travel blogs, digital nomads, work wirelessly, career choices
(Photo above: My office for a day in San Pedro, Guatemala, overlooking Lake Atitlan.  I have my blackberry, camera bag, notebook and Cuba libre.  Believe it or not, I got a lot of writing done that day, then returned back to my $8/night room.)

I recently came across an article on Computer World called, Why the Downturn Can Be Good for Digital Nomads (thanks to Jeanne Dee for the heads up) and it pointed out that in tight times, working remotely not only makes sense, but it will become easier too.

I’m doing it, my husband’s doing it, there are probably 100 bloggers out there doing it (and writing about it), but I often meet people who are just traveling for a week or two, but wish they could travel more– if only they could find a way to earn a living as they go.

So how do you go from cubicle dweller to digital nomad?

travel blogs, digital nomads, work wirelessly, career choices

Option 1:  Do what you do now, just remotely.

Consult. If you can get a job consulting in the States, you can get one working remotely.  Consultants by definition (although perhaps not in practice, if you’ve ever hired one) are experts in their field.  Companies hire consultants when the work they need done doesn’t justify hiring a full time person.  Or if they don’t have the resources to hire and train someone.  Or if they need it done Right Now.  How to tell if you’re consulting material?  Here’s a simple test.  Put your resume on Monster.  If you get emails in the first week, from headhunters looking for consultants, well then you have a very easily marketable skill.

Freelance. Where consultants typically work for an agency (and usually ones that have established relationships) freelancers are on their own.  There can be some overlap, but most freelancing jobs have a set deliverables.  Edit this book.  Make this website.  Create this logo.  (Consultants on the other hand, are often there to lend their expertise and determine what work needs to be done).  A way to check if your skills fall into the “independent freelancer” realm is to check out places like (just for reference), to see if you’d be a match for any of those jobs.  The key is to find out if there already is a market for your skill set.

Work Remotely. I’m including this one, because it is absolutely possible.  My husband does it.  But, a huge caveat:  it’s easier to convince someone to let you work remotely before you get hired then after.  If you live 30 minutes from the office and they’ve gotten used to your daily presence over the last few years, suddenly requesting to work from home is going to give some heartburn to your manager.  You can quickly evaluate your company with these three questions:  Is anyone else doing it?  Do I have a good relationship with my manager?  Am I already a high producer?

travel blogs, digital nomads, work wirelessly, career choices

Option 2: Change your career path to fit a remote lifestyle

Go down an ancillary path. If you’re struggling to find Consulting/Freelance/Remote work in your current field, can you make a 20 degree adjustment to something else?  For example, if you’re in HR, can you freelance writing policy manuals?  Or if you’re social worker, can you consult with non-profits looking for grant money?  Or if you work for a big corporate entity, can you help small business get off the ground?  The good news is that these types of changes (in the short term) are less jarring than big employment gaps, if you decide to pick up where you left off.

Demote yourself. Give up the title and get the freedom.  If you’re a manager or supervisor, but you used to be a staffer, you might find more opportunities at that lower level.  There are definitely remote opportunities for management level folks (my old boss lived in another state), but most companies are still squirmish about having a manager that no one ever sees and that is only available for meetings via teleconference.  So if you still have those programming/writing/PR/finance/accounting/etc skills that got you promoted in the first place, then you might have a skill that easily translates to a remote lifestyle.

Option 3:  Create your own job

Start an Online Business: This is probably the most popular option and the most risky.  Building a business is tough, and building it online doesn’t make it any easier.  With 50% of small business failing in the first year and 95% failing in the first 5 years, the prospects aren’t any better just because it’s online.  But many people are making it work with less– spreading out their risk with multiple websites, creating ebooks, leveraging large brands (like amazon) to do the heavy lifting and using social media to promote your product.  Gut check:  Are you willing to work really hard for little pay in the beginning?  Do you like networking, making connections with people, and communicating?  Do you have a passion for what you’re selling or creating?

travel blogs, digital nomads, work wirelessly, career choices

Once you pick your path:

1.  Don’t forget that living overseas is often much cheaper than living in the States. While it might take $60,000 to live comfortably in Connecticut, a mere $20,000 somewhere else could be sufficient.  If you take into account that freelancers make more per hour, plus the reduced cost of living, you could be looking for 10 hours of freelance a week, to replace your full time job.  A single three month project could fund your travels for the year, so take this into account when researching.

2.  Give yourself time. You’re boss may take a while to convince, with several test runs.  Or you may find it takes a while to build up enough freelance work.  Or if you start an online business, it could take a year just to earn a living wage.  By insisting on working remotely, you’ve just narrowed the field, so adjust accordingly.  Depending on your industry, if it takes 3 months to find a new job, give yourself at least twice as much to find remote work.  It’s out there.

3.  Plan to travel slower. You’ll be working during the day, running around at night and time passes so much quicker when you try to combine travel and work.  You’ll want to plan your travel days on weekends, or around your work schedule.  Depending on where you are, you also have to try out a few cafes to find the strongest wifi signal.  If you make calls for your job, you’ll have to find somewhere quiet with a good signal (or internet connection for Skype).  It takes a bit to get settled in (when you have to be productive at the same time), so think of your travel in terms of months instead of days.

4.  Remember it’s still work. The flip side to all of this is that once you pull it off, you might find yourself sitting on a beautiful beach (like I did last week in Belize) and instead of playing all day, you’re stuck on your laptop trying to finish an assignment.  While everyone at home is thinking I’m laying on the beach, I’m actually slapping flies away and trying to upload something with a painfully slow internet connection.  But you know what?  For me, it’s worth it.  If you want it, you’ll find a way to make it work.

Photos: Christine Gilbert Bitterjug Paullyoung Angela7 Soctech