Reflecting On Two Years Of Freedom From Work

Why work when you can SCUBA? - Reflecting On Two Years Of Freedom From Work

March 2014 officially marks my two year anniversary since I last held a full-time job. It's been an amazing two years, filled with uncertainty and excitement as I worked to balance play with trying to feel useful. Let me do some reflecting on two years of freedom so far.

To keep some discipline, I created a “production schedule” that officially began at 7:30am and ended at 11:30am. Sometimes I'd cheat by calling it quits before 10am because there was nothing left to do.

Other times I'd keep going because I'd get hooked on what was happening in the stock market until it closed at 1pm PST. By spending three to four hours a day trying to produce something – writing in my case – I would never feel guilty spending the rest of the day doing whatever I wanted.

“Feeling useful” is probably the single most important attribute I've needed to experience during this time away. I've spoken to other people who no longer have to work and everyone agreed they need something meaningful to do in order to feel fulfilled. I'm thankful this site provides an easy way to add some value to society, no matter how small it may be. If you're an early retiree who is bored and would like to share some insights, I'd be happy to publish your post here.

Reflecting on two years of freedom from the days of always wanting to get paid and promoted faster is my goal. I've written a similar post about what early retirement feels like, but that post was written immediately after emancipation – like when Andy Dufresne from Shawshank Redemption finally broke free. 

Reflecting On Two Years Of Freedom

Wondering Is this it?

After spending an entire lifetime getting educated and making enough money to live, it feels very puzzling to not have to struggle any longer. It doesn't matter whether your retirement number is $500,000 or $5 million, the feeling of wonder and bewilderment is the same. You've already won, but the thrill doesn't last forever. Instead, you wonder what's next.

You start to think about ways you can help ameliorate problems in the world. Most will fail to make a difference, but some might be genius enough to succeed like Elon Musk who wants to rid our addiction to fossil fuels through the creation of Solar City and Tesla Motors.

The main thing I'm interested in doing is writing online. But I do have this curiosity of starting a scalable advisory business that employs only the most experienced and smartest minds in finance to help the consumer. I don't want any of this “fake it 'til you make it” crap that is basically leading so many people down suboptimal paths. I'll let you know if I give it a go this year.

You'll miss the commotion. 

Staying at home gets very lonely after a while. You'll begin to miss shooting the shit with colleagues about their weekends, gossiping about interoffice romances, complaining about absurd client demands, and so forth. Hearing stories about other people's lives often times gives inspiration or glee into your own. I completely feel for stay at home parents who can't wait to get back to work.

To gain more human interaction over the past couple of years I would go to Golden Gate Park and play pick up tennis with the regulars. None of them seemed to have jobs as they were always there no matter what time I went. I got to know plenty of folks with alternative lifestyles.

One fella drove for Uber from 4pm until midnight so he could enjoy the day. Discovering how other people lived was enlightening. You'll be amazed how so many people are so happy without a lot of money. (See My Poorest Friend Is One Of The Richest People I Know)

You'll wonder whether you're falling behind.

Even though you've already won the race so to speak, you'll continuously wonder whether you should get back into the mix to keep up with your peers. Maybe the reality is you selfishly want to keep the distance between you and your peers. Instead of waiting to give them a high-five at the finish line, you'd like to stretch out the finish line for as far as possible so they never catch up. After all, if everybody is living a life of freedom, the value of freedom gets diluted.

No matter when I'd go out in San Francisco, Honolulu or New York City, there'd always be hoards of people just hanging out. I began to realize that plenty of people either don't work, are always on holiday, or have an amazing amount of freedom from work.

I always thought in order to get ahead, you had to work more than 40 hours a week and be cooped up in an office all day long. But I realize now that my situation of early financial independence is nothing special. There is much more money and freedom out there than you know.

Update 2021: I didn't fall behind because I grew Financial Samurai into a cash cow.

You'll eventually find what you really want to do. 

I've tried a number of things I thought I should do during this time off: 1) Write a book, 2) travel for an extended period of time to see how much is too much, and 3) start an ad network business to name a few. I've changed the design on this site for the first time in four years and I've also tried different types of revenue generating strategies as well. All were worthwhile experiences. In the end, what I found was that all I like to do is write.

After not writing for two days I start getting withdrawal symptoms. It's as if I'm addicted to putting thoughts into words. No other activity gives me withdrawal symptoms – not even tennis or SCUBA diving. There's something extremely satisfying about constructing a 2,000 word article that gets a point across.

Writing online provides instant gratification because it allows me to make sense of confusion. The key now is to figure out how I can scale my love for writing with a viable business. Financial Samurai and being a stay-at-home dad is really my purpose. This took longer than reflecting on two years to realize. More like six years.

You'll constantly wonder why You and not someone else.

Luck is a very amorphous animal. When you're free to do whatever you want, it's easy to take your days for granted. It's when you've got to take a crowded bus to work in the rain when you realize how miserable life can really be.

