How To Plan For Your Retirement The Second Time Around

How To Plan For Retirement The Second Time Around

The main reason why I've gotten more conservative with my investments is not because valuation for the S&P 500 is near an all-time high and earnings growth is decelerating.

Nor have I gotten more defensive because housing inventory has shot up across major parts of the country and prices are clearly declining.

No. The main reason why I've gotten more conservative with my investments is because I'm very close to retiring for a second time.

Let me recap my background and share some retirement preparation plans if you're also planning on retiring soon.

The Return To Retirement Living

After first retiring in 2012, I spent about nine months living the early retirement lifestyle. I wrote a book about my experience negotiating a severance and my wife and I traveled around the world for about 12 weeks.

By the beginning of 2013, I no longer told anybody I was retired. People gave me funny looks whenever I mentioned I had left corporate America for good. I also felt stupid saying I was retired in my mid-30s.

I longed for more purpose and a more acceptable identity that didn't require explaining my background each time. So I decided to pivot from early retiree to full-time writer and entrepreneur.

Almost immediately, I felt better about my new role in the world. Growing Financial Samurai all these years has been incredibly fun.

On average, I spend about three hours a day on the site, which is one of the main reasons why it's been so enjoyable. If I was forced to work 10 hours a day on FS and commute, I'd have probably started hating it after a year.

Having something intellectual to do, especially after my son was born in early 2017, has been a blessing. Being cooped up in the house all day is no fun for this stay at home dad.

Another thing I've enjoyed doing in my second career is mastering everything that relates to online publishing. From writing, to marketing, to business development, I now have a strong grasp on all the things it takes to build and run an online media company from the ground up.

Although it's been seven years since I left full-time work, it's been almost 10 years since I started Financial Samurai in 2009.

Back then, I had told myself that if I could reach various stretch goals by the summer of 2019, I would give myself the luxury of taking it easy once again.

The main stretch goal was to regularly generate over one million organic pageviews a month.

As fate would have it, I have the option to let go this summer and fully retire once more.

The Origin Of Luck And Fear

What I realize now is that whether by coincidence or on purpose, I'm living my life in 10-year cycles.

I first got a job out of college in 1999. Getting a job at a major investment bank was mostly luck because graduates out of a non-target public school usually don't get these front office jobs in NYC.

Although there was the dot com bust in 2000, the 10-year journey from 1999 to 2009 was an overall positive for my career.

After about two years at the first investment bank, I got my second lucky break when a recruiter placed me at a new firm in 2001 in San Francisco. If I had not changed jobs, I would have been kicked to the curb after my two years were up.

Then, of course, everything started crashing in 2008 – 2009. I was scared for my future given Lehman Brothers, Bear Sterns, Washington Mutual, and a bunch of other firms had collapsed. Friends were losing their jobs, their houses, and their savings.

Somehow, I managed to escape seven rounds of layoffs in a two year period at my firm. My immediate boss had left the firm to become a client the year prior. Thus, if the firm was to lay me off, it wouldn't have had anybody to run the business. Another lucky break.

I was so worried about my future in 2009 that I decided to finally start Financial Samurai, an idea I had had since graduating from business school in 2006, but had been putting off.

If you look at the chart of when Financial Samurai was started, you'll see that it was started at the exact bottom of the previous financial crisis in July 2009.

To start Financial Samurai at the bottom of the last financial crisis and then have a massive bull market help propel the site forward was also tremendously lucky.

Yes, I've spent many hours developing this site, but I fully admit that most of the growth is serendipitous. Living in San Francisco, the epicenter of technology and financial innovation has also helped me develop some key industry relationships.

If you started something in 2009, it would be relatively hard not to have successfully grown your business or your wealth.

The tailwind is like having a mentor who is actually the CEO of your company and also happens to be your dad who wants to give you the company. In such a scenario, how can you fail?

Since 1999 I've constantly wondered when my luck will run out. I've already talked about experiencing survivor's guilt after my friend passed away when I was 15. All the good that has transpired since has only made me wonder more about the future.

Don't Push Luck Too Far

Despite the good fortune, 2009 still burns deep in my psyche because of how badly my finances got crushed. Perhaps this is how survivors of the Great Depression felt for the rest of their lives.

I don't want to ever again suffer through a 2009-like experience. I recently got a taste of temporarily losing lots of money in 2018, and that was enough.

I'm so thankful we've recovered and I no longer wish to push my luck.

2019 is the year where I plan to retire again after 10 years of running Financial Samurai. I'll either sell the site, write less, or hire talented staff writers or guest writers to write using the Financial Samurai principles.

It's been a great run, and I want to leave on an up note. If you are thinking of retiring for a first or second time, here are some things you should consider.

Retirement Planning Checklist

1) Adjust your risk exposure down.

As with any classic retiree in their 60s or 70s, it's important to take down risk exposure because you no longer have the ability or the desire to work any longer.

Measure your risk tolerance in terms of the Financial SEER ratio. In other words, how many months are you willing to work to make up for a potential loss in retirement.

Once you've retired, you don't want to be forced to go back to work. Giving up precious time for money is one thing, but so is the embarrassment of having to go back to work because of poor financial planning.

Debt should be completely eliminated or reduced to a level that will never be able to sink your finances.

