A little preamble to start us off. I woke up this morning a little after 5 am to do some audio recordings with Jody on the beach in the Outer Hebrides in northern Scotland. We’ve been up here for almost a month now and there’s been a lot of time lately to ponder the scope of the expedition thus far: 50 countries, 50,000 miles, circumnavigation, etc. It all comes to an end in less than 3 months. Which begs the obvious question: “what’s next?” I suppose the best part of that question, and at the same time the most unsettling is the unknown. I’ve never been very good at stillness; I’m not much for contemplation. It’s something I’ve struggled with my entire life. I have to keep moving- have to be accomplishing something. To date I’ve had over 40 different jobs, more than one for every year I’ve been alive. Bartender, wildland firefighter, Outward Bound instructor, commercial fisherman in Alaska… I even had a brief stint after University in a suit and tie working for a small corporation in Boise, Idaho. It was there; at the age of 22 I learned the best lesson of my life. It wasn’t what I wanted to do; that’s a monster I’ve never been able to tackle, but what I didn’t want to do.

Paragliding in the Outer Hebrides, Scotland

I was dead broke, living in a windowless basement of a grungy house with an alcoholic roommate. Without any real plan I’d moved to Idaho thinking a buddy and I would open a pub.   To pay the bills I was waiting tables at night and working full time during the day at a small manufacturing facility. After college I’d planned on backpacking and climbing in the Andes for a year in South America. My trip lasted less than two months. I’d found it all way too easy wandering around mostly aimlessly without a care in the world and wanted to come back to the “real world” and see what I was capable of. I wanted more challenge.

For some reason I wasn't happy roaming around places like this!

After a month I found myself promoted to Director of Marketing and Sales at the small but promising high-tech plant and put in charge of accounts all over the world. We were engineering the platforms that microchips are etched on. Intel represented 78% of our business. This was 1995- business was BOOMING. The writing was on the wall- stick it out for a few years and I’d be a multimillionaire. My day usually began at 3 or 4 in the morning. Give the dog a walk in the dark, drive to work in the dark, call the accounts in Asia, blah blah blah. Come home in the dark, take the dog for a walk, watch an hour of TV, go to bed, start it all again the next day. In the spring, after 4 months of this I’d just returned from a tradeshow in Geneva, Switzerland and decided to do some whitewater paddling for the weekend. When I came to work on Monday morning I realized with some shock that the paddling was the only thing I could remember of the last 4 months of my life. I took out a piece of paper and drew two columns. One with a + sign, the other with a – sign. On the plus side was a symbol: $. On the negative I didn’t have enough space on the paper to put everything down. I quit that day.

Jamie Mitchell is one of the hardest workers I've ever met. But I think he's enjoying it!

In my youthful arrogance I even wrote a letter to the CEO of the company, a good friend of mine, and the father of my college buddy who was planning on being my partner in our pub, which thankfully never got started. In the letter I described in detail all the things that I thought were wrong with the company. Predictably he did not appreciate my adolescent rant. My father, who was living in Seattle flew over to Boise to “sit me down” and try to convince me that I was making a huge mistake. “Son”, he said “in your life you’re going to get 3 or 4 big opportunities. The difference between winners and losers are the ones who actually see them as opportunities and act on it. Right now you’ve got one of them. I know it sucks, I know you hate your job, I know you hate your life, but you’re going to be rich!” My father was right, I would have been rich. But at what cost?

Later that week I was cleaning out my desk and feeling very low. The owner of the company hated me, I didn’t have a job, and my dad’s words were ringing in my ear. The Vice President, whose office was next to mine came over and invited me to lunch. As we sat down he asked me what was wrong. I told him I felt terrible for letting the company down, for writing the letter, for losing a friendship with the owner. And then he told me something that I’ll never forget. “Gavin, the CEO isn’t mad at you about the letter. He’s angry because he didn’t do what you’re doing when he was your age. We’ve lived our whole lives in this town we don’t even like. Our wives and kids hate us because we’re married to our jobs. You think we like this reality we’ve created for ourselves? He’s pissed because he sees in you what he should have done with his own life. He’s mad at himself because now it’s too late.”

Kiting in the Marshall Islands onboard The Best Odyssey

I know it’s arrogant to espouse what’s the “right” and “wrong” way to live. I fully admit to having no idea and I know what works for one may not for another. My opinion is that if I’d stuck it out in Boise and made all that money I would not have lived a fraction of how I’ve lived to date. There’s no way of course to know if I’m right or not. I’ve never made any real money. I don’t own a house or a car. I don’t have an emergency fund or a “portfolio”. A lot of people will read this and think “wow, that’s really reckless.” And it probably is. But over the years I do know that because of what we do- where we’ve brought people, what we’ve exposed them to- well it’s made a lot of those people think very hard about what they do. I know for a fact that several of those people have quit at least in part because of their experiences with us. And I’m proud of that. Let’s put it this way- I’ve never met a banker who said “I love my job!” I think if life doesn’t have a lot of meaning it catches up with you.

One more story then I’ll get to the meat. One of my very best friends growing up was diagnosed with adult onset diabetes when he was in his late teens, which of course is manageable with diet and medication, but your average life expectancy is greatly reduced. One year when I was home for Christmas while in college, when we were maybe 20 years old this buddy laid out his life plan: Graduate; get a job in accounting; find a wife; have 2-3 kids; make over a million dollars by working hard; and retire at 45. I remember instantly feeling two things. 1) Envy that someone could actually know what they wanted to do with their life and 2) Sadness that someone would do that with their life. My reply went something like this: “So you’re going to work in an office slaving away for hours at really boring shit while your kids grow up without you being around so you can retire with all this money when you’re 45; at which time if you’re lucky you’ll have maybe a couple more years to live? Are you out of your mind?”

John Amundson has made a living shaping boards, and traveling the world ripping waves

What I didn’t know at the time was that my friend’s plan mirrors most people’s plan. So when I hear people complain about their work I always ask why they don’t quit? And they look at me like my friend did 20 years ago- like I’m crazy. I know I have a penchant for the absurd, but I think I can make a good case that they are the ones who are nuts!

