If I Could Retire All Over Again These Are The Things I’d Do Differently

I've been writing about early retirement (FIRE) since 2009. During this time period, I've made some suboptimal pre-retirement and post-retirement moves. Therefore, if I could retire all over again, I want to share some of the things I would do differently.

The first two years of Financial Samurai's existence was me mainly trying to figure out how to retire early. The subsequent years has been me touching upon various aspects of post-retirement life.

For the most part, early retirement has been everything I hoped for. Freedom is priceless, especially as you get older. But I've also highlighted a lot of negatives that I could not have expected until living as an early retiree for several years.

We can pontificate all we want about what it's like to do something or be in a particular scenario. But until you experience retirement for yourself, there's no amount of planning that can prepare you for some of life's big moments.

Now that I haven't had a job for a while, I'd like to share what I'd do differently if I could rewind time and go back to when I first left work in 2012. Yes, there are some surprising benefits of early retirement as well. But not everything will be perfect.

If you are planning on retiring early, this post should help you reveal some blindspots.

Things I'd Change If I Could Do My Retirement Differently

1) Work at least one more year.

In 2013, I wrote about the trap of the one more year syndrome where people can't leave their jobs due to the money and security it provides. It's always one more year to see if you can get a promotion or one more bonus to feel more secure financially that locks people in.

I left work at 34 years old. Now that I'm 45 years old, I look back and think how absurdly young that was to retire. Leaving a good job at that age now seems irresponsible and reckless.

I left because I was sick of office politics, bored with my job, and wanted to do something new. These reasons all sound like I was an entitled, impatient brat.

Suck it up already, I may have told my younger self. Maybe even do more quiet quitting, where I stopped stressing about getting ahead and just did enough to keep my job.

But in my defense, I had already been with my firm for 11 consecutive years. That's a rarity in this day and age of job hopping.

The Benefits Of Working A Little Longer

Working for one more year would have given me more time to prepare for my post-work future.

I would have lived like a pauper my final year and saved another $100,000+ for retirement. On my firm's dime, I would have gone on more international business trips. I would have taken out for lunch or drinks all my colleagues, competitors, and clients I had gotten to know over my 13 years in the business.

Overall, I would have been able to better savor my final year at work.

Instead, I rushed my departure. I only came up with the concept of negotiating a severance in November 2011, five months before I ultimately did. Therefore, I made some mistakes like taking a week of vacation the year I left. This action ultimately resulted in me receiving a week's worth of pay less in my severance.

If I had stayed at least one more year, I would have aggressively tried to find a new role within the firm in a different office. It was always a dream of mine to work overseas since I grew up overseas for 13 years.

If I had been able to find a new job within the firm in Hong Kong, Taiwan, Beijing, or London, I think my interest in work would have been rejuvenated. With more interest comes more happiness. I could have worked for at least another three years and made a lot more money.

Always Try To Negotiate Your Severance Before Retiring

If you already know a year from now you're going to negotiate a severance, your work life could become much less stressful and much more interesting. Think back to when you were a senior in high school when you already knew where you were going to college or work.

By leaving so quickly, I failed to uncover more financial and professional opportunities.

Today, I encourage folks to try and gut it out until age 40. If you can, find meaningful work until age 45, the ideal age to retire in my opinion. At age 45, you will have worked for 22-27 years after high school or college. You will have saved enough to take things easier.

If you're burning out, take a sabbatical or an extended vacation more often to recharge. Not only will your finances be stronger, but you'll also be able to eliminate more completely any potential regret. You will maximize your chances of never returning.

2) I would have tried to have children while working.

One of my regrets was waiting until 37, or three years after I left work, to try having children. My wife was 34 at the time and had just negotiated her severance.

We waited so long mainly because I was overly focused on my career. I didn't think I was mentally ready to be a dad without first having an enormous financial buffer. Logically, I felt that having children would delay my permanent escape from work.

Friends kept telling me that once their children were born, they felt they had to work until they graduated college. Working for another 21-23 more years sounded like a prison sentence! Therefore, I decided to avoid prison altogether and selfishly focus on me.

But there's no escaping biology. The chances of conceiving declines every year one waits. For the average couple, it takes about 7-8 months to get pregnant. Staying pregnant is another challenge. For us, it took almost three years to have our son.

I would have preferred to be a first-time dad in my early 30s than at 39 years old. Yes, I wouldn't have been able to spend as much time with him as I do now since I'd be thick into work. But being able to spend a greater percentage of my overall life with him would be priceless.

Thankfully, my wife was able to have a boy and a girl by age 40. I also realized as older parents, we can actually spend way more time with our children than younger working parents. So having children later can work out as well.

Children Are The Greatest Blessing

Having our son while I was still working would have likely made me better appreciate work and all its benefits more. Overall, having children has also made me richer and a better person.

My wife could have taken three months of paid maternity leave. I could have also taken one month of paid paternity leave spread throughout the first three months of our son's life. When you're working to take care of the person you love most, you can't help but cherish your job more.

If your finances are not bulletproof, having a kid when both you and your partner don't have jobs will likely make you feel extremely stressed. Going from a dual income to single income is also very stressful. I definitely felt more financial pressure after our son was born in 2017, regardless of our retirement income.

Although work is a luxurious safety net for parents, I'm sure I would have eventually started resenting work for keeping me away from our son. Therefore, if I negotiated a severance at least a year after my son was born, I think I would appreciate my early retirement even more.

In retrospect, I would have ideally liked to have my first at age 33, have another little one by age 36, and like my job enough to retire at age 40 after 19 years with my firm. A severance package after 19 years would have been so sweet!

Thankfully, we were able to have a second child at the end of 2019. Perhaps things have worked out fine after all since we always thought about having just two kids. My wife and I both have one sibling.

3) I would have worked on my side hustles sooner and more aggressively.

The key to maintaining a steady state of happiness is being able to consistently forecast your potential misery. Once you've made your forecast, you must take steps beforehand to counteract that misery. Ideally, we can all consistently plan 3-5 years ahead. But it's not a natural act.

I didn't start seriously forecasting my misery until 2008 after the financial crisis hit. Before then, I was just a super-motivated guy who wanted to climb a never-ending corporate ladder for bigger titles and more money. Until then, the correlation between effort and reward had been strong.

After the stock market started melting down, I realized that no matter how well I performed, I was no longer going to get paid and ascend at the rate I was used to. Instead, I would stall out in my career and actually get paid less the more I did because the industry was in a structural decline.

The good times up until 2008 had made me too lazy to start Financial Samurai until 2009. I also had a lot of pride and honor by wanting to wait until I had 10 years of finance work experience before launching.

Should Have Just Launched ASAP

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

If I had started Financial Samurai in 2006 when I first came up with the idea, perhaps I would have felt much more settled than I did when I left work in 2012. I've written a step-by-step guide on how to start your own website so you don't make my same mistake.

With more financial certainty, more confidence, and a clearer purpose, I may have had the guts to try having children three years sooner as well. But the desire for money and the necessity to live in an expensive city for this money got me.

Some of you might think I'm being too hard on myself for not foreseeing the recession and starting to work on my side hustle sooner.

But ever since I started in the finance industry in 1999, I've always felt my years were numbered because of the accompanying long hours and great stress.

Today, Financial Samurai is an established site. But goodness knows how much work and luck it took to get here. Without some lucky breaks, Financial Samurai could have easily died.

Related: 10 Reasons Why You Need To Start An Online Business Today

4) I should have bought more real estate in 2010-2012.

Because I was so focused on engineering my layoff in 2012, the last thing on my mind was leveraging up to buy more property. In fact, I tried to sell my primary residence in 2012 but couldn't because the market was so soft.

If I had planned on working until 40 years old, I would have had greater financial confidence to buy at the bottom of the existing cycle. A $900K rental property I would have bought in 2012 would be worth roughly $1.8 million today.

The failure to buy in 2012 was partially offset with a property home purchase in 2014. It was a lovely fixer in a quiet neighborhood with panoramic ocean views. The house was 40% cheaper than the house we were living in.

Further, I continued to contribute to my tax-advantageous retirement accounts. But boy could I have supercharged our net worth if I not only bought more investments back then. If I also worked five more years through a bull market that would have boosted our net worth greatly as well.

Luckily, I have been buying up many heartland real estate projects with real estate crowdfunding since 2016. The long term migration to lower cost of living areas is in tact. Once the pandemic hit, real estate values in the Sunbelt / Heartland rocketed higher.

However, I'm also going to buy more San Francisco real estate. I think there's going to be a huge rebound in demand for urban living post pandemic.

Further, I anticipate foreign investors to buy up more coastal city real estate in America to diversify their assets. America has proven to be one of the best countries in the world to make money and enjoy life.

You can dollar-cost average into real estate with Fundrise, my favorite private real estate company.


5) I didn't fully capitalize on my position as an early retiree.

Although I've been writing about early retirement since 2009, Financial Samurai is often left out of the mainstream FIRE conversation. This is partly because I write about so many topics in addition to early retirement. Once you retire early, there's no need to keep on talking about retiring early. Instead, you just live your life.

Further, I'm not very self-promotional. I'm not a public figure doing video, magazine, and TV interviews. But this changed starting in 2H 2022 with my instant WSJ bestseller, Buy This, Not That: How To Spend Your Way To Wealth And Freedom.