Because you realize how lucky you are, you start feeling some guilt as to why other more deserving people don't have the same freedom. If you keep thinking about your luck, you'll eventually go crazy because there will always be millions of people less fortunate than you. You'll naturally gravitate towards activities designed to help other people, such as volunteer work, joining school boards, or writing online.

See: Your Wealth Is Mostly Due To Luck: Be Grateful

All you want is the freedom to choose.

The only thing that bummed me out during my last year of work was the diminishing lack of freedom. There was a new boss who wanted to shake things up. He had a tendency to micro manage and not trust his veteran troops to do the right thing for the business. As a result, work was no longer as enjoyable.

Once you've experienced the freedom to choose what you want to do when you want to do it, you will fight tooth and nail to hold onto your freedom forever. Since money is no longer as big of a requirement, you will happily accept less money for more freedom if you ever return to work. In fact, you may even find it rather ludicrous that you once put up with so much crap in the past. Hopefully many of you will discover this fact sooner, rather than later.

You maintain your same financial habits. 

Just like a goldfish who tends to grow in relation to its habitat, we are wonderfully adaptive beings. Since 2000, I've been saving over 50% of my after tax income first out of necessity and then out of habit. When I left Corporate America, my total compensation took a ~70% hit.

Somehow I kept on saving 50% of my passive income within a couple months because that's what I had grown accustomed to. At the same time, I didn't feel like my quality of life declined at all because I had so much more freedom.

Now that my earnings have continued to grow, I'm saving even more because I feel like I need to “catch up” from the first year of under-saving based on the absolute dollar amount. It's really quite silly really, but that's what happens when you develop strong financial habits. They follow you no matter how much or how little you make! 

See: How Much Savings Should I Have By Age

Time moves even faster.

I still remember the last day of work very clearly. It wasn't a celebratory exit, just a firm handshake and a good-bye after I had spent a couple weeks helping my subordinate take over the accounts. But I have a hard time remembering the rest of 2012 because it went by so quickly.

I finished my book on negotiating a severance package by June 2012, and then went on this amazing two-week cruise that started in Amsterdam and went all the way up to St Petersburg, Copenhagen, and Helsinki. The cruise should be more vivid in my memory, but it isn't for some reason. Perhaps it's because things were so hazy in Amsterdam.

I can't remember what I did the first half of 2013. I know I must have gone up to my place in Tahoe for some snowboarding and writing. The summer in NYC for the US Open, and traveling around Switzerland and Mallorca for five weeks was amazing.

I don't like forgetting what I've done because it feels like I wasted my time. Perhaps this is part of the reason why I like to write so much. Since time gets more precious the older we get, it's important we all take a moment to record every single month with more enthusiasm.

You won't be as afraid to spend money.

One of my biggest fears I had before leaving my job was going from being a prodigious saver to a wanton spender. The ideal withdrawal rate in retirement touches no principal, after all. But my fears were unfounded because I naturally made sure I did everything possible not to run out of money before I started spending money. You will do the exact same thing.

For example, I spent about $20,000 on myself during the summer of 2013 traveling even though I was making less money. The most I ever spent on travel before was roughly $10,000 for two for two weeks. I was able to get over my frugality by compartmentalizing my money, creating a business plan, and telling myself that now was the time to go all out because I might not have this chance to travel so much again.

Given you will maintain your financial habits, you'll start saving aggressively again or figuring out ways to make more money when you return. (See The Key To Taking Guilt-Free Expensive Vacations)

Update 2021: Check out my Proper Safe Withdrawal Rate post

You wonder when it will all end. 

I remember telling myself in January 2013 that there was no way this type of growth on FS could continue. How many people out there really want to learn how to better manage their 401k for a nicer retirement? I guess a whole lot more since the viewership more than doubled again a year later.

I also wonder whether I'll ever be forced to get a “real job” again. Will a violent downturn in the stock market crush my net worth? How about Google suddenly blacklisting Financial Samurai for no apparent reason? Will I get into an accident that requires expensive medical treatment? In the back of my mind, I'm waiting for something bad to happen because surely the good times can't last forever. Can it? I guess this is why we save and have insurance.

This “pinch me” type of feeling is ubiquitously felt by many people I've met across different economic lines. The positive joy of freedom more than makes up for having less money by a ratio of 2:1. You've just got to have the courage to fight for what you want.

Biggest Realize: Don't Settle For A Job You Don't Like

After reflecting on two years of freedom, the clear realization is that nobody should settle for a bad job.

Most of us will probably start off working at a job out of necessity, rather than out of love. That's fine. Save your money and gain valuable experience so that you can move on to something more aligned with your interests. It might take several moves before you really find your calling, but trust me when I say that when you do, the clouds will part and you'll see how much better life really is.

Try figuring out the income level where one more dollar doesn't do anything more for your happiness. I thought I'd love to work in finance because I got hooked on online trading as a junior in college.

For 10 years between 1999-2009 I truly enjoyed work almost every single day. Then the downturn kicked my ass, government regulations started piling on and finance was no longer fun. But the financial crisis also kickstarted an old passion I had for writing. Let's see how long this ride lasts until my interest starts to wane.

