Living Vicariously Through You: The Joy Of Freedom

Dear Risk Takers, I enjoy living vicariously through you.

It makes me smile every time I read a story about someone who takes a chance and does something crazy with their lives. Make no mistake, as a personal finance blogger I think quitting your job to travel the world without several years worth of savings is kind of crazy, but I love it all the same!  Your risky actions shows the rest of us that we don't need that much to survive, especially those of us living in America.  We're spoiled by excess.

You are the lucky ones because you aren't encumbered with baggage. If you lose everything, you might have a moment of pity, but you never had much to lose in the first place. I originally wrote this post on November 19, 2010. At 32, I was thinking about what else there was to life. The 2008-2009 financial crisis really made me question the point of working in finance.

Thoughts On Breaking Free

For the rest of us, we're tied down. Many of us have mortgages to pay and mouths to feed.  How do we leave a job that doesn't inspire, but pays us just enough to show up?  

We've got spreadsheets and calculators where we pro-formalize our lives. If we work this long, and save this much every year, then we'll get to be free and travel the world!  But in the mean time, we have to patiently wait.

Living vicariously through others is the only thing we can do until we reach financial freedom.

Do you remember freshman year in college?  I don't know about you, but I felt like it was one big orgy. Everything was new, and we all had a sense of wonder, wanting to meet and do everybody! We were all accepting, because we had to be.  

There weren't any cliques formed yet, because we hadn't developed our good or bad perceptions. That's the way it should be, but we just can't help settling into a mold, doing what society tells us to do.

Two Choices When I Graduated From College

When I graduated college, I had two job offers and a half-dozen rejections.  One was to go on an adventure and work in a foreign country.  The company literally made widgets, and I was asked to manage the factory and develop a marketing plan for international expansion.  

The second offer was the dream corporate job offer where business majors and Ivy league grads would die for.  Seriously, every single stiff in a suit you see walking around campus holding a leather binder would have gone streaking just to land this job.

Of course I went with option #2 because I rationed that there must be a reason why so many folks study all day and join every little resume-building club for this job.  

True to form, the job was a ball buster, everyday for two years until I escaped to come to San Francisco. Now, I can still work all day. However, now the air is fresh and the tennis courts are plentiful and free. Living vicariously was no longer just a dream.

Wondering What If

At least once a month, I think about how my life would be different if I went with job offer #1.  I wonder about the different people I would have met and how my professional lives would compare.  

Maybe I'd be a tri-lingual mega-millionaire by now, or maybe I'd be light years behind where I currently am since the factory may have shut down. Who knows for sure, but I can't help thinking about how things might have been.  It's not an agonizing thought mind you.  It's just a fun thought to have.

There are seldom really bad choices in life, only sub-optimal or different choices.  If we're realistic enough, we can see the good and bad in everything we do.  The idea is to make the best choice possible, and minimize the potential annoyance of not taking the other one!

Living Vicariously: You Are The Lucky Ones!

People don't change their lives when they are happy.  People change their lives because something is bothering them sufficiently to change. You've been pricked so many times by your boss, that you quit.  

The work you're doing is so soul-less that you switch fields. You realize your life is half over and you don't want to die before seeing the pyramids so you take a sabbatical. Whatever the case may be, I'm happy for them all because of the stories they allow you to provide us.

It's unfortunate we can't live parallel lives, or be in two places at once.  Just that one choice will alter your life forever, so choose carefully, and have no regrets!  

Thanks again for writing all your inspiring stories. Don't let anybody keep you down because they're just jealous you're doing what they've always wanted to do. Perhaps I can join you in 10 years, when my career is over.  In the meantime, thank you for letting me live vicariously through you!

Related posts:

The Curse Of Making Too Much And Not Following Your Dreams

Taking A Leap Of Faith And Retiring On My Own Terms (I finally broke free in 2012, just two years after I wrote this post)!

Readers, do you consider yourself a risk taker or more on the conservative side of things when it comes to your career and investments?  Was there anytime in the past where you regretted or deeply wondered what could have been? Are you living vicariously through someone else?