I want more diversity in the personal finance and nonfiction finance author community. As a father of two children now, I will be the change I want to see in the world. As a minority, it's much harder to gain traction because people just gravitate toward people more similar to themselves. But I'll keep trying.

Instead of FIRE, which is becoming obsolete due to WFH, I'm more focused on wealth maximization through equity investing, entrepreneurship, career strategies, and real estate. Over the past couple of years, I've discovered new joy talking about family finances and estate planning.

I also didn't want to rub it in people's faces that I was done with work at a young age. As a result, I didn't incessantly talk about financial independence retire early. Instead, I just lived my life and now am focused on family finances.

After a year of telling folks who asked what I did that I was retired, I started changing my response. I felt stupid for saying I was retired at 34. Today, if anybody asks what I do, I tell them I'm an author.

Should Have Been More Focused In My Writing

If I had had the foresight and the chutzpah, I would have written more about early retirement life. If I did, I would have better branded this site and boosted its traffic. The more traffic this site gets, the more online revenue it generates. I should have been more proactively self-promoting, but I didn't because it felt unseemly to be constantly self-promoting.

I also naively believed more people would give Financial Samurai more credit for being one of the pioneers of the modern-day FIRE movement. But just like at work, those who self-promote the loudest, tend to get the most attention. While those who stay silent and believe their good work will get them recognized usually get left behind.

Despite half the U.S. population living on the coasts, I don't know many if any early retirement bloggers or people living off investment income in areas like San Francisco, LA, Boston or NYC. As a result, I sometimes feel like I'm on an island. It's more fun to have a tribe.

As a father now with rising costs to cover and a spouse who is an amazing full-time mom, I need to focus more on monetizing this site going forward. I've been way too lackadaisical about generating revenue. My desire has been to only write about things that interest me.

All told, I'm sure I've left at least $1.5 million on the table by being so carefree with this site. It's time to be more selfish for my family. That said, once my kids were born I began to focus more on monetization and less on retirement. As a result, online income has risen a lot since 2009.

6) I should have tried joining a different industry.

After 13 years of working in finance, I no longer found it interesting — and so I saw retirement as my way out.

Looking back, I wish I took the time to explore different industries. I often toyed with the idea of joining an innovative tech startup with explosive growth. After all, I was living in San Francisco, the tech capital of the world.

But because I was rushing to negotiate my severance, I didn’t even think to apply to companies like Uber, Airbnb and Pinterest.

I also could have leveraged my interests in real estate and technology to start a real estate crowdfunding company — or, at the very least, join one. I'm infatuated with real estate, passive income, and technology. Real estate is one of the most straightforward ways most Americans can build wealth over the long term.

Things could always change in the future, but right now, I feel too old and exhausted as a stay-at-home dad to pursue any of those dreams. It's much easier to get a new job when you have a job, than after years of being out of work. Please take a leap of faith while you're still young and full of energy!

Live In The Present, Plan For The Future

Why is it that when we're younger, we always seem to feel like we're in a rush to get things done? We've got to retire as early as possible, or else! Maybe it's because we lack patience and feel that we might all die an early death. I certainly felt like retiring early was a hedge against an untimely demise.

As I look forward, one of the main things I can do to mitigate my retirement mistakes is to live as long and as healthy a life as possible. If I can find some way to extend my life by five years, then everything will have worked out. Too bad I'll never know for sure whether I made a difference in my longevity.

On the positive side, maybe leaving work six years earlier than ideal helped extend my life after all. When I was 33, I started sprouting grey hairs. My hairline was also receding. But by age 36, all my grey hairs went away and my forehead stopped growing bigger probably because my stress level went way down.

The older you get, the more you will feel the race against time. The good thing is that money and status gradually fade away in your personal hierarchy of importance. Desiring to spend more time with family and enjoying more free time is a natural part of life.

If you're looking to retire early, please ask yourself the following questions:

1) Why am I rushing to retire early? Am I running away from something?

2) What will I do after I retire early? Am I running towards something?

3) How will retiring early change my life for better or worse?

4) Am I sacrificing too much to retire early?

5) Have I gained enough perspective from those who've already retired?

You'll Always Have Some Regrets

When it comes to retiring, there are no perfect answers nor is there perfect timing. You can only do your best with the information you know at the time. It's only after several years of living an early retirement lifestyle that you will know what you could have done differently to make it an even better one.

After more than 11 years of fake retirement, I've discovered the best reason to retire early is greater happiness. Not only do I feel consistently happier every day, I was able to experience greater happiness sooner for the rest of my life. Given feeling happy is priceless, leaving so much money on the table feels worth it!

Stay optimistic. Live in the present. And consistently spend time planning for the future. Chances are high you'll live to see another great day.

Related: A Pre-Retirement Checklist For Post-Pandemic Life

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Financial Samurai is one of the largest independently-owned personal finance sites that started in 2009. Everything is written based off firsthand experience. If I Could Retire All Over Again is a FS original post.

139 thoughts on “If I Could Retire All Over Again These Are The Things I’d Do Differently”

  1. Such an honest article! It’s rare to find someone looking so candidly at their own path, so thank you for that. While I’m sure you were this raw mostly for your readers benefit, i just wanted to share some of our story for perspective: my husband retired early at 35 just 6 months after the birth of our twin girls. This was not planned at all, but happened mostly out of necessity because we simply were not coping with him away at work so much.

    While we are mostly fine financially (I kept my job, we dont have a mortgage or lavish tastes, public schools are fine around here) I am not so sure he it was the best move for his mental health. Four years later, he feels a little trapped and isolated. Not many stay at home dads around here!

    So while you may now feel you rushed into retirement and should have waited until after your having kids – you probably planned this way better than we ever did.

    1. Hi Hannah,

      Thanks for reading. I can empathize with not a lot of stay at home dads. Hopefully, he can make new friends or go back to work now that the kids are in school? My son just returned to preschool and I’m itching to go back to work, especially since there is more flexibility: Best Time To Go To Work May Be During A Pandemic

      Being in community is nice and I’d like to get out of the house and do more mission-driven work. At the same time, I’m tired as hell and would like to relax.

      Let’s see where the future takes us! But I do know one thing, we need to take action to get what we want.



  2. Second Career Liz

    HI Sam,

    I really enjoy your blog and your reflections. For me, I was working in tech for 12 years and I switched jobs, locations, teams, you name it and I hated it. Hated it so much I thought of really unhealthy ways to leave. And then I took a year off. I had never heard of FIRE but I had saved enough money to afford a year off. And I decided to use it to figure out what made me interested and curious.

    I already knew I liked to travel and binge watch netflix and read books so this was going to be about what I hadn’t done. I took art classes, and spent whole days doing nothing, and started a business and took a class on psychology. And at the end of the year, instead of retiring, I went to grad school for counseling.

    It’s now nine years later and I have my own therapy practice. On dark days I question my decision because I would’ve met my FIRE goal if I had stayed in tech but I have so many other good days where I have purpose and focus and relationships in my life that create meaning for me. I won’t be retiring early but I will be spending the next twenty years with balance and purpose and family around me and retirement will be there eventually.

    Finally, it is so easy to be judgmental of the arts or the atypical career but I think you are selling yourself short if you don’t think you are in your second career as a writer. It’s just that this career gives you the time and space to relax and be with your family and be reflective. So embrace it!

    1. Hi Liz,

      Thanks for sharing your journey! I think it’s great you took the leap of faith to pursue something different!

      Balance and purpose is what it’s all about! It’s something I discuss in my X-Factor post.

      As I look to re-retire from the grind thanks to the pandemic wearing me down, I am focused on writing a traditionally published book with Penguin Random House for 2022 release. That might be my final cathartic moment as a write.

      Best to you!


  3. Hi Sam, I have been following your blog with interest over the last couple of years. Thank you for the insights and the information.

    Small side note about the vertical banner ads – they cover the main text of your blog and there is no way to move them out of the way :)

    I am 50 years old and I have been planning to retire early. Before Covid, I felt almost ready to retire, mentally and financially, but then decided to stay on the job given I would not have much to do at home if it wasn’t for work (fortunately I can work from home). My biggest barrier to taking the plunge is the cost of healthcare. I would have to set aside $20k /year at least for a comprehensive plan for my husband and me, but out-of-pocket expenses can be astronomical even with insurance. Do you have any advice or previous post on how to plan for healthcare in early retirement?

    Keep writing, I will keep reading. Thank you.

    1. Money Ronin

      I semi-retired 8 years ago, but my wife kept working in large part because of the healthcare benefits. We’re both 49 so it’s a long wait until Medicare kicks in. On top of that we have young kids who also need treatment for a condition. Healthcare costs are a tough nut to crack, short of just biting the bullet as Sam has done.

  4. Thanks for your series of questions in this article. I ended up using them as a journaling prompt for my life, and wanted to share my thoughts on them here.

    1) Why am I rushing to retire early? Am I running away from something?
    * I do not like to hit funder deadlines and people watching over my shoulder to see if I did it well enough. I like what I do. I will work endlessly. I do not like being watched.

