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 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.
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.
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.
Financial Samurai says
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.
Second Career Liz says
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!
Financial Samurai says
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!
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.
Money Ronin says
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.
Amanda G says
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.
Kevin B says
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 …
Financial Samurai says
I will say that having someone to share your life with during retirement is really great. This is why it’s funny to see WiFi (Wife Financial Independence) going around where the wife works and the man claims he’s retired.
Kevin B says
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.
Bettina Stahl says
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.
Financial Samurai says
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!
Taylor Anderson says
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
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 !
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.
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.
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 :).
Financial Samurai says
Good health is definitely a big one. I have a whole post dedicated to health:
The Health Benefits Of Early Retirement Are Priceless
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
D.D. Luby says
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.
Financial Samurai says
Thanks for sharing your thoughts! Sounds like a life well led, and one with plenty more great experiences to come!
Financial Nordic says
Good article, especially for us younger FI-guys/bloggers. There’s no rush :)
– Financial Nordic
Ann C says
I “retired twice” got bored and went back to work, so you can always go back :)
Randy from Seattle says
“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
Financial Samurai says
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.
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.
Financial Samurai says
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.
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.
Financial Samurai says
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?
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.
Financial Samurai says
Gotcha. That sounds like a very stressful business I could not handle.
Boredom is real. Check out: The Negatives Of Early Retirement Nobody Likes Talking About
Boredom is one of the highlights.
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.
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…
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!
Financial Samurai says
No need to wish! Make it happen! GL.
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.
Financial Samurai says
Congrats! The first 6-12 months is an amazing time. However, your views will change over time. Take note of them!
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.
Financial Samurai says
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.
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. ;-)
Financial Samurai says
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!
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!
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.
Financial Samurai says
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
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.
Financial Samurai says
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.
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!
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.
Financial Samurai says
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!
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)
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.
J. Quinn says
Sounds like my story; although, i haven’t pulled the trigger. Any lessons learned from your decision?
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.