2) Calculate your various income streams.

If after taxes, your income streams can sustain your desired retirement lifestyle, you're golden. If not, keep working or build more side hustle income. To be conservative, it's best to have at least a 20% cushion above your living expenses.

Plan out a tax-efficient safe withdrawal strategy based on a combination of your pre-tax and post-tax retirement accounts.

Those who want to stay conservative should try to only live off their after-tax passive income and never touch principal. Only when Required Minimum Distributions are in effect should you start drawing down principal.

3) Make sure you've accomplished all your goals.

When you leave your profession, you want to leave with as few regrets as possible. The best way to leave with few regrets is by fulfilling your stretch goals.

One of the reasons why professional athletes retire after winning the Super Bowl, a Major, or the NBA Championship is because there is no greater glory. During the rare times when such a champ tries to make a comeback, it's often a sad affair filled with struggle.

If you cannot reach the pinnacle of your profession, one thing you must ask yourself is whether you'll be leaving the place better than when you first started. If the answer is no, then you must take measures to rectify or continue working.

Retiring when your fund or company burned to the ground will make you feel like an unsettled ghost, unable to rest in peace. You want to go out on your own terms, which is why negotiating a severance can be incredibly powerful to your mental well-being.

4) Ensure your legacy will be left in good hands.

The longer you've worked, often the harder it is to walk away. The transition is made easier if you have someone you've trained or trust to take over once you're gone.

The last thing you want is to have all your good work get undone by someone with a completely different philosophy. If this happens, you will feel as if you wasted many years of your life. Find an excellent successor and don't leave until you do.

5) Have a next purpose.

You don't want to retire into nothingness. Going from working 12 hours a day to having all the free time in the world can be very disconcerting. After being so used to structure for so long, you might start wondering what else is there to life. Some of you might even get depressed if you don't have purpose.

Instead, diligently map out your retirement goals months or even years before you retire. You want to retire to something, not from something.

Start talking to people in the fields that interest you when you still have a job. Once you retire, it may be tougher to build relationships because society tends to look down on those who no longer work.

Having a clear purpose in retirement will make your remaining days at work even more meaningful. You'll also experience a much more joyful retirement life.

Retire As Many Times As You Can

There doesn't need to be only one retirement in your life. Instead, I encourage you to retire multiple times because that means you're challenging yourself with new endeavors.

Whether you decide to retire for six months or for six years is up to you. There's nothing more professionally fulfilling than mastering a new skill and enjoying its accompanying rewards.

Skills are highly fungible today thanks to technology. So long as you're able to work hard, communicate intelligently, get along with others, and produce more than you cost, you can do well at almost anything because the rest is learned on the job.

I truly hope we never see another 2008 – 2009, nor am I anticipating a correction of such magnitude. I'm just not willing to take unwarranted chances given I'm satisfied with what I have.

With now a wife and son to take care of and potentially zero active income if I sell Financial Samurai, I can no longer afford to take any excess risk. To go through another 40% loss as I did in 2009 at this stage in my life would be devastating.

Our passive income should keep us afloat, but I haven't truly been able to means test it yet due to my severance that paid out from 2012 – 2017 and the active income I've been generating from Financial Samurai.

From July 2019 – July 2029, I plan to spend my 40s primarily focused on raising my boy and spending time with my parents. If we relocate to Hawaii, we'll have more than enough activities to keep us busy in our second go around.

Let's pray the next 10 years are as lucky as the past 10!

Related Posts:

The First Rule Of Financial Independence: Never Lose Money

The Fear Of Running Out Of Money In Retirement Is Overblown

Readers, anybody on a 10-year cycle like me? How do you plan to ensure good fortune for the next 10 years of your life? Anybody retire a second or third time? How long did each retirement last and what did you do? What else should people do to prepare for retirement?

About The Author

101 thoughts on “How To Plan For Your Retirement The Second Time Around”

  1. Congrats on the great run, Sam!

    It will be interesting to see which of these you chose:

    “I’ll either sell the site, write less, or hire talented staff writers or guest writers to write using the Financial Samurai principles.”

    Sorry our paths never crossed. Somehow, I always figured they would. :)

    Enjoy the next decade!

  2. Congrats, Sam – I’m a long-time reader and have drawn a ton of inspiration from your site. I’ll be 45 in November and tendered my early retirement letter on March 1st, effective on June 30th. Planning on taking the rest of 2019 to re-charge then figure out what’s next. My wife has been incredibly supportive – she’s the only one who knows the toll that executive-level work for a long duration has taken on me (and us). I’ve been extremely lucky as well. Wish you all the best.

  3. Sam, in your interview with Art of Manliness podcast you recommended an asset mix of
    for a family in their 30’s/40’s

    5-10% CDs/money market
    30-40% Equities
    30-40% Real Estate

    What about bond/fixed income was that included in your 30-40% Equities mix or was bonds not included at all? This was different from your recommended networth allocation by age framework articles that included bonds.
    Seemed kind of off it was not included.

    1. The podcast was edited as he asked about what type of asset allocation I recommend. The thing is, the asset allocation depends on your age, risk tolerance, etc.

