One of the blogs I follow is called “Where’s My Office Now?” This site chronicles the adventures of a pair of freelancers, Corey Smith and Emily King, who decided to become modern nomads and live on the open road. Or, as they put it:

After many months of dreaming and planning, Apple [Corey] and Orange [Emily] set out to redefine their American Dream. On January 29th, 2013, they hit the road in a 1987 VW Vanagon and together journeyed into the unknown.

Being freelancers as well as nomads makes Corey and Emily’s work schedule a challenge, but not impossible. Because their clients are remote, Corey and Emily can logistically do their work and travel the country at the same time. Freelancing makes their chosen dream a reality.

While you may not be up for living the nomadic lifestyle, you can certainly travel more and have a more open schedule by telecommuting or going all out and finding your own freelance work. Or you can work from home, as I do. The possibility of such lifestyle design is the single biggest benefit of telecommuting and/or freelancing.

The question is, how do you start on this road to becoming a telecommuter or FREElancer and working just about anywhere in the world, even if that anywhere is simply from the comfort of your own home?

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It all starts with a work plan.

If you are currently employed, you may wish to read Tim Ferriss’ The 4-Hour Workweek, a book in which he describes how classic 9-to-5 workers can start telecommuting. In a nutshell, Tim advises workers to take a day off from work and spend it productively working at home. Then, based on this amazing productivity, Tim advises workers to broach the topic of telecommuting with their bosses, noting how they were much more efficient thanks to fewer at-work distractions, meetings, etc.

If you need help “proving” how telecommuting makes you more efficient, the Global Workplace Analytics website offers different statistics on telecommuting and its benefits.

Workers are well-advised to ease into this telecommuting arrangement slowly. Tim also notes that, while many bosses will be open to some telecommuting, they probably won’t permit total telecommuting. However, a work schedule that involves being home two workdays out of five is still better for work-life balance than being in the office all five days.

What if your boss says no to telecommuting, or what if your job entails manual or on-site labor that simply can’t be replicated at home?

Focus on remote work as part of your plan.

No doubt, you will never unhitch yourself from your job if it requires on-site labor or physical care of others. This is where, depending on how much you like your work and/or have the capacity to retrain, you will need to take a long, hard look at which aspects of your job, if any, could be completed remotely. For example, if you work in a lab, would it be possible for you to perform only data analysis or report writing? Are there current job openings at your place of employment where you might only have to do data analysis and report writing?

Alternately, would you be open to applying for jobs that take advantage of your current skills yet allow you to work remotely? Before you say no, take a look at this list of 100 companies, provided by the FlexJobs website, where remote workers are regularly hired.

If you can’t telecommute, focus on freelancing.

You might be stuck at a job where your boss feels it is her duty to micromanage you no matter what. In such a case, you are better off perfecting your skills by freelancing. Thus, if you can write well, for example, start pitching your writing services to potential clients when you come home from work. Or offer up your programming, graphic design or other services to private clients.

Yes, doing this type of moonlighting will mean that you work two jobs for a while. However, having the security of paid employment while you transition into freelancing carries many benefits including additional training and/or specialization, possible future clients, and a financial safety net.

Build up your niche expertise and client base- then resign.

Use your moonlighting time as an opportunity to try out different client acquisition strategies. Also, use this time to hone your negotiation skills- especially those related to per-hour and/or per-project pay rates. Become comfortable, and then confident, in your freelancing abilities. Keep acquiring new and higher paying clients.

Once you have an assortment of clients that are paying you well for your niche expertise, it’s time to consider resigning from your current job. And yes, you should consider resigning from, and not getting fired by, your current employer. Even if you end up not getting unemployment compensation because you’ve resigned, it’s just not worth the risk of losing out on this possible future client and/or referral.

Don’t give up on telecommuting or remote work.

As you freelance with bigger and better paying clients, you may eventually receive the offer of part-time or full-time employment. Carefully consider the offer and find out if this is work that you can complete remotely. If you can, negotiate for a telecommuting arrangement. After all, there are benefits to employment, including health insurance, training, retirement plans, etc. Plus, you don’t have to always be marketing your services in order to win new clients.

Also, check out where your potential employer maintains its offices worldwide. You might find out that your favorite winter destination, where you were planning to do freelance work anyway, also houses one of your potential employer’s offices. If such a fortuitous discovery occurs, you might happily “settle down” into employment for a bit, or at least until another remote location starts calling to you.

Have you worked remotely or explored different parts of the world as a result of freelancing? If yes, please tell us about your experiences in the comments below.

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