more time to work on the business.

At our peak, we had three employees working for no salary but only equity and belief in the company. Everyone worked extremely hard but, unfortunately, we went as most small businesses go and we couldn’t survive. Thinking about that business still makes my heart ache to this day. We started to repay the loans and I was exhausted, disillusioned, but I think wiser for the ordeal. The main lesson I took away was that businesses have to have a strong cashflow to survive.

Then, there were some talks of layoffs and, sure enough, they came. I was spared, but others were not so lucky. Still, it could have been me, and the little voice that talked of freedom became even more insistent. I was forced to ask the now-painful question, “What’s next?” Is early retirement worth it?

The Economic Crisis of 2009 – Surviving With About A $200,000 Net Worth

By this time, I had a long resume along with some biz experience and was ready to make another move. I was now qualified for the highest-level jobs in my field and I switched to what I saw as an up-and-coming company and a very healthy raise.

That first year or two, however, was near-insanity and some days it took all I had to just not walk right out of that place and never look back. But, with the ever-looming potential immigration problems it would cause, I said nothing.

It was during this time that I met the woman who would eventually be my wife. She was my ray of sunshine in a hard world and was responsible for keeping me sane during these years when things seemed like they were going off the tracks. Without her continuing support, I don’t know how I made it each day – I love you, Honey!

Then, one fine day, the whole world went straight down the tubes: Mortgage meltdown, stock market collapse, waves of massive unemployment, and bank bailouts. I braced myself for impact… but none came for me.

For whatever reason, not only was I spared but the company I was working at started posting excellent numbers and growing. I was not only safe for the time being, but doing better than ever financially. My instincts, now honed for disaster detection, practically shrieked at me to capitalize on this temporary windfall in whatever way I could.

“What’s next!?!” Is early retirement worth it?

Moving On Up

Up until now, I was living in an apartment downtown. The rent was as low as the clientele and there were a host of issues that up until this point, I was tolerating: the constant street noise, the threat of crime, the dirtiness, you get the picture. I decided I would buy myself a house.

I had saved up a very good downpayment and was following the news about foreclosures being at record lows. But even then, the houses that were in safe, quiet neighborhoods and not too far from work were still more than I could just pay outright. I would need a mortgage.

Debt was always an anathema to me – my Dad told me stories about paying off his house before he was 30 and living debt free throughout his life. I tried to learn from him, paying cash for everything, and not even getting a credit card until I was almost 30. But, this was not the 1950’s and I resigned myself to it.

I still think back to when I signed the papers. Such a large amount of debt to owe. I remember the feeling of mentally rolling up my sleeves. I was ready to pound that number into the ground. It was exciting to have a house. But I viewed the mortgage as just a lot of work to do. I would do my best to pay it off as quickly as possible.

Then I wondered again: Is early retirement worth it?

Still Controlling Living Expenses

As I lived in the house, I started doing little projects. Little projects became bigger ones, and tools started to inhabit my garage. I also started to read, mostly about houses. I read about Real Estate; about investing, about rentals and foreclosures and cash flow, about cap rates and tenants. And I found websites where I could look all over my area and see dozens of inexpensive abandoned homes for sale within less than an hours drive of where I lived.

I also read about people having a secure future owning rentals. 401ks, stocks, bonds and most other investments from a retirement perspective are what I like to call depletive; when you collect a payment, the amount of whatever product you have goes down.

Given enough time and withdrawing, you will eventually hit zero. (This is exactly why tools like FIRECalc are so popular; no-one wants to hit zero) But rentals are non-depletive. Given a renter willing to pay, the money will continue to flow.

“What’s next?”, said the voice. Is early retirement worth it?

THIS would be next.

Seeing The Light – Is Early Retirement Worth It?

One of the toughest parts of deciding to try landlording was my battle with mindset. I had bought my house with the intention of paying it off quickly. But real estate investment nearly requires you to be OK with taking on a lot of debt. In fact, taking on debt makes the investment give a much better return. (See: The Ideal Mortgage Amount Is $750,000)

So, in order to make this work, I not only had to be OK with my own personal mortgage but also another one, possibly many. Before I signed the paper on my first rental (and many nights for years afterward), I would find myself unable to sleep, sitting downstairs with a stiff drink or three and wondering if this was indeed the right way forward; running the numbers in my head and on paper again and again to make sure that I hadn’t missed anything.

Oh, and did I mention that these rentals were foreclosures? They required work to make them rentable. So, after a long week of insanity at the office, we’d have to pack up the tools and air mattress and live at the rental all weekend. It’s kind of like going camping at a forced-labor facility.

Sure, at times it was fun, but more often than not, it was just hard. It’s corny but I imagined my 50-year-old self there, encouraging me to keep going and not to quit. As I sweated my bag off in the summer heat, I imagined him having a fantastic life, thanks to me.

We eventually rented it and, when I got that first rental payment, I felt so vindicated, so good that something finally went the way it should, that my business made money right out of the gate. I also knew deep in my bones that this would be the way forward, the way out.

Going Crazy And Facing Mortality

I started saving up more money for the next rental and studying real estate like crazy. I created a program that would comb the MLS for house listings, do all the calculations, and come up with a top-100-rental list for every city. Weekends were reserved for house showings of what I had dredged up during the previous week.

It got to the point where I could look at a home listing and if it was in any of about 5 or 6 cities, I would just know what the rent on it would be and could estimate the ROI (return on investment) in my head. I would buy and rehab two more rentals in this crazy period of time in addition to managing existing tenant issues.

My income and net worth also spiked way up way during this time – I remember seeing my end-of-year statement and thought it was a mistake. The company was doing awesome because everyone left it all on the field every single day. But, the weird thing was that I still felt hard-done-by. Sure, my bills were paid, but everything else was already spent in my head even before I got my mitts on it. All my eggs went into the basket marked “retirement”.