      So I’d follow the charts and posts I’ve writing on FS for specifics. thx

  4. Regardless of your decision, I wish you nothing but happiness. I would also like to share an article with you that I put on Quora, that was later published on Business Insider that I think speaks to this point:

    Talented people such as yourself will never have a problem making money – unfortunately, none of us can make more time.

    I only wish I had done the same.

    1. Thanks for sharing. It is partly because I fear regret, that I’ve been so diligent in planning for the future. For example, I’m a HS boys tennis coach partly because I want to know what it’s like to coach/mentor teenage boys in preparation when my boy is a teenager 12 years from now. I want to understand how they speak, their insecurities, what they like etc.

      I know I can’t account for all variables, but I’m pretty methodical in my efforts.

      Retiring is no easy decision, but to play 6 months ahead and write everything out is helpful b/c other people help highlight some blindspots.

      I read the BI post and I know I’ve done the best I can in most of those categories… and i certainly don’t want to regret not spending as much time with my boy as possible. thx for the share.

  5. Sam, I am a new comer to your news letter. Love your combo of personal and professional, esp. parenthood. Selfishly wish you’d write once a week.

    But I get it. You are ready to dive into full time parenting so to speak. Coaching. Homework. Driving. Friggin driving everywhere. Hey— your child deserves your full attention if you are so lucky to be able to give it.

    I retired early from social work, in time for my daughter at age 11. Teen years are just as important if not more than elementary school. I meet her friends after school. I attend all her BB games. The other parent must hate me cause they have to work full time and do all this. It is the biggest luxury in the world.

    In case you didn’t hear me THE BIGGEST LUXURY IN THE WORLD

    so THANK YOU for the time and wisdom you shared. You will not look back.

      1. beth o'malley

        i blinked my eyes and……from diapers to kindergarten to snarky tweens to friggin driving lessons and boys.

        ps what makes me happiest? my kid talks with me. not every day but enough.

  6. Sam,
    Thank you for the many insightful posts you have written over the years.
    Maybe you could post 1 – 2 times a week instead of 3 – 4 times a week. I feel that you could still maintain or even continue to grow your readership while posting half as much. You could try that till the end of the year to see how it goes and then make a decision. Just my 2 cents worth.

  7. Personally, I was thinking that if your son shows the same interests as you why not keep the site and pass it down to him at a later date? You have the platform already built and he could just take over (you even mention leaving a legacy in good hands in your post). I’m sure there are plenty of people here that could offer to post guest blogs in your place and allow you as much freedom as you need. Either way, good luck Sam.

  8. Please Sam, don’t go. I just found your amazing site less than a year ago, and I’m a loyal follower and first time commenter. You have shared so much invaluable knowledge that has really educated and made a difference in many of our lives.

    Please stay with us, we need you. Don’t sell. If you don’t want to publish as often, then don’t, maybe once a week instead of 3-4 times a week…but please, for the greater good, stay with us.

    1. Hi Nicole – Good thing for you is that there is 10 years of content to go back through!

      It’s like finding a good show on Netflix after its heyday and realizing there are 10 seasons!

  9. Sell the blog…

    An American investment banker was at the pier of a small coastal Mexican village when a small boat with just one fisherman docked. Inside the small boat were several large yellowfin tuna. The American complimented the Mexican on the quality of his fish and asked how long it took to catch them.

    The Mexican replied, “only a little while. The American then asked why didn’t he stay out longer and catch more fish? The Mexican said he had enough to support his family’s immediate needs. The American then asked, “but what do you do with the rest of your time?”

    The Mexican fisherman said, “I sleep late, fish a little, play with my children, take siestas with my wife, Maria, stroll into the village each evening where I sip wine, and play guitar with my amigos. I have a full and busy life.” The American scoffed, “I am a Harvard MBA and could help you. You should spend more time fishing and with the proceeds, buy a bigger boat. With the proceeds from the bigger boat, you could buy several boats, eventually you would have a fleet of fishing boats. Instead of selling your catch to a middleman you would sell directly to the processor, eventually opening your own cannery. You would control the product, processing, and distribution. You would need to leave this small coastal fishing village and move to Mexico City, then LA and eventually New York City, where you will run your expanding enterprise.”

    The Mexican fisherman asked, “But, how long will this all take?”

    To which the American replied, “15 – 20 years.”

    “But what then?” Asked the Mexican.

    The American laughed and said, “That’s the best part. When the time is right you would announce an IPO and sell your company stock to the public and become very rich, you would make millions!”

    “Millions – then what?”

    The American said, “Then you would retire. Move to a small coastal fishing village where you would sleep late, fish a little, play with your kids, take siestas with your wife, stroll to the village in the evenings where you could sip wine and play your guitar with your amigos.”

  10. Sam, I’m still hoping it’s an early April Fools joke…but in the event you are really getting out…Thank you. I’ve been a background reader since the earliest days. I rarely comment, but I’ve read weekly for nearly the entire ten years. There are a handful of “super” saved links that I pull up regularly. I read many others blogger too, but never a week goes by without checking for new articles on MMM, MadFIEntist, ESI, JLCollins, and your site FS. Your writing would be seriously missed.

