Taking A Sabbatical And Potentially Never Coming Back!

As of right now, I’m on sabbatical!  Yeah baby, yeah!  After some discussion with my various colleagues, I’ve decided to take a one month paid sabbatical to rest, rediscover, and go on an adventure.  I could have done longer, but the second month is only 80% paid, and the third month is even less at 60% of paid salary.

You thought I was kidding when I wrote, “Should I Take A Sabbatical: Fears, Preparation, and Execution!” didn’t you?  Now you know when I write lengthy posts about making a change and enjoying life that I’m not messing around!  I’ve spent 13 consecutive years working in my same job.  I’ve saved up a good chunk of change and I’ve been itching to do something new ever since I launched Financial Samurai three years ago.

Taking a sabbatical is the first step towards discovering whether or not I can take the leap of faith and do something fully on my own.  Do anything for a while, and it becomes increasingly harder to cut the chord.  Why do you think swans die when their mate passes?

One of my biggest fears is looking back on life and regretting not taking more chances.  Living in any developed country like the USA is easy compared to hundreds of other countries around the world.  I’m not afraid of dying, I’m just afraid of not living life to the fullest.


Fear of failure is what’s driven me to work hard, save, stop complaining, and invest aggressively for so long.  My target ever since college was to be somebody by age 30.  I had 8 years to either feel like a success, or know that I was at least heading in the right direction.  I didn’t want to be an unemployed 30 year old, living in momma’s basement with no woman, no savings, and no friends.

My fears made me get into work at 5:30am and leave after everyone else so long as I could still breathe the first two years out of college. My fears during the 2000-2003 downturn made me go back to school and get an MBA, even though that meant putting an additional 20-30 hours of studying and class on top of my already 65 hour work weeks.  My fears led me to go travel abroad every year for 13 years straight because if I died early from a heart attack, at least I would have seen Sugar Loaf and the Taj Mahal.

I have new fears now:

* Am I being too rash with my career as someone in their mid-30s?

* Will I discover during my sabbatical that I will never want to go back to working for someone else?

* Will I realize that working online is only fun because there’s no pressure to make any money since I’ve got a job?

* Will I miss my friends, clients, and colleagues?

* Could the value of freedom actually be worth less than the value of money?!

There’s no big fear about not having enough money because that’s what saving and investing for the first 13 years post college was for.  I knew after I got my ass repeatedly kicked by rough bosses for the first two years in NYC that I would need to save a boatload in order to extricate myself away from the 5:30am-to-7:30pm+ life.

When 9/11 occurred, all I wanted to do was become a fireman or some sort of public servant, rather than work in the private sector whose sole purpose is to make more profits.  When the terrorist attacks occurred in Mumbai in 2008 at the Oberoi and Taj Mahal Hotels, I wanted to give up again because I had just stayed at the Oberoi two weeks prior!  Yet, I continued on.


Ignorance is bliss, but I tend not to be too ignorant.  I tend to analyze everything as thoroughly as possible and set up alternative scenarios to plan accordingly.  In most cases, thorough anticipation is a positive.  However, in other cases, I can see the over analysis of situations as completely debilitating.

Folks right out of college have it good (unless they are saddled in debt).  Recent grads aren’t making much money, don’t have anybody to support, and hopefully haven’t gotten into any sort of heavy consumer credit card debt yet.  When you’re young, you’re free to do anything! The world is your filet mignon sandwich.

As you get older, you see the world as it really is, a structure of mazes which may or may not lead you to what you really want.  You can choose one path, work your butt off, but end up getting sideswiped by an economic collapse or an evil nemesis at work.  The only person you can really count on is yourself, which is kind of scary!

Whatever chance you get, please speak to someone older, or someone whose gone through what you think you’ll be going through.  Having a mentor is a powerful, powerful asset that will help provide you a more fulfilling life.  They’ll help you overcome what you don’t know.


One month is going to go by in a cheetah’s eye.  As a result, I’ve created a plan:

* Work on Financial Samurai Online Services (FSOS Consulting).  I recently launched my online services to help aspiring or frustrated bloggers “Get On The Map“.  I plan to launch new service offerings related to getting into b-school, career, and financial consulting.  It’s been hard work, but very rewarding.

* Hire a developer to rework Yakezie.com and add new features.  If you know anybody, please let me know as I have money to spend.