Finally, before I get into the 10 reasons you should quit your job I’m going to anticipate some of the feedback from this article. I know it’s going to make some people angry. People don’t like to be reminded or told that the way they are living their life should be questioned or changed. But it should. People will also say that I’ve been lucky; or fortunate; or that I had good parents; or that because I don’t have typical “responsibilities” like children or a mortgage that it’s a lot easier for me to choose to live a different way than the norm. Fine, I can live with that. And it’s probably true. Anyone who knows me knows that I got here, wherever “here” is, the same way that some of the our insanely wealthy clients did: by working hard.  I’m not associating money success with life success though.  I’ve observed many who have found that balance, but I know for sure that one does not equal the other.  For some strange reason I’ve chosen jobs that require an impossible work load for very little monetary reward, so following my advice is definitely reckless! So let’s not call it advice at all, but the observations of someone who’s chosen a very different way to live life and had the fortune to meet a lot of successful and inspirational people along the way. But by “successful”, I don’t necessarily mean money success. In fact none of my heroes are wealthy by monetary standards at all, but they are successful in this little thing we are all doing called life.

Mauricio Abreu in Kosrae

Professional Kiteboarder Mauricio Abreu ponders another day of work in Micronesia

Ok, so here we go. 10 signs you should quit your job and admittedly a little personal push to help make it happen:

1) One day…

I hate this one more than anything. You can’t believe how many times I’ve heard this. “One day I’m going to sail around the world.” “One day I’m going to climb Everest.” “One day I’m going to bike to Tierra Del Fuego.” No you aren’t. This may be too simplistic or maybe not even fair, but in my experience there are two types of people- people that DO, and people that talk about what they are going to DO. The ones who talk are just that- talkers. You know how many people have promised me they are coming out here on the boat? Just as soon as they get the money, get the time, find the right job…Yeah ok, sure. They aren’t coming out here. They want to think of themselves as the type of person who would…but just can’t right now.

2) You like to sleep in.

Definite cause for concern. If you are happy in your work, you’re probably happy in your life. Which means you want to live it, and you can’t live it in bed. Parents listen up- DO NOT LET YOUR KIDS SLEEP IN! When I used to instruct for Outward Bound, our program director and one of my very favorite people on earth Doug Mann used to say “you can sleep when you’re dead.” He was right. Life is too short to spend it in bed.  Be wary of the couch too!

3) You can’t wait to watch TV when you get home from work.

TV sucks. Period. End of story. Throw a brick through that piece of crap. Grow a garden, read a book, talk to the neighbors, go for a walk. Kill your TV and life will look very different immediately in a very good way. Real dreams will take hold, network fantasyland will die. When I had a corporate job I couldn’t wait to get home to the TV so I could just shut off my brain. Time is precious. None of us knows how much of it we’ll get, but one thing is certain- it will run out. If you’re watching too much TV, have a close look at your work.

artist, photographer, father and wave ripper, Pete Cabrinha follows his passions

4) You want to quit, but you’re scared.

Being out of your comfort zone is going to open up all kinds of possibilities. Go on, take the step you know you should take. Once you take the step you’re going to realize the world is your oyster- the possibilities will literally overwhelm you. This is a nice predicament to have.

5) You find yourself saying or thinking “I wish” a lot.

Everyone dreams at night. But it’s the day dreamers, the ones who act on their dreams who are doing amazing things with their lives. You’ve probably met a couple people like this in your life. Those people who just seem to have really clear and excited eyes. People who are full of life, full of joy, hope, and seem to inspire the people around them. If you aren’t one of those people, take a good look at your job. It’s pretty hard to be full of life and energy if your job is sapping it out of you.  I’m not advocating any TYPE of job, and I’m not advocating something like I do at all- but whatever job you have should be something you can take a lot of satisfaction from.  Something you can be passionate about.  Taking care of a family, being a nurse, being a social working, volunteering.  The best jobs invigorate and motivate you to do great things. These jobs exist or you can create them. Do it! Don’t wish it.

Finding nirvana like this in the Pacific takes a lot of WORK. Nice work though.

6) You’re doing it for your family.

This is western society 101. It’s what we learn in school, it’s what’s preached in the magazines, it’s what’s going to magically “make us happy.” Consumerism and having “stuff” isn’t going to do diddly for your well being and you know it. Shopping isn’t buying things- it’s selling a piece of your soul. Want to do something for your family? If you hate your job quit it. Pare back and get back to simplicity. Take time with your kids and your dog. Instead of working weekends teach basketball or volunteer. Try buying food from the local farmers. Start a food co-op with your neighbors. The average American child gets 70 toys a year! If you’re working to sustain that then you are GUILTY of buying into the biggest sham of all and all you’re doing is selling out yourself, and your kids. If your kids are more into Gameboy and Nintendo than playing in the outdoors or learning music you are doing a poor job of being a parent, which probably means you’ve got a poor job to go with it. Sorry, but the truth hurts. If you are thinking right now “but all the other kids have them” then double shame on you.  The most joyful, happiest, most fulfilled people we meet over and over again have nothing in western terms.  They live simple lives, in simple places.  And to compare the two is way beyond the scope of this article, but suffice it to say I’m convinced we live rather complicated lives in comparison.  And I put myself in this category!

7) I’m just going to work until I get XXX amount of money.

You’re lying to yourself and you know it. It’s a stupid game of keeping up with the Joneses and if you’re playing it you’re a pawn and not a queen. Get out of this race it’s not one you can win.  I’ll even go so far as saying this- the more you “have”, the more miserable you’re going to be.

Mauricio Abreu is a father of 3, business man, and one of the world's best kiters

8) I’ve always wanted to be….