    You should know your impact… We have been happily FIRE’d for two years. We were able to do so because of knowledge you and others have shared on your sites. Your impact reaches farther than you can imagine. My two late-20 year old daughters are now also well on their way to FI also thanks to the many articles and posts provided by a small group of people who dared to do something different. If you are truly retiring, I hope you enjoy retirement as much as we are enjoying ours. You deserve it! Thank you…and Cheers!

  11. Best wishes, and thanks for your years of compelling ideas and content. I have a seven year cycle- changed careers every 7 years or so. I think that once you get past the excitement of the learning phase and achieve some degree of mastery/maintenence, it’s time to find a new “S curve” to climb up, whether work or personal. When I leave this Earth, it will be in the middle of trying to learn a new challenge. Your website helped me redefine success and what is important. Working on guitar right now (son is teaching me), along with tax optimization, etc.

    1. Yeah, I get it. After a while, you just want to move on and learn and master something new.

      I should probably create more products under FS. But what a PITA. Let’s see.

  12. Go for it, Sam. Financial independence is, as they say, having FU money to do what makes you happy. One thing that sticks in from my time in management is that we do our tour of duties, and for everything, even good things, there’s a natural end. Our next tour of duty may be in the same company, or completely different, but it’s good to have closure and new beginnings.

  13. You should do what makes you happy and feel like is best for your family. You have a curious mind, and no doubt will find things to keep you busy and to earn income. With that said, I would miss reading your columns.

  14. Sam, I’ve been thinking for a while that you would be smart to sell. I’m older and seen so many cycles of “sure bets”. The opportunity to realize a big pile of principle is rare. Don’t pass it up.

    1. That’s what I’ve been thinking too. Like selling stocks, real estate, anything you bought in 2009. What a ride. Not like I can’t just start another site and share some thoughts right?

  15. More of a lurker here, been perusing the blog for about a year as you have some different insights compared to other FI bloggers which I appreciate. I think that 10+ years is a long time to do any one thing and finding new challenges is great. You have a lot of somewhat “evergreen” advice that I look forward reviewing in the future. I want to take a minute to thank you and wish you well on your future endeavors.

  16. Sam, thank you so much for all your posts. I’ve been reading your blog religiously several times a week for the past 1.5 years since I’ve discovered it. I’ve recommended your blog to all my friends and family. I’ve learned so much and much more useful knowledge than I have ever learned in college and my MBA program. Wishing you the best with your family in Hawaii.

  17. Sad to hear you are thinking of no longer writing here.

    I’ll join others in saying that I don’t particularly care about reading posts 3x/week, but when you released an extra profound/detailed/contrarian post that you clearly enjoyed writing, I also greatly enjoyed reading it. If the schedule were changed, even to “when I feel like it”, I’d be quite happy with that (although I recognize the change is for what makes YOU happy, not me!)

    I also wouldn’t mind more writers – the guest posts you have selected in the recent months have been great. You could even get some VA/writer to massage your voice-to-text into a nicely structured post (I believe you often use this for commenting, right?) Less editing, more writing.

    Regardless the choice is, of course, yours. Just some feedback that I hope will be useful.

    I have been reading a couple of books recently – Zen and the Art of Motorcycle Maintenance, and Atlas Shrugged. About the idea of quality – how it’s instantly recognizable – and about the morality in doing quality work. Although I’d be sad to see your ‘final’ post, I’d be reassured to know you would simply carry this quality to another domain of life. Until then, I will keep reading.


  18. Sam, have you done any analysis instead of retiring bottom of the market in 2009, if you would have continue to work and retired today… what would be your net worth , financial independent and importantantly quality of life…

    1. I think I would’ve been poorer bc I wouldn’t have bought my Golden Gate Height fixer in 2014 and I wouldn’t have been as focused in growing FS.

      I definitely would be much more stressed and unhappy. I was developing a lot of health issues due to the stress of work as well.

      I don’t think it matters how much more or less wealthy I would’ve been as a result. After a certain threshold, enough is enough.

  19. Congratulations on your success, and good luck with whatever you choose to do with FS. You’ve gone far and wide, covering excellent topics, in great depth and analysis, and with a unique perspective. All other financial blogs are pure fluff, and are marred with dishonestly, conflicts, mundane useless garbage and self promotion. You are not afraid to take a stance, as you have arrived at it through much research and testing. I know that you work hard on these posts, the comments, and follow-ups – it clearly shows. I also understand that this hard work can wear you down, and at some point it makes sense to do something else, if the finances allow it. Personally, I couldn’t do what you do, it is hard work and you have to appease random strangers on the internet in order to build pageviews and readership. Yes you don’t have a ‘boss’ and that is awesome, but your advertisers, financial sponsors and readers are in a way clients/bosses and you do have to answer to them in some way. Hiring people, editing their posts and managing them would be an entirely new headache. If I were you, I’d do what you are proposing to do. Sell the blog. Finish out at the top. Retire to something new and exciting. Move to Hawaii, maybe Virginia. You’ve been great, and congratulations again on your success and impeccable service you have provided to readers like myself.

  20. Though I haven’t always agreed with your articles, I have always benefited greatly from the perspective and experiences shared. Therefore, I better say much thanks before it’s too late and best of luck with your next endeavor.

  21. Interesting reading these comments. It makes one wonder what is the true marketable value of FS? Most commenters seem to feel that YOU are FS. I would also acknowledge that fact.