* Meet online advertisement or consulting clients face-to-face or connect over the phone to develop deeper relationships.

* Work on solidifying at least one premier client whom I plan to invest a good amount of money in who will be a pillar advertiser on Financial Samurai.

* Figure out how to maximize a chunk of savings that’s sitting around in a 0.3% money market account to increase my passive income.

* Look for any other job opportunities (in paradise) out there in various industries.

* Test out the real estate market and put my house on the market after Facebook goes public on May 18, 2012.

* Take a week off and go to Hawaii to boogie board, hike, golf, and eat.

Holy $(@#!  Out of the eight things I’ve listed, seven of them are work!  Furthermore, I have no doubt that when I’m in Hawaii I’ll work at least 2-3 hours a day every day.

Newest Fear:

* Not feeling recharged and ready to take on the world after my sabbatical.


The reason why I titled this post, “Taking A Sabbatical And Never Coming Back” is because one of the most likely scenarios I see is that I’ll get back to work for a couple weeks and decide to engineer my own layoff (70% chance).  Another scenario is that I ask to do something different within the firm from some other location (10% chance, what’s better than SF?).  And the final scenario is that I realize how lucky I am to make good money and have a job (20% chance)!

I already know how lucky I am to have a job that allows me to eat the occasional toro sashimi dinner.  These past 10 years have been brutal in the economy, and I’m sure I had more close calls than I know.  I distinctly remember losing hundreds of thousands of dollars in my net worth in early 2009, hence the cathartic birth of Financial Samurai!  That said, the past is in the past and I’m focused on now.

Stability and money is very hard to give up, especially if a family is on the way.  But, how much do we really need anyway?  Do I really need $15,000 a month in gross passive income to really feel secure?  Or, is that just a fun goal to challenge myself?  Some people say that people get addicted to money once they start making a lot.  I say people start getting sick of money once they have money.  Instead, people with financial security tend to work on other things such as charitable initiatives, hobbies, travel, and so forth.  What say you?


Change is stressful, but oh so exciting.  Being an entrepreneur is a completely different animal.  You never, ever feel like you can go on vacation or are on vacation.  I’ve tried many times over the past several years to change my state of mind, but I couldn’t.  There’s always someone asking you for something, and always something you can optimize and do more of.

All I know is that I’ve had the entrepreneurial bug in me the day I graduated from college.  I’ve told myself several times in the 13 years of work that I should quit and do something else, but didn’t.  Taking a sabbatical is that first step.  I just hope I don’t step on a landmine or fall off a cliff!

Untemplaters, what would you do if you had a one month sabbatical right now?  Would you completely go see the world, or would you work overtime on your own potential full-time business given you know the end might be near?

I’d love to hear some specific suggestions on what you would do, and what you would do if you were me.

Post Sabbatical Update One Month Later: Wrote a summary post entitled, “What I Learned While On Sabbatical“.  Learned some interesting stuff about the economy and myself.

Personal Story: I was able to negotiate a severance package equal to six years of living expenses. Learn how to negotiate a great severance for yourself in my new book How to Engineer Your Layoff! Never quit, always get laid off so you can collect a severance, health care insurance, deferred compensation, unused vacation days, and be eligible for unemployment. If for whatever reason you do not find the book helpful, you can have a full refund.

How To Make Money Quitting Your Job

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Sam is the founder of Financial Samurai, America's fastest growing personal finance site. We believe in reaching financial independence sooner, rather than later. Slice through money's mysteries!


  1. says

    I think I would do exactly what you are doing. I would like a good two week period to focus on content for my site, as well as product creation.

    Given the choices you have to make, I don’t think you’ll be able to relax the whole time, so it is good that you will be working 2-3 per day.

    • says

      One of the best feelings was yesterday, Sunday evening when I realized I didn’t have to get dressed, hop on the bus, and go into the office. Priceless feeling perhaps!

      I’m working hard every morning til lunch. Then I take about a 6 hour break, have fune, then work again for about an hour in the night w/ international clients.

  2. Sydney says

    Wow that’s exciting Sam! I’m impressed you are so focused on doing so many things in one month. You’re so gung ho! That’s nice you’ll spend a week in Hawaii too to get a change of pace.