Ok maybe this is too simple, but…..go be it! Unless you believe in reincarnation or the afterlife this, right now, right here is your ONE chance.  Life is not a dress rehearsal.  Do you have any regrets? Most people do. Think about 5 years down the line- do you want more regrets, or less? I met a guy once who had always dreamed of being a geologist. Loved volcanoes, rocks, dirt, earth. He felt connected to it. He worked for some massive corporation that made shampoo and perfume and cosmetics. He despised his job but his wife said he couldn’t be a geologist because it wouldn’t “pay the bills.” He was “doing the right thing.” What a crock. I gently suggested they should just cut the bills a bit. You would have thought I’d suggested he become a comedian for how hard she laughed at me. But he wasn’t laughing.

9) You don’t look forward to going to work.

Unless you’re one of the truly lucky (or unlucky, as history often proves) who doesn’t need to work at all you’ll be spending at least 1/3rd of your time on earth working. And another 1/3rd sleeping. Which leaves 33% to play. I’ve met a lot of people in our wanderings around the world who don’t consider work to be work at all. Work should be something you love, something you’re passionate about, something that excites you. Suddenly then you’re playing 66% of the time! The most rewarding job I’ve ever had was instructing youth and adult populations when I worked for Outward Bound, an outdoor education school. They paid me $50 USD per day. I couldn’t believe I got paid at all. When I wasn’t working I was doing the same thing as when I was- playing in the mountains and in the rivers. And so were all my co-workers. Each of us was passionate about what we were doing because you could see the amazing impact on the kids and adults in the program. When you have a job like that money is not a concern. Life just has a way of working out when you’re doing the right thing.

Ben Wilson in Indonesia

Ben Wilson is one of the hardest working people I've ever met. Humble, kind, intelligent- and absolutely radical at what he does.

10) Deep down you know you should

Those of you who have the right job probably left this article a long time ago. Those of you who are still here are probably here because you’re somehow connecting with what I’m saying. You’re nodding your head to some of this stuff, trying to build courage to do something that unfortunately you probably won’t. Excuses are already filtering into your conscience. Maybe next year…Maybe after the recession…Maybe when the kids grow a bit older. If I just caught you thinking anything like this then I’ll leave you with this one thought. Making excuses just gets easier and easier and eventually those dreams and aspirations you have will become distant memories. You’ll be like I was all those years ago sitting in my office in Boise Idaho, wondering what happened to the last months of my life. For many people those months turn into years and then decades and then comes the inevitable for all of us. I said very honestly in one of our very first videos when we started this expedition, “life is about living, it’s about right now, this moment- because this moment is never going to happen again.”

It isn’t.

Here’s that video:

I’ll leave you with this quote from Edward Abbey, my favorite author:

“One final paragraph of advice: do not burn yourselves out. Be as I am – a reluctant enthusiast….a part-time crusader, a half-hearted fanatic. Save the other half of yourselves and your lives for pleasure and adventure. It is not enough to fight for the land; it is even more important to enjoy it. While you can. While it’s still here. So get out there and hunt and fish and mess around with your friends, ramble out yonder and explore the forests, climb the mountains, bag the peaks, run the rivers, breathe deep of that yet sweet and lucid air, sit quietly for a while and contemplate the precious stillness, the lovely, mysterious, and awesome space. Enjoy yourselves, keep your brain in your head and your head firmly attached to the body, the body active and alive, and I promise you this much; I promise you this one sweet victory over our enemies, over those desk-bound men and women with their hearts in a safe deposit box, and their eyes hypnotized by desk calculators. I promise you this; You will outlive the bastards.“


Pete Cabrinha balances running a kite company, family, and dropping into mammoth waves


  1. I can totally relate to this Gavin! I have made similar choices, and while I know I have chosen the more difficult path perhaps, I can safely say I have lived life to the fullest (so far), and love every minute of it.

    My definition of success is very similar to yours… success is happiness and living your dream lifestyle (whatever that might be), as opposed to making tons of money, or having a high powered position.

    A truly brilliant piece and wise words my friend.

  2. It’s always a delight to find your newsletter in my inbox. I’ve been trying very hard to pursue your lifestyle (as you might remember), but the everlasting necessity for money seems to catch up with me every time.

    Here you hit the nail on the head. I was sailing 8 months ago and now I’m earning money to ‘sustain’ that lifestyle but haven’t set foot on a boat since. I’m saving for the ‘big moment’ when I can pick up where I left. You’re absolutely right! Not a day goes by that I gaze to pictures that resemble this aim while killing time at work. I hate that and should be lucky enough I have no other obligations but to pursue my own dreams.

    Thanks for another great article. A useful source of inspiration. Know it’s not going un-utilized.

  3. Very cool Gavin! I agree with everything you wrote. I killed TV many years ago and don’t miss it at all. I have so much more time in my life to work on projects, which I enjoy doing. Next I’m working to quit the j-o-b.

  4. Relating to you in a mighty way!!! Thanks for putting it in words! Powerful stuff, Gavin. ‘Will have to share with others so I can actually look at them and say, “See? We’re alright.” HAHA Love seeing the adventures at each step of the way.

  5. If we were all Peter Pan, the human race would cease to exist in a generation. Is that what you’re advocating?

      • If we were all Peter Pan, you wouldn’t be able to sustain your lifestyle. Who could be bothered building you a new kite board or boat when yours breaks? Who could be bothered doing boring farm work to feed you? Who could be bothered producing the medicine to heal you when you get sick? Who could be bothered doing shitty oil-rig work to produce the oil needed to produce everything you consume?

        Not to mention the terrible crowds and destruction of wild places if everyone else set off to find their own unexplored island.

        Your lifestyle sounds great, but can be sustained only if few others pursue it.

        • Fair enough and of course you are right. That wasn’t what I meant by Peter Pan and what I’m advocating is not to avoid work- it’s to find work that you can be passionate about, something that is meaningful, something you can take honor in doing. Taking care of kids, feeding your family, even cleaning the streets- just about any job can be fulfilling, of this I am sure but I believe if people are working for an endgame that is simply dollar signs doing something they aren’t enjoying to get there- well I think that is no way to live.

          Thanks for your comments Tristan. Helps me refine!