See: How To Get More Life Insurance Coverage For Less Money

Health Scare

Sadly, this would also be the year that made me confront my own mortality. I had been working very hard and decided to take a break one weekend to visit a friend in the city. There we were, just talking when my entire vision went “white” for a few seconds and I instantly felt like I was on a roller-coaster.

My friend called an ambulance and I was rushed to the hospital where they did some scans on me. They didn’t find anything, but for the next couple of days, I could barely walk.

This was definitely a wake-up call and I was afraid and also conflicted. I felt like I was on a long march through the desert. If I slowed down or stopped for too long, I’d run out of water and dehydrate. If I went too fast, I could drop dead from heat exhaustion.

It was finally time to think about early retirement. Is early retirement worth it?

Reality Check And Burning Out

After that incident, I decided to take a week-long vacation and see my family back home. I had been averaging less than a week vacation (actually, more like a stay-cation) a year for the past four years, so taking an extra week that year seemed positively luxurious.

Meeting up with family I hadn’t seen in a while made me feel like I had landed on a different planet. Their lives were so different than mine. For example, I was stunned when I was informed that one of my cousins take their whole family every year on a four-week vacation! Absolutely unheard-of!

Oh, but it gets better! Another family member declared that they took TEN YEARS off to raise their children at home! I would have been less surprised if they would have just slapped me right across the face. In fact, I may have preferred the slap, looking back on it.

Damn, early retirement is worth it to her!

Struggling With The Life I Lived

The rest of that vacation was emotionally hard. I felt cheated and very, very stupid. Nearly 20 years of striving, risking, putting it all on the line, while other people have great lives? Throwing my best years away like logs on a fire, just to watch them burn. What have I done?

At this point, I also discovered the early-retirement community, a collection of 30-to-40-somethings that had the means to pull the pin and live a life of relaxation. I won’t lie, reading their stories made me very angry. Angry at them, but even more angry at myself.

I was working as hard as I could at both a demanding full-time job, grinding on investment projects and felt like I was still so many years away. What was I doing wrong?

Disgust With Early Retirement

For a long time, I couldn’t bear to read anything about FIRE (Financial Independence Retire Early). When I did, I just got really down. I tried to analyze where I went wrong in my life, every decision, every move, and I always came up with nothing.

As I started to read more about some of these stories, though, to dig a bit deeper, I noticed something. What people don’t say is even more important than what they do say. The basic assumption about ER is that living frugally is pretty necessary even after you retire.

Except for a few cases, the stories I’ve read involve building a small passive investment income, reducing your outlay on (or even canceling) a lot of luxuries, possibly moving to a cheaper area of the country, and finding something part-time to supplement your income to ease the financial pressure.

I felt like this was the piece of the puzzle I was missing. Looking at my situation with new eyes, I realized something interesting: I actually could retire. Now. if I moved to somewhere cheaper (this wouldn’t be hard to find), paid cash for a house, and lived like they did on Gilligan’s Island (everyone together now… no lights, no phone, no motor car, not a single luxurieeee…) my rental income and savings could definitely support us.

Did I want to do it? No, definitely not – it wouldn’t feel legitimate. I’d feel that I cheated myself – working for 20 years so that I could hole up in a shack somewhere and do nothing? Things were just starting to take off. But then, to fully reap the rewards of my efforts, I’d have to be tied to this type of life for quite a while to come.

So, that’s where I am now; feeling trapped. It’s hard to enjoy the “now” with all of the stress and I am unable (or maybe just too stubborn) to get off the treadmill.

What’s Next?

This question is now one that depresses me a bit. The way forward, the way out, is clear, but it simply boils down to making the calculation of time vs. money and staying the course. My current expenses are roughly $4,000-$5,000 a month and my current cash flow from rentals is about $4,000 a month so I'm just about covered.

I’m no stranger to hard work, but I’m now getting older and I am worried about my stress-level and my health. I also ask myself if all this is going to be worth it. Five more years of saving and perhaps one more rental should allow for my wife and I to be fully free. My current current net worth is about $800,000.

There are some things that I am very thankful for. Firstly, I could not have done this without my wife. She’s supported me through thick and thin and is truly a life partner in every sense. Secondly, is that I have a plan on how to move forward; continue to learn about investing and execute the plan.

Afterward: When I was first asked to do this article, I was told that it would be cathartic and it definitely was. Revisiting the hard times and reflecting on the years past was very emotional. I’m generally positive about the future, but reflecting on my life, I feel like there were a lot of things I’ve missed. I don’t expect sympathy, mind you – I realize that life is hard for nearly everyone these days. And, at least there’s an end in sight for me and I try to count my blessings. You will only know when early retirement is worth it until at least a year after you retire.

Related: How To Retire Early And Never Have To Work Again


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71 thoughts on “Is Early Retirement Worth It? Thinking Of Quitting My Job”

  1. House investment require a long time (20+ year ) to have a positive cash flow ( assume you buy and hold ) , Proper asset allocation allow you to withdraw 4% of the value every year, assuming you are not a person take chance ( flipping house or stock for profit ), House return is 3% + rent – your payment. Asset allocation return is about 8 to 9% if you do it correctly ( buy low sell high, rebalance ) . House has another problem when you return, if you need money, you cannot sell a piece of house, you have to sell the whole thing unlike asset allocation ( stock/bond/gold/cash ) you can sell a piece of it and only paid tax on that piece.
    Retirement is no magic, your total expense in retire needs asset to generate income whether it is a house or portfolio, there is no express way to retirement by investing in house or stock, you just have to give it time and keep accumulate until you have a big pension or a large side asset or both.

  2. I want to work toward a lifestyle where I can work on my own terms. I want to have my expenses well below my income so that I can take risks, work part time, start a business, etc.

