How I Went From the Cubicle to the Caribbean

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sunset cube to caribbean

Do you have certain dreams and goals that you are going after?

Today, I thought that I would give you a little insight into my backstory with a look at how I went from the cube to the Caribbean.

To be sure, my story about searching for personal freedom might be a little different than most as I now live in the Caribbean and I am currently trying to develop my web presence from here.

But, whatever your small business, social media, or web worker dreams are, this story should hopefully resonate with many readers because I am truly “everyman.”

I do not come from money and have done every possible job from working as a waiter, landscaper, and warehouse worker to presenting technical data and policy to high-level government officials.

My goal to live in the Caribbean is most likely quite analogous to *your* situation, whatever your objective might be – starting your own business, telecommuting a couple of days a week, or traveling the globe, and most likely my journey was not too much different from what many experience.

The Beginning of the Journey

Strangely enough, my journey out of the corporate world actually began when I was about fifteen (I turn 42 this year) and I don’t think I even knew what a cubicle was back then.

During my second year of high school I had the chance to go to Hawaii with a friend and his family. To this day, I can still remember stepping off the United Airlines plane and having my feet touch the sand and soil of the tropics for the very first time.

Certainly, my life would never be the same.

While I was in Hawaii I witnessed a completely different way of life and I soon realized that there was way more to living than snow and cold.

Additionally, the trip actually ignited my entrepreneurial spirit because from the time I returned, and for many months thereafter, I started drawing design ideas for a lifestyle and beach themed t-shirt line that I wanted to start (to help support my new beach life).

The Middle Part of the Journey

As my aspirations and priorities shifted over the years my desire to live in the Caribbean never wavered. Even when I tried to follow the norm, and began down the career track in a few corporations, I quickly realized that corporate mentality (at least in the offices that I experienced) was killing me.

Don’t get me wrong, there are some great companies to work for, I just never had the opportunity to work for them.

I guess this turned out to be a positive thing because all of the office scenarios that I experienced provided the initial catalyst and impetus to keep pushing forward toward my objective.

During the times of uncertainty and speculation about how I would actually make a living in the Caribbean, I always felt that preparation (e.g. acquiring unique technical skills) was the key if I was going to have success.

These days, I am quite certain that many established web workers could probably pick up tomorrow and go travel the world, or start their own practices without much of a negative effect on their income generation potential.

In addition to the above-mentioned preparation, I feel that the following key ingredients allowed for my successful journey:

  • A general disdain for petty office politics.
  • Careful preparation and research.
  • A willingness to take risks and stepping stone positions.
  • Networking with a wide variety of people.
  • Serving in the Peace Corps.
  • A strong desire to be an entrepreneur.
  • An unwavering focus on my final goal.

So how did you get there?


From my story, it appears as though my preparation phase was quite long, and indeed the idea had been planted early. To make matters more difficult, a good majority of my research work was done pre-blog era. Meaning, there weren’t great resources around like Escape From Cubicle Nation, Location Independent, and The Art of Non-Conformity to help dispel myths about how to take control of your life and pursue an existence that would allow you to work and be free at the same time.

I think that preparation can be the most arduous and frustrating of steps to success because you will not necessarily derive any tangible results, especially in the beginning. But, if you stick it out, you might just find a golden opportunity, or at the very least come across a “stepping stone position.”

Stepping Stone Positions

When my wife and I determined that we did indeed want to live in the Caribbean it was then time to find work that would help us to get there. After undertaking our initial preparation and determining that we could not quite fill our financial needs in the Caribbean just yet, we decided to seek various positions elsewhere that would help get us to our final goal.

These are what I like to call “stepping stone positions.” Furthermore, this type of employment is great for freelancers who don’t necessarily want to stay in one place or need to gain some experience before they can finally settle in their desired destination.

Our stepping stone positions had us working in Papua New Guinea, American Samoa, Tortola, and even briefly back at home in Massachusetts. However, we always tried to keep in mind that as long as we were heading in the right direction (i.e. towards the Caribbean) all of our jobs had value.

Also, I have found that pursuing new opportunities typically has a snowball effect and will generally lead to more employment prospects and enhanced chances to participate in new projects.

Focusing on the final goal

One key point that I have taken away from my experience is that unless you are really lucky, tremendously gifted, or possess a technical skill that really is rare, success does not come overnight.

Even forgoing my initial Caribbean dream as a fifteen year old, my journey to the Caribbean took approximately ten years.

A long-term focus will serve you well.

My nine tips based on my experience of going from the cube to the Caribbean are:

  1. Maintain your focus.
  2. Be prepared – make yourself the best candidate for every situation.
  3. Take some sabbaticals or extended research trips to various destinations.
  4. Don’t be afraid to utilize stepping stone positions.
  5. Take risks.
  6. Network effectively (do this early and often).
  7. Control your destiny.
  8. Deal with failure and setbacks and move on.
  9. Remember to have fun and enjoy the complete experience.

I once read, “You can’t learn how to play if you don’t get off the sidelines and get into the game.”

Whatever you would like to pursue – a new job, home based employment, overseas travel, or just to telecommute one day a week, you REALLY can do it! Now go get in the game.

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Mark Hayward


8 thoughts on “How I Went From the Cubicle to the Caribbean

  1. Hi Mark,

    Thanks for the great post. I think it’s amazing that you’ve maintained your dream for so many years, and continued to work toward it. Your dream of living in the Caribbean included more than a location, but also a way of life. I’m proud of you for staying with it and making it happen.

    My dreams are less specific, in terms of geography, but every bit as real. I have a very clear picture of what my life will look like. Many thanks to people like you who share your experience, helping those of us who are on a similar path to authenticity to keep moving forward.

    Take good care, and congrats!

  2. Hi Mark.

    A great post, I agree with Jane.

    I also agree with the petty office politics being a very valid reason on its own to leave the cubicle.

    Whe I read the title, though, I thought: Taxi, Airport, Aeroplane. What is so hard about that? :)

  3. @jane – thank you! I’m about to start chasing some new dreams and goals and thought that this post might keep me on track…

    @dave – Ha! “Taxi, Airport, Aeroplane” gave me a good chuckle. Thank you. :-)

  4. Mark,

    its awesome to read posts like this. When I come across little hurdles in the day I start doubting if I will truly get to all my goals – but when I read a post like this it gives me a boost to know that if someone else got what he wanted than why can’t I.

    Your point of it taking a while to get there was also great to read – when I first began my true journey out of the corporate world (age 22 – I’m 33 now) my most frustrating thing was that it didn’t happen overnight. It seemed so fricking easy when you see most people in the newspapers as you only read about the “overnight” success – but good to see someone that worked for it and admits that it wasn’t “overnight”. I think a lot more entrepreneurs/cublicle bound people will find this a great read.



  5. Hi Amir – thanks for your contribution! Just had a look through your website and noticed you are doing a lot of amazing things…keep up the great work.

  6. Love it, Mark :-). It’s amazing how hard we can make life sometimes. I think in a way, Dave’s comment is spot on. It really is just a matter of buy a ticket and go when it comes right down to it. Keep on keepin’ on!

  7. Hey Mark,

    I just ran across this post from a tweet. Congrats on reaching your goal and thanks for posting info on your journey. I especially liked this qoute you mentioneded “You can’t learn how to play if you don’t get off the sidelines and get into the game.” Seems so very very true.


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