          • Hi Gavin
            Yes I agree with you, and I think there alot that people should learn about life that sailing around the world as much as it looks good on paper there alot they might not like. I personally have a reverse story to yours, where I grew up on a deck of a yacht, and now work in a city for one of the worlds largest clothing companies. I wouldnt trade my years on yachts and being free and I spend most of my time in the city walking around bare foot and turning up to board room meetings with shorts on but the most important thing is that im extremely happy in where i am and what I have achieved and can do. So yes your are right each to their own and the most important thing is to be happy and not listen to all the social BS of what you should do and just do what you want to do.

        • I must respectfully disagree, Tristan. People doing what they are passionate about, following their bliss so to speak, make the world a better place for everyone. Some people are passionate about building kite boards, or farming, or healing… eg. some people are passionate about kiting. so they build a viable business around this passion. Beautiful places that are enjoyed for their beauty are rarely destroyed by crowds, rather, appreciated and protected. besides, “Setting off to find your own unexplored island” is easily understood as metaphor. So even the people who literally climb mountains or sail around the world serve as inspiration to the rest of us to follow our dreams. which could be to cure cancer …or poverty etc. etc.

          • Exactly! We’re saying the same thing, just in different ways. I don’t pretend to be the most articulate in my rants. Passion is passion- and it’s a beautiful thing, in any endeavor.

          • No one is passionate about working on a oil rig, being an auditor, selling insurance. its all about $$. We make choices, we live with them. Congrats, you live a dream life to some. I see it as empty, no home, no children, no legacy. However, No strings, no “responsibility” you get to see cool things, do cool things. Its a wonderful feeling to see the look in my daughter’s eyes as I teach her something new, or she watches me and learns. whether its fixing dry wall or catching a fish. its all in your choices. If we all followed your advice, how would anything get done. No one is passionate about picking up the garbage.

          • Hey Cameron. I think you missed the point, sorry to be blunt. I’m not proposing or encouraging anyone to follow what I’ve done- what works for me isn’t going to work for most people, as you’ve pointed out. What I’m encouraging people to do is follow their passions and their dreams. Obviously that’s not available to everyone- as westerners we live very privileged lives, and yes- much of that life can be vapid and irresponsible which is why we are also the most medicated and largely depressed society that the Earth has ever seen. Raising a child, being a great mother or father, passing on a legacy- these are WONDERFUL things that I’m glad good parents are passionate about! It is my theory that if you live a life like you say- simply to make $$ you’re going to be miserable. Because there is no end to that pursuit, you’ll never reach a place of peace. You’re letting so many beautiful, wonderful things pass you buy in your quest for “more”- things like looking into your daughter’s eyes. There is a comment above from Waller about this that I think is perfect. It’s about managing expectations and dropping the “if then” attitude. Like he says- it’s not necessarily about the end result, but the process. “If you are content enough to really enjoy the process of cruising, you are probably pretty content at home. And if you are not content enough, the passion will only carry you for a short while.” But thank you for your comment, always great to get all the different perspectives.

  6. Hi Gavin….

    I came across your post this morning, and it reminded me about when I was thinking about a change after working at Kona Village Resort, where I was employed for 14 years.
    I saw how disgusted the “elders” were with their predicament, same job, same drill, day after day…. No way to get out, all this “seniority” they’ve worked so hard to achieve,
    that they were too afraid give up, and take a chance on something new….. because where would they go? All they know is waiting tables, and want to remain in their
    “comfort zone”…. ” Well, one day I’ll be able to “retire”…..” What, work like hell for 30 years, then “live” when you’re 60? Naw, LIVE NOW! I’m doing it….
    I rolled the dice, took a chance, had FAITH that I could throw caution to the wind, and go out and get what I want out of life. It’s not about “stuff”, material possessions, or social status.
    It’s about being successfully content with who you are, to yourself, in your own mind. Not in other people’s eyes. Who friggin’ cares about what the “Joneses” think, have, or do.
    I’m so excited about life I cannot sit still…. I want to experience as much as humanly possible in this life…. And I AM, and WILL continue to do so.

    When it’s my time to go, I will look back at everything I’ve seen, felt, experienced and achieved, and be able to say that I can happily accept that it’s time to move on……..

    …….to the next chapter!

    Thanks for the dose of reality, Gav…. My trip on board with you guys really opened my eyes, and after reading your “10 reasons”, they’re like a 1.4 aperture….. WIDE OPEN….. Mahlo Nui Loa, E Piha Hauoli….. LONO

    • Lono that’s exactly it buddy. My dream, my mission is to surf 10% as well as you do- then I’ll really have lived! You rock buddy, can’t wait to see you again- been way, way, way too long. Keep chargin’ on this little mission we have going called life!

  7. Gavin, I saw this video and thought it fit your article. http://vimeo.com/27582815
    Hopefully not too many people will follow your advice, or all of your secret spots will be getting crowded!
    Thank you and Jody for sharing your fabulous adventures.

    • cool video Kyle! Don’t worry about people following the advice- people unfortunately (thank goodness!) just don’t work that way. You’re right- so nice to have it all alone.

      Cheers buddy,

  8. Preaching to the converted , Gavin
    Nice peice though , stuck in Europe for the last 2 months , Immigration passport blah blah , 2 weeks left and cant imagine how people do it
    Traffic tubes busses mayhem , but at 7 billion lets hope some of them remain fearfull

    Live today , plenty of time for dead later

  9. Haha , reading the replys it seems the biggest fear among the converted is to many people converting

    Might have to sail a little further

  10. Hi Gavin,

    Some advice please… what do you suggest if you have a partner (husband of 6 years) that can not see from this point of view? Leave them behind? I’m ready to step off the ledge… but how do you do it if you know that you have to give up half of yourself?

    I know you won’t have ‘the’ answer and that only I can decide, but unfortunately it is a decision that has to be made because I’ve asked him to join me… and he thinks I’m nuts.

    Thanks for your article, its fantastic to know someone else decided to make the jump and is happy with the decision.