    Please post some periodic follow-ups. I found this very thought-provoking!

    1. Hi Mike, thanks for responding

      Best of luck in pursuing your life goals and I look forward to hearing about your journey. When I read your enthusiasm about what a FIRE lifestyle can bring to someone (working on your own terms, take risks, work part-time), it gives me positive motivation to stay the course when things get tough.

      I can do some periodic follow-ups if everyone would like. Maybe I’ll do another guest-post in about a year if Sam thinks it would be an interesting article. It will also help me to keep accountable to my own goals.

      If you’d like to keep in touch, Financial Samurai has my email.

  3. I must say, I usually never comment but in your case I can’t help it. The thing is that I hear you. You seem to be the person that I was always scared of becoming. But after reading this I am sure that I won’t.
    I think I learned to value time much more now. I haven’t read anything about your ambitions, things you really cherish and I don’t mean gardening and family (no children?). Deferring gratitude is much easier if you have something to look forward too. When I was steering your way I felt the pull and I have the feeling that once you cross a line, you can’t go back to frugal and free without feeling miserable.
    I think extensive traveling helps a lot to change ones mindset. At least in your earlier years though. I am looking forward to phase out with 30.

    1. Hi Mart

      Yes, motivation is key to this whole thing. Realistically, the pursuit of ER is unsatisfying in the short-term and tiring in the long-term. I think for most people, it’s just too abstract a concept and too long-term to keep their motivation up.

      My positive motivation (carrot) is pretty abstract and is just the idea that life “will be better” and that the demands will finally stop. My negative motivation (stick) is pretty concrete, though. I’m a focused person and am not good at balancing working and fun. So if I do the traditional retirement route, I’ll just continue to march forward blindly and only when it’s too late, I’ll realize that I haven’t done anything, gone anywhere, met anyone new, etc. That’s not acceptable.

      Right now, there are shorter-term goals on the radar (finally take a vacation, do projects around the house, etc.) but my only long-term goal is to FIRE. I don’t think about what comes after that because I want there to be nothing for a long while. Then, in my own time, I can discover who I’ve become and what this new person wants out of life.

      Good luck with your goals!

      1. I can relate to your points, as for ambitions, I have a whole list and a million other things in my mind that I want to do when I retire. I am also reshuffling a top 100 books list I am looking forward to go through. I already look for apartments at the town I intend to escape to first in northern Africa.

        Sometimes I have to sneak to the bathroom at work to hide my vicious smile and the happiness that is pouring out of me when I think about what is coming next because all the others will keep being little hamsters.

        I am sure I won’t stay still. I am a workhorse and a proper day has at least 12 hours. I disrespect people who leave at 5 to be home on time for their favorite soap.

        One incident that I found important was a job for which I didn’t need to do anything. Not even show up. This lasted almost a year and has given me the opportunity to pursue all kinds of things that crossed my path, dancing, politics, business ventures, startup weekends, philosophy, love affairs, traveling, more education, languages, personal finance, ERE, books, acting, writing, dreaming, sleeping!, etc..
        After that I realized that I enjoy things I would have ever dared to think about before and that would like to know and master so many more things. This was my little trust-fund-kid experience. I duly recommend it, but make sure that you have at least a fake occupation like studying, writing, teaching or translating with a fixed-term!!! otherwise the workhorse in yourself will make it a shitty experience by giving you a constant feeling of futility.

  4. Hi JC

    I’m glad to hear that you still will feel productive after FI. If you have the energy, I’d say there’s nothing wrong with pursuing a project or career that’s interest-driven rather than income-driven.

    For me, a life that’s NOT income-driven will be a very strange world indeed. It reminds me of a documentary I saw about the parole system, where prisoners who were let out after many years have trouble adjusting because there’s no-one there to tell them where to go or what to do next. And, consequently, a lot of them have trouble adjusting to their new life and end up just going back to jail. I just hope that I’m able to adjust instead of going back to my familiar ways.

    I wonder what the recidivism rate is for early retirees? :)

  5. Hi Jason,
    My career choice allows me the opportunity to work with successful people like yourself. The conclusion I’ve come to is that it’s not about “retirement” as much as becoming “work optional”. It’s often not about the money or free time, it’s about feeling motivated, productive, and enjoying how you are spending your day. It sounds like you hate where you are, and that you’ve realized you are only there to pay the bills. I know the feeling, it drove me to a drastic career change in my mid-thirties, which I thank my stars for every day.

    I think RJACK above had it right. Worry less about future outcomes; they will turn out differently anyway. Concentrate more on how fortunate you are to be where you’re at, and the flexibility you have. If you hate your current career, live off your rentals and move to another. You’ll wonder why you didn’t do it sooner. Retirement is a myth for successful people. After a while, you’ll be looking for volunteer projects to keep you busy. Engineering your life and career, with a balance of cash flow, fulfillment and free time, while keeping your brain and body active, is a great way to go.

    Yvon Chouinard (owner of Patagonia) wrote and interesting book called “Let my people surf”. About the philosophy around the company, his initial desires to build it and sell it, and why he decided not to when he had the chance. Good food for thought.


    1. Very interesting points, RJE

      I’ve heard the idea of transitioning to a “work optional” life rather than “retirement” before. But, right now, I don’t allow myself to think that far ahead. Maybe, I’m saving the “what’s next” question as TBD so I’ll have something to do in my old age. :)

      I wouldn’t say I hate where I am but I hate that all of my motivation is based in fear right now. That’s what I want to be, is free from the “prepare for looming disaster” mentality. It’s exhausting but it won’t go away.

      When you say “retirement is a myth”, though, I hope that it’s not true for me. I eventually want to find some peace.

        1. Well, until I’ve grown my passive income stream more, I feel vulnerable to layoffs, illness, etc. The real situation is no different than it was when I started except for the fact that I’m older and have more to lose if things go south. Starting from zero at my age, no thanks!