    If I were to take a sabbatical I’d probably try to do half blogging half travel. I’d feel weird not doing any blogging and I also think it’s a lot more fun when I have more time during the day. There are so many places I still want to travel but I wouldn’t want to spent a fortune either so I’d probably pick one or two countries and go exploring for about two-two and a half weeks. Enjoy your sabbatical!!

    • says

      I totally want to go travel the world for 30 consecutive days, but I don’t want to leave a special friend behind :)

      BUT, maybe after the sabbatical, if I decide I’m never coming back, then I will take a 30 day tour regardless. I think it will be fun, and I’ll have good posting material!

  3. says

    That sounds great Sam. If you love what you do, working on vacation is not work at all right? At least that’s what Confucius told us.

  4. says

    “decide to engineer my own layoff (70% chance)” – sounds like you’re serious! That combined with the Facebook IPO means you might not be in the Bay Area much longer; you’ll be missed. One thing is you might want to wait for the Facebook lockup period to be up before you list (so the regular employees can sell); I think it’ll be 6 months post-IPO. That way the paper millionaires will be guaranteed to have down payments.

    No matter what you choose, I wish you luck!

    • says

      I will have a pied-a-terre in SF and Lake Tahoe always, so don’t worry! They are my rentals, which will be rented out until the mortgages are paid off, and then if I make enough money, I might just let my SF rental stay vacant so I can go back whenever and enjoy the city for however long at a time.

      I’ve thought about the IPO 6 month lock up a lot, and it makes sense to wait til then. However, Nov/Dec is not the best selling season, and what if more inventory comes aboard by then? Right now, inventory is down 40% YoY.

      Also, employees will be selling some during the IPO, so there is an influx of cash this month. I figure, test it out whiel I’m away on vacay, and if I don’t get the aggressive price I want after 2 weeks, then try again in a couple years. I strongly believe prices will continue higher.

  5. says

    Im very curious to see what the sabbatical brings! I really wish I could take one here, but it’s not really allowed, I could barely take a month to recover from surgery lol, they had my working from home.

    Great to see you putting in your best efforts on this. I very much think that you can replace your career with your online endeavors, and find the same fulfillment (if not more). I don’t ever intend to use my online ventures to replace my day job, however, I would like to live in a comparable home as I do now, but on a lake. Around my area, the same house on a lake is nearly double the price. Once I have that, I’d certainly like to relax my efforts a bit, so this is inspiring to see you take the lead!

    • says

      Thanks Justin. You sure about not being able to take a sabbatical? I know many companies who allow sabbaticals after 5 years of service, and definitely 10 years of service. You might be surprised! How long you been?

      I’ve had “the lake house” for a long time now and I have done my best since high school actually to pretend it is not there so I could prove to myself I could do my own thing. With the work online and the decade plus working, I’m at peace with myself knowing that I have. This will be a topic of another post!

      • says

        Ive been with my company just shy of two years, I was part of a failed IPO at my previous company and our department was let go…such is life at a turnaround/restructuring company as the economy improves. But I like the current company much more, just too many hours right now, definitely cutting into my online life.

        You are right that they allow sabbaticals after so many years, but Im at one of those places that thrives on face time to move up, as such I rarely take my month of allowed vacation, fortunately we do have about 17 company paid holidays a year…but even then I work sometimes.

        I look forward to that next post as well.

  6. says

    Is this how you see your retirement/independence? I expect to fill my time with just a few things everyday to get me out of bed or out of the house to keep myself stimulated. I started blogging as one things I want to do in retirement. Volunteering will be another and I expect to start in a few months.

    I think your sabbatical should be revealing to you, but a month is too short!

    • says

      Working for myself? Yes. Working this much continuously? No. The irony is that one needs to work hard so as to not have to work as hard since nothing is given.

      I’ve enjoyed taking 6 weeks off a year for the past 3 years and downshifting from work. Now, it’s time for a different shift, but I have to upshift first before I can downshift.

      I agree, 1 month is too short….

  7. says

    Very awesome stuff, Sam! “Being an entrepreneur is a completely different animal. You never, ever feel like you can go on vacation or are on vacation.” Haha, definitely agreed! But, my girlfriend told me I better not take out the laptop during the day when we’re on the islands. I’ll probably be wise to listen, haha. 😉

    • says

      I am willing to bet anything you will spend more time on the laptop than your GF will like! It’s an addiction that you won’t be able to conquer, ESP since this is your FT job!