    (typing from my desk in a windowless office in Central London)

    • Hi Rosie,

      Thanks for your message. Ok, first things first- I’m not a professional and should not be giving any advice. I’m certainly not in a position to give advice on relationships. HOWEVER, I am an opinionated SOB and while I should probably say something daft like “well your role is to be a loving wife and stand by your man” that just isn’t what I believe, so here goes. I shared your comment with my girlfriend of 8 years and my business partner, Jody MacDonald (www.jodymacdonaldphotography.com). And I’ll tell you what she said as it pretty much mirrors my own thoughts, and actually mirrors how we live. It’s a pretty basic philosophy actually: If your partner loves you, and has any confidence in himself HE HAS to let you do what you want to do. I don’t care what came up- if Jody comes to me tomorrow and says she wants to go on a shooting assignment in Timbuktoo for 6 months I would smile and say- MAKE IT HAPPEN! Sounds awesome. And she would do, and has always done the same for me (it’s the reason we’re still together after 8 years, I’m convinced of this). We believe if you don’t do this your doomed in a relationship anyway at some point because partner A (the one who wants to make a change, or pursue an opportunity, etc.) is going to resent that they can’t…and that resentment is going to grow.

      We’ve all got this one chance, this one opportunity to live our lives. If we don’t do it now, well then when?

      So my advice would be to explain to your husband fully where you are, and why you want to do what you want to do. Present your position, take a stand, be convincing. You don’t have to lose half of yourself, hopefully you can help him see that making the leap is going to be good for you both. But if he still says no to LIVING, then well- I think you won’t be losing half of yourself anyway, you’ll be getting half of it back!

      Anyway, my two cents. Good luck!

        • I know I am reading this thread two years later but I am DYING to know what happened to Rosie.

          In 8 months when the lease is up, My husband and I are making a big change. We have decided that spending 5 days a week in traffic, working jobs we hate to spend our weekends in traffic trying to get to surf isn’t the way we want to live. We already live very modestly but are ready to abandon material security to embrace the lifestyle that will truly bring us happiness… surfing everyday (waves permitting), spearfishing, and trail running with our dog. We are ditching the mainland for Hawaii and accept the risks inherent in our decision. We may never have children, own a nice house or a new car, but we don’t care… the ocean is where we belong (the dog included).

  11. Thank you for putting into word what’s been scratching at the inside of my skull for the past year. My first year out of school and in the corporate coma. Exactly what I need to hear, Thank you.

  12. Such a great article, Gavin.
    It couldn’t have come at a better time for me, as I’ve arrived back in Perth after 4 years travelling to be faced with friends, ex-partners, siblings, all focussed on buying houses, commuting up the freeway, putting plasma screens on lay-by, while I try to make sense of it all.
    It’s good to know there are other people looking for something bigger and more fulfilling than a suburban existence in the town they grew up in.
    I still haven’t figured out the answer, how to balance living and ‘earning’ just right [and sadly, I’m not a world-class kiteboarder or surfer!].
    But I am about to jump on a yacht thru Thailand and Indo for a few months, so I intend to have a think about it over there.
    cheers mate

  13. Hello Gavin,
    I must say the best article at the right time for me. I already made agreement with my boss,that I will quit job in November. It took me few years to finally make this decision. Now I have quite few reasons. Because working something I don’t like and It’s poorly paid, I don’t want to waste time like this any more and I’ll rather spend It outside in nature. I love open seas,big waves,sailing,surfing…things I can’t do here in Slovenia. There is no future here for creative, adveturer,outdoor people like me, this country needs changes and until It gets better I want to see the world and try somewhere else. I hope I’ll get working visa for New Zealand or Australia soon. There is the place where I can start my new chapter of life. Place where I can achieve my goals.
    I will share your article, I’m sure there’s too many people in the world which has to read It and start changing lives. We don’t need to be a human robots.

    take care


  14. Gavin,
    I did enjoy your article, if for nothing else, provoking thought. I admire your “spit into the wind” look at life and your seize the moment attitude. Too many people have chosen the “easy path” and not gotten out of their comfort zones to experience their dreams while chasing the capitalistic dollar.
    Although I don’t know for sure other than from your writings, your father was just such a person. He was one of those people who got up every morning, went to work at a job he may or may not have enjoyed, faithfully brought his meager check home to your mother, who went to the evil cooperate stores to buy you the necessities, and more, of life. Once you became a rebellious teen, and thought you knew all there was to know about life, they sent you off to college, (the largest invisible capitalist cooperation in the world, demanding large sums of money for little return on your investment) which I am sure they helped pay for and when you graduated and found a lucrative job, you chose to repay them by doing what made you feel good. Oh, if only your father and mother had done the same.
    I have to echo Tristan’s observations about your life style being afforded to you by the hard work of others. Do you actually think the person who pumps out the holding tank on your boat grew up wanting that to be their life’s ambition? And yet, where would you be without that person? Being the environmentalist that you are, I doubt you would send your waste over the side so that leaves you in a sticky, if not stinky situation. I also took note, that while you were criticizing “western” civilization, you mentioned your “business partner”, your photographer girlfriend. If not for that western society, the simple life you espouse would not exist at the level you have come accustom. I doubt too much of the third world population purchases your girlfriend’s work.
    Although I probably doesn’t sound like it, I agree with most of what you wrote, I just think you could say the same thing without denigrating your support system. Case in point, I noticed that the site this blog is posted on, is littered with big cooperate advertisers, many of whom most likely sponsor your lifestyle while you are ‘ripping waves” and were good enough to post your thoughts. By the way, are your girlfriend’s photos reproducible without fees? Just asking?
    I am a firm believer of your philosophy and everyone should follow their dream(s) and more importantly, never stop dreaming! Just don’t crap on those who help you make that dream possible in the process. If the world follows your advice, your lifestyle would come to an end overnight.