          But I feel like I’m also *really* close to realizing my dream and feel like I only need a few more years of compounding to make a huge difference. So I don’t want to rock the boat and lose momentum. Again, going back to the “one more year” syndrome.

          That’s why I’ve set the bar at 45 years old. It gives me time to compound, but also prevents me from “one-more-yearing” myself. Until then, I’m going to take care of myself better, take more time off, and try to enjoy the journey, even though I’m a little car-sick. :)

          Enjoy Hawaii, FS!

  6. ^^^ Truth. I feel the same way, but have some previous tendencies towards asceticism anyways (we share the weight of the term, MFIJ!), so I ended up leaning much more towards the “very low expenses” end. This means I don’t take tons of risk/leverage because I value the security, but since I should make FI at 30 even with a very conservative outlook I am instead looking at new careers to keep things interesting.

    As for this:

    “I’m actually looking for confirmation or denial of this. If there’s comments allowed on this blog, please share your thoughts.”

    I have tended towards extreme frugality and I feel many do chase it for the sake of freedom even without seriously asking themselves how they view the tradeoffs; blind pursuit of FI is still not ideal. My personal path is get there very quickly, and then have fun poking around and exploring. Since I’ll be able to invest my time without need for compensation (although I still plan to make a solid income), I can try a few new things without feeling bad because I know I have a pretty sweet deal going (in software, too =P).

    But I also feel that I have shown to myself I can be genuinely happy with very little, and that itself is very useful, and perhaps even more meaningful when it’s not simply the only option.

    1. Greg, you’re in an great place. I wish these ideas would have been around (or at least accessible to me) when I was your age. I would have been in a much better place at this point.

      I think the internet has really opened things up for everyone and the younger people really have more options open to them just because of the information that’s available to them at the click of a mouse.

  7. Jason,

    My response to: “What people don’t say is even more important than what they do say. The basic assumption about ER is that living frugally is pretty necessary even after you retire.”

    The flip side of this is the basic assumption of regular retirement @65. Work 30-40 years, but not be frugal and save just 15% of income. Spend 85%, and with compound interest of 15% savings rate, your nest egg will cover your 85% spending into retirement.

    ER people and ‘regular’ people make different trades with work/time for money.

    Actually frugal living aint that bad. I’ve cut my expenses (or got close to) by 50% (followed advice from MMM and ERE). So I just cut the nest egg I need by 50% too! I reduced my time to retirement by 1/2! My standard of living changed, but not go down by 50%. You just get smarter and more efficient with how you spend. You focus on others things in life that is not so money/consumer driven. Also you adapt (like lifestyle inflation, but in the opposite direction).

    Best of luck! Your health and having time to spend it outside of work is more important than money.

    1. Thanks for your input VC

      I’m definitely on-board with some of the frugality concepts. I think what hurts me is that I’m living in an expensive part of the country. But, this is where my job is, so I’ve got to work around that.

      I don’t think I’m doing too badly with cutting our expenses. Most of our expenses come from housing (no surprise, that’s 80+% of US households) so the past couple of years, that’s been the main target. Because of a couple of refis and some property tax battles, I’ve managed to shave about 600/mo off of just by filling out (many, many) forms.

      A couple of years ago, we were considering moving to a smaller place, but by the time we got our act together, the housing around here got into an upswing mode and it wouldn’t have saved us any money.

      We have been talking about if / where we want to move after we close shop. My inner caveman would like to just live in a trailer in the woods, but Mrs. Caveman would surely say “No”. A nice mountain cabin or a small condo in a beach town sounds pretty good, though. It’s funny, as I type, I’m running the numbers in my head, but when the day comes where this choice matters, the numbers will be a small concern.

      I’m glad you’ve managed to make things easier for yourself. You’re also the second person that has mentioned the ERE book. That will be next on my list.

  8. Darwin's Money

    Congrats on being able to retire from a W-2 income job. But are you really retired if you have to manage a real estate portfolio? Or just changing careers? Sounds like a nicer, more flexible job, but it’s still a job, right? I’m dealing with some tenant issues as I write this…

    1. Hi DM

      First off, I’m definitely not able to retire from my W2 just yet – I feel like I still have about 5 years left. I’m hoping I can find more ways to make it more enjoyable while still growing my passive income.

      As I said in my previous posts, because of scale and distance, I now need to work with a property management company. I will still keep managing my own rentals that are local, but when all of my out-of-state deals come online, the majority of the tenant work will be out of my hands.

      That being said, if I never put my local properties under someone else’s care, I’d still consider myself retired as it doesn’t amount to that much time spent.

  9. Jason, thank you for sharing your experience and thoughts. Your honesty made me respect you more even though my husband and I are not thinking of early retirement. When I was younger, I really dreamed of retiring early but realizing that I am still productive at my age, I decided to pursue my career and continue working as much as I can. I am enjoying my job so why should I leave it? Besides, I am not obliged to work at least 8 hours a day to write for my blogs.

    1. I’m glad to hear that there are so many people out there that enjoy what they do.

      But, yes, I think if you were doing full-time work and doing it for someone else, you’d definitely be in a different mindset.

      Good for you for breaking free!