    2) What will I do after I retire early? Am I running towards something?
    * I want to do similar things, actually. I am hoping COVID changed expectations for the better, as I really would enjoy working out of my Intl NGO’s country offices for 1-2 months at a time to gain different perspectives, instead of being tied to the DC office, and taking occasional 1-2 week trips 2-3 times per year. Much like you said, Sam — If you like what you do, then you won’t retire.

    **Travel and the chance to learn from others has really been what I’ve been seeking.**

    I had the faint hope that I’d be able to do that when I joined this organization. But I also realized the expectations to go to work every day in the HQ office, build relationships with teammates, prove your worth. So, I didn’t really expect it to happen in the first 2-3 years of working there. Then COVID hit, I’ve been making stronger relationships with my colleagues in India, Mexico, Brazil and Ethiopia. And everyone is on Zoom so much that I can’t see the org having a real problem with me taking my work on the road to work out of our various international offices once COVID is over. With this hope in mind, it does seem that I can achieve my goals while staying at work, finally. AND — I also appreciate your idea to take a sabbatical. In my case, it may need to be leave without pay… as I’ve only been at my job a little over a year, though I’m 13 years into my career. But, having not had sufficient enough time to rest and recharge. 2 months off could do a lot to renew my perspective.

    Also, like you had mentioned, I am just using this Pandemic era to focus on work and building my base. I’ve had the luck to purchase 5 investment properties this year, and I’m currently working on buying a 4-unit before 2020 is out. After this purchase I *could* retire early as soon as Jan 2021. However, the exciting thing will be to finally have enough income to really save, save, save, and build a nice cushion by making a few more real estate investments, completely clearing out ALL debt (except mortgages), and even purchase a condo with cash that I would call home. That’s the kind of safe base I would want… and your site helped inspire it. And staying on the job 3 more years will probably be all I need to achieve those goals. And like you pointed out, since I like my job, then it’s really not a big deal to stay on either.

    For context, I’m 35 working in the non-profit field. I accidentally stumbled upon real estate investing in 2016 and now have 8 mortgages, 7 are producing income, one is my owner-occupied. Without house hacking, as a non-profit kid from a low-income background — it would have been mathematically impossible to save enough to generate actual levels of passive income. But, real estate helped with that. Now I earn around $80K profit from my real estate each year. Next year my rental profits will be more and more, as I always add to the passive income flow with each new property I buy.

  5. Interesting read. I too retired early and never looked back. I get the idea of “living on an island without a tribe”. It’s different for me as I’m single and there are exactly zero women who are single and retired it seems :-) Once this corona thing is over I’ll start traveling again (75 countries and counting…).

    I live in Vancouver BC, also one of the most expensive cities to live and even less likely here to bump into others like me. I think, BTW, that you are better off without much attention from the FIRE people. I follow a few things here and there and it all seems very ill thought out, with hair-raising assumptions and financial advice.

    Enjoying this site …


      1. Well I could live with that arrangement LOL.

        No such traditional path on this end. I’ve hacked up my career in pieces; worked for a few years, travel. Work for a few years, travel. Usually the travel was 1-2 years. It mostly worked to slot right back into work since I am incorporated and used to consult here and there. So kids, mortgages, wife etc. are all streams I avoided by choice.

  6. Bettina Stahl

    Came to this article after reading your “darkside of early retirement” post. This is definitely better. You seem to have found some humility. I want to quibble with your use of the word “retirement” though. It seems to me you’ve been working all along.

    1. Sure. Thanks for not being as excoriating as you were in the other post, but I’m OK with criticism and judgement if there are tips to improve.

      In 2009, I made a commitment to publish 3X a week for 10 years. I finished that up in July 2019 and haven’t stopped here in 2020 and beyond.

      I really love to write and help others achieve financial independence as well. One of the things readers have found helpful is if I share the negatives and the things I would do differently. I personally love those types of posts and perspectives from others.

      I’m lucky to be able to write in retirement. It is like work, but 100X better because I love it. If I didn’t love to write, I wouldn’t. That’s the beauty of having enough passive income to do what you want.

      BTW, I think you’ll enjoy this post: The Internet Retirement Police Are Coming For Ya!

  7. Taylor Anderson

    My father is getting close to retirement age, and he isn’t quite sure what to do after. I like how you mentioned that he should consider working another year, as it will give him more money to have in the future. These tips could help my father out with retiring, but what tips do you have for finding purpose after retirement?f

  8. Orangethecat

    Great reflection and insight. I agree with the part about having kids earlier.. I have both mine at 24 and 26. Very early in my generation here. 19 years later…. I am now 45 and feel confident to be able to retire financially…but instead I chose to wind down my commitment at work to part time. Now I work 3 days a week. It keeps me socially engaged and gives me time to explore new areas that I hope to engage in post full retirement.
    Please keep writing as I share your great insights with my friends and family !

  9. Retiring in your 30s ??!! That’s unheard of here in the UK, we have a Conservative government who think that people can/should carry on working into their 70s or until they drop. We can’t even get the State Pension until age 67, and it’s a pittance that means living like a pauper. I’m nearly 58 and have many more years to go until I can Retire, and I am worn out now. Many people I’ve known have already died in their 50s, so the chances of living long enough to get your Pension are quite slim here in the UK, unless you’re rich.

  10. There are many forks in the road of life. We make many decisions along the way and end up in our current destination. Our past looks so clear in hindsight. But right now at this point in time, we can not see what the future will bring. Did we make the right decision today? It may take years to find out. That is life.

  11. I think you did a great job juggling resources after your exit. You gloss over something that matters more than money: health. I retired at 50 from an extremely stressful job. I discovered shortly afterward that my health had been suffering, and the job literally could have killed me. So, you cannot say for sure how your own health was being affected. Unlike you, my hair never grew back though :).

      1. Hi Sam, do you have any post about, “ What to do best with 401K after Retirement” for continued growth (if it’s still possible at this late stage). I’m 62 and retirement thoughts are kind of starting to sprout. So far, I’ve about “Roll Overs to IRA(Roth & Traditional), or just leave it in place. Would appreciate your thoughts about this. Thanks

  12. Hi Sam, as always, your blog is entertaining, educational, and, in my case, therapeutic. Just wanted to take a moment to add my personal thoughts, experiences and confirmations on a few points you made.

    Like you, I decided early on to pursue early retirement. The result of too much stress and back-stabbing office politics (it eventually will wear the best of us down). To that end, to self-educate on maximizing savings/returns, protecting assets, and retiring early. Got pretty good at the game and socked away a chunk. Could have retired at 45, but changed jobs and, luckily, it was like a shot of adrenalin. So, I believe you are correct in your premise that a good “job-change” could be a way to extend a career. This change allowed me to work a several more joyful,profitable years.

    Which brings me to another of your tenets. Because in my high-earning years I got caught up in the “one-more-year” trap (that you so aptly describe), I ended up retiring on my 62nd birthday. A little longer (even with the joyful job change) than I intended. Again, to your point, at this stage, the money was too good and I kept pushing it out…and pushing it out…over and over. I think a lot of us who commit to the financial discipline it takes to prepare for early retirement struggle with this. It is a very hard switch to turn off. Unfortunately, for some, I believe enough will never be enough.

    Which brings me to your thought about the post-retirement struggle with loss of former identity. That has been one of my biggest struggles. I had 150 employees who I genuinely cared about. Safe to say I really liked and respected that team. They, light-heartedly, called me “Captain.” An unofficial title, but one I grew to love. There were lots of meetings, gatherings, teaching moments, victories, defeats, lunches, weddings, baptisms, graduations, sicknesses and yes, even deaths. When I retired, I gave up being a direct part of all that. To this day, got to admit, I still miss it.

    And finally, you are spot-on on the baby front. I, like you, was totally driven to retire relatively young. To that end, I relentlessly pushed hard. Hence, having children was put on hold while I waited to have the “perfect amount” saved. My wife was 34 (I was 42) when we began trying in earnest to have a baby. But, as you well know, it’s not always an easy process and the older you get, the more difficult it becomes. We tried hard for five years. Spent a fortune and, ultimately, were not successful. Tough news for two over-achievers who had always been able to get what they want by hard work and determination. For us, it didn’t work out. So, would have to add this to my regret list.

    All in all, good advice in your “what would I do differently” blog. Hoping these words will help some readers to better understand and address the risk/reward dynamics at play that some of us who have gone before you have dealt with.

  13. Financial Nordic

    Good article, especially for us younger FI-guys/bloggers. There’s no rush :)

    – Financial Nordic

  14. Randy from Seattle

    “Woulda, shoulda, coulda.” “Hindsight is always 20/20.” “If I had my life to live over.” It is human nature to look back and rethink many of life’s personal and professional decisions. I retired six years ago at age 63 – the FIRE movement didn’t exist during most of my career and the notion of retiring at even age 50 seemed unthinkable – yet, even I, look back and play imaginary scenarios of what my life would be like with different decisions along the way. Life is life. It is filled with risk. We all must live with the outcomes/consequences of the choices we make, which is why making rational life decisions are a mark of emotional maturity. Still, the road of life is bound to be paved with some regrets.

    Introspection is how we learn. Depending on one’s station in life, you’ll never think you have enough money saved (when with budgeting you probably do). You’ll never find the perfect job (but probably do); however, there are times a change of employment can be rewarding in many ways. I know. Life is full of surprises, rewards and disappointments. No one’s life is “perfect” whether working or retired.