For more resources check out my:

Financial Samurai has been online since 2009 and is one of the most trusted and largest independently-run personal finances today. You can sign up for my free newsletter for more insights. I'm still living vicariously through many of you. I just have a lot going on with two young kids to raise.


Sam @ Financial Samurai – “Slicing Through Money’s Mysteries”

About The Author

34 thoughts on “Living Vicariously Through You: The Joy Of Freedom”

  1. I have tended to be a risk-taker, but there are times I have been cautious, conservative… the thing that always sticks in my mind is hearing about research with octogenarians – the only thing they said they regretted? NOT taking risks. Everytime I have the chance, I think about living with regret for another 50 years… that helps me level out the risks somewhat. My life is small, rewarding, and free. In 3 months I take a new risk of quitting the very part-time job that provides a steady income and going fulltime to work for myself…no fallback plan! Scary? Sure. Exhilarating? Definitely!

  2. This really resonates with me. I fall into the category of the “crazy ones,” by most people’s standards. (I moved to China when I was 22, shortly after graduating with a degree in Latin American Studies.) However, on more than one occasion, friends have told me that I’m more conservative than I like to think I am. I have been very lucky in life. Thanks for giving me a different way to look at this :)

    1. Well done! What made you move to China with a Latin American Studies degree? Why not South America or something? Where are you currently residing now?

      Anyhoo, it’s great that you do what you do. Keep it up and I’m gonna visit your site now! :)

  3. I took a big step and decided to “take a break” from college to find a full time job at the age of 19. I went a few months without paid work, but kept doing unpaid internships. I found a paid internship that eventually became my job. I then took that opportunity to move in with my now fiance, out “on my own” for the first time. I think that was the biggest risk I’ve ever taken. I was so sure I was going all the way through college without stopping. Some of my friends still question my motives, but looking back, I couldn’t do it any other way. I’m looking to do more risk taking, including starting my own business. I hear that so many of them fail, and I’m aware of that, but I’m still going for it.

  4. Kay Lynn @ Bucksome Boomer

    It’s funny but as I’ve gotten older the less I think about the path not taken. Instead I’m focusing big time on making the most out of the bed I’m in.

  5. I wish I could tear away from my current job and move on to a job that really excites me. I have reached a dead end here and the people I work with are in bearable. I know there are other jobs out there but the fear off how I would perform or will I be able to perform, what if I don’t perform and get fired, what if I feel more miserable there etc etc scare me. Also, the fact that I am comfortable and secure in a place makes the jump more difficult. I am not sure what will be the last straw that will make me take the jump.

    I have always played it safe in life and would not mind sailing through life with the only the bear necessities. Of course after marriage and with other responsibilities, you tend to get even more cautious.

    1. Just wondering though, is it dangerous you are saying you are bored of your job if you are linking your Credit Cards of Canada job here? Or, do you not work for this company?

  6. I’m definitely a risk taker….but I do “calculated risks”….just like in poker.

    When I quit my fancy corp gig 10 years ago without a job it was so liberating!

    And after I got back from a couple weeks partying in Key West, I found a job at a start-up. We ran out of cash pretty quickly but I kept working for equity. The day I decided to do that was the most invigorating of all. Knowing that I was essentially working for myself and that I was in complete control of my future was life-changing. Not getting paid didn’t make me slack, it made me work 10 times harder! And it sent me down the entreprenuerial path, never to stray again.

    1. Wow Geoff! That’s great to hear! I didn’t realize you worked for a good 10 years in your corporate gig before going out to a start up. You said it was liberating, but was it also scary too? Did you have a good chunk saved after 10 years?

  7. I did not regret anything from my past but I mostly considered them as a key to whatever and who I am now. I have learned my lessons for every failure or mistakes I have done in my younger years. We cannot achieve anything if we do not take the risk of doing whatever we have to do, whether it is a failure or success the important thing is the lesson we learned from every journey we take.