  10. Lindsey @ Cents & Sensibilty

    Hi Jason!
    I have to say, I really enjoyed your post. You are obviously a very bright and driven individual who thrives in the face of challenge. I really connected with what you said about your jobs and projects and more projects. I have no idea what I’d do with myself if I didn’t have my plans and projects to engage myself in but, like you mention, the money is already spent before I’ve gotten it.
    However, retiring early to move to the country and discover my love of gardening sounds like an early attempt at boring myself to death.
    Anyway, it’s definitely a question that’s going to have very different answers for each individual. It sounds like you’re well on your way to answering it though.
    Good luck! Lindsey

  11. I could still be working and trying to eek out a few more percent on a COLA’d pension. ( The one more year syndrome) My plan was to retire when my kids finished high school in 2016. Last year I did the math and rethought my original plan. I wanted to be with my kids more than have the extra money. Savings outside of the pension put me into a zone of comfort in my decision. I don’t know if I am considered early retired at 51 but I have no regrets at all. The freedom is wonderful. Just so happens my mom started needing help in her old age. A couple of months ago, she broke her back. I feel blessed that I have the freedom to help her out without thought of time constraints. I don’t know if I would feel the same about cutting loose early if I had worked in the private sector where I would be accountable for all my retirement savings. Each situation is different. Deep down, you will know if the time is right for your personality and circumstance. I love life every day. Retirement is the greatest thing ever…for me.

    1. Hi Steve

      I hear you about the one-more-year syndrome. I think that’s going to be a challenge for me too since I sometimes think that I’m a delayed-gratification junkie. Although, there is strong incentive on the other side for me to pull the plug too.

      And, really, as some of the other posters say, how much is enough? It’s simply never going to get to the point where it’s obvious and you just have to go with your instinct and call it good enough.

      At this point, I definitely cannot hang up my skates, but as that 5-year mark approaches, I’m going to be heavily weighing the options. Give up a year of life and roll the long-term-illness dice again for another X dollars per month? It’s a tough call.

  12. Jason,

    There’s no time like the present to do what you want to do. If it means taking 6 or more weeks of vacation, go do it! You will never get that time back and I’m sure you have plenty of sick leave you haven’t used as well.

    Making money is an endless pursuit that gets pretty meaningless after a while. $800,000 is a handsome sum of money. Once you get to $1 million, you will feel no different as you wonder what $2 million would be like and so forth. You need less than you think in retirement, especially since you won’t have to save for retirement any longer.

    Consider a sabbatical as well. It’ll do wonders! Btw, how is your net worth currently allocated?


    1. Hi Sam and Bobby

      I can definitely see that net worth can become like a pinball score eventually, but I don’t think I’m there just yet. I don’t consider my NW to be very high, actually, but I also don’t really believe that net-worth is that useful of an indicator. For me, everything revolves around my monthlies. How much am I getting in passively each month vs. how much goes out each month. This year will be a milestone because I’ll be nearing breaking-even for the first time.

      I have actually talked about one of the management team about taking a sabbatical. I think I’ve got the seniority there to do it and that would be far more likely than a 6-week vacation.

      My net worth right now is a little skewed toward cash, since it’s buying season and I need to have liquid funds. But, once it’s allocated, I’ll be 35% stocks and 65% RE. There’s a little cash in there, too for reserves for each rental, but it’s not much. The reason why my stock allocation is so high is because of stock options – they haven’t started paying me in real estate yet. :)

      But, Sam, I can tell you’ve been out of the loop for awhile. Many companies have dispensed with sick leave and vacation time for their regular staffers completely. Now, what you’re likely to see is “approval-based” vacations, where you apply for whatever vacations you want and they will approve or deny you based on the current company needs, your performance at work, the current grumpiness of your manager, etc. It’s a monstrous policy.

  13. Jason, excellent article!
    I too came to some realization that I wasn’t cut out for doing rental properties, since my wife and I actually bought a fixer-upper property nearby our own house (convenient since I was working a full time job).
    Serious modifications to the house because we just wanted to flip it came up to me doing a large portion of the structural repairs (lowering the 2nd floor by 4 inches, and raising the 2nd floor ceiling by 3 inches to get 8′ ceilings on both floors, and a very odd thing which was a well literally covered by some old rotting wood underneath of the kitchen floor!). We sold the house for a small loss after all that work and time away from my family.
    It was definitely a learning experience that I will never forget and appreciate everything that I learned in doing that.

    1. Hi Rich

      Sorry if I misled you here – let’s be clear, I’m still very much on board with the concept of rentals. But it sounds like you did a flip, which is a completely different beast. I feel filps are not appropriate for someone working full-time and is especially not good for someone wanting to FIRE. It’s not an investment, it’s a job with a large work and risk component. I do believe you about it being super-hard, especially when you start talking structural changes. The company I’m working with now absolutely will not touch anything with that type of problem.

      Don’t let your flip experience sour you on real estate, though. Try a rental instead and see how you like it. Just make sure that you’re cashflowing from day 1!

      1. Oh no, I didn’t feel misled at all. I realize that the flip is completely different than a rental. My wife and I were considering rental of the house, but at some point it seemed better to simply flip it because the rentals in the area were quickly approaching the point where rentals might have just barely covered our out-of-pocket costs. Like you said, we didn’t want to hold it if it was barely cashflowing for us.
        Several people actually told me that I had a talent for doing house renovation. After all, how many people really know how to physically rebuild floors in a balloon frame house without the walls falling in? :-)

      2. Incidentally, my goal once was to FIRE around 55, but the age had to shift up another decade or so due to our having 4 kids and putting away enough to cover everything in our retirement age.

  14. My husband and I are in our mid 30’s and have 2 young children. We worked two full-time 6 figure jobs for years and while we had a lot of cash, it killed us. We weren’t happy, we spent our weekends grocery shopping, working on the yard and doing kid stuff. So, I quit my job going on 3 years now to stay home with my kids and while we had to sell a beautiful house to do it, it’s been worth having a less chaotic and stressful life.

    Yes, we aren’t saving nearly the amount of money we used but we also have no debt, with the exception of one rental property (that cash flows $250/month).

    These intentional choices have allowed us to spend time on things that value: frequent domestic and international travel, skiing, biking, camping, and sports for our kids. Our plan is to live comfortably now so we can live comfortably later. Not luxurious (so we can save for retirement) and not denying ourselves the things we really enjoy (should we never make it to retirement).