    But one thing is for sure: life is short. For everyone. And we tend to take it for granted. It is said that at the end of life many people have one common regret: they wish they’d taken more chances. My advice: Nothing wrong with being practical and responsible…but learn to take some risk and “color outside the lines.” It makes life’s adventure more interesting. Thanks, Sam

    1. Absolutely true about life being short and taking it for granted.

      When my friend died at 15, when i was 13, that scared me into not wasting my life. I try to appreciate everything and not take things for granted. His death is one of the reasons why I continue to forge on post work with Financial Samurai.

  15. I retired at 36 from being an attorney. I worked through my IVF and pregnancy, but stayed home after having our daughter. I worked almost 10 years. My husband is still working- he is in commercial development and likes his job for the most part. We also have very good health insurance through his job. I think my biggest regret is not starting a side hustle beforehand. Once I started IVF, I didn’t have the time or mental space to spend on anything else. I didn’t anticipate it being as difficult as it was. If I had taken the time to start something before IVF, I may have avoided some of the boredom I’ve experienced now. I also agree that having some other purpose is a good thing- eventually children grow up and won’t need you as much. I better start the side hustle when she goes to preschool this fall.

    1. Congrats on your little one!

      Thoughts on going back to work once preschool starts?

      I’m thinking of doing something myself. 29 months is a long time to be a stay at home parent so far for me.

      Utilizing this free time should be good.

  16. My spouse and I retired in our mid 40’s after we sold our business. We no longer need to work. Although we travel to different countries on long vacations, we often feel bored. Early retirement is not for everyone.

    1. Thanks for sharing. I have a really strong offer to buy my online business as well. But I keep thinking that we will be absolutely bored if we sell. There’s something to be said about doing something productive every day, and also teaching my son Abad online communications and business so he doesn’t have to go in cold after graduating from school and not having to stress so much about trying to get a job working for someone else.

      In retrospect, would you have rather held on and kept running the business? What type of business was it?

      1. Our business was in-home care. At the time, the business was often stressful and had long hours. We had about 20 full time employees and a few hundred independent contractors. The offer to buy our business was several millions dollars so we couldn’t refuse. We have more than enough for our retirement but early retirement has many downsides for us. The main one being boredom.

  17. Sam: Thanks for writing this article: I think even though FIRE is great for some people, for others it could be FINS (Financial Independent Not Slave). I was researching what to do when I retire since 2013 by talking to many who did retire early (in their 30s and 40s), and I can’t really find any whose lives I want to live – the only ones who are having fun are those who retire in their 20s or 30s and simply started their own companies, but I’m now 52 and really not in the shape or mood to work hard.

    It’s 2019 and I still come to work even though my passive incomes already equal my pre-tax income, but instead of focusing on finding my retirement hobby, I now try to find interesting teams/companies to join and fun projects to work on.

    Even though this has been hit-and-miss in the last few years (great teams became boring, good projects/products became stale and i’m too stupid/un-motivated to fix them, etc..) I end up switching teams a lot and this is my 3rd team in 6 years, I rather come to work to make money and donate to charity then staying home and watch Youtube.

    I noticed after FINS, every time I go on two week vacations, I no longer think about work and it became really hard to motivate myself to come back to work. This is a huge contrast compared to earlier during my career when I still need the paychecks, I would psychologically conditioned myself to embrace work and my coworkers and always looking forward to come back to work no matter how nasty the people or stupid the projects. Office politics that used to bother me now seemed so blah and I’m no longer affected by negative things (as much). One thing I find still important is to be surrounded by smart and interesting people, and that means young people, since most people in their late 30s and older in Silicon Valley, if they are still not financial independent and have a big mortgages, can be ruthless and not pleasant to be around, especially if you are their object of their envy.

  18. You hit the nail on the head: no one likes the corp politics and the grind, we all dream of retiring early, but how early? I agree with you that besides getting the finances ready, we need to ask ourselves questions, like what are we running away from?

    For my sister and I who don’t have children, the answer is easy: to take care of our aging parents in Taiwan. My sister hates her job (in Taipei) and I am fine with mine (in Boston). Like you said, I would rather enjoy the perks of having a sense of security for a few more years. We have argued so many times and after I did the numbers and the life after quitting my job would not be sustainable… I hope I can be patient enough to build enough wealth so I can retire early…

  19. What a great article, Sam! And a timely one. Your points resonated with me so much….how I wish I can be in your position. And to arrive at that, I really need to do something you have done already…proven!

  20. Hi,

    I just retired a month plus ago. This is one of the best decision which I have made. The sheer long hours of work (about 80 hours a week) is no joke and would definitely shorten the lifespan if I continue to do so. Life is about enjoyment and doing the things one like, as per my perspective.


  21. Interesting post. Like many I see the FI part of FIRE as way more important than the RE part. As far as I can see from reading FIRE blogs almost no FIRE bloggers actually retire they simply use FI to leave their old mainstream corporate employment and take up other more fulfilling work instead – part time, blogging, self employed etc etc. It would be preposterous for most people to retire early anyway as what would they do with their time? Most people could not just mope around for decades as their mental health would suffer. Some form of productive use of time is essential. The exceptions would be those who have a particularly demanding and all consuming hobby or non remunerative talent and being FI can avoid the need to earn.

    1. Yes, that’s right. It doesn’t seem like most are truly FIRE because their investment income is not enough to cover their living expenses. You won’t see any numerical details. As a result, there’s an aggressive push to make as much money online as possible to fill their day job income hole.

      Upon Financial Samurai’s 10-year anniversary, I’m planning on monetizing the site more by being more strategic. Lots of low hanging fruit.

  22. Thanks for this article. As a single 34 year-old with a decent job who follows the FIRE movement and saves >50% of income, this article was highly timely. The points about having children earlier, and balancing the trade-offs of working longer from the perspective of somebody who’s lived it were especially thought-provoking. Self-promotion at work was another good one – I think I’m the work quietly and expect to be noticed guy. ;-)

    1. You’ve definitely got to spend as much time selling yourself internally as you do doing good work and selling yourself externally to get ahead.

      Believing you will naturally ascend without self-promotion is likely not going to happen b/c so many other people are aggressively self-promoting. It’s just how the world works. GL!

  23. Very thorough reflection! Thanks for sharing your thoughts. I can understand the thought on having kids earlier. I was never one to have a ton after I graduated college, but I still had a ton more energy in my 20s than I do now in my late 30s. Kids really do take a ton of energy and focus when you’re with them. And they expect you to be 100% every day even when you’re exhausted or sick. You’ve done a fantastic job with your accomplishments and really do amaze us all with how much you can get done and multitask so hats off to you!

  24. Sam – it’s great that you are playing devil’s advocate vs yourself to uncover your blindspots, but really you have done very as an ‘early retiree’. You rode the SF real estate wave, milked your tenants for good rents, played and improved your tennis, dabbled in coaching and consulting, more than doubled your banking income while working less hours, tripled your net worth without salaryman W-2 income, worked with less stress, on your terms and even managed to have a healthy kid at your advanced age. One might even say this post is a humble brag. I only really agree with your point #2, you could have had kids earlier on. You can outsmart your career path and financial goals, but hard to beat biology. You are clearly in the top 1% in wealth and income and the top 0.01% in retirement age. You won the game very early and continue to be way ahead of the pack. Congratulations! Yes you could have done better, but everyone in the world except Bezos could say that too.

    1. Thanks for the feedback. Very different from the others.

      Tell me about yourself. When did you have kids if any? And when did you retire if you did? What would you have done differently? Thanks

      1. Sure, you’re welcome.
        I had my 1st kid at 35, 2nd at 37 and lost my 3rd one at 40. Life is tough, and sometimes brutal. I am 41, and not retired yet. Very very few people retire in their 40s, and even fewer in their 30s, despite the FIRE movement, besides everyone’s definition of retirement these days seems to vary. I might retire soon but more likely 45-50, as I don’ think I have enough, I enjoy my work as it is intellectually stimulating with no corporate bs, high pay and upside, 35-45 hours, enough vacation, stability, no commute, lots of autonomy and freedom.

        What would I have done differently? I wish I had invested more aggressively in stocks, coastal real estate and alternative investments. I saved 50% or more of my earnings even with very high tax rates and HCOL, but probably only annualized 5% in returns over 2 decades as I was to afraid to lose my hard earned capital. I could have had kids earlier, but I would have regretted suppressing my desire to travel the world freely during my 20s and 30s. I would have continued playing tennis instead of stopping in my early years. I would liked to have lived and worked in different places globally and in SoCal. I don’t regret not starting a business or ever owning a primary home. I don’t regret not having a side hustle as I used my extra bandwidth for family time, traveling, outdoor activities, cooking, relaxing, sleeping. If I retire, investing my portfolio will be by side hustle and I’m happy with that.

        1. Sorry to hear about your child. I cannot imagine.

          Sounds like you are in a great place with work since you enjoy it. That’s the dream scenario, to enjoy what you do!

          No need to take excess risk or save more because of your work enjoyment. I was not as lucky so I had to save a lot and take a lot of risk. Just got lucky with the 10 year bull market.

    2. Mysticaltyger

      Ehh, Bezos could have done better, too. Otherwise, he wouldn’t be getting divorced. Winning at the money and career game is not the same as winning at relationships and at life!