    • Hi Paul,

      There isn’t a person who would agree with much that you said there about me personally- not about my work ethic (by the way- I was ALWAYS the one who took care of the heads- not my crew!), or where I came from, and definitely not my parents! I think my crew would say that what they were doing on our boat WAS actually what they wanted to aspire to. Way off base there I’m afraid. Jody gives a TON of her photos to great causes, but I don’t need nor want nor need to bolster my (or our) position. It is just an opinion and I put it out there knowing it would antagonize and definitely knowing I’m not right nor more “together” that anyone else because of my life choices. The purpose was only to help push people towards chasing their dreams, and dreams come in many forms. Tristan and you both make some fantastic points, and I agree with all of them. We are part of the bigger problem, we are part of a broken system, and yes the system is and has allowed us to pursue some terrifically fun and selfish things, but my point is that we should do them consciously. My life style is being afforded by hard work, period. If you knew how little money we had (and this hasn’t changed) and what we put on the line to start this you would be gobsmacked. Granted, and I am very conscious of this- It’s a lifestyle that I could never have if I was born into a different place, in a different environment. As I pointed out in the article- some of the most joyous people I’ve run across in the world have the least of the things our corporate sponsors spew out to the world- you’re right, we need none of this stuff to be happy. Which brings me back to passion- that’s the point I was trying to make. But you’re right, I am denigrating the support system- because I think it’s broken and it’s unsustainable, and I’m very conscious that we are part of that system. And it makes promises that are false- buy this and be HAPPY! It’s crap. Thank you for your comments. I knew I would take some heat on this, and that keeps it all real. Thank you.

      • Gavin,
        Totally have to disagree with you on this new tact. The “system” is not broken. It is ever evolving and changing. The argument of “broken” is one that is made throughout history. It is naïve to think that the idea that the “system” is broken is a new one or a revelation. Since man came out of his cave, he (and she) has strived for greater “things” to make their lives easier. Do we now have the ability to own more than we need, maybe but who is to say how much is too much? You have repeatedly stated how little you make or have and yet you are rich in some economic circles. Many would claim you have too much. I have lived in some of the poorest countries in the world and what you state is factual, they are happy with what they have….until they get the chance to have something better. A man blind at birth knows not what the world actually looks like and learns to adapt. However, that doesn’t mean the man would choose to be blind if given the opportunity to see. The difference between the simple life you have and that of the world’s poor is that you have chosen to live the lifestyle you do, they have no choice. However given the choice, most would forgo defecating in the same stream they wash their clothes in for indoor plumbing and a Maytag. If you choose to not participate, you are well within your God given right, but that doesn’t mean the system is broken. It just means you feel it’s broken. Ask the Chinese if they think the system is broken.
        I think you missed the point totally about pumping out your holding tank. Not going to try to expand that here. I am sure your girlfriend does give away TONS of photos and she has a talent, but there is a capitalist venture there, part of the system, whether you want to think of that way or not. I am sure you would agree that Bill Gates and the late Steve Jobs are part of the “system” and they give TONS of their stuff and money away as well but that does not make them any less part of the “system”. I would also venture to say their wealth gained from the system has helped far many more of the world’s poor than those who have dropped out of the system.
        And my friend, I don’t think I made any assumptions about your work ethic. Not sure why you felt the need to defend something that was not stated. I based my conclusions on your stated facts that your father flew out to Boise to help you regain your sanity. I am sure as a good father, he was doing what he thought was best for his son and I am sure the work ethic you state you have can be directly contributed to you parents. NO foul intended, sorry you took it that way.
        Claiming the system is broken is an opinion, not a fact, depending on where you are standing on the big blue ball. You are using the very system you claim is broken to spread your opinion that the system is broken. That was my point.
        I do applaud you for taking the big leap into the unknown and following your heart. Most great men were told by society’s torchbearer that they were dreamers and chasing pipe dreams. Some men dream of changing the world through ones and zeros and phones without wires that take pictures and some men dream of leaving that world behind for a passive existence. Each man would think the dream of the other odd but neither would deny them their vision if they truly believed in dreams coming true. And you are smart enough to be able to make your point and inspire others to live their dreams without vandalizing straw man rhetoric.
        I appreciate your response and I defend your right to your opinion.

  15. Gavin,

    My wife and I have been working towards this goal of sailing away. We are under 30, and before we started liquidating we had a nice condo, a sailboat, two vehicles, and had no time to enjoy them because we working opposite hours to afford these “luxuries”. Jennie, my wife lost her grandmother, and job within a month and we decided to go ahead full steam. All that’s left is our condo to sell.

    All this rings so true to me because I just lost my 21 year old brother unexpectedly last week, and we were faced with the *** life is for the living*** “dilema”. Jennie, my wife, had to fly out the next day to buy our boat on the other side of the continent. We looked at our options and said our only choice is to move forward.

    So what I take from this is life is about taking action, you neverwill regret doing something, it’s what you don’t do that that will always haunt you. That and don’t listen to others, work hard and focus on your dream.

    Anyways, a bit of a sob story, but it’s guys like you who inspired us, thank you.


    • Thank you Dave for your wonderful comment. Jody’s family has just gone through a similar tragedy and these things force us to reevaluate and make hard decisions…and hopefully we make the right ones. Tough lessons…which is life. Thanks and good luck to you both!!!

  16. Great philosophy. Let the dead bury the dead.
    I am 66. No retirement other than SS.
    I had a good paying, easy job in Quality Control. In September, I quit, and am now a full time Boatschool student. I won’t be making as much money, by any estimation, but low stress and a fun challenge. I finally get to do what I like doing.

  17. Hey… a man after my own heart!
    I’ve just quite my job.
    Plan to find travel opportunities, somehow, through Southern Africa… even the simplest weekend away.
    I had a wonderful job – exceptional view of the sea from my window. Part of my job was to take photos of seals, whales etc .. basically I’m in online marketing and I carved out a fantastic job for myself at this place… however, regardless of how exquisite the environment, when politics creeps in… it becomes evil.

    I quite.

    I’m 39 years old and, although I’ve lived in various cities in South Africa, lived in the UK travelled Europe, I’ve yet to discover so much more… minus the politics.

    My final day in my job is next Wednesday. I cannot wait to begin my new journey so I’m going away for the weekend to a place I’ve never been… taking my traveling facebook friends with me…

    I never felt better. I’ve never felt freer . I’m totally liberated from all social norms.