  8. Agree, I read about these people and even preach their message, yet I’m stuck at my desk job. I am getting set up for the point where I can live “free” by being out of debt and eliminating things, but I don’t have the urge to travel and not own a car. I’m halfway between, not ecstatic but not mad enough to go crazy. I preach this lifestyle to my friends, but maybe I’m just as bad because I’m not even living it. Who knows? Still only 24 and in a good position. Even just having this mindset would have freaked me our 3 years ago. I have been to Australia to study, but could never imagine just living like a nomad.

    1. Ahhh, to be 24 again. I encourage you to do whatever you really want to do at this age, while keeping your finances in disciplined mode. You’re only in your 20s once, so make the most of it!

  9. I’m a Risk Taker and so far it worked and I’ll be 50. I own my own home; work for myself; and I’m Happy.

    I do live month to month (yikes); but I have backup plans and backup for those backup plans..

    I can live in my small unit and rent the larger unit of my house someday… etc.. here in NYC.

    Or leave NYC (sell the home and live someone where I can have a home paid off and still have a 100,000 in savings and social security.


    scary to work for oneselves.. great post

    1. Sounds great Betty Ann. You can definitely always leave NYC for a cheaper place, which is why I like living in an expensive place curiously enough.

      Do you own your home free and clear?

  10. I swing back and forth between risk-taker and conservative. Seven years ago, I was much more of a risk-taker but that risk landed me in debt. Now that I’m older (and according to your calculations, almost middle-aged!) I’m more conservative. However the risk-taker is still rolling around in my mind; every now and then I think of selling all of my possessions and roaming the globe. Until then, I’ll just read Wandering Earl. ;)

      1. Well, if that risk-taker spirit ever decides to make its presence felt once again and you do sell all of your possessions, I look forward to meeting you out here somewhere! This is an interesting topic because even though it appears that I may have taken great risks, it isn’t so much the case. When I left to travel at the age of 22 I really had nothing to lose as I knew that if things didn’t work out, I could always return home, find a job and start again. It just happened to work out that I continued to find opportunity after opportunity that has allowed me to continue this lifestyle but luckily, I really didn’t have to put much on the table to begin with.

        And as always, I appreciate you both as readers of my site and thank you for your kind comments!

  11. Very true, people will make that change when they are unhappy. I had made several life changing decisions but the thought of what if never crossed my mind. It may well just make me frustrated if I may found out that my decision was a bad one. Anyway, the most important aspect is that you are happy where you are now.

  12. Financial Samurai

    @Sandy – Don’t worry, middle age when your life is half over isn’t until 39 since the median lifespan is 78, so you still got a few years!

    I do wonder about debt though. There’s always a joy or a return for taking on debt, otherwise one wouldn’t take on debt, no?

    @Kevin – Still searching for the dream mate! I feel I am too conservative and methodical when it comes to personal finances and life. I already have a 5 and 10 year plan in place as well as all my financial targets in a spreadsheet, for example. Sometimes, I wonder if I should just say “what the heck” and do something completely different. So much is at stake though. At the very least I’m close to taking all my vacation this year!

  13. Kevin@InvestItWisely

    I guess right now definitely more on the conservative side, and in part due to those anchors. There are many ways we can explore without betting the farm though, like you said, whether it be the part-time biz or something else like that. I think it’s important not to become too stagnant and set in one’s ways because there is risk in that, too: the risk of not growing and realizing one’s potential.

    Sounds like you definitely found the dream, Sam. :)

  14. Believe it or not, Sam, I think about this question a lot.

    I’m currently an officer in the military. Although I enjoy and am gratious to serve my country, the assignments that I receive are far from what I want to ultimately do–teach people the ins and outs of personal finance and start my own teaching network.

    So what’s the dilemma? I can get out the military now, with 12 years of service to maybe be able to do what I enjoy OR I can finish out at least 8 years, retire, and be in a position to never have to work a day in my life (plan to have no mortgage with a $4000 monthly pension at retirement).