    Curious then- How would it be marketed? How do you get potential suitors to see the value and pony up what you would need to part with it?

    If a company value is so tied to the founder, how do others leverage the brand and keep the advertisers that ultimately are needed to create the value? If you walked, would advertisers stay?

    1. Good questions. ~70% of the traffic comes from organic search, while the rest come from other websites like CNBC, newsletters, and direct traffic b/c the person heard of FS somewhere.

      Less 1% of traffic comes from regular commenters and people who ask me for things etc. To be operationally efficient, I would eliminate comments, which also eliminates all spammers (1000X normal commenters), make contact info hidden etc.

      This would save me lots of time. For example, it’s taken me time to read your comment, filter out spammers, and write a reply. So far I like the camaraderie and reading different perspectives. But this might change after year 10, b/c often, when I respond to a comment and ask a question back, there is no response or appreciation of my response.

      It’s extremely easy to invite more guest posters and hire staff writers and just pop in on occasion and share my thoughts like usual.

      How about you? How is your side hustle or business being run? What are some contingency plans you’ve thought of? thx

      1. Thanks so much for reading my comment and talking time to reply. I very much appreciate it and am even humbled a bit that you would do this.

        My side is hustle is consulting with small companies on setting up programs to ensure good liability and product safety/certification practices. This is done to stay current in the field, I like the work and I enjoy the clients. The money made is a bonus. When I am done, the practice dies. I have no plan nor intention of turning this into anything more.

        Although your questions got me thinking – hmmm.

      2. Refugee from Academia

        Respectfully, I offer a contrarian view. The most enjoyable posts for me, and the ones I learned the most from, are those that offer a “case study of stupid” if you will. In particular, the high earners in NYC who are “poor” because they don’t budget. The article, and the 100+ comments, made for great reading and I really learned something.

        So comments add value for me. They are half the fun of most of the stuff I read on the Internet.

  22. Are you selling FS? I can’t see another person taking over and doing a better job than you.
    More freedom would be good, but what would you do with 3 extra hours every day?

  23. Sam, we would all hate for you to stop writing.

    Alternatively, you can hire a CEO for FS who can build a path to more revenue to support a team. You retain significant ownership and guide strategic direction.

    With your newfound time, you can raise $ and step into the cushy VC job you’ve been writing about, focused on fintech and/or media.

    1. Hi Eric – How are things going for you post retirement?

      One of the biggest bummers I could experience is having to manage people again. People are great, but people also cause a lot of stress.

      I spent the weekend with a couple VCs, and one big one from KP where I invested in their new fund. It’s a pretty sweet gig, but also a battle field. Could be a really exciting 3rd, 10-year career!

      1. Honestly Sam I am back to hustling like in the startup days, just not having any boss, board or employees.

        I do fully embrace the flexibility of schedule and don’t go into the city every day, take 11am yoga or Jiu-Jitsu classes, be there for all the kids stuff etc.

        Invested in a bunch of companies and did some consulting to pay the bills since I’m not yet there mentally to start withdrawing or taking dividends.

        Sounds like you need a change in some way, I hear that.

  24. I hope you continue to write for FS, but I completely understand your position. However, I think this post made me realize we need to start re-thinking retirement. Instead of focusing on the 4% rule exclusively, we should also consider other options like side hustles or maybe a second career. For example: Say you’re 55, hate your corporate job, and have $1mm saved, but now you have a side hustle that’s making $40k a year. Instead of continuing to grind, maybe “retire”, take 3% a year from savings and see if you can increase the income from your side hustle. There are so many more options today than just grinding it out until 65.

  25. Thanks for the post Sam. Congrats on achieving your stretch goal to regularly generate over one million organic pageviews a month. That’s a big achievement!

    I can fully understand that after working hard for so long providing wonderful content on this site, you want to take a step back. But selling FS? It probably feels like giving up your baby?

    But probably you give up your ‘FS baby’ to spend more time with the most wonderful gift in life. Your own kid.

    Personally, selling FS would feel a bit too definitive. Not easy to come back to blogging afterwards. But probably you will figure something out! Good luck with you 2nd retirement!

    1. Sometimes your baby grows up, and you’ve got to let him go on his own path.

      To me, nothing comes close to taking care of my boy and being with him. Before him, I loved FS so much and had so much fun. I still have fun, but I discovered a NEXT LEVEL of joy and love with him.

      I’m probably still in my honeymoon phase of fatherhood, and as time goes on, I’ll take my fatherhood more for granted. We shall see!

      1. I couldn’t agree more. Kids can be real energy drainers, but there is nothing more rewarding then spending time with them and watching them grow! Enjoy it 100%!

        All the best!

  26. Well I know it will be a bittersweet moment if you do sell Financial Samurai/walk away from it. What you have accomplished with this site is truly remarkable.

    As a reader I am selfish and hope that you decide never to retire from FS but as a blogger I know the type of effort, time commitment etc you have to pour into it to make it something that you are happy to be associated with.

    Regardless of what happens, I do hope you don’t leave your readers hanging as we have really developed a lot of online connections. We definitely want to know what happens, whether you go to Hawaii, etc and how your 2nd retirement turns out. It would be akin to watching a TV series that you get wrapped up in and the network cancels it leaving everyone hanging.