I never dreamed I would one day make enough to survive off writing alone. Perhaps writing would be a nice side hobby that could generate $500 – $1,000 a month, but no more. I was wrong. Two years later, my writing generates more revenue than income from my last year of work with 70% less effort, 80% more fun, and 90% less stress! I would not have gotten to this point if I did not take some risks. If you are wondering whether hard work and sacrifice is worth it, I fully believe that it is, even if you don't quite live up to your goals.

If you don't like what you currently do for a living I implore you to not settle. You will seriously regret more of the things you don't do than the things you do.


Start your own business/website. If you feel you're not getting paid what you're worth and want to boost your income, start your own business online on the side! It used to cost a fortune and a lot of employees to start your business. Now you can start it for next to nothing with a hosting company like Bluehost for under $4/month and they'll give you a free domain for a year to boot.

Brand yourself online, connect with like-minded people, find new consulting gigs, and potentially make a good amount of income online one day by selling your product or recommending other great products. Not a day goes by where I'm not thankful for starting Financial Samurai in 2009. Here's my step-by-step guide to for how to start your own website like mine in under 30 minutes.

Blogging For A Living Income Example: $300,000+
A real income statement example from a blogger. Look at all the income possibilities. CLICK the graph to learn how to start your own site in under 15 minutes.

Negotiate A Severance Package. After reflecting on two years post work, never quit your job, get laid off instead. Negotiating a severance package provided me with six years worth of living expenses to help me focus on my online media business.

Check out my book, How To Engineer Your Layoff: Make A Small Fortune By Saying Good-bye. It is the only book on the market that teaches you how to negotiate a severance. The book has been expanded from 120 pages to 200 pages in the latest version.

About The Author

74 thoughts on “Reflecting On Two Years Of Freedom From Work”

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  5. Has it already been two years Sam? Wow time really flies! Funny you mentioned seeing other people around you not having to work. I sometimes go to lunch at Costco and the first thing that enters my mind is, “Do any of you work?!?!?!” Interesting how some of your travel memories are hazy. Could it be your vacation times are not as precious since you no longer have a dreadful job that makes you long for a vacation break? Thanks for sharing!

  6. Fascinating article. My goal down the road is to someday be where you are now. It is inspiring to see people like you out there and it just gives me more motivation to work hard now.

    Keep up the great work!

    1. Hey Court,

      You and me both, would love to support each other in our journeys..
      What are your thoughts on this i.e. keeping each other accountable and motivated?



  7. Hi Sam,
    I am floored to have found your website. I have been fighting through contradicting a advice for a few years now and your story is helping me sort through it.

    Question: What are you doing for health insurance coverage now that you are “unemployed”? That seems to be a considerable benefit to being employed but surely not enough to keep one from pursuing freedom.

      1. Hi Sam,

        I found you in the middle of the night after reading about LEAP and being very disappointed. In frustration I grabbed my smartphone and googled “wealth accumulation for 30 yr olds” and your “How Much Should I Have Accumulated” article came up. I loved the candid tone and the dialogue in the comments and now I’m on my 15th article! Thanks for your generous sharing of knowledge.

        You can’t complain about those health care costs. I’m sure this is a bigger problem for older folks though. Thanks for dispelling that concern for me.


  8. I am not financially free yet, but I know if I were to retire I’d go absolutely crazy with 10+ hours per day of idle time. I have a feeling you are the same way, Sam.

    There’s a difference between doing things that are fun (tennis in your case) and things that are fulfilling. I think it’s only a matter of time before you are back in the saddle. :)

  9. Hey Sam!

    “some might be genius enough to succeed like Elon Musk who wants to rid our addiction to fossil fuels through the creation of Solar City and Tesla Motors.”

    — Great example. Elon Musk is definitely one of my heroes.

    “I’ve changed the design on this site for the first time in four years”

    — You did a good job. The site looks WAY better than it did before.

  10. Freedom to choose is the one that resonates with me the most. Will I ever quit “working”? No, not likely. There was once a time where I wanted to be on a trajectory towards parking my rear end on the beach endlessly. I learned more about myself, though, and it is now clear that the parking it on the beach isn’t what I want. It’s the choice of getting up on any given day and parking it on the beach. That’s the goal for me.

  11. Man, you hit the nail on the head for me with the luck/waiting for the other shoe to drop thing. I stumbled into a very good career out of law school that did not entail the brutal, de-humanizing aspect of Big Law practice, one that provides excellent benefits including a pension and generous 401k matching. In just over 5 years, I will be retired/FI after 22 years of working in this job, to pursue other things (I have some serious recreational passions that I intend to convert into part-time work). Lucky? Oh hell yes, am I lucky! But I’m also pretty sure a good portion of my “luck” was not pre-ordained but rather flowed naturally from choices I made. But for sure, plain dumb luck has played a part, and I am super-grateful for it. And like you mentioned, I keep waiting for something terrible to derail my good fortune, because there is so much misfortune in the world, and I can’t help but thinking “why hasn’t it found me?” I don’t obsess over it by any means, but it’s an occasional nagging little thought in the back of my brain.

    Anyway, great article.

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