  25. Great article, as always. Personally, I feel the FIRE movement has altered the definition of retirement significantly and thus it causes confusion and resentment amongst people outside the movement.

    The original term retirement meant a COMPLETE stoppage of paid work (whether the work was enjoyed or not). It seems FIRE views retirement now as stoppage of disliked work but commencing work that is enjoyed (still paid / productive work though) and working is a “choice”.
    I think that’s where outsiders feel its not honest to say you’ve retired when you’re still earning money actively (be it from blogging, side hustles, managing investment properties / stock portfolios etc.). It is still active work, you’re just not working for someone else.

    I don’t mean to get all tied up in semantics, but the confusion in this simple term of retirement, does turn off the people outside the movement as it means different things to different people.

    1. I agree. I don’t tell anybody offline that I’m retired anymore. Haven’t since 2013. I tell folks that I’m a writer or a high school tennis coach. Some folks still look at my funny, but that’s truth.

      But then when I’ve said I’m a HS tennis coach online, then the Internet Retirement Police come after me. It’s pretty entertaining!

      1. Why don’t you just tell people you’re a retired financial analyst who is now blogging?

        I imagine the conversation will go something like this:

        X:Sam, what do you do?
        Sam: I’m a retired financial analyst.
        X: What!? You’re so young.
        Sam: Well, I worked hard, saved a lot of money, and invested it well.
        X: Wow, that’s fantastic! So, what do you do with your free time?
        Sam: I created a finance blog called financialsamurai.com.
        X: So how do I retire early like you? You have any stock tips?
        Sam: Just read my blog…
        X: (pulls out smart phone)

  26. I waited until age 52 to ‘take a break’. Similar to Sam, I’ve worked in the financial services (since 1986), and I’ve definitely worked hard during these years. I’ve gone on a personal sabbatical now to develop my own blog site which I plan to monetize, something I’ve been wanting to do for the past 3 years. With the hours I used to worked, there was no time to pursue this as a side hustle, so I planned carefully and then decided on the date to take the plunge to quit my job and focus on it full time.

    1. Sounds like my story; although, i haven’t pulled the trigger. Any lessons learned from your decision?

      1. The main lesson so far, consistent with Sam’s post, is to wait as long as possible to pull the trigger.

        But also don’t wait too long. I figure at 52 I’m still young enough mentally and physically to undertake starting a new business and all the learning and trials/tribulations that go along with it, versus doing it when I’m retired in my early sixties and finding out I haven’t the drive to do it.

  27. On #5, most of the media reporting on retirement and wealth are white. And most are white women. Hence; it’s natural they would cover more white people and also white women.

    If you were in Asia, you would get predominant coverage.

    So congrats for getting as far as you have despite the clear media bias!

  28. Great article Sam and definitely appreciate the references to the “prison sentence of working 30-40 years+” as well as the “rush to retire”. You’re mention of patience as well as Perspective have been where I’ve matured the most during my mid 30’s.

    You also hit it on the head with the thought of an untimely demise, but for me it was always the thought of “career shelf life/longevity”. For example, think about the high number of age discrimination cases that exist for those who are 40+ in high earning roles. But like you said, it’s your fault if you fail to forecast appropriately even if it’s an unjust elimination of your role. On the opposite end, look at md’s and surgeons who don’t really earn money (i.e. free cash flow with zero student debt) until they are 40+ but will need to work until 60+.

    In terms of your posting variety, I’m overly appreciative. For example, not every kid will be a high end pro athlete or pro blogger but that doesn’t mean there shouldn’t be other alternatives to financial independence obviously. Too many FIRE bloggers claim to be FIRE when they are actually working (i.e. blogging) and can’t maintain a fraction of their lifestyle without blogging. Yet, they speak down and never offer advice for the turtles in the race. Thx for the diversity Sam!!

    1. You’re welcome! Right now, it is smart branding to say you are a FIRE blogger or FIRE enthusiast, even if you’re far away from having enough investment income to cover your lifestyle. It’s the same thing with saying you are retired versus being a stay at home parent.

      Regardless, it’s everybody’s individual journey and only we can say whether we are satisfied with our financial progress.

  29. SkillfulWealth

    Thank you for the post. I am 38 now and plan on retiring at 42. In order to do so I have been asking others for advice on what to expect as well as planning for some “side hustle” as you call it. Not so much for the additional income, which I certainly won’t turn down, but for something to keep me busy and mentally sharp. I appreciate your insight as I struggle if I should retire earlier but am choosing to work some additional years for an added cushion. I’m glad to see that working the extra years may not be a regret.

  30. Financial Freedom Countdown

    Sam, I totally agree with your comment wrt lack of FIRE bloggers in HCOL. When I was reading about the movement I could not identify with the ones living on a shoestring budget in cheaper locales

    1. Should be something for everyone. And I’m glad to represent half of the US population and other people around the world we live in high cost of living areas who want to raise a family.

      1. Great point. Financial independence is for everyone. Just pick what you’re happy with and what you want your life to look like. No need to say “I need to live in a tiny house and not have kids” JUST to save enough money to retire early… unless that’s how you want to live! I don’t want kids, but has nothing to do with helping me retire earlier (though that’s a benefit). But, I want to make enough money to be able to give $50,000+ year to charities I believe in each year, and to spend $10,000 on flights each year, as well as $3,000/month on rent, so that no matter where I’m traveling or living, I can live in a comfortable apartment or hotel suite in a good neighborhood. And, that’s ok with me. It might take me longer to reach my FIRE… but everyone’s is different!

  31. Nice reflection post. You never know how life would have turned out if you’d made different decisions. Maybe you would have enjoyed work more and decided to keep working forever, maybe you would have become more exhausted anyway. I’ve always wanted to become an independent woman partly thanks to seeing my mom have a professional career. Now that I want to retire early or at least take the part-time route after turning 40, I wonder how my (future) children will perceive their mom and working women in general.

    1. I think your children will perceive you bc there’s always something interesting to do at home. I don’t think you will stay at home and do nothing. Everybody remains productive in some way.

  32. It’s easiest to have kids when you are young, rested, and dumb than when you are older, tired, and wise. The irony is when you are young you can’t afford it, or so you think, and when you are older it is some much more of a toll on you physically and mentally.

  33. I appreciated the candidness about leaving the workforce too soon, especially when we’re in our peak-earning years.

    I share your frustration about being unable to reach the mass market. As an anonymous financial literacy advocate myself, I feel it’s more difficult to reach one’s readers when they can’t see the face behind the words. it also limits ability to promote your site, being unable to participate in mainstream media interviews.

    Moreover, I’ve yet to even monetize my site despite some readers’ suggestions to do so. I fear that monetizing will turn my writing into industry, no longer art. Haha. I just console myself in the knowledge that the readership is limited anyway as people are less likely to get into finance than they are into fashion, gossip and shopping.

  34. Great article! It really reminded me to be reflective on all that has been going on. Sometimes you need to step back and reevaluate and continue to do so. We cannot change what is in the past or how we missed out on this or that but we can change what happens today to make a better tomorrow!

  35. “Having our son while I was still working would have likely made me better appreciate work and all its benefits more.”

    Total B.S.

    15 years from now, when your son is gone to college and your not dealing with the daily PITA that kids deliver to us you will look back and be so grateful that you were able to spend so much time with him.

    1. Probably.

      But my statement you quoted is about increasing my appreciation for work due to the stability, income, and benefits and not being so in rush to leave at 34.

      My subsequent writing talks about me likely despising work after a year for taking me away from my son. As a result, I would appreciate my early retirement more.

      1. I get it Sam. I read it as if you’re diminishing the impact that having both you and your wife at home is having on your son. I think by waiting until you were financially stable to have a child then being the primary caregivers is probably the least selfish thing parents can do.

        Not that it matters, I’m just a troll on the internet, but all that you’ve accomplished on this site, your success, your wealth, your profession pale in comparison to the effort you and your wife are putting into your son.

      2. MemberBerry42

        My wife and I are the same ages you and your wife were when you had your first child. We are trying to have our first child. When we started trying, I set a date of age 40 not to retire, but to find a way to minimize my work life through seasonal work and side hustles. I have a written list of 10 ideas. I have a little less than 3 years to figure out what life could be with less work. Once we have our first child, I will need to see if that makes sense. My plan seems to be exactly what you are wishing you would have done instead of retiring at 34. I’ll have to let you know how it goes as it happens.

      3. My children were born when I was 27 and 29 and I’m glad I become a father sooner rather than later. My kids are healthy and have a great life. As I approach 40, I don’t have the energy that I used to but I’m wiser. I’m retiring this year so that I can get rid of the stress of running a successful business and be able to spend more time coaching and tutoring my kids.

        1. Congrats on being able to have two kids and still retire by 40! Maybe you can share in a guest post how you did it. Any color you can provide in the comments section would be appreciated.

          I was definitely not ready to have kids at 27 and 29. Felt like I was still so green back then.

          1. Hi Sam,
            Yes, I’d love to write a guest post. I’d like to get my tax blog up and running first, so I’ll write the guest post before the end of the year.