    I’m not always a “all things in moderation” believer but this is one area my husband and I practice that method.

    1. Hi Tiffany

      I’ve definitely considered selling my house, but because of the hot market now, we couldn’t find something even a couple of steps lower for the same price. And, I’d have to find a new job if I were to move to another area.

      I’m curious about your situation now that you’re down to one income. You had said that you quit your your job – what changes did your husband do with his career to alleviate his stress?

      Personally, I would have a very hard time with my partner not contributing financially and would feel deeply betrayed.

  15. Thanks for sharing your story Jason. Having a partner for support and encouragement is priceless. Nice job with all of your accomplishments and that’s great you’ve been able to plan and prepare together with your wife for the future.

    Hilarious pic of the goat Sam. He is just chilling with his big belly plopped down on that bench lol. Animals are so funny!

    1. Thanks, UT – I know I love the goat picture too! Made me laugh because it’s so appropriate for the topic!

  16. I know that comparing myself to others is not the way, but I’m always trying to improve things for myself and so I do look to other ways that people live to get ideas. If I didn’t do that, I wouldn’t be able to improve things. I have seen some sad stories first-hand, though, and am grateful that I can even attempt what I’m doing. Things are just out-of-balance for me.

    I’m glad you are so positive about working. I can’t imagine doing much of anything after FIRE.

  17. I’ve been trying to slow down and I know that I can’t really “do it all” anymore without a significant impact on my happiness. I’ve also discovered that as I get more rentals, there’s no way I can keep up with the demands of the units AND do my day-job AND grow my business. So, I’ve been working with a property company that finds and manages rentals. Plus I get the benefits of out-of-state prices.

    I’ll read that ERE book, thanks for the recommendation

  18. Before I start replying to comments, I’d like to thank Sam for hosting my little story. It was really emotional to revisit all of the hard times, but I think I’m now much more mentally tough than even a few years ago.

    I also like the goat picture – that’s what I feel like some days. The only difference is that I still have the plow around my neck! LOL

  19. What’s the phrase… “comparison is the thief of joy”? We’re looking forward to financial independence sometime in the next 5 or 6 years when we’ll still be in our mid-thirties, but I personally don’t feel deprived in our current lifestyle – except of time. And that’s what we’re working so hard to get – to have our hours really be ours and not have to sell them to someone else. I don’t feel like tons of extra “stuff” would buy me more happiness than tons of extra time would. We have a friend Mr PoP just visited who feels completely differently. He can’t wait to sell his time to a mega-corp for the next 35 years and retire at 65 knowing that he’s eaten his way up and down the west coast. Since that’s what makes him happy, that’s great – but that’s not what makes us happy, so it’s not a comparison we want to draw.
    PS – math majors rule!

    1. Hi Mrs. Pop – that’s amazing that you’ll be financially independent before 40, that’s an incredible accomplishment. And much more so because you didn’t feel deprived.

      For me, the question is definitely not about deprivation since I don’t see the point in going overboard with frugality. Materially, I live in a nice place, eat nice food, etc. It is all about time and happiness.

  20. Thanks fro sharing! It reminds me of my journey in income property although I bought apartment buildings. I started with a 9 unit and traded it for a 24 unit. Then refinanced and bought a 10 unit. It took me 7 years to reach financial freedom and that was 28 years ago. I realize the quest is all consuming, but enjoy your life too. Time goes by very quickly and you need to enjoy your life. You seem to be very close, but have reserves and additional revenue because it is that kind of business. I sold all my holdings roughly 22 years ago and work at things I enjoy which is currently teaching.

    1. That’s great – I was thinking to get into apartment buildings too, but we’ve already got some purchases in the works for this year. So that will have to be further down the road.

      As for time, yes, it goes by so quickly. I’m already feeling like I’ve give up a lot to get where I am now and I get down because it seems like the situation is demanding even more. After I FIRE, though, because of all the time spent, I can’t imagine myself ever working again. It would feel as though all of that effort was pointless.

  21. There is nothing like a health scare to make you rethink how you live your life. I had some health problems too and I think most of it was due the the stress and unhappiness associated with my old job.
    We spend about $3500/month and we live in a nice vibrant city. I don’t think you need to go live in a hole to cut down your expenses.

    How about slowing down a bit and try to enjoy your life while working? Instead of going 110%. Try 80% and stretch the target date out to 10 years or so. It might be better for your health.

    1. Well, I can’t cut my work hours down but as I mentioned before, I’m trying to develop strategies where I can work with outside people to help me with my goals. If I’m to scale up, I’ll need to do that eventually anyway.

      I’m also trying to do more social things and add some joy to my life when I can. For a long while, things were very grim

  22. The First Million is the Hardest

    Thanks for sharing your story with us Jason.

    Early retirement doesn’t have to be shopping at thrift stores and eating ramen noodles all the time. Achieving FI or ER doesn’t even have to mean that you stop working. Most of the bloggers I read that are “retired” still work in some capacity. I think the goal is to be able to check out of the traditional corporate world and be able to structure whatever it is you choose to do for work around however you want to enjoy life.

    1. The original article that I sent to this site was about double the length of what you see here and in that one, I talk about my attitudes toward frugality. Basically, my view is that frugality is like hygiene – definitely necessary, but subject to a steep curve of diminishing returns. So, although I take care not to buy stupid things or have too many services, I still have things like cable TV, I go out to eat with friends, etc.

      IMHO, *extreme* frugality is for the birds. FIRE is hard enough on people, mentally. I concentrate on being frugal with BIG things and I don’t sweat the smaller stuff.

  23. Hi Jason,

    You perhaps can take a year off and then come back- ideally you would like your rental income to be double your living expenses and also for the rental income to be growing faster than your expenses are growing.