  8. says

    Way to go Sam–at least you won’t be looking back 30 years from now and wondering why you never even gave a sabbatical a shot;).

    If I was in your position (thinking extensively about working for yourself), then I would spend the month doing work instead of traveling. It will give you a good preview of how it will be to work for yourself, to work from home, etc.

    One other thing I would do is research lower cost-of-living places. I know that you love San Francisco, but if you are truly thinking of working for yourself full-time, you might want to have a lower cost of living place to take some pressure off of you (at least as an alternative).

    P.S. Houston has very cheap housing, and we don’t pay state income tax! Just saying:).

    • says

      I hope I live for 30 more years! haha.

      If I work too much, I might need a sabbatical from my sabbatical! That is what I fear the most.

      I would consider Texas if… I had never discovered California and Hawaii. Alas, I’ve experienced the good life, hence it’s hard to go back!

  9. says

    Every summer for me is sort of like a sabbatical, but without pay. So I work my butt off working towards a goal: making money doing something I like. Usually that ends up being teaching; teaching summer school (I get to design my own curriculum for the class), tutoring, blogging, or helping Mr. LH with his work load. Right now, I’m working at securing a full time teaching gig – not easy with the economy. So I’m thinking outside the box and figuring out how to blend teaching with personal finance (because don’t all HS kids needs this kind of education?!) and getting paid to do it. We’ll see how that pans out.

    Enjoy your sabbatical and I’m sure whatever you decide will be the right decision.

    • says

      If you can pioneer a personal finance mandatory summer course for kids, and make money, that would be wonderful!

      BTW, YWC launching next week. There is a Pforum post on it if you want to join Sydney and I.


  10. says

    I’m thrilled for you! And I want to cry a little bit, because I’m scared for you, too! Can your next post be about what your special friend thinks of all this? Unless I somehow misread, and that special friend has four legs and fur.

  11. says

    I’m extremely excited and not the least bit nervous for you. I know you’ve done your share of thinking around “worst case scenarios.” You’ve done such a good job of diversifying income streams as well as building up specific skills that you’ll forever be able to make money – even if its teaching tennis.
    If everything somehow falls apart, you have a lot of fans that would be willing to take you in.

    • says

      Thanks mate. It is a little nerve-wracking, but that’s b/c of done my same routine for so long I’ve become a little delusional on what I think is the proper way. Different perspectives have helped me think differently!

  12. says

    I think this is a great idea. This will allow you to build up your online business, and focus on the other things that you have planned. If you are still unsure after 1 month, will you be able to extend it at 80%, or did you have to make that decision at the very beginning?

    I work at a major university, and only the tenured and tenure-track faculty are given the option to take a paid sabbatical. They usually use the time to work on a book or become a visiting professor at a university in another country.

    It definitely sounds like you’ve been preparing for this for a very long time. I really hope this works out well for you, and that you gain more clarity on your desired future!

    • says

      I have a strong feeling that 1 month is not enough, but better than no months I guess.

      Time for you to get on the tenure-track then Khaleef?!

      I really have been preparing for a long time now. I was going to stick it out for 5-6 more years, but things have changed.

  13. Tidy Husband says


    It’s only money and your adventures on financial samurai are great stories to tell. It seems like you’ve got savings, and the feeling from turning nothing into something like you’ve done with your site and the network is priceless.

    You’ll never look back on your life and say “I wish I worked more”. Especially when it’s for somebody else.

  14. says

    I am still fortunate that i don’t have to think through all of these. i love my job. I love to see people waiting for my decision, I like power. Not that i don’t love my blog..i love my job more..still after 1 and almost half years of blogging.

    Its your life do what your heart says.

  15. says

    what would i do? As a five time career breaker/sabbatical taker i’ve worked on various things. from living in Japan, travelling, working on my business, to raising my kids. Having said that, i think you are doing the right thing, what feels right to you.. Glad that more and more people are seeing the value in taking time off to invest in themselves, vacations aside..

  16. DeniseGabbard says

    Coming in on the tail end, and I was wondering how things went. Were you able to relax and decompress, or did you end up working harder than you would have if at your “day job?”
    Our local news did a story about the United States mandating less paid time off than so many other countries that I thought was interesting. Visitors to Rome or Paris in August experience that firsthand–when everyone is off on holiday. Could be one of the reasons why those folks always seem less stressed than Americans.

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