    My soul, spirit and heart are finally free!

    Living life the way it’s meant to be – for ME.

    Thank you for sharing your story – makes me believe even more, that I’m doing the right thing for me.


  18. I enjoyed living a transient life in my 20s, but now I am in my thirties and grateful for my job that puts food on the table and allows me to buy presents for my loved ones. I think people should take a few years off after college, or high school, and explore the world. Live in hostels. Would like to see a USA put all high school grads into a mandatory public service program so that we could learn the value of cooperation and helping others. Helping others trumps any amount of surfing, hiking, and exploring I could ever DO.

  19. Amazing article!

    I’ve been living aboard for over 2 years now, escaped from the NE about a year ago, and I’m slowly making my way down that path. Typing this aboard my measly little Gemini catamaran, anchored off of South Beach. I’m going bet your few critics typed their comments from a miserable cubicle somewhere.

  20. Hi Gavin,

    I enjoyed reading your story. It is nice to hear about someone who grabs life fully and makes the most of all that precious life has to offer! I just wanted to share that, while I respect your life choices, they are not right for everyone, including me. I am a mother of four children and find tremendous joy and fulfillment in caring for them. Perhaps I do get caught up in some of the “snags” that you mentioned, but I love my children and do think that I am a good parent. I think it would be totality unrealistic for my husband or myself I to quit our jobs, thinking that we could just cut out some of those “unnecessary extras.” What if, God forbid, one of us became very ill or had a life altering accident? How would we pay medical bills? For my part, I made a decision when I brought children into the world and I have a responsibility to them. Perhaps I will not see as much of the world as you, but I certainly am not lying in bed regretting this. When my little one puts his hand in mine, or my daughter blows me a kiss before she gets on the bus, my heart is full. When I see my older daughters volunteer and pay a kindness to others, I smile inside. And when I go for a walk with my husband, arm in arm, I know that I am right where I want to be. Happiness and fulfillment come in all shapes and sizes. Some days we do not love our jobs, but each day we love our lives and would not trade with anyone in the world! Finally, we are able to spend a lot of time together as a family. My husband has coached three of my daughter’s teams, I have volunteered in their schools, and we are at nearly every event that they participate in. Yes those people who are truly unhappy should rethink their job (or the source of their unhappiness) but (especially when children are involved) each person should think carefully before walking away from a job when it is their only source of income. Yes, life goes way too fast and we should all make the most of each day, but no one wants to wind up homeless, on welfare, or have their children go to bed hungry.

    I wish you lasting happiness!

    • Hi Mary. Thanks so much for sharing this. As I hope is clear from my comments above- the purpose of this article was definitely NOT to encourage people to live like I do, but just to take stock of their situation as I see a lot of people living quietly desperate lives without passion. Clearly you are living a fulfilled and extraordinary life, and this is all that I was ever hoping to encourage- to LIVE! Well done!

  21. I was re-reading your old blogs and came across this one, which I have to say rang a little hollow for me when I first read it.

    Let me say again that in many ways you are my hero. I admire what you have done.

    Let me also say that I don’t know the answer, and I write this only to engage with you to progress toward it together.

    So here is the meat of it – what dreamers sometimes do is not unlike what pragmatic conventional acheivers do. If X, then I will be happy. Conventional acheivers: If I get promoted to VP I will buy the new BMW and the larger house, and then I will be happy. Dreamer: If I quit my job and go exploring, then I will be happy.

    There is a great TED talk (which I was unable to find for you) about this If…then approach to happiness. The author is clear: you have to thow that out entirely and adopt the “I am going to be happy…period.” approach.

    I don’t entirely subscribe to that message either. Indecision may or may not be my problem, but I think you need a combination of passion and contentment. The “if …then” approach is related to passion, and the “happy…period” approach is related to contentment. I think passionate contentment is where it is at.

    I said that the “If…then” mindset is related to passion. A purer form of passion is a passion for a job well done, not the end product of that job. Doing the job well is living in the moment, even if you are rebuilding the head. I was recently focused on the end result of a kiting downwinder, and when the flukey wind repeatedly stalled my kite and it crashed into the surf line for the third or fourth time, I swore a blue streak. I probably will do the same next time, but a better apprach would have been to be content with the challenge, or with the other opportunities that the day offered.

    The more familiar form of passion is the “if…then”, which is about the result. This form is easily steered by outside influences, like advertising. Whether that advertising is for the new BMW, a diamond, or a cruising sailboat, watermaker or genset. So it is a little easier to take potshots at.

    If you have passion for the process, then you have something good, because you have not surrendered your hapiness to things out of your control. And I submit that it does not entirely matter whether your process is advancing in an organization, or reaching the next horizon.

    So what about contentment? Seems good for monks in monasteries. Being content with very little is probably better for the planet. Maybe it is best, but it does not work for me. I like to strain to do something. Being entirely content with the world as it is surrenders the worlds dominion to the “if…then” pragmatic acheivers. You don’t protest if you are content. You don’t act as an agent for change if you are content.

    I tried to have a humble approach, but now the ultimate conceit: I am going to quote myself. When I got back from a little 8 month cruise I wrote this about cruising. I should point out that my 8 months were nearly without incident (no storms, never had to rebuild the head, only minor engine issues, and when my anchor dragged off a shelf, another sailor retreived my boat before it hit the shallows on the other side of the harbor). So i refer only to irratants instead of the disasters that surely would have befallen me had I been out longer.

    But I think my blog may help may point out the real enigma – If you are content enough to really enjoy the process of cruising, you are probably pretty content at home. And if you are not content enough, the passion will only carry you for a short while.



  22. Great post!

    It kind of makes me wonder though… where do we start to “derail” and make wrong choices which causes unhappiness…?

    It’s normally something people realize late (they may feel too late) in life, and that makes it hard for them to break out of it.