            Looking back, I wasn’t mature enough to be a good husband and father at 27. On paper, I seemed pretty responsible by being married, having graduated from UC Berkeley, owning a home, and being a CPA, but I had average maturity for my age. I matured a little through the experience of being married with 2 kids, but I really started to mature when I started my business. I went from being a shy nerd in a cubicle to advising high-income clients and giving tax seminars.

            Living in the SF bay area is expensive so I think it’s even more crucial to save as much money for retirement. I found that what a person invests in doesn’t matter as much as having the attitude of being a saver. I tell clients “rich people don’t become rich by spending all their money.”


  36. I started reading Financial Samurai in 2013. I read your work (almost exclusively) because of who you are and the decisions you’ve made, e.g., living in a high cost city, having kids later, formerly having a high paying job, minority background, etc. I’ve reflected upon similar very similar “regrets” but have decided I wouldn’t change a thing.
    Although I think your content has a lot of value to anybody interested in FIRE, your “attention grabbing” articles about net worth and income can intimidate most people. Your target numbers are just too high for the average American. People like to read about the guy who retired with $2M because that’s more attainable. I like to read about stretch goals since we share a lot in common, but this is not mass market content. I’ve met or exceeded some of your numbers, but even I believe I can be perfectly happy financially with lower goals.
    Selfishly, I say don’t change a thing. You be you. If I put on my consulting hat about maximizing revenue and reach…well, I might have to charge you.

    1. I’m note sure if FIRE is something of interest to the average person or attainable for most people. But the concepts are applicable to all and can be used to I help others improve the quality of their lives.

      Oh my business standpoint, it’s probably best to go to mass market. So this is probably something I’ll do more of in the future.

    2. Such a great comment to a great blog. Fully agree – unfortunately (or fortunately?), HCOL + higher drive + having a family = very small percentage of FIRE internet people.. Another one reporting in from Australia.

      FS – Thanks for putting all this content out there, and perhaps consulting to monetise it with Ronin is a good idea!

      Just a few other 0.02c
      Some of your numbers to be honest about how much wealth is needed seem low (Australia has higher tax rate than US which probably explains it, actually our tax rates are similar our top one just kicks in at 2.2x avg earnings while yours is about 8x).

      Otherwise have an awesome day, and thanks again for the content. Peace!

  37. I quit in 2012. In hindsight, I should have stuck around just a bit longer and try to negotiate for a severance harder. I tried, but I was too impatient to leave. If I stuck around, I would have been able to get something. Anyway, it’s not a big deal and wouldn’t have changed anything much. Actually, I’d missed a really good year with my son (6m to 18m old.) I guess I really wouldn’t change anything. Life is great now. Who knows how it’d turn out if I worked longer? I might have had a heart attack before I retired.

    1. A heart attack would not be good! I remember feeling like you were much more exhausted than me, and really didn’t like work. I was more bored back then and wasn’t getting paid commensurate to my production, so was also very unmotivated. Glad things have worked out for you and your family so far.

      1. A couple of co-workers died the year before I left. One went in to get minor surgery and never came back. Another one got cancer. Life is short.
        Yes, I was really dragging back then. It wasn’t a good situation so one more year would feel like 5 more years… It’s too bad your book didn’t come out a year before I quit.

  38. I’d do differently: 1) live it up that last year like you said – more (justifiable as part of my job) travel, meals and entertainment on the company dime. 2) be even more aggressive in my severance negotiation. 3) plan to fill the void with non-work interests for a lot longer.

    All told though no complaints.

  39. Damn Sam! You’re so hard on yourself! I think every time you start to doubt yourself, just look at your son and the life you’ve carved out. You’re free! You’re a present parent with time, not a zoned out zombie from work! That is worth all the money in the world to your child.

    Every point you think you shoulda/woulda/coulda actually looks amazing to me but then I’m on the outside looking in.

    1) Why am I rushing to retire early? Am I running away from something?
    I’m running away from corporate politics and bosses.

    2) What will I do after I retire early? Am I running towards something?
    Write my novels full time. I am one of those people who are never bored. In fact I look forward to moments when my mind is not engaged, not overthinking, not stressed. I am running towards happiness. Hopefully I’ll have a nice house and yard by then. Not having to be forced to wake up every day and pretend you’re happy to your colleagues.

    3) How will retiring early change my life for better or worse?
    I will be less stressed which is good for my chronic health condition.

    4) Am I sacrificing too much to retire early?
    The answer would me no. I am more important than work.

    5) Have I gained enough perspective from those who’ve already retired?
    Yes. I have. I did the holiday break and found myself fully occupied from hobbies to writing (the writing research alone takes up a good deal of time!).

    Book link under website.

    1. Sounds like early retirement would suit you well! Glad you have thought things through. When is your target retirement date and how old will you be?

      I don’t think I’m being too hard on myself. I’m just thinking about things I would’ve done differently. It’s enjoyable for me to pontificate during the dog days of summer.

      1. I’m aiming for FI by 40 because the economy is tanking and there’s nowhere for me to run (emigrate). I won’t have enough in any first world currency to remain retired or even buy a house! At the least I will have enough to eat and live in my country but not if our currency continues devaluing.

        Your post sounded so serious like you had made huge mistakes and are unhappy. It’s good to think about what could’ve been but I hope at the end of your thoughts, you come away realising that you made the right choice for you.

        Sam, one more thing, I was recently in Central Park and you were right. Nannies to the left and right on cellphones or chatting away not paying attention to their charges and some very irritable. I only saw 2 nannies paying attention and enjoying it!

        1. Thanks for the feedback. I don’t believe I’ve made huge mistakes. Nor am I unhappy. I just like to reflect, and reflecting makes me happy because I know some of these points will help someone else on their journey to financial independence.

  40. Observations:

    I’m 67, at 42 you could start all over again and correct your mistakes.

    I’ve never worked for anyone other than myself. The word ‘severance’ has no meaning to me.

    I would expect you are in the 1% of Americans in terms of life and lifestyle, so I am not sure many can relate to you.

  41. “But just like at work, those who self-promote the loudest, tend to get the most attention. While those who stay silent and believe their good work will get them recognized usually get left behind.”

    This is a harsh reality for introverts. A little self promotion (I.e. communication) goes a long way toward rewards at work. The key is to do it in a way that feels genuine and adds value to your organization (e.g. a weekly summary of your work to key stakeholders).

    1. I can see that to be true. I’m not even an introvert, and I have a difficult time self-promoting.

      But once my son was born, it became easier because I Had the best reason to self promote ever. Doing things for someone else you love is truly one of the biggest motivators.

  42. Good article. Rather than retire early, is it fair to say you’ve transitioned into a different career as a small business owner/entrepreneur between FS and real estate? Maybe that would help with the “got out too soon” nagging feeling.

    1. Yes, I can reframe my occupation in that way to make myself feel better. But this post isn’t really about making me feel better, it’s more some revelations to help others make a better decision. Thanks though!

      I do forget how miserable I was at work in 2011/2012, so that’s another thing. Time heals most pain.

  43. Have no regrets, son. You’re doing phenomenal for someone who “retired.” You’re making as much if not more than you would be if you stayed traditionally employed, can’t be fired, and earn additional streams of passive income whether you sit at a desk all day or not. I believe that fire in your belly that you’re feeling is what propelled you to take charge of your finances and professional life, so I certainly understand. But take a true look at what you’ve accomplished and the current state of your portfolio and find some solace with that. Waiting it out another year at your fulltime job might have delayed all the mechanisms that are currently in place with your life. “Woulda, shoulda, coulda” are just fleeting thoughts.

    1. Thanks. I do like the fact I can’t get fired. But my wife can always fire me, hah.

      I like to spend time reflecting during the summer months. And then take action to rectify things over the coming years.

      What’s your current situation?

      1. I hear ya. I’ve been self-employed for over five years now, and I thought one of the biggest benefits was doing away with those bi-annual performance reviews. It turns out, my wife has taken them over from my old bosses and runs them on a daily basis!

        My current situation is that I’m in my mid-40s, married, and no kids. I live in the southeastern region of the country, so my COL is roughly about a third of what it would be in the Bay area or NY. For my age, I have an above average portfolio with a healthy mixture of cash/CDs, traditional investments, trusts, alternatives (real estate crowdfunding), and one property (primary). I have no personal debts, one fully paid off car, and about a 70% LTV ratio on my residence.

        Sometimes my work (voluntarily and involuntarily) allows me to take hiatuses and assess everything, but one significant benefit is that it allows me to see how much I would really need in retirement and beyond. Obviously not having kids is a huge factor (I did start and am ongoingly funding a 529 plan for my niece), but I’ve also have eliminated lifestyle aspects that my younger self enjoyed more than my current self (higher end restaurants, clothes, etc.). That being said, I never truly was indulgent nor into “toys” as some of us are, but I certainly do not live like a monk.

        Currently, I am attempting to establish other income workstreams similar to what you have done, but I still enjoy my primary occupation so there are no immediate plans to let that go. If anything, it continues to challenge me in a way that being a full-timer at a buy-side firm, bank, or asset management firm would never have done. (I think you can relate.)

        Thanks for all of your financial insights. I hope you continue to do so in some capacity even if or when you decide to sell FS.

        1. It’s great you still enjoy your work. I don’t know too many people who do after more than 20 years of working.

          My colleagues would have to be some of the most amazing people over for me to go back to work and spend 10 to 12 hours a day with them.

          Good luck on the establishing new income streams!