    Best of luck and thank you for all the work you have done in the past.

  27. I’m going to need another glass of tequila if Sam is leaving FS.

    Kramer and Mad money can’t compete with Sam.

  28. Hi Sam,

    I’ve thoroughly enjoyed reading your informative posts on an impressively wide array of topics! It seems to me that this site does so well because it fuels the dream that, with wise financial choices, we can all take control of what we do, when we do, and how we do it. That’s the American dream and you don’t owe anyone an explanation for realizing the natural culmination of all you’ve written about.

    We share a number of common life experiences. I played tennis in school, and my first job after college was as an associate equities analyst. I get the sense you are like me in that there was a point when you realized you never again wanted someone to have the power to dictate your day to day. Corporate America is all too often littered with ridiculous experiences dictated by incompetent and/or morally questionable decision makers. Following your advice empowers us all to break free from those destructive chains!

    After 23 years in the rat race, and by the grace of God, I’m lucky enough to have reached the neighborhood of where Susie Orman would bless my retirement. I have some ideas around teaching kids from difficult surroundings how to do the same via consistent reasonable work and the miracle of compound interest. I hope I can reach out to you at some point as I’m sure the project could greatly benefit. Thanks again for your service and inspiration!!

  29. I can understand the feeling. I think in terms of 2, 5, and 10 year cycles. I have been with the same company for a little over 10 years now, 5 years in the same position, and I’m feeling the itch to try something different.

    Good luck with your decision!

  30. Sam, if you stop blogging, the PF / FIRE space will lose an important voice. Your posts stand out from the crowd due to your sometimes contrarian views and nearly always unique perspective. I spent my entire pre-FIRE life (until last June) in the Bay Area (East Bay, SF, and the peninsula), so I’ve always appreciated your insight about living in a HCOLA.

    Your voice cuts through the echo chamber, so I hope you find a way to keep the spirit of your blog alive.

  31. Wow – I just started reading your blog a couple of years ago (and read more often when you started podcasting).

    Hopefully you will just post less often and not completely end it.

      1. Lol I was in PRC China 2009-16. Behind the Great Firewall. Even with a VPN it was so incredibly slow that I stopped using FB, Instagram, Google, etc.

        BTW – will u b at Fincon in DC this year?

        Now that I’ve started a blog (and am no longer gainfully employee) I’m thinking of going.

  32. I’ve enjoyed FS for many years and would be sad to see it without Sam.

    You should be happy, thankyou for that bit you have brought to me. Do what you want, it’s been a great 10 years!

  33. HI Sam … am a long time lurker and have benefited personally from your severance advice and many other tips. Totally understand the wisdom in enjoying your 40s and shifting towards a better version of your life well lived. You have a unique opportunity to see your kid grow up with your company and encouragement. Best of luck to you in whatever you decide to do!

  34. Not at all a finance related blog but worth a visit to another corner of the internet. The couple started a blog then eventually left day jobs, built a brand, published 2 books, created furnishing lines to go with their blog then decided to step away entirely. Eventually they returned and re-engineered their brand to a podcast based media “thing”. They took a break at the most hectic point in their life (parenting from 0-3 years).

    If it isn’t covered in the above podcast, they also shared the financial impacts to their page view based revenue when they stopped their old routine of daily posts. From their experience, organic page views were surprisingly fleeting. Apparently us internet strangers and trolls are fickle.

    Good luck with your decision!

    1. Very cool. Will have a listen as this is completely pertinent to our situation! “What we learned from quitting our blog so you don’t have to quit yours.”

      How perfect is that?

      I believe the internet is fickle and folks will go to the next shiny object. The one thingI figured out about three years ago was how to last online for longer without having to do as much work. But nobody sees the strategy b/c it is not obvious.

      1. Nicely done on the stealth improvements! It is frustrating that new and shiny has trumped thoughtful and intelligent. Thankfully there are times and blogs, like yours, that those two efforts come to my attention and I have enjoyed the content tremendously when they do.

  35. You’re writings are highly appreciated. If you decide to retire again, I will completely understand.

  36. Nice job Sam on the 10 year anniversary of your website and business. Your consistent schedule of publishing valuable content for your readers is greatly appreciated.

    I would imagine having one retirement is already great but to plan for a second one so early in life must take the cake (or even to be able to contemplate a second one regardless if you decide to move ahead).

    It must be a nice feeling indeed.

  37. A couple months back you said you were considering to return to a W2 job?

    You also mention in this post that having some intellectual stimulation since your son was born has been good.

    I’m confused…..

    Wishing you the best in whatever the next venture/adventure will be.

  38. Sam,

    Please whatever you do, don’t leave. I understand taking time away and not spending so much of your time on FS, but please don’t stop writing. You provide too much value to this world. Coming from an Econ grad/junkie, lover of personal finance, and husband to fellow W&M Tribe (er), please give us at least one Sam post a month. That’s all I am asking. I am begging you not to go. You have helped my wife and I get to such incredible places in our lives, we have gone from zero to hero and there is so much of our success we attribute to you and your teachings. This world is better off with Sam behind the keys of this site, even if it must be at a limited rate.