    You have come quite far so congratulations. Take a bit of time to take a break now won’t hurt you in the long run and may be great for your outlook.



    1. Thanks Mike – I definitely want to take a break but I suspect it would be impossible to take a year off and come back later. Maybe a three month sabbatical would be more likely – I have considered it. Right now, I’d even be happy with 2 weeks vacation per year.

      You are right about the income; just breaking even is not good enough. With the rentals come inevitable expenses so if we can get around 8k / month, we’ll be doing awesome. But, I predict a lot can happen between now and then, so who knows if I can last that long. On the other hand, the power of compounding is speed things up since I keep rolling the rental income into more purchases. (Maybe it’s time for some financial modeling…)

      One thing: To put all the cards on the table, FS did do some rounding-off in reporting my situation. My expenses are about 4-5k but the 4k / month is the higher-end a projection after we finish all of our RE purchases this year. I suspect it’ll be more like 3500. I just want to come clean on that.

      1. Thanks Jason. Maybe take the 2 weeks off and switch off your company phone and email, and maybe you will feel ok about waiting a little bit longer.

        Like I said, you are doing great!


  24. First of all, thanks for sharing your personal story.

    Observations: You have a strong work ethic (most of us on these forums do!)
    You have been burning the candle at both ends for quite a while-to the detriment of your health
    Step #1 is an important step-Free your mind first from the illusion that things or status will bring happiness!

    Kudos for such a strong work ethic in the rental world-I’m trying to follow down the same path.

    Consider deciding on a mindset-what truly makes you happy and chase it (Hint-it doesn’t involve things)
    If your health fails, then everything is for not-I struggle with stress too.
    If/When you retire, remember, frugality is not deprivation, live simply so you can chase after the things that truly make you happy and in turn are low stress.
    Whatever avocation you assume in retirement will most likely still make you money, hopefully in a deeply satisfying and low stress manner. Best wishes!

    *You are slightly ahead of me in the retirement game, therefore, lest I sound smug in my advice, I feel compelled to give this disclaimer. My advice is meant to be emotional support to a brother in the same game of life!

    1. Thanks for your support, Chris. I’ll take the advice in the spirit it was given. I think my key challenge is finding some balance and cultivating health.

      Also congratulations on taking steps into the world of REI. In my opinion, it’s the most powerful investment known to man and it’s been very good to me.

      I’ve seen many of your posts on this blog, let’s stay in touch. Sam has my email. I’d like to hear more about what you have planned for your real estate stuff, maybe we can trade war stories.

  25. Thanks for sharing Jason as well as for your openness and honesty. We’re really not pursuing ER ourselves, for much of the same reasons. At the end of the day it’s not what we’re wanting. We have started our own business in the last year and that has been quite an adjustment or us, but we love being able to directly benefit from what we do and who knows where it’ll go…likely we’ll not be pursuing ER.

    1. I definitely respect that decision. It’s not for everyone.

      I think for some, though, they fall into it by accident. Living a simple life, both partners making good money, I can see it becoming a reality by about 55 even if it wasn’t the overriding concern. Just wake up one day and say, “huh, looks like we’re free! Honey, call work and tell ’em I ain’t comin’ in. We’re taking a cruise!”

      Ideally, that’s what I would have wanted, but there was no way I could last working for that long, so it forced my hand.

  26. Jason, really great of you to share your thoughts and experience. All of those things you are feeling, and past obstacles you have overcome, are told in a very relatable way. Everybody has a story, and yours in one of the ones in which you emerge victorious and redeemed. Congratulations for giving yourself choices; what you do with those choices will be interesting to follow.

    btw, my favorite parts of your post are the ones where you learn tools, educate yourself through reading, and mostly about your wonderful wife. You can tell a lot about a person by the way they talk about their spouse/partner. It reflects very well on her, and you. Thanks again.

    1. Thanks, I appreciate that.

      I think it’s key to have the support of your spouse when doing a major life shift like this. Without her being on-board and right there beside me, I simply could not have done it. I’m also grateful that she’s such an upbeat person, since I can be so serious.

      The learning and reading about new things were the most enjoyable part. I still like doing things around the house. But I’d say the most important part was changing my mindset about debt, risk, and investment. Many a sleepless night went into “remapping my neurons” to the new situation:

      * Money working for you is better than you working for money.
      * Risk is necessary for reward.
      * Debt is a powerful investment tool.

      1. How did you get over the commitment to long term debt, even if it goes well in the short term? Just as Financial Sam is probably nervously eyeballing his AAPL structured note these days, I have walked away from investment property investing because I can see worst case and it could be pretty bad – vacancies while paying the mortgage, renter losing their job, rising property taxes, insufficient insurance (I live in a hurricane area)…

        1. It’s a mindset thing and a business decision. Businesses, even large ones, take on debt all the time to help with their cashflow and take advantage of cash infusions. This is no different.

          Really, you can’t believe all the hype these days about ALL debt being bad, because it’s not. What most people REALLY mean by debt is credit card debt. But, even in THAT case, it’s prudent to take that on if the terms are right. I have an example of this.

          Last year, I bought some appliances for a rental and put everything on the store credit card because they gave me 12 months zero-percent interest. As the year went on, the cashflow from the rental whittled that away completely. In the meantime, I conserved my cash from that purchase as a reserve fund in case anything went wrong with the rental. It was completely win-win.

          The mentality in REI is all about cash conservation, since everything is so big-ticket. There are some investors even talking about financing properties on credit cards to minimize their outlay. Crazy? At first, yes, but once they start talking about 60% ROI, now they’ve got my attention. Hell, I’d probably do it as an experiment just to say I did it. :) That’s the way the game is played.

  27. Jenny @ Frugal Guru Guide

    I am in no way interested in scrimping and saving so we can quit our jobs in order to….scrimp and save the rest of our lives. Just not impressed.