  44. “Retired” June 2018 at 50yo. Was doing the ‘one more year’ thing for a couple years and a couple of reasons but I finally based my FIRE decision on answering two foundational questions:

    1) How much money is enough? There are lots of articles here and elsewhere on approaches to determine your ‘number’, but, one can always make the case you need a little bit more or y you have more than enough today – depending on your lifestyle decisions and sacrifices you may be willing to make to that. Ultimately, it comes down to a personal decision of your own.

    For me, the FI number is high (eight digit FI) as this number truly minimizes almost all market risks and allows one to freely travel, have nice things, and also do some charitable giving of consequence. And, eight digit FI is really my definition of a true ‘millionaire’ today = adjusted for inflation, $10mil today equates to roughly $1mil or being a ‘millionaire’ at the end of WWII when that valuation really meant something…

    Anyway, once you answer this first question for yourself, then the next question is really the key to successful FIRE….

    2) What makes you happy? I believe this is the core question of a successful FIRE decision. Some people enjoy what they are doing. Even if they feel they can comfortably answer #1, they still decide to continue working hard at their current job because they like it and they can’t envision something better they’d like to be doing.

    For me, I was really passionate about work for many years but eventually grew weary of the politics, extensive travel, long hours, business calls at all hours, etc. (and my wife and I became empty nesters which is also a big factor for many I think)
    Although I could have retired earlier from a purely FI perspective, this question is really what drove my decision – even though I couldn’t really answer it!
    I knew I no longer wanted to continue to do the job/industry I was in so I negotiated my exit (very happy with that) But, now 1yr into FIRE I am still trying to figure out what really makes me happy. Working my way through it but surprisingly hard to answer this question as a type A personality who still would like to be being busy on activities of consequence.

    Some people seem to know very clearly what they want to do before they make their FIRE decision but I suspect many (most?) do not. Appreciate people’s input on this….

      1. Hi Sam,

        Just for interesting debate, I created a new a new post to your “3 million is the new 1 million” blog.

        I try to make my case in more detail that ’10 million is the new 1 million’ if one wants to live a truly luxurious retirement lifestyle. I hope it generates some discussion.

        Anyway, keep up the great work! Really enjoy your thought provoking posts on many topics. I thought about starting a blog myself but realize I am not nearly as engaging a writer as you and others!

        1. I think the best thing people with time can do is to figure out how they can truly HELP people. Whether that is finding businesses you can be an angel to, non-profits where you like their work, or actually volunteering as a consultant or mentor. Try to figure out how you can make a DIFFERENCE in this world. Make that your goal. It is a puzzle you can never perfect, but I think that kind of thought process is worth pursuing. If you do it, can you let me know!?

    1. I was in a similar situation as you about 5 years ago and here is what I did to find my happy place post retirement. I asked myself what were the happiest 10 days of the last 10 years of my life….for me they all revolved around being on the water and exploring new places. Being an avid boater this lead me to learn how to sail on the big water. In doing so through a series of just living life events I met my soon to be wife, she is ridiculously amazing and in about 2 years she can pull the retirement plug as well. With 8 figures we of course already could, but she’s less than 24 months away from a lifetime retirement benefit that’s worth a couple million and loves her gig and only works 50 hours or so a month. This leaves us plenty of free time, this year we will go sailing in Europe and then again for a few weeks through French Polynesia. We are treating this time as practice and making sure it is something we would both want to do full time with a home base someplace tropical to take breaks to. In the mean time I’m doing a little consulting and its a ton of fun to still get a little challenge and stay connected to the industry your expertise is in…plus you end up making a ton for working 1/4 of the time. Good luck finding your happy place, I guarantee you though it is not in a cubicle or having customers/bosses breathing down your neck about some project that is truly meaningless in the grand scheme of life.

      1. Hi nbsdmp,

        It’s a good suggestion. I think most of my top 10 would be around traveling which I am doing a lot of now. Also a bit of competitive racquet sports – which I am also doing now but realize as I get older, that will become more difficult. However, those don’t necessarily give me meaning or activity of consequence in the life.

        Definitely more confident each month that I don’t want to go back to the 9-5 rat race but less confident that I wouldn’t want to do something more ‘work’ related. I got my first BOD position this month. That has been a great experience so far and I’d like to do more of that. I’ve also been doing some consulting which has also been rewarding but not that consistent – at best a few hours per month. Lastly, I’ve been looking at charitable organizations and ways I can contribute. All these are still a work in progress but my thought direction so far on how to engage more in ‘activities of consequence’…

        Doing lots of travel now (almost once/month international trip) but I don’t see that continuing forever – maybe another year (2.5yr total) until I’ll scale that back. Your thought on how long the travel bug will stick with you…?

  45. Great post, initially I looked forward to reading things that I’d empathize with but oddly I didn’t share any of these regrets. I’m guessing because I worked a long career until I was 60 to retire. I still considered it early because I had planned to work until 70, something very common among oil industry executives. I did work one more year for the last two years I was there, and I made twice my annual income both years so that certainly boosted my investments significantly. I also left exactly at the point our industry slid into a depression so that if I had stayed a third “one more year” my compensation would have dropped to only 40% of what it had been. So I got out when the getting out was good! We did have our three kids while I was working and I had prepped my side gigs long in advance, over ten years in planning. Didn’t do the real estate thing, it just isn’t something I like and I don’t share your acumen or pleasure in it. I’m too lazy to be good at it. But the only reason for no regrets in my case is I loved my job and it was too fun to quit earlier. That’s not talent, just circumstance. It is fascinating to see your perspective, I am certain I could not have navigated retirement at your age, it takes extreme discipline I think, something you’ve got that isn’t my strong suit.

  46. I would not be so harsh on yourself Sam. Looking through the retroscope with 20/20 hindsight vision makes everyone have regret.

    You have truly won the game and should be proud of your accomplishments. Not many people could have done what you did and help as many people as you have.

    I had my daughter at the age of 34. I thought the stress of medical school and residency would be too tough to start a family.

    1. Tell me more about having your daughter at 34 and the stress of med school.

      You glad she came when she did? Or would you have preferred later, like my situation at 39?

      1. Although there were people who were married and had kids during residency it was a lot less common in medical school (though some did).

        For me the financial stress on top of having to cram so much knowledge in so little time in medical school and awful hours during residency would have made me feel guilty about leaving my partner if I had one at the time to take care of the kids on her own as well as spending so much time away from the baby.

        I am happy about having my daughter at 34. When she is 18 and graduating and going to college I will still be relatively young at 53 or so. For me I didn’t want to wait too long and be over 60 when she graduates high school.

        Lot of docs start families late because of the extra training

        1. Bob, from New Joysie

          Med school and residency – can’t imagine having kids during that time, especially if you had a working spouse.

          Two of our 4 were born while I was in law school and working (as was my wife), but LS was seriously a cake walk, nothing like getting through MS/residency.

          Our first was born when I was 34, then the 2nd at age 35 (16 month spread), then 37, then 40.

  47. Great post Sam! Since I’ve been saving for retirement from around 15 or 16, I used to say, “I’m going to be PISSED if I can’t retire by 45.” A lot of this was due to our frugal lifestyle that was self-imposed. Now that I’m 3 yrs into an “extended break”, I still don’t feel 100% comfortable with it. I’m only now re-evaluating what options might work best for me. Especially, since my wife is still employed full time and is unsure of when her retirement date might be. Thanks for taking the time to put it together and some great advice over the years.

  48. Writing from my home in Zurich, transferred from my company’s LA office last year. Really loving the experience. I have a 2 year old son and one benefit of living abroad is my son is learning a foreign language in a native environment. Definitely not too late for you to take a foreign position for a few years if you feel like that would be rewarding. And I think we all wish we would have gone harder on RE in 2012…just got to be glad for the acquisitions I did make. Anyway, I appreciate the candid perspective that comes through in your writing.

    1. This isn’t to put down Sam in any way, but it is way too late for him to take a foreign position for a few years. He is almost certainly unhireable in his old industry. In any competitive, dynamic white collar business you have a 2, maybe 3 year window to go back in. After that, technology, strategy, and contacts have all mixed on. He has nothing to offer that a younger version of him at a firm (or from a competitor) wouldn’t provide.

      The moral of this post is do not leave a 6 figure job expecting it to be available again at any point in the future.

      1. No problem. Can you share more about yourself as to why you think people over 40 years old are un hireable?

        Did you go through a Situation of trying to go back to work after 40 and could not due to an extended break?

        1. No, its not the over 40 (though that is an additional bias), it’s the time out of industry. I’ve interviewed dozens of women (mostly, some men) who left work for an extended time. There is no reason to hire them over someone with better current contacts in the industry.

          “Important people like to deal with other important people. Are you one?”

  49. This is a very helpful post. It particularly spoke to me, because I’m currently in the midst of OMYS (one-more-year syndrome). Your suggestion of taking a long vacation to re-charge is great, and one I would definitely recommend to people who aren’t quite ready to retire — I’ve found that real vacations, though they may be a bit expensive in terms of lost income, pay for themselves many times over in that they allow me to keep enjoying my work rather than quitting due to burnout.
    So here’s my question: given that you would have stayed at least one more year, how would you ultimately have known when it was time to go (given the wisdom of hindsight)? Would there have been a number (perhaps as a ratio of passive income to annual expenditures) that you would have felt comfortable with? I definitely don’t see you as a 25x expenses guy (you seem more holistically oriented, and also a bit more cautious), but is there a ratio you would currently recommend to us OMYS sufferers who are worried about sequence of return risk in today’s environment of elevated PE ratios, etc?