    And at retirement, it would be easier to start a business in fail because I would have my pension to fall back on. But here I sit, also living vicariously through the many successful blog authors doing what I would love to do as a all-day job.

    1. Romeo, it’s hard to say since I’m not in your shoes but as an observer, I would stick it out for 8 more years for sure to get the kidding pension! Let me help you. Take 40,000$ and multiply it by your remaining life expectancy. That’s how much your pension is worth! Would you work 8 more years for chance to “win” $1.2million+?

  15. Sandy @yesiamcheap

    I’m conservative because I have to be because the risks that I have taken have landed me in a place of debt and uncertainty. But when I dream, my true self likes to get just close enough to the ledge to look over, then back away. I know that it’s causing some angst and midlife (is 32 mid-life?!!!!) mental crisis but right now I have to suck it up and act like an adult is supposed to act. I guess.

  16. Financial Samurai

    @IJ – A WTF fund sounds like a good outlet and idea. It’s very likely you will not lose all your money and may hit it big based on an ROI. I have a similar fund where I’ve used the money to invest in a couple private firms and vacation properties for fun and potential return. Otherwise, I’m very conservative and am happy with a 4% risk free rate of return.

    @Retireby40 – Ill have to check out your guest post when I return. Do you have a set savings goal or cash flow goal you need to achieve before hanging it up and doing something else?

    @MJTM – it’s great and interesting to follow Baker’s adventure. Hope he and other lifestyle bloggers can go out and travel more and share with us their trips. With 6 weeks vacay a year, I try and go on at least two international trips a year if not 4, and the rest are in the US or staycations. Not sure I could travel for more than 1 or 2 months at a time bc I’d miss work and SF. Lots of exciting stuff right here at home!

    1. Investor Junkie

      Lucky you. I assume you don’t have children (at least not young). We can’t take a vacation because of our kids, not because we can’t afford it. Staycation it is at least for another 3-4 years.

    2. I do have a set of saving goals and a draft cash flow plan. I’ll write a post on this topic near the end of the year to go with my net worth post.
      2 international trips a year, wow such luxuries. :)
      Have fun! I love international travel.

  17. I’m in agreement with you there.

    When I was younger, I lived in Seattle and decided to leave. I gave away all my possessions and hitchhiked around the US to see where I’d like to live. Certainly it was a highlight of my life.

    Years later I’m now ensconced in a comfortable life.

    Two of my favorite blogs about perpetual travel is Andy Hobo Traveler and Wade’s Travelogue.

  18. Anyone living their dream interests me. Whether their dream is that boring #2 option or a nutty guy like Baker from Man Vs Debt who traveled the pacific for 8 months.

    Do you remember freshman year in college? Some of it lol. But I had a chance at the end of freshman year to transfer to a completely different school for a 5 year MBA program. I didn’t, and not doing it led me to my wife, my life here, my J.D. etc. WEIRD to think what my life would have been like.

  19. I am definitely more conservative. My job has lost its luster and I’m looking for a way out. I can’t just up and leave though (bills to pay and all that you listed.) I’m giving myself 3 years to get the hell out of Dodge and we’ll see how it goes.
    Did you see my guest post earlier this week? She wrote about quitting her office job and becoming an entrepreneur doing what she loves. I think that was pretty vicarious. I only know a few people like that and really need to meet more of them.

  20. Investor Junkie

    One of the overall things you are implying is people get set in their ways and don’t take enough risk in life. I agree, and was the reason for my post:

    I too have fallen into this trap.

    I’m not suggesting bet the farm, but if you take some calculated risks in life at worst case you’ll learn something from it. Go start that biz part time, go ask that girl you wanted to date, go find a new job, etc. etc… Do something! Just don’t sit on the fence and not do anything at all. Life is too short.

    For me, I personally plan on creating a WTF Fund on my site and making somewhat risky calculated bets on the market. Everyone will be able to see my good and bad investments I make. Could I loose it all? Sure! But the amount of money I’m risking is less than 1% of our total net worth. The is more upside risk than overall downside.

    So you’ll be able to live vicariously through my trades ;-)

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