    I don’t think work is that terrible. If you do something you believe in, you have friends, you’re making a positive contribution to the world, what is so terrible about it? Why should our #1 goal be to stop working at any cost? I’m just not interested. When we do retire, it will probably be a working retirement, too–not fulltime, of course, but part-time, meaningful work that we care about.

    1. I totally agree with you about scrimping and saving – not only is it a false economy before retirement, but it also doesn’t make for a fun-filled life in general. Unfortunately, the non-scrimping attitude makes ER even harder because our passive income needs to support these fun activities.

      I’m glad you’ve found a job that you can see yourself working for a long time.

  28. This is a great post, I’ve been at this point for 2 years now (even the love/hate of ER)! However, I come to new realizations everytime I look at ER from my current situation working and from a future-FS-like situation. I have weeks where I just want to live within my 3 – 4% withdrawl rate and be with the family 24 x 7, but I also realize that FI is a fluid term. To some, it is living on poverty-like withdrawl rates and hoping a Black Swan doesn’t land, for 40 or more years, and I wonder how they will do if they do have to return to work in their 50’s… To me, FI is optimizing between the risk of retiring too early (if I had to, I’d rather have a chronic illness hit when I’m employed thanks) vs. working myself into a chronic illness. Luckily, each year I put in, the more I get relaxed about work, getting older, and getting laid off… Ultimately, FI to me is like when I was commuting weekly to a job outside the state, I got reimbursed $700 per week in lieu of plane tickets – Although I would get a speeding ticket once in a while, this was not longer the gut wrenching, ‘oh why me’ moment. Sure, it’s still a bummer, but in the whole scheme of things I could afford it as compared to all the other motorists I’d see getting pulled over. I now had a new perspective about how money can buy some cushion from life’s inevitable travails and freedom to speed a little more than I normally would. In closing, now that we’ve laid the foundation for minimalist, risky ER, it’s just a matter of optimization (the tradeoff of ‘one more year’ vs. retire now), pat yourself on the back on the way in to work!

    1. Sounds like you’re on your way – is all of your money in the market right now? You may want to consider some real estate ventures while the getting is still good.

      1. Jason, I hear this a lot from many people and plan to make an entry eventually. Any good, thorough sources you have that accurately depict the issues that come up with contracts/legal, maintenance, vacancy and other risk would be appreciated =)

        1. I’d start with joining the site – it’s an amazing resource for everything REI. The only complaint I have is that it tends to be skewed toward flippers rather than buy-and-hold guys like myself.

          You may even find my profile on there!

          I’d also be happy to answer questions so email FS if you’d like to get hold of me.

    1. No, neither of us talked all that much about children and it wasn’t a priority for either one of us. So it just never happened.

      1. There is never right time to have kids, and never will be. Just have them – they will bring a lot into your life…..

  29. Jason, I’ve battled the same things that go through your head…it is tough seeing other people live supposedly a simple and easy life. Trust me, everybody has problems! I think you are doing great and should keep up the good fight, you’ll be happy you did…the only difference is take time for yourself and your family FIRST. This is what I’ve been guilty of most in the past, (and stiill a little bit currently), but for the most part I kind of live my life as a “working retirement” I enjoy what I do, but don’t take the ups and downs too seriously. Work to live, not the other way around!

    1. Thanks for your encouragement!

      Deep down, I know other people have their own challenges, but you have to admit, sometimes it’s really hard to see. Someone doing a cushy government job with a pension and 4 weeks of vacation a year, that sounds awesome. But, maybe what sounds even more awesome to me is not having to do any of that at all… :)

      I play board games and card games frequently. In some of the more complex games, the players are not equivalent. Each player starts with different handicaps and strengths. Some players get a more balanced, vanilla mix of characteristics, while others are heavily skewed.

      What this does is make sure that everyone needs to adopt different strategies in order to be the most effective. Maybe it’s the same with us all. I just happened to get the card that was heavily skewed so I have to play my hand really differently to get where I’m going.

      1. Jason, your comment about a cushy job with 4 weeks of vacation and a pension is the exact comment that inspired me personally. My “mentor” at my first real job was probably my age (42) when said to me “yep, only 16 more years and I’ll be able to put all of this behind me”…I translated that into my own situation and said holy s#%t, I’m going to be doing this for 35 years sitting in a cube, just so I can be looking forward to the day retirement comes…well guess what, the company pension he was counting on is now guaranteed (and cut in half) by the goverment because the company we worked at declared bankruptcy. He spent the next 16 years slaving away miserable in his job, I left exactly 16 years ago this year to go to buy into a small company…I’m now financially independent, and he’ll have to count on SS to supliment his retiretment. Moral of the story, you are doing great, the grass it nice and green where you are at, & never lose focus on your goals!

        1. That’s quite a story! I’m glad you made it out and decided to pursue something new. There’s so many positives to pulling the ripcord early. What kind of business did you buy into? Was it related to your job or was it something totally new?

          One of the reasons I like rental income is that you’re the main decision-maker instead of counting on others to make good decisions.

          My wife sometimes talks about buying into a business afterward if she gets bored. I’d support her if she’d want to do it, I’m sure it would be a good idea for her.

  30. I love reading these type of posts. Sounds like you are doing great, Jason!

    I would say your best bet is to continue to find hobbies and other things you are extremely passionate about. You have the where-with-all right now to dig into those without worrying about making money at them. Find what you love to do and transition into doing it part time. You will make some money and love every minute. Then you win!

    1. Yes, I definitely have bee told that developing hobbies is something that I should do. For a while, ER was my constant companion, a monkey on my back that kept pushing me.

      But, I’m trying to develop hobbies and my wife and I are now more social. We’re doing some gardening and other work around the house.

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