    1. Good question. Will have to think about it more. Maybe even in a new post!

      My severance was my catalyst. No severance, I would have gutted it out for at least one more year if not 6.

      Other catalyst may have been hitting a certain traffic or revenue target on FS.

      I’m not a 25X guy bc that is a bare minimum barometer. It’s a good one, but I had thought way beyond 25X by age 30.

      Let me get back to you.

  50. Sam, interesting perspective. I retired 368 days ago, and ironically achieved all of your “Things I’d Change” excluding SanFran real estate. It’s been a very smooth transition into retirement, and I have no regrets.

    Most important of all your points raised: “Live In The Present”. Don’t dwell on regrets from the past, and don’t waste all your life waiting for a tomorrow that may never arrive. Great post.

    1. Congratulations! I think age of retirement has a lot to do with it. And at some point, one will have regrets on whether they should have retired sooner. Do you have any of those regrets of working until you did?

      1. Interestingly, I’ve never wished I’d retired earlier. I was always intentional in enjoying The Moment, and made sincere efforts to treasure life as I lived it. We took our full vacation time every year, traveled the world, and enjoyed the work I was doing. I’ve been fortunate, and I recognize that. I sometimes worry that die hard FIRE advocates sacrifice a bit too much of The Moment for The Future. Life’s an interesting game of balance, and I’m pleased with how I’ve played the game thus far.

  51. Great reflection. I really enjoyed reading this one.

    On #2, I like what you wrote on having kids sooner. While there are clear benefits of waiting (getting to be a SAHD, which you’ve written very nice posts about), the greater shared overlap of life from earlier fatherhood is also worth a lot. Of course, there’s no single best way to do it, and the path you’ve taken has created great financial stability and opportunity for your son, maybe more than if you’d had him earlier (and/or had another). But it’s interesting to hear you reflect on it from the perspective of your 40s.

    More generally, why do you think the conversation is so focused on retiring early, as opposed to reducing hours or just working less? Why not reducing to 3/4 time, or 1/2 time? It seems to me that most people should aim for what you’ve done, which is generating a new career or work opportunity with less-than-full-time hours. That seems more middle-ground and much more fulfilling than full-on retirement.

    Anyway, just my two cents. Again, I really liked this post.

    – DeForest

    1. I absolutely agree that there’s an under-discussed middle ground between full time and no time. Full time is going to get old, but no time sounds boring. I’m 10-15 years away from needing it, but the fact that I don’t have an appealing Plan B worries me.

      Sam, loved this deeply introspective post. You’ve given me a lot to chew on.

    2. I would imagine in many industries part time is just a myth like remote working is for many. Before I retired I reduced my hours to 4 days a week. All that did was reduce my paycheck by 20%, my workload did not change, nor did expectations of what I should be able to accomplish. If in any kind of senior position reduced hours would be tough to negotiate, especially if staff supervision is required. I can’t imagine in tech or finance these reduced hours would be a reality.

      1. This is spot on. Moving to a reduced hours role could be an alternative to negotiating a severance, but it is no way to sustain a career. As soon as somebody is unavailable even a day a week, they get put in this “other / weird / not part of the team” pigeonhole regardless of their output. If you’re going to do it, stick to your guns, work only your set hours, and run out the clock. Don’t do this thinking it is sustainable.

    3. I think the ideal number of hours to work a week is 20. Maybe 25 hours. We get at least 80% done if we work 3-4 hours a day, was my case.

      I would have love to work three days a week and get 40% less pay. Unfortunately, the workforce is just way too competitive and everybody wants full-time all the time. But maybe that’s a blind spot of mine because I think several female colleagues work part time.

      I never bothered to ask. The solution or a bid to figure out a new job within the firm that was less stressful with less travel to be at home with family more.

      1. Hi Sam, Catching up on some of your posts, which I always enjoy and want to say “thank you!”.

        Perhaps there are some nuances to working part time? I would have loved to find a way to tele-work during my career, but as a veterinarian, it’s not possible. Working 2-3 days a week, though, is, when I want to slow down a little (very possible, now that I’m 53). I think your observation about females and working fewer hours is on target– it was only when we (women) began to dominate in the profession that part time work was not looked down upon.

        Thanks again!

  52. Retired in Jan of 2019, at 43. Was a NYC cop for almost 22 years. Wife retired 3 years ago at 41.

    No regrets from my wife. She was running away from finance/wall st. I wasn’t really running away from anything, as my gig was quite nice and very close to home. But, I was getting bored and wanted to spend more time with wife and kids.

    Anyway, I’d already worked 2 more years than required/expected. So, one day, it just said screw it.

    No regrets so far. Keeping busy with daily workouts, as I’ve done for most of my life. Started playing the piano; got back into remote control cars with my buddies/fellow retired cops; I volunteer a couple times a month. Also, we just started planning more trips overseas.

    Maybe I’ll feel differently in a few years? Right now, no regrets. Except, last month, I suddenly started feeling like I “needed” a paying job, despite keeping busy everyday. But, I talked to a bunch of retirees and they said it was natural and to just keep busy.

    1. Congratulations! I found that the first couple years after early retirement was more like the honeymoon. So it was hard to know exactly how to feel about the experience. But after about three years to five years everything is pretty calibrated and you adjust. So it‘ll be interesting to see how you feel several years from now.

    2. Congrats on retiring so young and enjoying what you are doing post retirement. Just curious – how good is the retirement benefit from your NYC Police pension? I ask because I am a public employee in a different state and always heard NYC had a very good benefit.

    3. Congrats John! I posted below in this thread. I’m a retired firefighter from a big city FD in Florida. I was a military reservist my whole career (even before I started on the FD) and my last 6 years on the FD I was actually on military leave. I’m still on active duty and will be able to collect my military pension at the age of 50 (most reservists have to wait until 60). So, I’m almost 49 and will have two pensions at the age of 50 (plus a VA disability rating which will be another $1500/month or so). My biggest regret about leaving the FD early (at 20 years) is not getting any time on the DROP (Deferred Retirement Option Plan). As a lieutenant I could have walked with another $300K if I did 5 more years…but I’m happier on active duty so leaving the FD early was probably best.

      Good luck in retirement, sounds like you planned well!

  53. 1) Why am I rushing to retire early? Am I running away from something?

    Because I am lazy. Running away from hard work.

    2) What will I do after I retire early? Am I running towards something?

    Exercise, travel, family, friends, sports, volunteer.

    3) How will retiring early change my life for better or worse?

    I’m not sure yet. Good question.

    4) Am I sacrificing too much to retire early?


    5) Have I gained enough perspective from those who’ve already retired?

    Probably not. I should ask more questions about the negatives of early retirement.

    Thanks for this post it’s really insightful

  54. Question for you Sam: Have you read the book titled “Straight to Hell”? It is by John Lefevre about his time working in debt capital markets between 2001-2010. He seems to have a similar timeline as you in terms of work experience. I believe he was with Citi in NY, London and Hong Kong. I just read this and found it was very funny and crazy….

  55. Good article Sam.

    I’m 48 and will retire next summer from the military. I have a job lined up making low 6 figures and plan to bank my pension checks for as long as I can…but I want to get out (retire) within a few years. One thing that almost everyone I talk to who is retired says is “make sure you have a plan”. Basically, a lot of these people who retire (at any age) get bored. So that’s my priority right now; figuring out what I want to do with my time. I don’t fish, golf, hunt, play video games, have poker night w/ the boys, etc. So I need something to do!

    1. Hi Chris,
      I have the similar perspective and just created a post to expand upon this point.

      I think “the” key question to FIRE is clearly answering the question of “what makes you happy?” And, I think this is surprisingly hard for most people…

      1. some dude on the internet

        I retired 6 years ago at 46.

        I can’t for the life of me understand the root of questions like this, but I hear them all the time.

        Being retired is the best thing I ever did.

        What is it about the human species that seems to need someone to tell them what to do all day, in order to be happy?

        If you have the wherewithal to retire, you have the wherewithal to live a life that doesn’t include someone telling where to sit for at least 8 hours each day.

        1. Yeah, that’s what I said, “Hey, somebody tell me where to sit for 8 hours a day”.

          I’m talking about “doing something”. I don’t play golf, I don’t fish, I don’t play video games, I don’t have poker night with the boys, etc. I go to the gym and I run – usually 40+ miles per week, so those two activities kill about two hours/day. I’m sure I can find things to do, but I want to be productive or “have fun”. Some people volunteer, some work part-time, some start a business, some travel, etc. I’m sure I’ll do a combination of those things….but right now, at 48 years old if I walked out tomorrow I’m not sure what I’d do with my time besides go to the gym and run. I’d occasionally surf, travel, go to concerts, etc (but I don those things now). I’m simply talking about filling my days…. I’m glad you had no problem finding something to do besides being a d*ck on the internet.

          1. Some dude on the internet

            Well, I think I see your problem.

            But I don’t think it has anything to do with whether or not you retire.

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