    A beloved reader

    1. Go W&M! Thank you for your kind words.

      The great thing about the internet is that there is such a massive space out there to discover. If and when I am gone, there will be a new Sam or a new Financial Samurai to readily take my place.

      This impermanence is actually a type of relief. There’s something for everyone.

      1. Sam,

        Thank you so much for your response! Much appreciated. I wish you and your family all the best in retirement and I hope that everyone will be able to continue to benefit from your value like you want for your own son. I hope that in the very least, you might keep us up to date with an Instagram or some form of media for us to follow you on your 2nd retirement journey. So excited for you! You are an incredible mentor and I truly appreciate everything you have taught me. If you do end up needing any ghost writers or any contributors, let me know. I would do anything to help pay you back for the value you have provided in my life.

  39. Jim @ Route To Retire

    Wow, this is some big news! Although this would be a big loss for the PF community, I’m very excited for you. The opportunity to spend all the time in the world you want with your family is a true blessing.

    Good luck to you, Sam!

    — Jim

  40. 10 years of sticking to something is huge especially blogging and even more so at the rate you’ve kept it up! It is so much harder than people’s realize who have never tried operating a blog. There are so many things that go into making it hum and grow. So congrats to you on all of your progress so far and I totally get where you’re coming from. Makes sense to try to preserve as much capital as possible!

  41. Congratulations, Sam. Long time reader here, I’m sure you’ll get some interesting replies to this plan but if it’s what you want then you should do it. Happiness is the goal here. Best of luck.

  42. Financial Freedom Countdown

    Sam, I don’t identify with 99% PF writers cause they don’t live in HCOL :( As a fellow Bay Area resident, hope you continue writing (even if it is at a reduced frequency). In fact your last post inspired me to start a blog!

  43. Sam-my gut says this is an early April fool’s joke…Selfishly, I certainly hope so. Whatever you decide, you don’t owe any of us an explanation. While you have experienced immense personal/financial satisfaction from FS, we (reader) can never adequately thank you.
    We have never met and I seldom comment, but you have always been part of my journey financially and as new dad. I have much to thank you for. Your content and insight has always been refreshing, invaluable, and served as a vital foundation for my success.
    Best of luck with your next chapter and I hope I have the opportunity to hear or play a role in whatever the next stage has in store for you. Thanks again for all you have done.


    1. ^ Bump —

      Don’t go anywhere! Instead, use the next 10 years to take the gas off of writing articles and becoming an editor and providing a platform for other aspiring to try their hand at writing about finances. You could still write once in a while and serve as editor / overlord of some sort. You would be changing more people’s lives because of it!

      1. Amen! I’m happy to submit potential contributions. Sit back, kid in lap, and let us do the daily work. You just edit, contribute now and then and live how you want to. :)

      2. The funny thing is, editing often takes just as long, with less satisfaction since you’re not producing your own work.

        I don’t enjoy editing as much as I enjoy writing. Hmm.

        1. Kathy Abell

          I LOVE to edit other people’s writing. Back in my wage slave days in the cubicle farm my red pen was LEGENDARY. I’d be happy to serve as one of your remote editors. :)

  44. Dave @ Accidental FIRE

    But wait, you haven’t even won a Plutus Award yet!


    Duuuude. This sucks. Maybe you could start a podcast and run episodes from time to time on the site. I’m sure the new owners would do it, and they’ll know that your audience would love to keep up with your story, whether it be in Hawaii or Virginia.

    1. Hah! Never gonna win one of those!

      A podcast takes a lot of time… but I should probably do one for this current article to chronicle some thoughts. The podcast is really for my son to get to know me and his mom when he grows up and wonders what his parents are thinking when he was a toddler.

      If anybody else wants to listen, sounds good.

  45. Seriously? you’re going to stop writing FS? I feel like I’m going to need a support group to get through this. Ugh…

    BTW, I thought you were going to become a VC? Is this an early april fool’s joke?

  46. Little Seeds of Wealth

    Thanks for building FS and inspiring many of us to pursue financial independence. However, don’t leave completely because we’ll miss your writing!

  47. Hi Sam,

    Unless you have a new endeavor in mind I just can’t see a guy like you selling or retiring from Financial Samurai. I completely understand after hitting a milestone or getting negative feedback the urge to do so, but my guess the satisfaction you get from building a business from scratch and the peace of mind that comes with regular income outweighs the negative.

    I am in a similar situation. It took 5 years of careful planning to get to the point of being semi retired. Hiring and training people as well as giving them the control they need in order to run the day to day operations was extremely difficult. However, now I have the best of both worlds. I can work when I want, and I can play when I want. Even better I still get a check every 2 weeks along with the perks of owning your own business.

    Best of luck with whatever you decide.

  48. I guess I don’t understand where you’re coming from here. You want to retire from FS, the job you love and is your baby, that costs you around 3 hours a day and gives you fulfillment, a creative outlet, and capital? I get wanting to take on help to grow the site and give it more unique voices and content, but not that you want to walk away because of some made up construct of 10 year luck cycles, or the fear of riding this website’s husk to the ground.

