Anywired - Wired self-employment tips.

This is a guest-post from Mark Hayward, writing from the Palmetto Guesthouse in Culebra, Puerto Rico.

In one of my previous guest posts here at Anywired I discussed how to remove yourself from the office and take your show on the road. Today, I thought that I would give you a little insight and look into how I went from the cubicle to the Caribbean.

My story of searching for personal freedom might be a little different than most as I now live in the Caribbean and am currently trying to develop my web presence from here. But, whatever your web worker dreams are, this story should hopefully resonate with many Anywired readers, because I’m truly an “everyman.” I do not come from money and have done every possible job from working as a waiter, landscaper, and warehouse worker to presenting data and policy to high-level government officials.

To be sure, my goal to live in the Caribbean is most likely quite analogous to your situation, whatever your objective might be, whether it’s starting your own business, telecommuting a couple of days a week, or traveling the globe. My journey was probably not too different to what many of you are hoping to achieve.

The Beginning of the Journey

Strangely enough, my journey out of the corporate world actually began when I was about fifteen (I turn 40 this year) and I don’t think I even knew what a cubicle was. 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. I soon realized that there was way more to living than snow and cold. The trip also ignited my entrepreneurial spirit and 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 career paths 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 corporate structure

• careful preparation and research

• a willingness to take risks and stepping stone positions

• networking with people

• serving in the Peace Corps

• a strong desire to be an entrepreneur

• unwavering focus on my final goal

So how did I get here?

Preparation

From my story, it appears as though my preparation phase was quite long, and indeed the idea had been planted early, but my true groundwork only began a few years ago. A good majority of my research work was done pre-blog era, meaning that there weren’t great resources around like Anywired (Thanks! — Ed) and MyTropicalEscape to help dispel myths about how to take control of your life and pursue an existence that allows you to work and be free at the same time.

Preparation can be the most arduous and frustrating of steps to success because you won’t 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.”

Photo by yasmapaz

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 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.” Moreover 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, and even briefly back at home in Massachusetts.

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

You’re probably someone who wants to pursue some sense of personal freedom in your life. 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 over night. 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.” More recently, Scott Rigsby told me, “you can’t steer a parked car.” So, with those two final thoughts in mind I would like to close by stating, “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!

What are you hoping to do? Travel the globe? Become a self supported freelancer? Or, how did you get to where you are today?

Mark writes about blogging, personal freedom, and entrepreneurship over at mytropicalescape.com and if you liked this post then you might consider signing up for his RSS feed.

Editor’s note: Mark has asked that if you found this post particularly useful or informative that you please help to support the Special Olympics.

Photo by hal990.