  23. I was working in a corporete in a big city, i don`t fell happy but everithing was ok, my career was groving up! I quite the job, i take 700 euros and i star to travel around the world discovering amazing places amazing people and kiting kiting kiting. That was my life 4 years, i was working a little bit for paying next ticket fly and yes, i do good money in really short times. So i was traveling, working less than never in my life and enjoying a lot! 15 countrys and more than 100 differents towns. But (is always a but) i start to miss city, culture, theatres, cinema, museaums and the complexity of corporations works. So i come back to a big city and i am triyng to have again a corporation working life.

    I don`t know if really i am the city corporation girl or the adventurous girl or maybe i need both??? Or maybe i only like challenges and prouvit myself… I don`t know, i hope to know some day…

    What do you think about this expirience?

  24. Hi Gavin, I wanted to add another point under the list of ’10 reasons to quit your job’… you turn to excessive drinking to deal with the monotony! A few years ago I got a ‘good’ corporate job in Hong Kong and joined the throngs of black suits and money movers. While the job was high paying and offered a lot of security, and allowed me to travel all over Asia and enjoy a very good lifestyle. But slowly I became more and more depressed about my daily life and my work, and began self medicating myself on a daily basis. Get home, put down the handbag, make a gin and tonic. Repeat, repeat, repeat. Like a drunk hamster on the wheel.

    After the third year I decided once and for all to quit the job. My husband and I took off for Thailand for a few months with more than enough savings to get by. But after a while, that too became boring too. Everyone there was retired and enjoying the slow life, but here I was at 30, young and full of energy and potential, with pretty much nothing to do. I then spent months travelling around which was great, but now, a year and a half later after quitting my job, I still find myself trying to figure out what to do with this life. In fact, I miss having a job. I miss having something useful to do, a goal to achieve every day. So I’ve learnt that quitting the job is actually only half the battle — you still have to figure out what you want to DO. Just being free and bouncing around the globe and backpacking might sound all fun and romantic, but the truth is it gets old if you have no purpose.

    So to the people out there thinking of quitting their jobs, my advice would be to start thinking ahead to what you REALLY want to do, and I don’t just mean sitting on the beach drinking rum and relaxing. By all means, yes quit the job you hate, the job you dread going to every day. But don’t just drop out — go and find something GOOD to do.

    • Very sound comment and thoughts. Thanks so much for this. I find traveling without a purpose pretty hollow. Found that out right out of college bumming around South America climbing in the Andes. Thought it would be a challenge, a great learning experience…but really it was all very easy and very quickly grew pretty self-indulgent and I also felt like all my energy was being underutilized. So yes, before cutting the umbilical cord, pretty good idea to think about more than just taking off and wandering. Driven people will quickly find you can’t run fast enough.

      • After reading the article and some of the comments and watching the video I would say that I agree on almost all your reasons to quit your job. However people are different.
        I have switched jobs many times and never had a job for more then 1 year, and for me all the new jobs have given me LOADS of experiences, contacts and so on. I’m generally a person who must plan and be sure to have savings and so on, so I have trouble being spontaneous, however I found out that buying a single ticket to London to find work there actually is no problem. The same goes for travelling around the world without booking hotels or hostels in advance. BUT, I am a very driven person, so I can manage situations like this. And as The Travelling Trini say, sometimes I can miss to have a permanent job and location to live at. So I guess even we driven people can envy others in ways that we don’t compare ourselves with.

        To sum up: As long as you have a PURPOSE of what your doing, do it! If your life has no purpose, GET A PURPOSE! Either by travelling, getting another job or maybe just start your own company, but do the things you like and make a living out of it. If people can make a living out kite-boarding…you can make a living out of anything!

  25. You’re my hero brother, I know what you’ve been through and would still follow you to edge and beyond. Stand strong, your words and path are changing lives, and creating this great debate above, which is golden in itself! I’m ready to go!!

  26. its not that you have to quit your job just because of the sport that you love..you can have the sport and your job together..having a sport is pretty cool it can also make you relax specially if you are being stress of your work..

    kiteboard barcelona

  27. Aw, this was a very nice post. Taking a few minutes and actual effort to produce a superb article… but what can I say… I hesitate a lot and don’t manage to get nearly anything done.

  28. Hey Guys!!
    I’m 24, I live in Chicago. I spent one year in Prague and one year in Argentina trekking patagonia and the like. I speak fluent spanish and czech. When I graduated I knew I could never work for anyone else so I went to work for myself. I started WalknTalk. It grew out of a love affair I had in Argentina when I made a journal for a girl, then moved in with her, build a workshop, and began making and selling them in a Fair in the city. It’s 2 and a half years later now and my journals are in 22 countries and I had a scholarship for study abroad called the Dream Box @dreamboxjourney. It has $150 dollars in it but some day I dream that it will fund international education. My modow is Get Lost To Find Yourself! On that note I think you guys would be my best advocates so I’d love to send you some journals! Shoot me an email and we’ll be in touch. PS I’ve been first mate on a 100 year old wooden motorsailer in NY since I was 16. Love boats, love the water, love that feeling! LIVE WRITE NOW, Talk soon!


    585 703 4506

  29. I just wanted to take some time to thank you for this list and this post. After working in professional jobs for the past 7 years since college graduation, I found myself working in my dream job- but everything about it was causing me so much stress that my body was breaking down. I made one of the hardest decisions of my life to just up and quit that job. I am at a time in my life without kids or a mortgage and with very supporting parents. I moved from Ohio (where I was living) to Florida to live with my father. Every day is still a challenge. Do I still try to find another desk job that may be better than the last? Do I throw away all of my hard work on that piece of resume paper for bar tending or waiting tables? I don’t know what to do right now. All I know is that after reading this I need to find some way to mix my forgotten passions with a new life. I’m only going to get this opportunity once. I went kayaking out on the ocean the other day and I felt so free in the water. Being back near the ocean has helped to heal me a bit. I used to snowboard for over 10 years when I lived up north. I am going to look into kiteboarding or SUP. Thank you for the reassurance that what I did wasn’t absolutely insane. I felt very alone for some time after. I believe the ocean is helping me to heal.

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