    FS is just getting started. The Forums are starting to take off, and it looks to me like engagement is up in the comments. No… I don’t think you’re done yet. The reasons you gave above aren’t solid enough. You know can spend time with your boy and family while working this site. You are incredibly well leveraged to do that. If you simply are bored, ok, but at least acknowledge if that’s the reason, and not that you’re guilty of surviving in spite of yourself. Let’s talk about it again in 2029 ;) Oh, and if you’re serious about wanting some freelance writers to help out, I’ll be in touch to see what I can do. This site is worth growing.

    1. Sounds good. One of my greatest joys is not having to listen to anybody, but myself and my family. It feels awesome to be free.

      How about you? Tell me about your background.

      1. I can’t claim to have the total freedom you do, though that’s something I am working toward (and will say I have been helped, even if just through inspiration, by this and sites like it). I’m second generation in this country, my parents were both first borns in the US. Pretty new overall, and no real family here or legacy to call from, which I actually think helped me a lot. I was a nerdy kid, into computers and games, and that parlayed into a job with a major tech company when I was 18. I gave up school, was head hunted by another major tech company and moved out to Los Angeles, but this was shortly after the crash and I can’t pretend the money then was anything like it is today.

        Still, I did well enough that I could start stowing away money in a 401K when I started my first job, thanks to some advice my brother-in-law shared with me. He told me, “Just set it at 10% and forget it as soon as you get the job… You’ll never miss the money and you’ll be amazed what it will do over time.”

        I did that… Then a few years later increased my deduction to max out my contributions, and have maxed every year since 2004. I went back to school a few years later, got a degree in Econ, and then I worked my way up the corporate ladder to the point I got offered a killer job at Amazon in 2012 with $200,000 in shares at $183, plus a crazy sign on bonus to go with a sweet manager position for a secret project. I turned it down, because I didn’t want to move to Seattle at the time.

        LOL. That’s a bit of a regret. But, I didn’t rest on my hands. I was running a nice side hustle that was making just about as much as my day job, and I was working on fiction and short stories on the side to increase my own intellectual property worth. The goal was to one day spend as much time on my own work as I did for others… Knowing if I did, I would be the one reaping the profits.

        Flash forward to today, I’m far and away from being able to retire as I near the big 4-0, but I have a large retirement nest egg, the side hustle grew the after-tax savings to very comfy levels where I could raise a middle-finger and walk away from it all for several years and just work on my own stuff, and I’m being courted currently to keep in the game with one of the companies that are going IPO this year in the Bay Area, though… My equity would be dripped over four years, so who knows if people will still find a certain Messaging app as cool when I can fully profit, would be fun though… But still, I feel I’m like you. I like to beat my own drum, walk my own path.

        So yeah, I’m 100% serious when I say I would love to contribute to this site, share some trials and tribulations, and maybe not be able to talk about retiring early, but I’d be happy to shine a light on what busting a hump can do in a high-cost-area and the drive and insane pressure it takes to keep busting that hump as the years march on. Though, no matter what happens, Financial Samurai, without Sam, isn’t Financial Samurai to me.

        1. Sure! I welcome a guest post with you with some insights and stories about your journey, as well as lessons learned.

          $200,000 worth of Amazon at $183 sounds good, but best case, it would have turned into $2 million right? Most employees sell their stock along the way and diversify.

          Surely, you earned a similar comp package elsewhere to turn that down and did pretty good these past few years too.

          1. I am also an early retiree, but waited until my 50s. I have been playing around with many new identities, one of which is as a financial blogger (just getting started). It’s been inspiring to see what you have accomplished and I too would be more than happy to guest blog or freelance. Most people don’t like diving into the details of tax laws and investment strategies so it’s always fun to share with others what I have learned. Good luck with whatever you decide.

  49. Interesting post Sam. You mentioned having a next purpose being important and in broad terms you plan to move to Hawaii and raise family. Like myself, you seem to get bored quickly if not doing something and I would love to hear more specifics on that next purpose if you are open to sharing. Also any regrets to the blogging or anything you may have been unfair about in the blog? Best of luck on your next retirement.

    1. There are many endless challenges one can have. It can be as easily as joining a USTA tennis league in Hawaii and competing against other teams.

      I no longer get easily bored, especially since I have a son to raise.

      I am not sure I understand your question about things I am may not have been unfair about with my blog.

      I have no regret starting something on the side and sticking with it for this long. A huge regret would’ve been not trying at all.

      1. Life Outside The Maze

        Thanks for the reply Sam, as far as my question about any regrets in blogging or anything you may have been unfair about in the blog, I guess the question is after posting hundreds of articles is there anything that you posted that you might now amend after further reflection or new information and as far as the regrets part have you experienced any personal costs to being a blogger or unforeseen side effects to having a most successful blog (semi-fame? many people wanting to connect? negative reactions of family and close friends to what you say on the blog)? Full disclosure, I have some concern over putting myself out there and possible downsides and am hoping to learn from someone who has been through it. Thanks and best of luck working on your USTA rating and eating spam musubi at your local ABC store ;)

        1. Nothing stands out. I wish I started FS in 2006, when I first came up with the name and discovered the wonderful world of blogging.

          I’ve never had a single negative reaction from friends or family towards the path I lead.

          The only one negative reaction I can think of is from an ex-coworker, who is still stuck in the grid 10 years later.

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